INFORM January 2018.5

inform January 2018 Volume 29 (1)
inform
International News on Fats, Oils, and Related Materials
THE “SHEAR” MAGIC OF

ROLL-IN
SHORTENINGS
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January 2018 inform
CONTENTS
6 What makes your shortening
suitable for fancy croissants,
puff and Danish pastry?
Large oscillatory shear tests explain why roll-in shortenings can bear the stresses
of lamination.
10 Unraveling the fusty/musty off-flavor in native cold-pressed

rapeseed oil by application of the molecular sensory science concept
Learn how the 2017 AOCS Analytical Division Student Award winner applied this
unique concept to identify marker compounds that can be used to develop a
quick method for determining the quality of native cold-pressed rapeseed oil.
10 14 18
14 Production of food-grade canola proteins by membrane-based process
A membrane-based, scalable process uses defatted canola meal to produce high
yields of glucosinate-free proteins.
18 From laboratory to full-scale degumming: a new efficient

phospholipase A
Researchers describe the development of Quara® LowP, including the properties
and benefits that have been documented in Novozymes laboratories and
full-scale trials.
22 Extraction of proteins and active substances from microalgae

A new process extracts more value from microalgae by recovering proteins in
tandem with other high-priced products.
26 Tall oil, its chemistries and applications

Tall oil compounds are used in adhesives, paints, mining, and other applications.
This article reviews their unique chemistry and properties.
DEPARTMENTS
5 Index to Advertisers Analysis/commentary Publications and more
21 Classified Advertising 31 Olio 36 Patents
17 AOCS Meeting Watch 32 Regulatory Review 38 AOCS Journals
34 Latin America Update 40 Extracts & Distillates
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6 • inform January 2018, Vol. 29 (1)
What makes your

shortening suitable
for fancy croissants,
puff and Danish pastry?
Braulio A. Macias-Rodriguez and Alejandro G. Marangoni
Shortenings are fats used for many applications, including cakes, icings, and laminated doughs,
among others. As indicated by their name, their main role is to “shorten” baked products by pre-
venting interaction of gluten and starch particles. Other important functions include structuring,
lubricating, foaming, emulsifying, and so on. According to the functional requirements, shortenings
fall into various categories including those intended for roll-in applications.
A roll-in shortening, used in laminated doughs, serves as barrier
• Roll-in shortenings are firm yet by forming continuous thin fat films that prevent fusion of dough lay-
ers. To do so, this roll-in material must “survive” deformations imparted
malleable specialty fats used in the during co-extrusion, sheeting, and folding of dough. If the shortening is
manufacture of laminated doughs. too soft, it will be absorbed into the dough or squeezed out; if it is too
firm and brittle, it will rupture the dough. Either case yields the same
disastrous result: small pastries with poor crumb structure, low lift and
• Their functionality or mechanical volume.
performance is largely determined by To achieve good roll-in functionality, formulation and crystallization
conditions are adequately customized to meet a set of physical criteria.
their bulk rheological properties at Roll-in shortenings are formulated with higher contents of tri-saturated,
large deformations. and tri-unsaturated triacylglycerols (TAGs) consisting of trans fatty acids
in some cases. This represents a major shortcoming as the industry aims
to rid fat products of industrial trans fats to comply with the current reg-
• Large oscillatory shear tests reveal that ulatory framework.
roll-in shortenings are more effective Roll-in shortenings are crystallized under substantial cooling and
shear conditions using a scraped-surface heat exchanger, worker units,
at dissipating energy than other and extrusion passages, which contribute to breakage of crystal aggre-
bakery fats, a property that explains gates, and their orientation into layer-like microstructures. Some of the
physical parameters that are believed to describe roll-in functionality
their ability to bear stresses during include higher solid fat content and melting points, β’ polymorphism, and
lamination. high yield values. Nevertheless, it was recently found that bakery short-
enings may share similar physical properties. For example, an icing short-
ening may share a similar melting point, solid fat content (though wider
melting ranges), and polymorphic behavior with a roll-in shortening.
Likewise, viscoelastic attributes, such as yield values, could not be cor-
inform January 2018, Vol. 29 (1) • 7
EDIBLE APPLICATIONS
FIG. 1. Side views of shortenings during compression. A roll-in shortening deforms plastically without
forming cracks, whereas an all-purpose shortening displays macroscopic cleavage fracture.
related with the usability of shortenings. These findings were

particularly important (yet puzzling) since these properties had
been long used to design for baking functionality.
Rheologically speaking, a glimpse into the differences
among shortenings may be gained partly by tactile percep-
tion (using the so-called “thumb or finger” test) and partly by
visual observation during deformation—still common indus- this purpose, large amplitude oscillatory shear (LAOS) tests
try practices. A roll-in shortening may be perceived as firm yet were conducted and applied to understand yielding dynam-
malleable (“shape” retaining) during handling in contrast to an ics of a wide range of soft matter and complex fluids. Unlike
all-purpose shortening that would be perceived as a firm yet more traditional large deformation tests (cone penetrometry
brittle material. Indeed, during compression a roll-in short- or compression), LAOS oscillations provide controlled yield-
ening does not seem to develop visible cracks, whereas an ing, allow the decomposition of elastic and viscous moduli, and
all-purpose shortening does (Fig. 1). These characteristics are better resemble the flow experienced in use as they probed
important factors in determining the quality of lamination, and strains and frequencies relevant to lamination. For example,
whether the dough bakes into a puff and flaky pastry. under small amplitude oscillatory shear (SAOS), bakery short-
So far, a direct measure of these properties has been enings behave in a similar fashion; i.e., both fats act as soft
impossible, partly because of continued reliance on subjective viscoelastic solids (G′ >G′′ ) with similar viscoelastic moduli,
or empirical tests established over half a century ago [1]. These critical strains, and stresses uncorrelated to solid fat content.
tests have been used to determine “hardness,” “spreadability,” Rohm and Weidinger [2] reached similar conclusions in com-
the “consistency” index, and similar attributes typically found mercial butters. Nevertheless, visualization of the same data in
in the industry lexicon. The challenge in using such tests lies strain versus stress curves makes it possible to realize rheologi-
not so much in their ill-defined physical properties, as in the cal differences between samples.
degree to which such properties can be said to exist at all. This Beyond γcritical≈ 0.05%, both shortenings reached yield
motivated the search for alternative tests or physical measures stresses (taken as stress maximums) of τ1≈4000Pa (roll-in)
of roll-in functionality. and τ1≈4900 (all-purpose), respectively. Above the yield stress
Considering that roll-in shortenings (and fats in general) (failure point), the stress in roll-in exhibits a plateau com-
experience substantial deformations during use, it seemed rel- pared to an all-purpose shortening in which the stress under-
evant to investigate their nonlinear rheological behavior. For goes abrupt decrease and quick stress relaxation. Strong stress
FIG 2. (a) Viscoelastic moduli G′ and G′′ as a function of strain input γ0. Enlarged data points reflect average responses (G′, G′′) calculated
from the raw waveforms. (b) Stress versus strain as obtained from (a) for strain deformations γ0≤15%. (c) Curves of stress versus strain–
elastic projection, and shear rate–viscous projection recorded at ω= 3.6 rads-1and γ0=0.01-10 % for laminating and all-purpose shortenings.
Arrows highlight the observed qualitative differences. Adapted from [5].
overshoots result from the growth of macroscopic fractures in both shortenings display similar features; i.e., stress “upturns”
the nonlinear regime, as shown in Fig 1. and stress “bends” within an oscillatory cycle, specially at maxi-
To capture the observed behavior, several methods have mum strains or shear rates (local measures). However, it seems
been proposed to analyze the nonlinear LAOS response. These that a roll-in shortening experiences less local strain stiffening; i.e.,
include Lissajous-Bowditch (L-B) curves and Fourier-transform milder stress upturn, and less shear-thinning, higher viscosity as
(FT) rheology, and stress-decomposition via FT-Chebyshev seen by larger area enclosed by the elastic L-B figures, and weaker
polynomials, among others. For a comprehensive review on stress bending shown in the viscous L-B figures.
the fundamentals, analysis, and applications of the technique, Quantification of these responses can be done via a
readers can consult the work of Hyun, et. al. [3], while read- Fourier transform (FT) analysis to reconstruct the LAOS wave-
ers wanting to know more about use of the technique in lipid forms. In the linear regime, Fourier series show the presence
materials may refer to Macias-Rodriguez and Marangoni [4]. of one or “fundamental” harmonic (n=1), whereas in the non-
L-B are parametric plots of strain versus stress (elastic per- linear regime, higher-order odd harmonics (n=1, 3, 5…) grow
spective) or strain-rate versus stress (viscous perspective) that unboundly in the nonlinear regime. Fig 2 shows the intensity
appear as ellipsoidal shapes in the linear regime, but progressively of the leading-order harmonic (n=3) as a function of strain.
distort in the nonlinear regime (Fig. 2). In the nonlinear regime, Compared to an all-purpose shortening, roll-in shortenings
FIG. 3. Nonlinear elastic and viscous local measures at ω= 3.6 rads-1and γ0=0.01-10 % for roll-in and all-purpose shortenings. Viscous mea-
sures are parametrized by the linear dynamic viscosity ηLVE’ at γ0= 0.01%. Inset shows absolute values of dynamic viscosities. Adapted
from [5].
gradually transition into the nonlinear regime, suggesting

superior ability to bear stresses for the primer.
To gain physical insight into the nonlinear regime, we use
the FT-Chebyshev framework to isolate storage- and loss-
energy mechanisms in the stress response (Fig. 3). While minor
differences appear in the local elastic response (GL’-GM’)/ GL’,
substantial variations, such as dynamic viscosities at min-
imum- (ηM’) and maximum- (ηL’) shear rates, show in the
viscous response (viscosities are related to plastic flow). To
illustrate, a roll-in shortening exhibits at least twice the rela-
tive dynamic viscosities than an all-purpose shortening does.
Increased viscosities mean that a roll-in shortening dissipates
energy more effectively during deformation than an all-pur-
pose shortening does, and thus the primer withstands higher
stresses than is the case when using all-purpose shortening.
Remarkably, it has been found that multiple formulations (e.g.,
palm-oil based, soybean-oil based, trans-containing, trans-
free) meet the same rheological criteria. This suggests that
novel and functional roll-in shortenings may be designed as
long as the rheological properties are adequately matched.
Braulio A. Macias-Rodriguez is a postdoctoral fellow in the

Department of Food Science, University of Guelph (Ontario,
Canada). He may be contacted at bmaciasr@uoguelph.ca.
Alejandro Marangoni is a professor in the Department of Food

Science, University of Guelph (Ontario, Canada). He may be
contacted at amarango@uoguelph.ca.
Further reading
1. Haighton, A.J. (1959) The measurement of
the hardness of margarine and fats with cone
penetrometers. J. Am. Oil Chem. Soc. 36: 345–348.
http://dx.doi.org/10.1007/BF02640051
2. Rohm, H. and K.H. Weidinger (1993) Rheological
behaviour of butter at small deformations.
J. Texture Stud. 24: 157–172. http://dx.doi.org/
10.1111/j.1745-4603.1993.tb00041.x
3. Hyun, K, M. Wilhelm, and C.O. Klein, et al. (2011)
Progress in polymer science a review of nonlinear
oscillatory shear tests : analysis and application of
large amplitude oscillatory shear ( LAOS ). Prog. Polym.
Sci. 36: 1697–1753. http://dx.doi.org/10.1016/
j.progpolymsci.2011.02.002
4. Macias-Rodriguez, B.A. and A.G. Marangoni (2017)
Linear and nonlinear rheological behavior of fat crystal
networks. Crit. Rev. Food Sci. Nutr. 8398: 1–18.
http://dx.doi.org/10.1080/10408398.2017.1325835
5. Macias-Rodriguez, B.A, Marangoni AG (2017)
Understanding the functionality of lipid-based materials
under large-amplitude nonlinear deformations.
Lipid Technol. 29: 23–27. http://dx.doi.org/10.1002/
lite.201700008
Unraveling the fusty/musty

off-flavor in native
cold-pressed
Katrin Matheis and Michael Granvogl
rapeseed oil by application

of the molecular
sensory science concept
The molecular sensory science concept is aimed at
• Sensomics combines sensory and identifying, quantifying, characterizing, and, finally,
instrumental analytical techniques to simulating the characteristic aromas of specific foods.
analyze odorants. This state-of-the-art sensomics approach for the anal-
ysis of key odorants combines sensory and instru-
• The molecular sensory science concept mental-analytical techniques. The first step is a gentle
uses the sensomics approach to isolation of the volatiles using high-vacuum distillation
identify, quantify, and simulate the at temperatures of 35°C to prevent artifact formation
characteristic aromas of specific foods. either caused by degradation of present aroma-active
compounds or by formation of odorants from other
• In this article, 2017 AOCS Analytical present compounds, such as thermolabile precursors.
Division Student Award winner Katrin
Matheis and her Ph.D. supervisor Next, aroma extract dilution analysis (AEDA) as a screening method
via gas chromatography-olfactometry (GC-O) is applied to reduce the
Michael Granvogl describe how large number of volatiles to a smaller set of characteristic aroma-ac-
they used this concept to identify tive compounds. This is followed by identification experiments based
marker compounds that can be on comparison of retention indices on two GC columns with different
polarities, odor quality and intensity, and mass spectra in electron ion-
used to develop a quick method for ization (EI) and chemical ionization (CI) mode obtained for the analytes
determining the quality of native cold- and their respective reference compounds. A precise quantitation using
stable isotope dilution analysis (SIDA) in combination with the calcula-
pressed rapeseed oil. tion of so-called odor activity values (OAVs; ratio of concentration to
the respective odor threshold) and, finally, simulation of the aroma in a
respective food matrix finalize the concept.
In the first part of the study, this approach was applied to native
cold-pressed rapeseed oil (NPC, native positive control). The volatiles
ANALYTICAL METHODS
were isolated by a two-step high-vacuum distillation consisting The characterization of the key odorants in native cold-
of thin-film distillation, followed by the so-called solvent-as- pressed rapeseed oil with desired sensory attributes was the
sisted flavor evaporation (SAFE) technique [1] to remove basis for unraveling the odorants responsible for the fusty/
remaining oil droplets. After gently concentrating the obtained musty off-flavor in a native cold-pressed rapeseed oil (NOF,
distillate using a Vigreux column, the concentrate (~ 100 µL) native off-flavor oil). In the next step, the key odorants evoking
was stepwise diluted 1+1 (v+v) with solvent and AEDA was the fusty/musty off-flavor in NOF were characterized by
applied, which yielded so-called flavor dilution (FD) factors. application of the molecular sensory science concept. Eighteen
The FD factor correlates with the dilution step and represents aroma-active compounds with OAVs ≥ 1 were found and,
the highest/last dilution, in which the respective odorant was again, the reconstitution model was in perfect accordance
perceivable at the sniffing port during GC-O for the last time. with the original oil. Thereby, 12 compounds were increased
In NPC, 52 aroma-active compounds with FD factors at least by a factor of five compared to NPC and showed OAVs
between 8 and 2048 were detected and identified by their ≥ 1 including 2-sec-butyl-3-methoxypyrazine (earthy, pea-like),
aroma qualities and intensities, retention indices on two GC col- dimethyl trisulfide (cabbage-like), ethyl 2-methylbutanoate
(fruity), 2-isobutyl-3-methoxypyrazine (bell pepper-like), 2- and
umns of different polarities, and mass spectra (EI and CI mode)
3-methylbutanal (both malty), 2- and 3-methylbutanoic acid
using data of reference compounds available in an in-house
(both sweaty), 2-methoxyphenol (gammon-like, smoky), and
database containing more than 1,000 aroma-active volatiles.
4-methylphenol (fecal).
Thirty-one odorants with an FD factor ≥ 64 were quantitated by
In addition to the reconstitution model, a spiking exper-
stable isotope dilution analysis (SIDA), the most accurate meth-
iment was performed to further validate that the odorants
odology, especially for volatile and/or reactive compounds. In responsible for the musty/musty off-flavor had been char-
addition, odor thresholds in oil were determined and used to acterized correctly. Therefore, the 12 compounds clearly
calculate the corresponding OAVs. increased in NOF were added in the respective amounts to
Only 11 compounds showed concentrations above their NPC. In parallel, butanoic acid, (E,E)-2,4-decadienal, dimethyl
respective odor thresholds and, thus, contributed to the overall sulfide, 2-isopropyl-3-methoxypyrazine, and octanal were
aroma of NPC. High OAVs were obtained for 2-isopropyl-3-me- added to NOF to compensate for slightly higher concentra-
thoxypyrazine (330) and dimethyl trisulfide (37), followed by tions in NPC. Finally, the sensory panel was not able to distin-
butanoic acid, dimethyl sulfide (both 7), 2-isobutyl-3-methoxy- guish both model solutions (A: NPC + 12 compounds present at
pyrazine (5), 2-sec-butyl-3-methoxypyrazine, octanal (both 3), higher concentrations in NOF; B: NOF + 5 compounds present
hexanal, 3-hydroxy-4,5-dimethylfuran-2(5H)-one (sotolon), and at higher concentrations in NPC) using the six odor attributes
3-methylbutanal (all 2). mentioned above for evaluation.
For aroma reconstitution, all odorants showing OAVs ≥ 1 Next, omission experiments were performed to verify if
were added in their naturally occurring concentrations to an all 18 odorants with OAVs ≥ 1 are necessary to evoke the char-
odorless oily matrix (refined rapeseed oil). The comparison of acteristic fusty/musty off-flavor. Therefore, single as well as
this reconstitution model with the original oil using the odor groups of odorants were systematically left out in the model
descriptors cabbage-like, nutty/fatty, earthy/pea-like, malty, solution. In a triangle test, this “omission sample” was com-
sweaty, and seasoning-like matched very well [2]. pared to the full recombinate using the forced-choice prin-
FIG. 1. Heat map illustrating the clustering of oil samples with desired sensory attributes (PC, PC1-PC5) or a fusty/musty “off-flavor” (OF,
OF1-OF8), as well as the two corresponding seeds (OFS and OFS8), from which OF and OF8 were pressed. Concentrations (µg/kg) are dis-
played in colors with the highest in red and the lowest in white.
ciple. In summary, the sensory

experiments revealed that a mixture
of the six odorants dimethyl trisul-
fide, 2-methoxyphenol, 4-methylphe-
nol, 2- and 3-methylbutanoic acid,
and sotolon in their naturally occur-
ring concentrations was not distin-
guishable (at a significance level of α
= 0.05) from the full recombinate con-
taining all 18 odorants. Thus, these six
odorants are responsible for the for-
mation of the fusty/musty off-flavor
in cold-pressed rapeseed oils [3].
To find marker compounds for
oils eliciting the fusty/musty sensory
defect, all compounds, which showed
a clearly increased concentration in
NOF, were quantitated in another
eight rapeseed oils eliciting the off-fla-
vor and in five oils with the desired
sensory attributes. These data, clus-
tered pairwise in a heat map, showed
that all of the off-flavor oils showed a
very similar pattern—as was also the
case with the good rapeseed oil sam-
ples. Additionally, the above-men-
tioned increase of selected odorants FIG. 2. Biplot of the PCA showing a clear separation of oil samples with desired sensory
in the off-flavor oils was clearly visi- attributes (PC, PC1-PC5) and with a fusty/musty “off-flavor” (OF, OF1-OF8), as well as of the
two corresponding seeds (OFS and OFS8), from which OF and OF8 were pressed.
ble. Interestingly, the pattern of the
seeds (OFS and OFS8), from which
the off-flavor oils (OF and OF8) were
pressed, and the pattern of the oils OF
or fungi. Consequently, the storing temperature and the

Further reading residual moisture in the seeds play a crucial role in the off-fla-
vor formation [3].
1. Engel, W., W. Bahr, and P. Schieberle, Solvent assisted Additionally, data obtained for the off-flavor oils were sta-
flavor evaporation—a new and versatile technique for tistically evaluated using principal component analysis (PCA).
the careful and direct isolation of aroma compounds The right top quarter in the biplot shows the compounds,
from complex food matrices, Eur. Food Res. Technol. 209: which revealed the highest increase in the off-flavor samples;
237–241, 1999. therefore, 2- and 3-methylbutanoic acid, 4-methylphenol, and
2-phenylethanol were proven to have a high influence on the
2. Matheis, K. and M. Granvogl, Characterization of
separation of the group containing the off-flavor oils and the
the key aroma compounds in commercial native cold-
group containing the oils eliciting good sensory attributes.
pressed rapeseed oil by means of the sensomics
Again, the seeds and the corresponding oils were likewise
approach, Eur. Food Res. Technol. 242: 1565–1575, 2016.
coordinated representing their similarity (Fig. 2).
3. Matheis, K. and M. Granvogl, Characterization of In a final step, the above-mentioned marker compounds
key odorants causing a fusty/musty off-flavor in native were used for the development of a quick method based on
cold-pressed rapeseed oil by means of the sensomics headspace-solid phase microextraction-high resolution gas
approach, J. Agric. Food Chem. 64: 8168–8178, 2016. chromatography-mass spectrometry (HS-SPME-HRGC-MS) to
determine the quality of rapeseed, which can be used as a pre-
diction tool for the quality of the corresponding native cold-
pressed rapeseed oil.
and OF8 themselves were very similar (Fig. 1). Due to the fact
that exactly the same key odorants were characterized in the Katrin Matheis, a graduate student in the Department of
seeds, an influence of the pressing process on the oil quality Chemistry at the Technical University of Munich, received the
could be excluded. 2017 AOCS Analytical Division Student Award. She can be
It was noticeable that all compounds that increased contacted at katrin.matheis@tum.de. Her Ph.D. supervisor is
in the oils eliciting the sensory defect can be formed from Michael Granvogl, Chair for Food Chemistry in the Department
respective precursors, such as amino acids or phenolic acids, of Chemistry at the Technical University of Munich. He can be
via degradation pathways caused by microorganisms, yeasts, contacted at michael.granvogl@ch.tum.de.
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OLFB_inform_AOCS_2017.indd 1 3/10/2017 3:11:51 PM

Production of
food-grade canola
proteins by
Bih-King Chen and Levente L. Diosady
membrane-based process
Canola with very low erucic acid (0.01% in oil)
• A patented process developed by our research and glucosinolate (10 μmole/g seed) levels
group was used to isolate protein from defatted is now grown in Canada. With its high oil
canola meal. The process involves a series of content (45%), low concentration of saturated
well-designed unit operations. In the bench-top fats (7%), and balanced amino acid profile,
experiments, all of these individual steps were it is Canada’s most valuable oilseed crop.
optimized to ensure the quality and yield of the So far the most valuable part of canola is
final products. its oil, which is considered to be one of the
healthiest edible vegetable oils. At present,
• The process yields three products: a precipitated canola oil is produced by prepress solvent
protein isolate with 83% protein, a soluble extraction [1]. In this process, the seed is
protein isolate with 91% protein (both are on cleaned, preconditioned, and flaked; then its
dry basis, N×6.25), and a meal residue with 26% oil is removed by mechanical pressing followed
protein suitable for animal feed. The isolates by solvent extraction. After the hexane is
are light in color and bland in taste. They are recovered from the miscella, the crude oil is
essentially free of glucosinolates, and have very degummed and then refined to produce edible
low phenolics content. oil. The meal is desolventized, then toasted to
remove any residual solvent. Due to its poor
• The process was readily scaled up, resulting in a taste, unattractive dark color, and antinutrients,
precipitated protein isolate and a soluble protein the defatted meal produced is used only as
isolate with qualities similar to the lab products. animal feed despite its high nutritional value.
The high protein content (35–40%) in canola meal, along
with its balanced amino acid profile, makes it attractive for
food applications. In this article we describe, though not at
length, our investigation into converting canola meal to food-
grade protein products. One of the major interests of our
research group is developing processes to isolate proteins from
Brassica oilseeds. Patents [2, 3] have been granted after years
PROTEIN AND CO-PRODUCTS
of research optimizing the process, which yields two main
products: a soluble protein isolate (SPI) and a precipitated pro-
tein isolate (PPI). It also yields a third product, meal residue
(MR), which can be used as a food ingredient if made from
mustard meal, and as animal feed from canola meal.
The process involves a series of unit operations: protein
dissolution, chemical treatment, centrifugation, membrane
operations of ultrafiltration and diafiltration, isoelectric pre-
cipitation, and drying. While each step plays its role in the
production, the operations indispensable for the high qual-
ity of the final products are centrifugation and membrane
operations. Effective centrifugation eliminates fine suspended
particles, resulting in a clear protein extract. This is doubly
important, as a clear solution with no fine solid particles makes
membrane filtration much less prone to clogging, and the pro-
tein isolates have a higher quality since they contain no undis-
solved meal residue. Membrane filtration is a powerful tool
used to separate micro-molecules from macro-molecules in a
true solution, diverting them into two separate streams. Once
the membrane with correct pore size is selected, and the pro-
cess liquid is appropriately pre-treated, the dual operation of
ultrafiltration and diafiltration will remove essentially all small,
low-molecular-weight antinutritional components, and thus
purify the protein solution.
Defatted meals were acquired from different suppliers: (1)
two commercial meals from two different suppliers (pressed,
hexane-extracted, desolventized, and toasted during manu-
facturing), (2) non-toasted meal (pressed, hexane-extracted,
desolventized, but not toasted), and (3) expeller-pressed meal
(pressed twice, without solvent extraction). Aside from these
materials, a meal was also prepared in our lab by defatting the
ground seeds with hexane, followed by air-drying. Table 1 pres-
ents the protein extractability at pH 11.5 and room tempera-
ture (21–25°C).
Compared to the non-toasted meal or the lab-prepared
meal, the commercial meal and the expeller-pressed meals The addition of ascorbic acid reduced oxidization during
had significantly decreased extractability. Obviously, this was the extraction stage. After completing an extraction that
due to the thermal damage to the meal caused by toasting or lasted for 45 min, centrifugation separated the alkaline extract
extensive mechanical pressing. Given that the expeller-pressed solution from the wet solids, which were immediately washed
meal had very low protein extractability, it was not processed twice with water. The extract solution and the two wash solu-
further. tions were combined. The wet solids were freeze-dried to
In a typical bench-scale experiment, 80g of defatted meal produce the meal residue. NaCl was added into the alkaline
was used for protein isolation. The processing started with extract solution, and heated at 50–55°C for 30 min. Then the
aqueous alkaline extraction at pH 11, which was maintained solution was cooled to 45°C, without exceeding the maximum
by 25% or 50% NaOH solution. The extraction of non-toasted operating temperature of our ultrafiltration membrane.
meal or lab-prepared meal was carried out at room tempera- The membrane was made of polyethersulphone, with a
ture (21°C). However, the commercial meal was extracted at molecular weight cut-off of 5,000 Daltons. The extract solu-
50°C to achieve higher protein solubility and higher product tion was split into two streams by ultrafiltration: The retentate
yield. (At 50°C and pH 11 its protein extractability was 65.0%.) containing largely concentrated protein and some micro-mo-
TABLE 1. Protein extractability from various canola meals at pH 11.5
Meal Commercial meal Non-toasted meal Expeller-pressed meal Lab-prepared meal

64.0%
Extractability 45.5% 68.2% 28.5%
(at pH 11)
TABLE 2. Protein content in the starting meals and their final products
Commercial meal* Non-toasted meal# Lab-prepared meal#
Starting meal 35.3% 37.8% 37.0%
Products:
25.4%
Meal residue (MR) 24.9% 23.0%
(25.9% dry basis)
79.3%
Precipitated protein (PPI) 76.5% 90.7%
(83.0% dry basis)
86.1%
Soluble protein (SPI) 81.6% 89.4%
(90.6% dry basis)
* Meal was extracted at 50°C
#
Meal was extracted at room temperature (21°C)
lecular impurities, and the permeate containing undesirable The two major final products from the commercial meal
low molecular weight impurities. The protein in the retentate were noticeably lower in protein content; they were also
was further purified by subsequent diafiltration, in which fresh darker in color, and moderately harsh in taste. The protein
0.05M NaCl solution (adjusted to pH 11) was continuously isolates from the non-toasted or the lab-prepared meal were
added into the retentate while the permeate was removed. beige in color and bland in taste. They were essentially free of
The pH of the diafiltration retentate was lowered to 4 by glucosinolates and had a very low phenolics content (~0.15%).
the addition of 6M H3PO4. This precipitated the proteins. The The process recovered 88.5% of the protein present in the
solid slurries collected after the centrifugation were washed lab-prepared meal; more than 50% was distributed in two iso-
with water, centrifuged, and then freeze-dried to produce the lates, and 35% in the meal residue. The protein distribution
precipitated protein isolate. The clear liquid, which contained among the three products from this meal is shown in Figure 1.
the acid-soluble proteins, was ultrafiltered to reduce its vol- A semi-pilot scale experiment of protein isolation was
ume, and then diafiltered with fresh water. The retentate was conducted with defatted Estonian rapeseed, resulting in two
freeze-dried to produce the soluble protein isolate. major final products, PPI and SPI, with 84% and 91% pro-
Table 2 shows the crude protein content (N×6.25, as is) of tein, respectively. Very similar to canola, the seed also con-
the starting meals and the products made from them. tains low concentrations of erucic acid and glucosinolates. The
meal used for this scale-up test was prepared by defatting the
ground seeds with hexane, followed by air-drying. It was not
heated during desolventization.
Higher protein extractability and better final protein prod-
ucts are attainable if the starting meal is:
• low in oil content;
• low in residual solvent;
• free of contaminants, such as other seeds, weeds,
leaves, stems, soil, or sand;
References
[1] CCC, 2015. Canola Meal Feeding Guide. Feed Industry
Guide, 5th Edition, Canola Council of Canada.
[2] Diosady, L.L., L. Xu, and B-K. Chen, Production of high-
quality protein isolates from defatted meals of Brassica
Seeds, US Patent 6,905,713 (2005).
[3] Diosady, L.L., L. Xu, and B-K. Chen, Production of
high-quality protein isolated from oil seeds, US Patent
8,048,463 (2011).
FIG. 1. Protein distribution among products from lab-prepared
defatted canola
• finely ground;
• dehulled; and
• not thermally damaged.
This work clearly points out that currently available com-
AOCS MEETING WATCH
mercial canola meal or expeller-pressed meal is not a suitable May 6–9, 2018. AOCS Annual Meeting & Expo,
starting material for the process of protein isolation. However, Minneapolis Convention Center, Minneapolis,
we have clearly demonstrated that, when our scaleable pro- Minnesota, USA.
cess is used, high-quality food-grade protein isolates can be
September 6, 2018. JOCS AOCS Joint Symposium, Kobe
made from canola seed that has been gently defatted and
Gakuin University, Arise Campus, Kobe, Japan.
desolventized.
October 28–31, 2018. Fabric and Home Care World
Bih-King Chen is a senior research associate in Conference, Boca Raton Resort & Club, Boca Raton,
the Department of Chemical Engineering and Florida, USA.
Applied Chemistry at the University of Toronto,
Ontario, Canada. He can be contacted at May 5–8, 2019. AOCS Annual Meeting & Expo,
bk.chen@utoronto.ca. Cervantes Convention Center at America’s Center, St.
Louis, Missouri, USA.
Levente L. Diosady is a professor of food
engineering in the Department of Chemical For in-depth details on these and other upcoming
Engineering and Applied Chemistry at the meetings, visit http://aocs.org/meetings or contact the
University of Toronto, Ontario, Canada. He can AOCS Meetings Department (email: meetings@aocs.org;
be contacted at l.diosady@utoronto.ca. phone: +1 217-693-4821; fax: +1 217-693-4865).
AOCS Call for Nominations for the

Thomas H. Smouse 2018–2019 Academic Year
Memorial Nominations for the Smouse Fellowship must be submitted using the official
Fellowship
application. The application is available at aocs.org/awards.
Completed applications must be returned to AOCS by February 1, 2018.
Do you know an exceptional graduate student?

Major Contributors: The purpose of this graduate fellowship is to encourage and support
AOCS outstanding research by recognizing a graduate student pursuing an
AOCS Foundation advanced degree in a field of study consistent with the areas of interest
Archer Daniels Midland Foundation of AOCS. Thomas Smouse was President of AOCS in 1983 and a noted
industrial researcher into the flavor chemistry of fats and oils.
Benefactors:
American Fats and Oils Association The award consists of a US $10,000 Fellowship and up to US $5,000 for travel
Mr. and Mrs. Edward Campbell and research related expenditures related to the student’s graduate program.
Dr. Stephen S. Chang
Fabrica De Jabon la Corona, S.A. DE C.V. Eligibility
National Institute of Oilseed Products This award is open to graduate students with a strong aptitude for research,
Mrs. Bernetta Smouse who are scholastically outstanding, and have
Mrs. Elizabeth Smouse and children additional interests and involvement outside the
Thomas, Deirdre, and Robert academic discipline. Student and major professor
Unichema North America must be current members of AOCS.
For more detailed eligibility requirements,

please visit aocs.org/awards.
Smouse 18-19 Awd Nom Ad-NovDec17i-halfH.indd 1 9/21/17 11:49 AM

From laboratory to
full-scale degumming:
a new efficient
P.M. Nielsen
phospholipase A
Enzymatic degumming is a robust process that consistently ensures a low level of phosphorous (P)
in degummed oil while achieving a higher yield than other physical refining processes. The yield
increase is a result of releasing fatty acids from the phospholipids and reduced binding of neutral
oil in the gum phase.
The enzymatic degumming process was first introduced

• Enzymatic degumming is a highly effective using the expensive porcine pancreatic phospholipase in 2000
[1, 2]. A few years later, a microbial phospholipase A1 (PLA1),
technology to remove phosphorous from oil Lecitase Ultra, was introduced to refineries globally (Fig. 1),
with limited yield loss. and 5–6 years ago Verenium introduced a phospholipase C
(PLC) for the water degumming application. In water degum-
ming, the PLC cleaves off a diglyceride (DG) and significantly
• Phospholipase A Lecitase® Ultra has been widely increases the yield. However, the PLCs available today do not
used since 2003. In 2016, a new thermostable react with all phospholipids.This has led refineries to use a PLC/
PLA combination enzyme product to achieve the highest possi-
and acid-stable enzyme called Quara® LowP was ble yield and DG—within acceptable enzyme costs.
introduced. A new PLA for full degumming has been in development
for some time and was launched as Novozymes Quara LowP in
November 2016. Since June 2016, full-scale testing has been
• This article describes the development of running successfully at our partner plant in the United States.
Quara® LowP, including the properties and
benefits that have been documented in
Novozymes laboratories and full-scale trials.
FIG. 1. The historical development of phospholipase A in refining

PROCESSING
together with additional neutral oil yield, while PLC produces
DG. The most important parameters for a successful enzyme
reaction are temperature and pH in the water phase.
The reaction temperature for enzymatic degumming
has historically been 50–55oC, which corresponds with the
enzyme’s thermostability. It has therefore been necessary to
cool and heat the oil during the process to get the tempera-
ture right for the acid chelating step, the enzyme reaction, and
the separation. The pH in the water phase is also dictated by
the optimum conditions for the enzyme, and normally caustic
must be added to adjust the pH. When adding caustic, a small
amount of soap formation, which can impact the centrifuga-
tion efficiency, is unavoidable.
Recent R&D work addresses some of the challenges of
FIG. 2. Relative activity of Lecitase Ultra (dotted line) and Quara
LowP (solid line) using enzymes for degumming. This has resulted in develop-
ment of a new phospholipase—Quara LowP—which origi-
nates from the thermophilic microbe Talaromyces leycettanus.
BACKGROUND ON DEGUMMING This PLA’s heat-denaturation temperature is 17oC higher than
There are many different technologies available for physical Lecitase Ultra, making it fully active at 70oC and both active
refining of vegetable oils. The oil yield increase is what makes and stable at low pH. The activity at pH 3–7 compared with
enzymatic degumming attractive. The enzyme’s hydrolysis of Lecitase Ultra is illustrated in Figure 2.
phospholipids changes the properties of these molecules dra- With the increased heat stability and the activity at low
matically, making it possible to wash out the gums without pH, the process becomes simpler and easier to control. This is
losing much oil. So the higher the phospholipid content in the evident from the typical process layout for enzymatic degum-
crude oil, the larger the savings will be. ming (with Quara LowP); see Figure 3.
Today there are several suppliers of enzymes for degum- Quara LowP simplifies the process by eliminating the tem-
ming. The enzymes differ with respect to specificity and opti- perature-controlling steps after acid treatment, although the
mum operational conditions. PLA releases free fatty acids (FFA) temperature still needs to be increased to 85oC during centrif-
FIG. 3. Process layout for enzymatic degumming using Quara LowP

ugation for optimum separation and to deactivate the enzyme.

Furthermore, there is no need to add caustic to control the pH.
The low pH coming out of the reaction is expected to reduce
fouling of downstream equipment such as heat exchangers
and centrifuges. In cases when enzymatic degumming is per-
formed at higher pHs, fouling can be prevented by adding acid
after degumming [3].
Quara LowP for full enzymatic degumming has also
demonstrated a significant oil yield increase in laboratory test-
ing (Fig. 4). The figure shows the gum phase in the centrifu-
gation tube after degumming using Lecitase Ultra (55oC) and
Quara LowP (70oC), respectively. The difference in oil yield is
0.8%. Why is that?
First, there is a clear difference in FFA-release during the
reaction. The FFA content in oil is typically 0.3% higher with
Quara LowP. This is because of more efficient hydrolysis of the
phospholipids. Table 1 illustrates how the reaction rate of each
type of phospholipid differs for the two enzymes. This data
was collected from a reaction test at 40oC, and we expect a
significant increase in the reaction rate for both enzymes when
they are used at their respective recommended tempera-
tures of 55oC (Lecitase Ultra) and 70oC (Quara LowP). In addi-
tion, the new enzyme is hydrolyzing off fatty acids from the
lyso-phopsholipids.
FULL-SCALE TESTING
The US-based soybean plant, which has been using Lecitase
FIG. 4. Degumming of crude soybean oil using Lecitase Ultra and
Ultra for three years, has experienced a simple and robust Quara LowP
process with enzymatic degumming that consistently delivers
less than 20 ppm phosphorous after one-step centrifugation.
flow rate, the low dosage at 10 ppm required changes in the
The degumming section consists of three reactors with four
dosage pump This confirmed that the enzyme should be for-
compartments each. These make up the efficient continuous-
mulated in accordance with the dosage of 30 ppm that fit the
ly-stirred tank system with a total of 5 hours retention time.
dosage pumps in the plants.
In the trial, different dosages of Quara LowP were tested
It was immediately evident that Quara LowP produced
to identify the minimum dosage needed to achieve the same
higher FFA than Lecitase Ultra. Further, the new enzyme
performance as the plant could achieve with the Lecitase
changed the gum properties so that viscosity was lower, which
Ultra standard dose of 30 ppm. The process conditions were
impacted the centrifuge. It was then necessary to lower the
changed to meet the temperature and pH optimum of the new
water content in the gums for better operation of the centri-
PLA (70oC and pH of 4 in the water phase). The parameters
fuge. This turned out to be a benefit, because water usage
measured were:
was reduced from 2.5% to 2.2%. During the first two months
• FFA
of trials with the new enzyme, the plant sent samples to the
• P-content by ICP
Novozymes laboratory for analysis. The data analysis com-
• Centrifuge test
bined with plant data documented an FFA increase of 0.3%,
• Yield by flowmeter
and a yield increase of 0.4%, which meant that the yield
Samples were collected on a daily basis, and the conver-
increase was partly FFA (75%) and partly neutral oil (25%). The
sion of the phospholipids was confirmed by NMR analysis.
additional FFA produced by Quara LowP came from the reac-
The Quara LowP test formulation was used at different
tion with lyso-phospholipids (Fig. 5). The first part of the reac-
dosages ranging from 40 to 10 ppm.To be able to deliver a low
TABLE 1. Initial reaction rate for degumming crude soybean oil with Lecitase Ultra and Quara LowP at 40°C measured as ppmP/
(Minutes*ppm enzyme protein). Analyzed by 31P-NMR.
PC PE PI PA
Lecitase Ultra 3.25±0.02 3.50±0.12 0.06±0.03 2.50±0.14
Quara LowP 12.30±0.02 9.85±0.17 1.04±0.10 2.04±0.08
Laboratory tests confirmed that Quara LowP is more efficient than Lecitase Ultra. The next step was full-scale testing at a soybean
oil plant located in the United States.
References
1. Aalrust, E., Beyer, W., Ottofrickenstein, H., Penk, G.,
Plainer, H. and Reiner, R. Enzymatic treatment of edible
oils, US Patent 5,264,367 (1993).
2. Galhardo, F. and Dayton, C. Enzymatic degumming.
AOCS web August 2016: http://lipidlibrary.aocs.org/
content.cfm?ItemNumber=40324.
3. Dayton, C.L.G., Staller, K. and Berkshire, T.L. Process
for improving enzymatic degumming of vegetable oils
and reducing fouling of downstream process equipment,
US Patent 7,713,727 (2010).
The simplest analytical tools are required: FFA-analysis to

FIG. 5. Reaction data from converting phospholipids in crude soy- control the reaction of the enzyme, centrifuge test to check
bean oil 20 ppm dosage of Quara LowP. Analyzed by P-NMR. centrifuge performance, and the ICP for P-content analysis.
Thanks to the trials in the laboratory and at full scale,
tion produces lyso-phospholipids, which are hydrolyzed during Quara LowP was formulated to be used at the standard dosage
the last part of the reaction. of 30 ppm enzyme/ton of oil.
Because Quara LowP operates at a lower pH, it is expected
to lead to several benefits in addition to yield gain. First, NaOH P.M. Nielsen is senior science manager at Novozymes in Bagsvaerd,
dosing becomes redundant, which means that plants can elim- Denmark. He can be contacted at pmn@novozymes.com.
inate soap formation and save pumps and piping. Second, the
low pH can reduce deposits in centrifuge and heat exchangers
[2]. These benefits will take more time to prove, but during the
test period there were no signs of fouling of equipment, and
2.5 months of operation without a need to clean the centrifuge
indicates a significant reduction in deposits.
Extraction of proteins
and active
Halime Idakiev and Steffi Baecker
substances from
microalgae
Microalgae offer incredible potential as renew-
• Today, microalgae are mainly used to produce able raw material due to their ability to synthe-
high-priced products, such as dyes, antioxidants, size numerous valuable ingredients through
and unsaturated fatty acids. They are also sold in photosynthesis-based growth, and to bind
dried form as a food supplement. massive amounts of CO2. Their ability to repro-
duce quickly allows them to realize yields far
• Although proteins are a major constituent of superior to those of classical land plants. Con-
microalgae biomass, they are currently not sequently, algae biotechnology is developing
viewed as a quality product—even though into a major global industry.
many are enzymes with diverse functional
characteristics. Better use of the proteins in To date, 40,000 species of microalgae have been discov-
ered. Of these, only a few hundred species are character-
microalgae (between 30 and 60% [w/w]), could ized biochemically, and only 15 strains are used industrially.
make microalgae processing more profitable, Therefore, while the use of microalgae offers enormous poten-
and is an important step in realizing the concept tial, current use of this renewable raw material remains far
behind what is possible.
of a microalgae biorefinery. Most of the products obtained from microalgae are high-
value products, such as cosmetic ingredients, dyes and other
fine chemicals, antioxidants, and unsaturated fatty acids.
• The study described in this article focuses on Intact algae are also marketed in dried, pressed form, or as
recovering proteins in microalgae alongside the food supplements.
recovery of existing high-price products. More recent developments aim at mass markets such as
the fuel market. Research projects in this area tend to focus on
optimizing the use of individual key components. Meanwhile,
• Optimal conditions for the production of protein other components that are present in microalgae in relatively
high concentrations, such as proteins (Fig. 1), are generally dis-
and biopigment (phycocyanin, phycoerythrin) posed of, released for anaerobic digestion in biogas plants, or
from Arthrospira platensis and Porphyridium used to fuel the combustion process.
This is unfortunate, as many microalgae proteins have a
purpureum were determined during laboratory high-quality amino acid spectrum that would be of interest to
tests. A process flow chart is presented, and manufacturers of human nutrition, animal feed, cosmetics, and
possible applications are discussed. other products. For this reason, Pilot Pflanzenöltechnologie
Magdeburg e.V. (PPM), Magdeburg, Germany, initiated a proj-
ect to develop biorefining technologies for isolating proteins
PROTEIN AND CO-PRODUCTS
FIG. 1. Approximate composition of microalgae Arthrospira FIG. 2. Trial design for determining the optimal conditions for the
platensis and Nannochloropsis gaditana (Miyamoto, 1997; production of pigments and proteins from Arthrospira platensis
Radakovits, et al., 2012, original data) and Porphyridium purpureum
and other potentially valuable co-products in tandem with the proteins (pigment-protein complexes). Both pigments are
production of lipids or other active substances. The premise therefore water soluble, which we considered to be an import-
was that a more holistic use of microalgae could improve the ant factor in selecting an appropriate extraction process.
viability of microalgae cultivation. Phycocyanin (blue pigment) and phycoerythrin (red pigment)
have fluorescent and antioxidant properties. Thus, A. platen-
MICROALGAE SELECTION CRITERIA sis and P. purpureum are cultivated for the production of these
The intent of the project was to investigate five microalgae pigments, which are marketed as high-priced fluorescent dyes
species with different structural compositions and valuable in biological and biomedical research, and as food supple-
products, to see how the isolation procedures would differ. ments and natural dyes in the food and cosmetics sectors.
The algae were selected based on their: The process for extracting functional proteins in con-
• high content of valuable ingredients (a prerequisite for junction with phycocyanin and phycoerythrin extraction from
commercial production); Arthrospira platensis and Porphyridium purpureum was inves-
• ability to be produced on a technical scale; and tigated in laboratory tests, in which various methods of cell
• different cell wall structures and compositions, which disruption, such as high-pressure homogenization, ultrasound
would result in the application of different extraction methods. treatment, ultra-turrax homogenization,and cell lysis were
The microalgae species selected are illustrated in Table applied. The solubility behavior of proteins and pigments at
1. All are commercially available and have a high application various pH values and ionic strengths was determined, and the
potential. The first two microalgae species are currently being extracted proteins and pigments were also separated by pre-
evaluated, as the project is still ongoing. cipitation at different ammonium sulfate concentrations using
a salting-out method. Figure 2 provides an overview of the
methods and testing parameters that were used.
ARTHROSPIRA PLATENSIS AND The optimal cell disruption method for A. platensis turned
PORPHYRIDIUM PURPUREUM out to be high-pressure homogenization. Phycocyanin has
The most important active substances in the microalgae maximum solubility at pH 6, and is unstable within the alka-
Arthrospira platensis and Porphyridium purpureum are phyco- line pH range, where the majority of other proteins are most
cyanin and phycoerythrin, respectively. These are accessory soluble. The proteins of A. platensis are also highly soluble at
pigments in photosynthesis and belong to the phycobili- pH 6 and maximally soluble at pH 10. Therefore, the optimum
pH for extracting both substrates together is 6. Ion concen-
tration does not increase phycocyanin and protein solubility.
Therefore, to solubilize them more selectively, cell disrup-
tion can be conducted at pH 6 without adding salts. The phy-
cocyanin and proteins in the obtained extract can then be
separated from each other—for example, by precipitation at
different ammonium sulfate concentrations. The salting-out
process for microalga A. platensis is presented visually in
Figure 3 (page 28). Phycocyanin can be separated from pro-
teins at higher ammonium sulfate concentrations (25% and
35%), as the phycocyanin fractions are distinguished by their
typical blue color. However, the addition of ammonium sul-
fate introduces obstacles (eg., the high cost of adding and
recovering ammonium sulfate, possible impairment of solubil-
TABLE 1. Tested microalgae (free-access photos assembled from ity in water) which could be avoided with another separation
Culture Collection of Algae (SAG) at Goettingen University) method. Another possibility would be to use ultrafiltration. In
FIG. 3. Phycocyanin and protein separation by precipitation at

different ammonium sulfate concentrations
this case, using membranes with different molecular weight

cut-offs could achieve effective separation, as the pigment and FIG. 4. Process design for obtaining the phycocyanin and proteins
protein have different molecular weights. from Arthrospira platensis
The residue from cell disruption still contains a large por-
tion of the proteins, which can be subsequently extracted
under basic conditions. The protein solution recovered by cen-
trifugation can also be purified by precipitation at the isoelec-
tric point (pH 4) or, alternatively, by ultrafiltration. The process
diagram for extraction of proteins and phycocyanin from A.
platensis is shown in Figure 4.
In the case of P. purpureum microalga, most of the cells
can be disrupted using ultrasound. Phycoerythrin is max-
imally soluble at pH 7, unstable at the alkaline pH range,
and less soluble in saline solution. In contrast, P. purpureum
proteins are poorly soluble at a neutral pH range. They are
most soluble at pH 11 and less soluble in saline solution.
Therefore, these two products cannot be extracted simulta-
neously. By applying successive extraction, both products can
be obtained with high yields and quality. In this case the P.
purpureum cells should be disrupted first at pH 7 to solubi-
lize phycoerythrin more selectively. Since just small fraction
of P. purpureum proteins will be recovered, separation can
be omitted if high purity is not desired. The extract obtained FIG. 5. Process design for obtaining the phycoerythrin and
by centrifugation can be marketed as a phycoerythrin-rich proteins from Porphyridium purpureum
product.
The residue can be subsequently extracted under basic
conditions to obtain the proteins. The protein solution recov- MICROALGAE PROTEINS AND
ered by centrifugation can be further purified by precipitation THEIR POSSIBLE APPLICATIONS
at the isoelectric point (pH 3) or by ultrafiltration. The process Today, the techno-functionality of proteins of only a few
scheme for extracting proteins and phycoerythrin from P. pur- microalgae species (Tetraselmis sp., Chlorella vulgaris, and
pureum is presented in Figure 5. Arthrospira platensis) is known.
Using the processes shown in Figures 4 and 5, proteins Protein extracted from the microalga Tetraselmis sp. are
were obtained as co-products of phycocyanin and phycoeryth- completely soluble at pH values of 5.5 and higher, independent of
rin extraction. Moreover, the techno-functional properties ionic strength. Such Insensitivity to ionic strength opens the door
of the proteins obtained can be studied, and their applica- to applications in a wide range of salt concentrations. In con-
tion possibilities determined based on their functionality. The trast, oil seed proteins are usually minimally soluble at pH values
extraction of other valuable compounds such as sulfated poly- of 5.5 to 6.5 and low ionic strengths (I ≤ 0.3). Due to the strong
saccharides, PUFAs remaining in the residue should also be influence of solubility behavior on the functional properties of
considered. These steps are necessary to use the full poten- a protein, this difference in the solubility behavior of microal-
tial of the microalgae Arthrospira platensis and Porphyridium gal protein extracts compared to the plant proteins can lead to
purpureum. unique techno-functional properties. For example, tetraselmis
References
Benelhadj, S., A. Gharsallaoui, P. Degraeve, H. Attia, and D. Morris, H.J., et al., Immunostimulant activity of an
Ghorbel, (2016), Effect of pH on the functional properties of enzymatic protein hydrolysate from green microalga
Arthrospira (Spirulina) platensis protein isolate, Food Chem. Chlorella vulgaris on undernourished mice, Enzyme Microb.
194: 1056–1063, 2016, Technol. 40, 2007.
http://dx.doi.org/10.1016/j.foodchem.2015.08.133 Radakovits, R., et al., Draft genome sequence and genetic
Buono, S., A.L. Langellotti, A. Martello, F. Rinna, and V. transformation of the oleaginous alga Nannochloropis
Fogliano, Functional ingredients from microalgae, Food gaditana, Nat. Commun. 3: 686, 2012, http://dx.doi.
Funct. 5: 1669–1685, 2014, http://dx.doi.org/10.1039/ org/10.1038/ncomms1688
c4fo00125g Samarakoon, K. and Y.-J. Jeon, Bio-functionalities of proteins
Kang, K.H.., et al., Antioxidant peptides from protein derived from algae: a review, Food Res. Int. 2: 948–960,
hydrolysate of microalgae Navicula incerta and their 2012, http://dx.doi.org/10.1016/j.foodres.2012.03.013
protective effects in HepG2/CYP2E1 cells induced by Schwenzfeier, A., P.A. Wierenga, and H. Gruppen,
ethanol, Phytother. Res. 26: 1555–1563, 2012, Isolation and characterization of soluble protein from
http://dx.doi.org/10.1002/ptr.4603 the green microalgae Tetraselmis sp., Bioresour. Technol.
Karawita, R., et al., Protective effect of enzymatic extracts 102: 9121–9127, 2011, http://dx.doi.org/10.1016/j.
from microalgae against DNA damage induced by H2O2., biortech.2011.07.046
Mar. Biotechnol. 9: 479–490, 2007 Ursu, A.V., et al., Extraction, fractionation and functional
Miyamoto, K. Renewable biological systems for alternative properties of proteins from the microalgae Chlorella
sustainable energy production, FAO Agricultural Services vulgaris. Bioresour. Technol. 157: 134–139, 2014,
Bulletin 128, 1997 http://dx.doi.org/ 10.1016/j.biortech.2014.01.071.
proteins exhibit stronger emulsifying behavior compared to the cyanin, phycoerythrin, astaxanthin, lipids, and other primary
sunflower protein helianthinin (Hel), and the emulsifier-stabiliz- active substances could open up additional revenue streams
ing abilities of the protease inhibitor protein isolated from potato and add value to microalgae processing.
juice (PIP) is comparable to that of whey protein isolate, the most
important protein-containing emulsifier in food applications Halime Idakiev is scientist at Pilot Pflanzenöltechnologie
(Schwenzfeier, et al., 2011). Protein extracts from Chlorella vul- Magdeburg e.V. in Magdeburg, Germany. She can be contacted
garis also show an excellent emulsifying capacity that is compara- at Idakiev@ppm-magdeburg.de.
ble to or higher than that of commercial proteins such as sodium
caseinate and soy proteins (Ursu, et al., 2014). The protein iso- Steffi Baecker is scientist at Pilot Pflanzenöltechnologie
late extracted from Arthrospira platensis (API) has relatively high Magdeburg e.V.
oil- and water-absorption capacities. Moreover, API was able to
form films when sorbitol (30% (w/w)) was used as plasticizer, and Acknowledgements
to form gels when the API concentration exceeded 12% (w/w) The authors thank the European Regional Development Fund
(Benelhadj, et al., 2016). (ERDF) for providing financial support for this research.
The functional properties of the proteins in the microalgae
species we investigated suggest that such proteins have a high
FAST FACT
potential as additives in numerous food as well as non-food
products, such as cosmetics. For example, microalgae proteins
and their derivatives have moisture-retention properties and
provide nutrients to skin and hair, making them good candi- FIND LIKE-MINDED
dates for functional cosmetics (Samarakoon, et al., 2012). They
can also serve as biological substitutes for commercial chemi-
PROFESSIONALS IN
cal emulsifiers and foaming agents in such personal care prod- YOUR GEOGRAPHICAL LOCATION.
ucts as moisturizing creams, lotions, shampoos, soaps, hair AOCS Sections bring members together based on
foam, shaving foam, and many others. In addition, many bio- geographical location. Can you name all seven AOCS
logical activities of microalgae (eg., antioxidant, hypotensive, Sections? Which Section was formed in 2016?
hepatoprotective, immunomodulatory, anti-cancer, and anti-
coagulant) are associated with their proteins, protein hydroly- The seven AOCS Sections are Asia, Australia, Canada,
zates, or peptides (Karawita, et al., 2007; Morris, et al., 2007; China, Europe, India, and Latin America. China is the
Kang, et al., 2012; Buon, et al., 2014). Thus, extracting such newest Section, formed in 2016.
proteins and other active compounds in tandem with phyco-
Tall oil, its chemistries

and applications
Bing Wang
Tall oil is a unique type of “oil” with properties that differ from those of common edible vegetable
oils, such as canola, coconut, corn, olive, palm, peanut, safflower, sesame, soybean, and sunflower,
as well as non-edible vegetable oils such as linseed oil and castor oil.
The term “tall oil” comes from the Swedish word for pine oil:
• Tall oil, which is derived from “Tallolja.” The term was anglicized to distinguish it from the essential
oil that is produced from the steam-distillation of pine stumps, needles,
sustainable and renewable sources twigs, and cones, and is referred to in English as pine oil.
of fatty acids and resins, has been Pine wood contains five major components, namely cellulose, hemi-
cellulose, lignin, tall oil, and turpentine (Fig. 1). While cellulose fibers are
produced commercially since the 1930s.
mainly used for papermaking, the remaining components are considered
to be by-products.
• Tall oil offers unique properties and a
wide range of applications. EXTRACTION PROCESS
For many years, tall oil was treated as waste or burned as fuel. Tall oil
products were not made on a commercial scale until the 1930s, when
• The pine chemical industry has a big the invention of the recovery boiler enabled recovery and reuse of
organic chemicals in the Kraft wood-pulping process that separates tall
impact on the global economy and is oil from wood chips. (Fig. 2, page 28).
evolving to find new applications. In the Kraft process, after the pine chips are digested and filtered,
the filtrate, called “black liquor,” is fed to an evaporator and skim tank
for soap making. The soap is then acidulated to make crude tall oil (CTO).
The CTO is then further fractionated at the refinery to get tall oil heads,
INDUSTRIAL OILS
FIG. 1. Composition of a pine tree
tall oil fatty acids (TOFA), distilled tall oil fatty acids (DTO), tall TALL OIL COMPOSITIONS
oil rosin (TOR), and tall oil pitch (TOP) (Fig. 3, page 28). With a composition similar to that of vegetable oils, TOFA is a
The most important components in CTO are tall oil fatty mixture of fatty acids with various chain lengths and satura-
acids (TOFA) and rosin acids (TOR). Unlike most vegetable oils tions. The most common components are oleic acid, linoleic
and animal fats, tall oil is not produced as triglycerides but as acid, linolenic acid, palmitic acid, and stearic acid. The carbon
straight fatty acids. Nevertheless, tall oil is considered to be chain distribution of tall oil is similar to that of sunflower and
from a renewable resource, just like vegetable oils. soybean oil, which have a higher prevalence of longer chains
With about 3% of total weight in pine wood chips, crude (C16 and higher) than coconut and palm kernel oil do.
tall oil(CTO) is valued at $243 million in world exports, contrib- A unique property of TOFA is that it contains various
uting to global revenues of $10 billion for the pine chemical amount of rosin (represented here are abietic and pimaric
industry (“Global impact of the modern pine chemical indus- acid). The presence of rosin creates physical properties that
try,” Pine Chemical Association, 2016, “https://pinechemicals. could not be obtained from vegetable and animal fats. For
site-ym.com/news/292194/GLOBAL-IMPACT-OF-THE- example, it reduces the bioactivity of TOFA in downstream for-
MODERN-PINE-CHEMICAL-INDUSTRY.htm).
Soap
Skimmings
Crude Tall Oil Heads

Tall
Oil
Plant Tall Oil Fatty Acids
DSTILLATION
CTO Distilled Tall Oil
Tall Oil Rosin
Tall Oil Pitch
FIG. 2. Flow diagram of a typical Kraft pulping process FIG.3. Components in tall oil fractionation
mulations, particularly in metalworking fluid and Household, ylates. Alkyd resins are a major application of TOFA esters.
Industrial, and Institutional (HI&I) products. Short-chain alcohol esters have been used in biodiesel, syn-
In addition to TOFA and rosin, there are other often-ig- thetic lubricants, and as surfactants. An example of a new
nored components of tall oil processing—unsaponifiables. product based on C-21 diacids is Altalub 5300, which has
These are neutral compounds that do not have carboxylic shown promise in lubricant applications (“Performance lubric-
functional groups and thus do not readily form soap when they ity additive for metalworking fluids,” Tribology & Lubrication
react with caustic. The main components of unsaponifiables Technology 72: 76, 2016).
are hydrocarbons, alcohols, and sterols. Although such com- TOFA amides are also being produced; applications include
pounds appear in all five fractions of tall oil distillation, they asphalt additives and mud drilling in oilfields.
are more dominant in tall oil heads and pitch. The extraction of TOFA in the forms of DTO, heads, and CTO or their mix-
sterols makes the unsaponifiables portion of tall oil more com- tures, have been used as anionic collectors in mineral flotation.
mercially attractive. The presence of rosin acids in TOFA can sometimes help to
improve the froth property of the collectors. In addition, TOFA
CHEMISTRIES AND APPLICATIONS amidoamines can also be used as cationic collectors in phos-
phate ore flotation (McSweeney, E., et al., 1987).
Derivatization of TOFA and rosin leads to their salts, esters, and
resins. While C36 dimer acids and C-21 diacids are unique to The Diels-Alder reaction is a very commonly practiced
TOFA, pitch can also be used to extract sterols for medical and reaction for both TOFA and rosin derivatization. For example,
fuel applications. maleic anhydride would be used as a reactant with a
Current applications of TOFA include adhesive, inks, sur- conjugated portion of TOFA (conjugated linoleic acid) or rosin
factants, painting and coatings, mining, and metalworking. (abietic-type acids).
Rosin is used in many applications, including adhesives, inks, Another common reaction in tall oil derivatization is dis-
tires, chewing gums, varnishes, electronics, papermaking, coat- proportionation—an isomerization reaction of TOFA or rosin
ing, and roadmaking. under heat, usually with a catalyst. In TOFA, iodine has been
Esters are one of the most common derivatives of TOFA used to catalyze disproportionation, thus converting non-con-
due to the esterification of polyols (glycerol, pentaerythri- jugated linoleic acid to conjugated linoleic acid, and eventually
tol, and trimethylolpropane), short chain alcohols, and ethox- to oleic acid.
Similarly, rosin can be disproportionated from its conju-
gated diene components, such as abietic and palustric acid, to
its aromatic form as dehydroabietic acid, which is widely used
in the rubber industry (Fig. 4).
Diene portions of rosin can be utilized for a Diels Alder
reaction with maleic acid or anhydrides—or fumaric acids—to
make tricarboxylic acids and further derivatizations for ink and
adhesive applications.
NEW POTENTIAL APPLICATIONS

In addition to traditional applications in rubber, adhesives,
and inks, new applications of tall oil products have been
FIG. 4. The molecular structures of two rosins found in tall oil fatty developed.
acids
MAY 14-16, 2018/ Norman, OK
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Novel applications were recently discovered by making istry and sustainability, tall oil offers alternative raw materials
ionic liquids based on TOFA and rosin (Klejdsz, T., et.al., 2016). and products to both petroleum oil and other natural oils.
In addition, new potential applications for rosin-based
chemistry related to flame retardants have been explored Bing Wang is a senior principal scientist at Ingevity Corporation.
(Zhang, M., et al., 2015, and Lei, et al., 2015). He has broad experience in the chemical industry involving such
TOFA and rosin have also been explored as renewable areas as flame retardants, water treatment, mining, oilfields,
hydrocarbon sources (Jenab, E., et al., 2014). and surfactants. His current research focuses on new applica-
Despite of its long history, the tall oil industry continues to tions of tall oil and its derivatives. He can be contacted at Bing.
evolve. As people pay more and more attention to green chem- wang@ingevity.com.
Information
Pine Chemical Association, “Global impact of the modern Wang, B., “Ionic liquids based on naturally derived fatty
pine chemical industry, 2016, “https://pinechemicals. acids and rosin,” 2017, patent pending
site-ym.com/news/292194/GLOBAL-IMPACT-OF-THE- Jenab, E., P. Mussone, G. Nam, and D. Bressler,
MODERN-PINE-CHEMICAL-INDUSTRY.htm “Production of renewable hydrocarbons from thermal
McSweeney, E., H. Arlt, and L. Russell, “Tall Oil and Its conversion of abietic acid and tall oil fatty acids,” Energy
Uses: II,” Pulp Chemical Association, Atlanta, GA, 1987 Fuels 28: 6988–6994, 2014
Ingevity New Product, “Performance lubricity additive for Zhang, M., Z. Luo, J. Zhang, S. Chen, and Y. Zhou, “Effects
metalworking fluids,” Tribology & Lubrication Technology of a novel phosphorus–nitrogen flame retardant on rosin-
72: 76, 2016 based rigid polyurethane foams,” Polymer Degradation and
Klejdsz, T., et.al., “Biobased ionic liquids with abietate Stability 120: 427–434, 2015
anion,” ACS Sustainable Chemistry & Engineering 4: 6543, Lei, G., S. Xu, and L. Weng, (2015) “Halogen-free rosin-
2016 based flame retardant and preparation method thereof,”
CN104558019A, 2015
Handbook of Advanced
Chromatography/Mass
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AdvanceChromaMassSpec-Oct17i-HalfH.indd 1 8/28/17 2:19 PM

OLIO
A conversation with
Scott Bloomer
Olio is an Inform column that highlights research, issues, trends, and
technologies of interest to the oils and fats community.
Laura Cassiday
In September 2017, AOCS welcomed Scott Bloomer as its new director of technical services,
following the retirement of Richard Cantrill earlier in the year. Bloomer will lead AOCS technical
products and services and represent the scientific interests of AOCS with key scientific and
technical stakeholders in government, academia, and industry.
Bloomer has over 20 years of experience First, we have an outstanding team, dedicated to provid-
in the fats and oils industry. Most recently, ing value to AOCS members. Our flagship production is the
he was a principal scientist and senior patent 7th Edition of the Official Methods and Recommended Practices
agent at Archer Daniels Midland Company. of the AOCS, which contains more than 450 analytical testing
In that role, he assessed the value of new methods used around the world. Our Laboratory Proficiency
process technology and product develop- Program (formerly the Smalley Check Sample Program) is also
ment and prosecuted patents in the areas of broadly used to demonstrate laboratory accuracy and reliabil-
food oil, biodiesel, and renewable chemicals ity. Our Certified Reference Materials are used to confirm the
from oils. He holds a doctorate in bioorganic absence of GMO in oilseeds and other traded food commodities.
chemistry from the University of Lund, Sweden.
I recently had a conversation with Bloomer about his
background, goals, and vision for AOCS technical services. Q: Are there areas that need improvement?
We are working hard to obtain ISO certification for our
Laboratory Proficiency Program. Because our program is 99
Q: How did your previous experience in the fats and oils

industry prepare you for your current role at AOCS?
I did research on many aspects of fats and oils process-
years old, it predates the ISO certification process by decades
and requires a bit of custom tailoring.
ing at Cargill, including degumming, alkali refining, deodoriza-

tion, and hydrogenation, as well as developing methods for Q: Do you have any specific plans for improving or advanc-
ing AOCS Technical Services?
Given the rapidly expanding consumer desire to see
biodiesel synthesis and emulsifier purification. I also worked
at Land O’Lakes doing basic and applied research on modi- organic foodstuffs, we need to expand the offerings of our
fying dairy fats and proteins with enzymes. Following that, I Certified Reference Material program to make more standards
worked at Archer Daniels Midland as a patent agent, where available to food industries around the world.
Q:
I drafted and prosecuted patents on fats and oils process- Thus far, what do you like most about your job as direc-
ing and on replacing petroleum-based ingredients with bio- tor of technical services?
based feedstocks. I also was able to spend much of my time Without a doubt, the AOCS staff. They are smart, hard
analyzing patents to identify opportunities for research and working, and genuinely invested in providing the best ser-
product development. vices to the AOCS membership and the broader fats and oils
Q: What was your involvement with AOCS prior to accept- community.
Q:
ing this position? What activities to do you enjoy when not working?
My first peer-reviewed paper was published in JAOCS. I I enjoy roasting my own coffee, driving my Triumph TR4A
was a peer reviewer and associate editor in the biotechnology (the 50-year-old British sports car I rebuilt), and training in
area for many years and have been providing patents for the martial arts.
Inform patent column for about 15 years.
Q: In your mind, what are the strengths of AOCS Technical Olio is produced by Inform’s associate editor, Laura Cassiday.
Services? She can be contacted at laura.cassiday@aocs.org.
REGULATORY REVIEW
Re-evaluation of mono- and

di-glycerides of fatty acids
(E 471) as food additives
Regulatory Review is a regular column featuring updates on regulatory
matters concerning oils- and fats-related industries.
European Food Safety Authority (EFSA) Panel on Food Additives
and Nutrient Sources added to Food (ANS)
Mono- and di-glycerides of fatty acids (E 471) is

authorized as a food additive in the European
Union (EU) in accordance with Annex II and
Annex III to Regulation (EC) No 1333/2008 on
food additives and specific purity criteria have
been defined in the Commission Regulation
(EU) No 231/2012. The Scientific Committee
on Food (SCF) concluded that the use of mono-
and di-glycerides of fatty acids in nutrient and that it had a composition rich in unsaturated fatty acids
preparations for use in infant formulae and fol- (> 95%). The Panel further noted that its composition made
this material acceptable with regard to the specifications of
low-on formulae is acceptable within the direct E 471. The Panel considered that the results of the toxicological
additive limit of 4 g/L and for use in weaning studies with these diacylglycerols can be used for the assess-
foods within the direct additive limit of 5 g/kg. ment of E 471.
No study was available to evaluate the acute toxicity of
The Panel noted that this food additive has not E 471. No evidence for adverse effects were reported in short-
been evaluated for its other authorized uses as term and subchronic studies in rats and hamsters even at the
highest dose tested of 2,500 mg diacylglycerol/kg body weight
a food additive in EU. (bw) per day in the rats and 7,500 mg glyceryl stearate/kg bw
The Panel considered that it is very likely that hydrolysis of per day in hamsters.
mono- and di-glycerides of fatty acids by lipases in the gastro- The Panel considered that the available studies did not
intestinal tract would occur, resulting in the release of glycerol raise any concern with regard to genotoxicity.
and fatty acids. Glycerol (E 422) and fatty acids (E 570) have No adverse effects were reported in chronic toxicity stud-
been re-evaluated, and the Panel concluded that there was no ies at doses as high as 7,800 and 2,000 mg diacylglycerol/kg bw
safety concern regarding their use as food additives. per day in mice and rats, respectively. In mice and rats, diacyl-
In rats, only traces of cottonseed oil monoglycerides were glycerol did neither show carcinogenic potential nor a promo-
found in the feces, indicating that after hydrolysis, the compo- tion effect in initiation/promotion studies.
nents were well absorbed (97.8 ± 0.4%). In another study, the The refined estimates were based on 31 out of 84 food
absorption of hydrolysis products from diglycerides of fatty categories in which mono- and di-glycerides of fatty acids
acids was calculated to be 58.8 ± 14.3%. (E 471) is authorized. The Panel considered that the uncertain-
The Panel noted that the diacylglycerol (diglyceride) used ties identified would, in general, result in an overestimation of
in several toxicity studies described below was intended to the exposure to mono- and di-glycerides of fatty acids (E 471)
be used for nutritional purposes (as an edible oil substitute) as a food additive in European countries for the refined sce-
nario as the food additive may not be used in food categories, • the contribution of mono- and di-glycerides of fatty
for which no usage data have been provided. acids (E 471) to the daily diet represented at the mean
However, the Panel noted that considering information only 0.8–3.5% of the recommended daily fat intake.
from the Mintel’s Global New Products Database (GNPD), mono- The Panel concluded that there was no need for a numer-
and di-glycerides of fatty acids (E 471) is used in food catego- ical acceptable daily intake (ADI) and that the food additive
ries for which no use levels have been provided to the European mono- and di-glycerides of fatty acids (E 471) was of no safety
Food Safety Authority (EFSA). The main food categories, in terms concern at the reported uses and use levels. The Panel recom-
of amount consumed, for which no use levels reported were: mended that:
unripened cheese; different kinds of pasta; processed fish and • the European Commission considers lowering the cur-
fishery products, including molluscs and crustaceans; processed rent limits for toxic elements (arsenic, lead, mercury
eggs and egg products; and salads and savory-based sandwich and cadmium) in the EU specifications for mono- and
spreads. The Panel further noted that the exposure to mono- di-glycerides of fatty acids (E 471) in order to ensure
and di-glycerides of fatty acids (E 471) from their use according that the food additive will not be a significant source of
the Annex III to Regulation (EC) No 1333/2008 (Parts 1, 2, 3, 4, exposure to these toxic elements in food;
and 5 A and B) was not considered in the exposure assessment. • the European Commission considers revising the EU
Therefore, the exposure to mono- and di-glycerides of fatty specifications for mono- and di-glycerides of fatty acids
acids (E 471) may be underestimated in all scenarios. (E 471) including maximum limits for impurities cur-
The Panel noted that in Annex II of Regulation (EC) rently included in the EU specifications for glycerol
No 1333/2008, use levels of mono- and di-glycerides of fatty (E 422) or recommended by the Panel in the re-evalua-
acids (E 471) in food for infants under the age of 12 weeks tion of glycerol (E 422) (EFSA ANS Panel, 2017b);
are included in category 13.1.1, 13.1.5.1 and 13.1.5.2. The • the European Commission considers revising the EU
Panel considered that these uses for infants under the age of specifications for mono- and di-glycerides of fatty
12 weeks would require a specific risk assessment in line with acids (E 471) including maximum limits for residual sol-
the recommendations given by the Joint FAO/WHO Expert vents which can be used when manufacturing mono-
Committee on Food Additives (JECFA) (1978), the SCF (1998) and di-glycerides of fatty acids (E 471), i.e. tert-butanol
and EFSA (EFSA Scientific Committee, 2017). Therefore, the or tert-pentanol;
current re-evaluation of mono- and di-glycerides of fatty acids • the European Commission considers revising the EU spec-
(E 471) as a food additive is not applicable for infants under the ifications for mono- and di-glycerides of fatty acids (E 471)
age of 12 weeks. including maximum limits for trans fatty acids because
The Panel noted that no specific clinical data address- mono- and di-glycerides of fatty acids (E 471) can be man-
ing the safety of use of mono- and di-glycerides of fatty ufactured by glycerolysis of hydrogenated fats and/or oils,
acids (E 471) in “dietary foods for infants for special medi- which contain significant amounts of trans fatty acids;
cal purposes and special formulae for infants” (food category • the European Commission considers revising the EU
13.1.5.1) and in ‘dietary foods for baby and young children for specifications for mono- and di-glycerides of fatty acids
special medical purposes as defined in Directive 1999/21/EC’ (E 471) including maximum limits for glycidyl esters
(food category 13.1.5.2) considering the defined maximum use because refined vegetable oil, which can be used for
levels were available to the Panel. manufacturing of mono- and di-glycerides of fatty acids
According to the conceptual framework for the risk assess- (E 471) is the only identified source of glycidyl esters of
ment of certain food additives re-evaluated under Commission fatty acids, which are formed during deodorization;
Regulation (EU) No 257/2010 (EFSA ANS Panel, 2014) and given • the European Commission considers revising the EU
that: specifications for mono- and di-glycerides of fatty acids
• in the current safety assessment carried out by the (E 471) including maximum limits for erucic acid because
Panel, the uses and use levels reported by the food erucic acid can be present among the fatty acids in edi-
industry in 46 out of 84 food categories in which ble oils which can be used for manufacturing of mono-
mono- and di-glycerides of fatty acids (E 471) is autho- and di-glycerides of fatty acids (E 471); and
rized were considered. However, only 31 food catego- • more data should be generated to decrease uncertainty
ries were taken into account for the refined exposure arising from the occurrence of compounds of toxico-
assessment; logical concern (e.g. 3-monochloropropane-1,2-diol
• mono- and di-glycerides of fatty acids are subjected to (3-MCPD) or glycidyl esters), which can be produced
hydrolysis by lipases in the gastrointestinal tract to liber- under certain processing conditions from the food addi-
ate glycerol and fatty acids; tive mono- and di-glycerides of fatty acids (E 471).
• data from the evaluation previously conducted for the
food additives glycerol (E 422) and fatty acids (E 570) This is the summary of the scientific opinion that that was
can be used for the evaluation of the food additive published online in the EFSA Journal on November 10, 2017 (
mono- and di-glycerides of fatty acids (E 471); https://doi.org/10.2903/j.efsa.2017.5045), and modified for
• there was no indication for a genotoxic, carcinogenic or Inform and republished under the terms of Creative Commons,
reprotoxic potential from the available data; and http://creativecommons.org/licenses/by/4.0/.
LATIN AMERICA UPDATE
Argentina: corn oil from the

6th worldwide producer of
fats and oils Leslie Kleiner
According to a recent article by the “Bolsa de
Comercio de Rosario (Rosario Stock Market-Argen-
tina),” Argentina’s production during 2016/2017
would change the country’s rank from 7th to 6th
worldwide oil and fats producer (with “oil and fat”
encompassing palm, soy, cotton, peanut, sunflower,
corn, and others) [1]. A positive growth of 10.5%
during 2016/2017 boosted the country’s estimated
total production to 10,231 thousand metric tons,
pushing it into 6th place behind Indonesia, China, the
European Union, Malaysia, and the United States,
and ahead of Brazil, which was bumped to 7th place
by negative growth during that period of-1.1%.
Since corn oil is one of the oils Argentina produces, I inter-
viewed Licenciada Silvana Lisi, Jefa de Desarrollo de Agronegocios
(Manager of Business Development- Agribusiness), Arcor Argentina,
to learn more about this oil’s production.
Q: In the United States, it is common to use soybean oil for

daily applications, and canola oil for frying. What are com-
mon uses for corn oil in Argentina?
In Argentina, the most common uses of corn oil are for the
preparation of salads and fried foods. Corn oil is also commonly
Latin America Update used in the preparation of mayonnaise and preserves.
is a regular Inform Q: What is the annual consumption of corn oil in Argentina?

Corn oil represents 2% of the oils consumed in Argentina, and
has an annual volume of 4,200 metric tons. Arcor’s corn oil (aceite
column that features de maíz Arcor) is leader in the field, with over 30% of the market
segment. Figure 1 depicts the evolution of corn oil consumption
information about per category (human consumption, or bioethanol and industrial
feed combined).
fats, oils, and related
materials in that region. Q: What does a characteristic fatty acid profile for corn oil look
like?
Corn oil has a low saturated fatty acid content (15%), most of
which (11%) is comprised of palmitic acid (C16:0). Instead, corn oil
has a high percentage of unsaturated fatty acids (>80%), which are of
Q: In general terms, how is corn oil produced?

Most of the corn oil is stored within the germ; there-
fore, corn oil production starts by removing the germ from the
grain. This can be achieved by physical and chemical processes
that lead to “wet milling,” or by a physical process alone that
instead leads to “dry milling.”
From the corn germ, the oil extraction process is not much
different than that used for soy and sunflower oil extraction:
pressing and/or solvent extraction. These extraction processes
first condition the germ by means of mills that break and lami-
nate; then, a press extracts a large oil portion, and the remain-
FIG. 1. Oil consumption per use. Y-Axis: kg/ person/year; ing cake is further processed to recover trapped oil by means
dark blue indicates bioethanol and industrial feed combined;
light blue indicates human consumption. Source: Ministerio of solvent extraction. The resulting crude oil is degummed to
de Agroindustria de la Nación – Subsecretaría de Mercados eliminate hydratable phospholipids (Fig. 2), and the product
Agropecuarios (http://www.agroindustria.gob.ar/) is then refined (neutralized, winterized, washed, dried, and
deodorized); see Figure 3. There are many variables that can
interest for their role in the reduction of cardiovascular diseases. be adjusted in the process, and these largely depend on the
Within the unsaturated fatty acids, linoleic acid (C18:2) com- type and quality of the available germ.
prises approximately 51% of the composition. This is followed
by oleic acid (C18:1), which represents approximately 32% of
Preparation Pressing Extraction Degumming
the content. In addition, due to the mild processing conditions,
Arcor corn oil has no trans fatty acids present in its composition.
FIG. 2. Process sequence to obtain crude and degummed corn oil
Q: What additional benefits may arise from the consump-

tion of corn oil?
Corn oil contains ~25 mg/100 g of vitamin E. Therefore,
Neutralization Winterization Washed Deodorization
a 13 mL serving (this equates to 1.5 soup spoons) yields 30%

FIG. 3. Process sequence to obtain refined corn oil
of the recommended daily value currently established in
Argentina. Vitamin E is an important component of the diet,
since it has antioxidant properties that help prevent cell dam-
age caused by the presence of free radicals. Latin America Update is produced by
In addition, corn oil has a larger content of phytosterols Leslie Kleiner, R&D Project Coordinator in
than olive and canola oil, respectively (0.77% phytosterols, by Confectionery Applications at Roquette
weight [2]). Phytosterols are plant-derived compounds that America, Geneva, Illinois, USA, and a
when consumed through diet, have been shown to reduce cir- contributing editor of Inform. She can be
culating LDL-cholesterol levels at a clinically significant level reached at LESLIE.KLEINER@roquette.com.
[3,4]. In particular, phytosterols from corn oil have been shown
to substantially reduce cholesterol absorption in humans [2].
References
[1] Informativo Semanal: Commodities: 6o en el mundo,
FAST FACT
Argentina produce más aceite que Brasil. Año XXXV, vol DID YOU KNOW THAT
(1810) June 2nd, 2017, https://www.bcr.com.ar/Pages/ 41% OF AOCS MEMBERS
Publicaciones/
RESIDE OUTSIDE THE UNITED STATES?
[2] Ostlund, R.E., S.B. Racette, A. Okeke, and W.F. Stenson,
AOCS membership puts you in touch with a network of
Phytosterols that are naturally present in commercial corn
like-minded leaders in nearly 90 countries, as evidenced
oil significantly reduce cholesterol absorption in humans,
by the high percentage of members with manager (19%),
Am. J. Clin. Nutr. 75: 1000–1004, 2002.
company officer (15%), director (13%) in their title. AOCS
[3] Marinangeli, C.P. and P.J. Jones, Deconstructing the members have a broad range of job functions. About
Paleolithic diet: components that reduce cardiovascular 43% reported that their job function is basic research;
disease risk, Curr. Nutr. Rep. 3: 149–161, 2014. 25% food manufacturing; 21% management; 20% QA/
[4] Racette, S.B., X. Lin, L. Ma, and R.E. Ostlund, Natural QC ; 14% marketing and sales; 13% teaching; and 12%
dietary phytosterols, J. AOAC Int. 98: 679–684, 2015. surfactants and detergents.
composition, size, and structure of the fat globules may improve
PATENTS
digestion. The disclosed nutritional compositions may provide
additive and or/synergistic beneficial health effects.
Botanical extract from the aqueous

Milk-based alternative product and stream of the palm oil milling process
method for producing the same for the prevention and inhibition
Domazakis, et al., Creta Farm Societe Anonyme Industrial and of oxidative stress and hemolysis in
Commercial, US9661863, May 30, 2017
The present invention concerns the production of a milk-based
human red blood cells
alternative product, using edible oil to substitute at least part of the Balasundram, et al., Malaysian Palm Oil Board, US9669065, June
milk fat. In particular, the present invention concerns the produc- 6, 2017
tion of a cheese alternative product, an ice cream alternative prod- The invention provides a composition for the prevention and
uct, a custard alternative product, or a chilled or frozen dessert inhibition of oxidative stress and hemolysis in human red blood cell
alternative product, using an edible oil to substitute at least part of wherein said composition compounds obtained from the aqueous
the milk fat. Further, a milk based alternative product, in particu- stream of palm oil milling (palm oil vegetation liquor), in particular
lar a cheese alternative product, an ice cream alternative product, a from vegetative liquor from the milling of palm oil fruit.
custard alternative product, or a chilled or frozen dessert alterna-
tive product, and the use of an edible oil, in particular olive oil, for
the production of the milk-based alternative product are disclosed.
Production of fatty acid alkyl esters
Nielsen, Novozymes A/S, US9670513, June 6, 2017
A method for producing fatty acid alkyl esters, wherein a solu-
Nanogel comprising water-soluble tion comprising triglyceride, alcohol, water, and glycerol is con-
active ingredients tacted with a lipolytic enzyme.
Ding, et al., DSM IP Assets B.V., US9661870, May 30, 2017

The present invention relates to a nanogel composition com- Separation systems for dewatering of
prising at least one water-soluble active ingredient, one or more
plant proteins, and one or more soy soluble polysaccharides. These
fog and biodiesel fuel production
compositions can be used for the enrichment, and/or fortification Bell, et al., Smartflow Technologies, Inc., US9670429, June 6, 2017
of food, beverages, animal feed, and/or cosmetics, and allow stabi- The present invention provides for methods and systems
lization of the active ingredient. The present invention also refers to that effectively separate dispersed FOG from emulsions and/
the process for the preparation of such nanogel compositions. The or free-floating FOG from a waste stream to provide dewatered
present invention furthermore refers to a process for the manufac- emulsions and/or separated fats, oils, and greases from emulsions
ture of a beverage by mixing the compositions with ingredients of thereby providing value added separated product while reducing
beverages. The present invention also refers to beverages obtainable disposal of solid or liquid waste matter into landfills or water treat-
by this process. ment facilities.
Nutritional compositions containing Methods, compositions, and devices

structured fat globules and uses for supplying dietary fatty acid needs
thereof Margolin, et al., Alcresta Therapeutics, Inc., US9668942, June 6,
2017
Banavara, et al., Mead Johnson Nutrition Company, US9661874, Nutritional formulas comprising long-chain polyunsaturated
May 30, 2017 fatty acids (LC-PUFAs) are provided, along with methods and
The present disclosure relates to a lipid source for nutritional devices for preparing and/or administering nutritional formulas.
compositions, comprising an enriched lipid fraction which com- In some embodiments, a percentage of the LC-PUFAs in the nutri-
prises structured fat globules. The enriched lipid fraction pro- tional formula are in the form of monoglycerides and/or free fatty
vides fat globules having a desired size and fatty acid composition acids. In some embodiments, the nutritional formulas do not com-
and may be stabilized by components such as phospholipids, cho- prise added lipase. Also provided are methods for providing nutri-
lesterol, milk-fat globule membrane protein, and combinations tion to a subject, methods for improving fat absorption, methods
thereof. Additionally, the disclosure relates to methods of support- for improving cognitive ability, methods for preventing chronic
ing lipid digestion in a pediatric subject by providing a nutritional lung disease, and methods for reducing the length of time a patient
composition comprising an enriched lipid fraction having struc- requires total parenteral nutrition.
tured fat globules that are more accessible to lipases. The chemical
Automatic frying machine nation results in substantial improvements in metabolic biomarkers

related to insulin resistance, diabetes, weight loss, and physical per-
Kim, et al., Kornic Automation Co., Ltd., US9668616, June 6, 2017 formance in a short period of time. Further, use of these supplements
The present invention relates to an automatic frying machine to achieve ketosis yields a significant elevation of blood ketones and
comprising: a frying process part having divided spaces, wherein reduction of blood glucose levels. Use of these substances does not
a plurality of module-type process units which carry out each of adversely affect lipid profiles. By initiating rapid ketosis and acceler-
predetermined frying processes are detachably disposed in the ating the rate of ketoadaptation, this invention is useful for the avoid-
divided spaces; and a transfer part which is in communication with ance of glucose withdrawal symptoms commonly experienced by
the plurality of process units of the frying process part and which individuals initiating a ketogenic diet, and minimizes the loss of lean
carries a basket having frying materials in and out of the plural- body mass during dietary restriction.
ity of process units and moves the basket, wherein the transfer
part comprises: a basket which carries the frying material in and
out through an opening formed on the plurality of process units; a Cooking aid
transfer unit which raises and lowers the basket and slides it back Krauch, J., et al., Nestec SA, US9675082, June 13, 2017
and forth; and a horizontal moving part which moves the transfer A cooking aid comprising a sheet of flexible burn-resistant
unit horizontally. material and a composition disposed on one face of the sheet, the
composition comprising a mixture of vegetable or animal oil with
Compositions and methods for a melting point below 20°C, vegetable or animal fat with a melt-
ing point above 20°C, and one or more herbs, spices, and flavor
producing elevated and sustained enhancers.
ketosis
D’Agostino, D.P., et al., US9675577, University of South Florida, Patent information was compiled by Scott
June 13, 2017 Bloomer, a registered US patent agent and
Beta-hydroxybutyrate mineral salts in combination with Director, Technical Services at AOCS. Contact
medium chain fatty acids or an ester thereof such as medium-chain him at scott.bloomer@aocs.org.
triglycerides were used to induce ketosis, achieving blood ketone lev-
els of (2-7 mmol/L), with or without dietary restriction. The combi-
Fatty Acids
Chemistry, Synthesis, and Applications
1st Edition
Edited by Moghis U. Ahmad
July 2017 | 600 pages
ISBN (softcover): 9780128095218 | ISBN (ebook): 9780128095447
Fatty Acids: Chemistry, Synthesis, and Applications is a compre-
hensive source of information about a wide range of industrially
important fatty acids. Written by a team of experts, the 18-chapter
book includes detailed descriptions of fatty acid crystallization,
enzymatic synthesis, and microbial production. The book serves
as a reference manual for the oleochemical industries and to a
new generation of lipid scientists and researchers.
List: $175 | Member: $123*
Available for purchase at store.elsevier.com/aocs
*AOCS Members use code AOCS30 at checkout to receive 30% discount and free shipping.
FattyAcidsCSA-Oct17i-HalfH.indd 1 8/28/17 2:18 PM

AOCS JOURNALS
2018: AOCS brings the

journals to the members
2017 was a year of change for AOCS journals. During the past several months, we have made the
transition to our new journal publishing partner, John Wiley & Sons. Wiley is one of the world’s
largest publishers of academic journals, with nearly half published in partnership with academic or
professional societies.
We look forward to increasing our readership, augment- • Wiley’s English language editing, translation, format-
ing our author pool, and improving our review times, and are ting, and figure formatting services to help present your
excited about the many other benefits this partnership offers. research in its best light
For members: • No charge for color figures in print issues of the journals
• Online journal access to current and back issues (Active, • No publishing page charges
Retired, Emeritus) • Virtual collections similar to this one in Lipids: http://bit.
• Access is to all three AOCS journals, which will promote ly/29VpWdO
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Journal of the American Oil Chemists’ Richard F. Wilson Thad A. Rosenberger
Society Oilseeds & Biosciences Consulting University of North Dakota
Raleigh, North Carolina, USA Grand Forks, North Dakota, USA
Editor-in- Chief
James A. Kenar Jill Winkler-Moser
Journal of Surfactants and Detergents
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Lipids Huntsman Performance Products
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a gas chromatograph–flame ionization detector equipped with an
EXTRACTS &
SLB-IL111 capillary column. Results showed that eight ALA iso-
mer standards were separated effectively using these optimized gas
chromatographic conditions. The coefficient of determination was
DISTILLATES
r2 > 0.9994 in the linear range of each ALA isomer. The obtained
limits of detection and limits of quantification of the ALA iso-
mers were 0.02–0.08 ppm and 0.05–0.22 ppm, respectively. A high
degree of reproducibility and percent recoveries between 96.2%
and 106.5%, with coefficients of variation ranging from 0.82% to
0.97%, were achieved. The developed method has been successfully
applied to the analysis of ALA isomers in heated pure trilinolenin
Seed development and hydroxy as well as to trilinolenin in various edible oils, and the TALA isom-
erization pathways in heated trilinolenin were verified.
fatty acid biosynthesis in Physaria
lindheimeri Economic feasibility analysis of
Chen, G.O, et al., Ind. Crops. Prod. 108: 410–415, 2017, https://doi. soybean oil production by hexane
org/10.1016/j.indcrop.2017.06.065.
Hydroxy fatty acids (HFAs) are valuable industrial raw mate-
extraction
rials used in many industries. Physaria lindheimeri accumulates Chenga, M.-H. and K.A. Rosentraterb, Ind. Crops. Prod. 108: 775–
over 80% HFA, in the form of lesquerolic acid (20:1OH), in its seed 785, 2017, https://doi.org/10.1016/j.indcrop.2017.07.036.
oil. Understanding the seed development of Physaria lindheimeri is Hexane extraction is the most common method used in the
an important step to utilizing this unique wild species as a genetic industry to produce soybean oil due to its high oil recovery and lower
source of HFAs biosynthesis. The changes of seed growth, lipid accu- production cost. With the demands of soybean oil increasing either
mulation, and fatty acid composition during seed development of P. in food or industrial applications, expansion plans are considered by
lindheimeri were examined from 14 days after pollination (DAP) to many companies to increase production capacity. Techno-economic
desiccation (56 DAP). The seed development could be divided into analysis is performed to evaluate the economic feasibility of soybean
three periods. During the early period (14 and 21 DAP), seed rapidly oil production by hexane extraction based on historical scenarios
increased in size and fresh weight. In mid-maturation period (28, 35, from 1980 to 2015. Capital investment, operating costs, revenues,
and 42 DAP), lipids and dry weights accumulated steadily. When and profits are main parameters to consider when estimating prof-
seeds developed to late-maturation/desiccation stages (49 and 56 its, gross margin, return on investment (ROI), and payback time and
DAP), fresh weight dropped significantly due to water loss, and the are the indices used to evaluate the profitability of the process. As the
dry weight and lipid accumulation reached their maximums. Seed plant capacity increases in scale to over 34.64 million kg of annual
color remained green up to 42 DAP and turned to orange-brown at soybean oil production, the break-even is met and the producing
49 and 56 DAP. The major fatty acid 20:1OH started accumulation stream is able to earn profits. Additionally, sensitivity analysis is also
when seeds developed into mid-maturation stage (28 DAP) and the applied to examine which factor affects profit the most. In the hexane
accumulation continued thereafter up to 56 DAP, eventually reach- extraction process, material costs, especially for soybean prices, have
ing up to 77% of the total seed oil. The HFA accumulation indicates the most significant effect on profit. However, soybean meal is the
embryonic storage tissue formation, thus 28 DAP defines a critical main driving force for soybean oil production due to its significant
time point for seed development entering reserve synthesis and accu- amount of productivity and revenues.
mulation. The information and knowledge obtained from this study
are essential to the success of HFA production using metabolic path-
way engineering approaches in commodity oilseed crops.
Production of seed-like storage
lipids and increase in oil bodies in
Highly sensitive method for the corn (maize; Zea mays l.) vegetative
quantification of trans-linolenic acid biomass
isomers in trilinolenin of edible oils Alameldina, H., et al., Ind. Crops. Prod. 108: 526–534, 2017,
using an ionic liquid capillary column https://doi.org/10.1016/j.indcrop.2017.07.021.
Triacylglycerides (TAGs) are high energy density lipids
Guo, Q., et al., J. Sci. Food Agric. 97: 4697–4703, https://doi. with a $25 billion commodity at international level. Plant TAGs
org/10.1002/jsfa.8337. are produced via a series of chemical reactions catalyzed by cer-
The polarities of linolenic acid isomers are very similar, and tain enzymes including diacylglycerol acyltransferases (DGATs)
only a few studies to date have attempted to separate α-linolenic and phospholipid diacylglycerol acyltransferases (PDATs). In
acid (ALA) isomers completely. The aim of this study was to fill this Arabidopsis, certain transcription factors including Wrinkled 1
gap by developing and validating an accurate method for the anal- (Wri1) and Leafy Cotyledons2 (LEC2) supply the necessary sub-
ysis of ALA isomers in trilinolenin at 200, 220, and 240°C using strates for synthesis of fatty acids and/or for packaging of the oil
bodies. TAGs will be stored as oil body structures which certain using glycine (RG), hydrochloric acid (RH), diethyl ether (RD),
proteins such as oleosin can protect them from enzymatic degrada- ethyl acetate (RE). Comparison analyses were performed through
tion. In this study, we overexpressed three major genes involved in NMR, FTIR techniques and viscosity, density measurements apart
the TAG biosynthesis and accumulation; 1) dgat1 as a key enzyme from determination of rhamnolipid yields. It can be concluded that
in TAGs biosynthesis, 2) wri1 which is the major transcription fac- rhamnolipid from diethyl ether for extraction is far from molecular
tor involved in supplies of fatty acids for TAG biosynthesis, and 3) structure to reference rhamnolipid molecule according to instru-
oleosin (Ole) gene which encodes for protein that protects TAGs mental analyses performed. Besides, the yield of this rhamnolipid is
from degradation. All three genes were integrated in maize genome much more than other rhamnolipids extracted through other meth-
under a constitutive promoter to allow the production of oil bod- ods but this is misleading because the value in there may be total
ies and seed storage oil-like TAG in maize vegetative biomass. Our sugar content apart from rhamnolipid. Therefore, RD extraction
results indicated an increase in the total leaf oil contents by 79% method can be said to be non-selective process for rhamnolipid
in the metabolically engineered line. GC-MS analysis detected obtained. In RH method, some functional group peaks belong-
a total of 13 fatty acids in the leaf oil extract samples, representing to rhamnolipid were not observed. NMR analysis showed that
ing ∼99.99% of the total fatty acids. Overall, the percentage of the some CH groups were not observed in the RG method. However,
leaf total saturated (SFA) were decreased while the percentage of especially NMR and FTIR analyses showed that rhamnolipid
monounsaturated fatty acids (MUFA) and polyunsaturated fatty obtained from RE method represented more accurate rhamnolipid
acids (PUFA) were increased in metabolically engineered plant based on reference molecule.
leaves. This is the first report of increasing TAG accumulation in
maize vegetative biomass (stover) via metabolic engineering, which
will open new dimension for creating new opportunities to comple- Application of β-cyclodextrin,
ment and expedite the cellulosic biofuels applications. chitosan, and collagen on the stability
of tocopherols and the oxidative
Fatty acid metabolism and prospects
stability in heated oils
for targeted therapy of cancer Gim, S.Y., et al., Eur. J. Lipid Sci. Technol. 119: 1700124, 2017,
Chen, T., et al., Eur. J. Lipid Sci. Technol. 119: 1600366, 2017, https://doi.org/10.1002/ejlt.201700124.
https://doi.org/10.1002/ejlt.201600366. Effects of beta-cyclodextrin (β-CD), chitosan, and collagen on
Fatty acids are fundamental substrates required for energy tocopherol and oxidative stability in heated oils were determined
storage, synthesis of membranes, generation of signaling mole- under moisture added condition at 180°C in this study. Collagen
cules, and lipid droplet formation in cancer cells. High levels of was added in the form of a mesh structure with different pore sizes
fatty acid metabolic activity are one of the most aberrant metabolic (50, 100, 200, and 300 μm) whereas chitosan was added in the form
alterations in cancer cells. The de novo fatty acid synthesis pathway of gel. Presence of 1% w/w β-CD significantly (p < 0.05) reduced the
is the primary source of fatty acids in cancer cells, but cancer cells formation of p-anisidine compared to controls. Collagens also acted
can also acquire fatty acids through the lipolytic pathway, which as antioxidants irrespective of pore sizes whereas chitosan gel failed
helps cells survive and maintain their invasiveness. Key enzymes, to act as antioxidant or prooxidant. Collagen and β-CD significantly
including ATP-citrate lyase (ACLY), fatty acid synthase (FASN), (p < 0.05) protected the decomposition of total tocopherols while
acetyl-coenzyme A (CoA) carboxylase (ACC), stearoyl-CoA desat- chitosan failed to show such protection. Collagen with pore size of
urase 1(SCD1), and monoacylglycerol lipase (MAGL), which are 300 μm significantly (p < 0.05) stabilized γ- and δ- tocopherols com-
involved in fatty acid synthesis and degradation, are overexpressed pared to controls and oils added with β-CD, chitosan, or collagen
in cancer cells. The alterations in fatty acid metabolomics in differ- with pore size of 50 μm. The addition of β-CD, chitosan, and collagen
ent cancers, at different stages of cancer, and in different tissues are significantly (p < 0.05) reduced the moisture content in heated oil
clinically significant. This review focuses on current research into compared to controls. β-CD or collagen mesh structure can be used
fatty acid metabolism to explore new targets against the fatty acid in heated oils like frying condition to control the rates of lipid oxida-
metabolic pathways for anticancer therapy. tion. Addition of biopolymers may extend the oxidative stability and
shelf-life of heated oils and help to produce more food products.
The true methodology for
rhamnolipid: various solvents affect Oryzanol modifies high-fat, diet-
rhamnolipid characteristics induced obesity, liver gene
Çakmak, H., et al., Eur. J. Lipid Sci. Technol. 119: 1700002, 2017, expression profile, and inflammation
https://doi.org/10.1002/ejlt.201700002.
Rhamnolipid, among the most effective biosurfactants, is a
response in mice
glycolipid-type biosurfactant primarily produced by Pseudomonas Wang, L., et al., J. Agric. Food Chem. 65: 8374–8385, 2017,
aeruginosa. In this study, rhamnolipid production was carried out https://doi.org/10.1021/acs.jafc.7b03230.
using a strain of P. aeruginosa and it is aimed to compare rham- In Western countries and China, the dietary habit of high
nolipid biopolymers obtained from various extraction methods calories usually results in hyperlipidemia, which is closely asso-
ciated with cardiovascular diseases. In the study, we investigated (P < 0.05) 1-y changes in 20 and 17 lipids, respectively, compared
the antihyperlipidemic effect of oryzanol and its molecular mech- with the control group. Of these changes, only those in CE(20:3)
anism in the high-fat diet (HFD) mouse model. In total, 60 ICR in the MedDiet + nuts group remained significant after correcting
mice were randomly divided into control group, HFD group, and for multiple testing. None of the 1-y changes was significantly asso-
HFD+Ory group. The mice from the HFD+Ory group were addi- ciated with CVD risk after correcting for multiple comparisons.
tionally fed with 100 mg/kg of oryzanol by intragastric adminis- Although the MedDiet interventions induced some significant 1-y
tration. Our data indicated that oryzanol treatment for 10 weeks changes in the lipidome, they were not significantly associated with
significantly reduced bodyweight, liver weight, and adipose tissues subsequent CVD risk. Lipid metabolites with a longer acyl chain
weight of the mice; lowered the contents of total cholesterol (TC), and higher number of double bonds at baseline were significantly
triglycerides (TG), and low density lipoprotein-cholesterol (LDL- and inversely associated with the risk of CVD.
C); and elevated high density lipoprotein-cholesterol (HDL-C) in
the plasma of HFD mice. Compared with the HFD group, H&E
staining showed that oryzanol treatment decreased the size of fat Solvent-free biodiesel production
droplets of liver tissues and the size of adipocytes. Gene chip data catalyzed by crude lipase
found that oryzanol administration caused 32 genes to increase
expressions while 60 genes had reduced expressions in the liver tis- powder from seeds: effects of
sues of HFD mice. IPA software was used to analyze the protein
interaction network and found that transcript factor NF-κB located
alcohol polarity, glycerol, and
in the central role of network, meaning NF-κB may have import- thermodynamic water activity
ant function in the lipid-lowering effect of oryzanol. Western blot- Kouteu, P.A.N., et al., J. Agric. Food Chem. 65: 8683–8690, 2017,
ting and RT-qPCR confirmed that lipid metabolism-related gene https://doi.org/10.1021/acs.jafc.7b03094.
expressions were obviously regulated by oryzanol administration. The aim of this work was to evaluate the potential of crude
Oryzanol also inhibited expressions of inflammatory factor in the lipase powders made from Adansonia grandidieri and Jatropha mah-
liver tissues of HDF mice. Taken together, our data indicate that afalensis seeds for the synthesis of fatty acid alkyl esters in a sol-
oryzanol treatment can regulate lipid metabolism-related gene vent-free system. The influence of the nature of the alcohol, the
expressions and inhibit HDF-caused obesity in mice. amount of glycerol, and hydration of the powder was investigated.
Results showed that the activity of these crude lipase powders was
Plasma lipidomic profiles and inversely proportional to the alcohol polarity and the amount of
the glycerol in the reaction medium. To ensure optimum activity,
cardiovascular events in a A. grandidieri and J. mahafalensis powders must be conditioned to
randomized intervention trial with the a water activity of 0.33 and 0.66. To obtain a fatty acid ethyl ester
yield greater than 95% with A. grandidieri, ethanol should be intro-
Mediterranean diet duced at an amount corresponding to a triacylglycerol to ethanol
molar ratio of 2:1 every 15 h for 96 h and use 25% of preconditioned
Toledo, E., et al., Am. J. Clin. Nutr. 106: 973–983, 2017,
crude lipase powders (2 additions of 12.5%).
https://doi.org/10.3945/ajcn.116.151159.
Lipid metabolites may partially explain the inverse associa-
tion between the Mediterranean diet (MedDiet) and cardiovas- They say coconut oil can aid weight
cular disease (CVD). We evaluated the associations between 1)
lipid species and the risk of CVD (myocardial infarction, stroke, or loss, but can it really?
cardiovascular death); 2) a MedDiet intervention [supplemented Clegg, M.E., Eur. J. Clin. Nutr. 71: 1139–1143, 2017, https://doi.
with extra virgin olive oil (EVOO) or nuts] and 1-y changes in org/10.1038/ejcn.2017.86.
these molecules; and 3) 1-y changes in lipid species and subsequent There has in recent years, been much media speculation and
CVD. With the use of a case-cohort design, we profiled 202 lipid consumer interest in the beneficial satiating properties of consum-
species at baseline and after 1 y of intervention in the PREDIMED ing coconut oil and its potential to aid weight loss. However, the
(PREvención con DIeta MEDiterránea) trial in 983 participants media has primarily cited studies using medium-chain triglycerides
[230 cases and a random subcohort of 790 participants (37 over- (MCT) oil. The current perspective looks at the research that
lapping cases)]. Baseline concentrations of cholesterol esters (CEs) is available on coconut oil. It examines if and how MCT-related
were inversely associated with CVD. A shorter chain length and research can be applied to coconut oil and if there is potential for
higher saturation of some lipids were directly associated with CVD. coconut oil to aid weight loss. The current report indicates a lack of
After adjusting for multiple testing, direct associations remained consistent evidence on the topic of coconut oil, satiety, and weight
significant for 20 lipids, and inverse associations remained signifi- loss. Given both the publicity and the increased consumption of
cant for six lipids. When lipid species were weighted by the number coconut oil further research, particularly long-term clinical trials,
of carbon atoms and double bonds, the strongest inverse associa- in this area are warranted.
tion was found for CEs [HR: 0.39 (95% CI: 0.22, 0.68)] between
extreme quintiles (P-trend = 0.002). Participants in the MedDiet +
EVOO and MedDiet + nut groups experienced significant
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was possibly the result from the downregulation of genes involved

Thinking outside the classical chain in lipogenesis in goat mammary glands.
reaction box of lipid oxidation:
evidence for alternate pathways and The physical state of emulsified edible
the importance of epoxides oil modulates its in vitro digestion
Guo, Q., et al., J. Agric. Food Chem. 65: 9120–9127, 2017, https://
Schaich, K.M., et al., Lipid Technol. 29: 91–96, 2017, https://doi.
doi.org/10.1021/acs.jafc.7b03368.
org/10.1002/lite.201700025.
Emulsified lipid digestion was tailored by manipulating the
Lipid oxidation has always been viewed as a simple free radical
physical state of dispersed oil droplets in whey protein stabilized
chain reaction with straightforward sequence of radicals → hydrop-
oil-in-water (O/W) emulsions, where the oil phase consisted of
eroxides → products. The first paper in this series proposed that
one of five ratios of soybean oil (SO) and fully hydrogenated soy-
alternate reactions of lipid peroxyl and alkoxyl radicals compete
bean oil (FHSO). The evolution in particle size distribution, struc-
with hydrogen abstraction to make the process much more com-
tural changes during oral, gastric, and intestinal digestion, and free
plex. This article provides experimental evidence for formation
fatty acid release during intestinal digestion were all investigated.
of epoxides as major products and shows how monitoring a broad
Irrespective of the physical state and structure of the dispersed oil/
spectrum of products is critical for accurate assessment of the
fat, all emulsions were stable against droplet size increases during
extent of lipid oxidation, elucidating reaction pathways, and antici-
oral digestion. During gastric digestion, the 50:50 SO:FHSO emul-
pating potential toxicity.
sion was more stable against physical breakdown than any other
emulsion. All emulsions underwent flocculation and coalescence or
trans-10,cis-12-conjugated linoleic acid partial coalescence upon intestinal digestion, with the SO emulsion
being hydrolyzed the most rapidly. The melting point of all emul-
affects expression of lipogenic genes sions containing FHSO was above 37°C, with the presence of solid
in mammary glands of lactating dairy fat within the dispersed oil droplets greatly limiting lipolysis. Fat
crystal polymorph and nanoplatelet size did not play an important
goats role in the rate and extent of lipid digestion. Free fatty acid release
Shi, H., et al., J. Agric. Food Chem. 65: 9460–9467, https://doi. modeled by the Weibull distribution function showed that the rate
org/10.1021/acs.jafc.7b02377. of lipid digestion (κ) decreased with increasing solid fat content,
The molecular mechanisms on milk fat depression (MFD) in and followed an exponential relationship (R 2 = 0.95). Overall, lipid
response to trans-10,cis-12-conjugated linoleic acid (t10,c12-CLA) digestion was heavily altered by the physical state of the dispersed
supplementation in ruminants were elucidated in this research with oil phase within O/W emulsions.
dairy goats. A total of 30 2-year-old Xinong Saanen dairy goats
[40 ± 5 days in milk (DIM)] at peak lactation stage were assigned
to a 3 × 3 Latin square design (14-day treatment period, followed
Effects of different lipophilized
with 14-day washout). Three CLA treatments included (a) control, ferulate esters in fish oil-enriched
fed the basal diet only without CLA supplementation; (b) orally
supplemented with 8 g/day of lipid-encapsulated CLA (low dose,
milk: partitioning, interaction, protein,
CLA-1); and (c) orally supplemented with 16 g/day of lipid-encap- and lipid oxidation
sulated CLA (high dose, CLA-2). Expression levels of fatty acid
Qiu, X., et al., J. Agric. Food Chem. 65: 9496–9505, 2017, https://
metabolism genes in the mammary tissues were analyzed by real-
doi.org/10.1021/acs.jafc.7b02994.
time quantitative polymerase chain reaction (RT-qPCR) in three
Antioxidant effects of ferulic acid and lipophilized ferulate
goats on day 1 and the other three goats on day 14 in each group
esters were investigated in fish oil-enriched milk. Methyl ferulate
after the discontinuation of CLA treatment in the third experi-
(C1) and ethyl ferulate (C2) more efficiently prevented lipid oxida-
mental period. Dietary supplementation of CLA led to a significant
tion than dodecyl ferulate (C12) did, followed by ferulic acid (C0).
decrease of milk fat compared to the control (p < 0.05). Milk fat
The combination of C1 or C2 with C12 could have a “synergis-
concentrations in CLA-1 and CLA-2 groups were 2.74 and 2.42%,
tic” effect indicated by peroxide value, hexanal, and 1-penten-3-ol
respectively, while the milk fat concentration in the control group
analysis results. These antioxidants also showed protein oxidation
was 2.99%. Decreases in short- and medium-chain fatty acids (<16
inhibition effects. The most effective antioxidants (C1 and C2) had
carbons) and increases in unsaturated fatty acids were observed
the highest concentration in the precipitate phase but the lowest
in the CLA-2 group (p < 0.05). The desaturation indexes of C16
concentration in the aqueous phase, which was the opposite of the
and C18 fatty acids were obviously increased (p < 0.01). RT-qPCR
partitioning of C0. C12 had the highest concentration in the oil and
results revealed decreases of the mRNA expression levels of
emulsion phase. In particular, the interaction between ferulates
SREBF1, PPARG, LPL, CD36, FABP3, ACSL1, FASN, ACACA,
esterified with short and medium alkyl chain lengths could lead
DGAT2, TIP47, ADRP, and BTN1A1 genes in mammary glands (p
to their “synergistic” effects in fish oil-enriched milk, which could
< 0.05) and an increase of the SCD gene because of CLA supple-
be caused by the change in their partitioning or localization at the
mentation (p < 0.05). In conclusion, t10,c12-CLA-induced MFD
interface.
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Associations between fatty acids and removal rate of GEs in palm oil was up to >95%, which was signifi-
cantly higher than other adsorbents used in this study. In batch
low-grade inflammation in children adsorption system, the adsorption efficiency and performance of
acid-washed OPAC were evaluated as a function of several exper-
from the LISAplus birth cohort study imental parameters such as contact time, initial glycidyl palmi-
Harris, C., et al., Eur. J Clin. Nutr. 71: 1303–1311, 2017, https://doi. tate (PGE) concentration, adsorbent dose, and temperature. The
org/doi:10.1038/ejcn.2017.73. Langmuir, Freundlich, and Dubinin–Radushkevich models were
Assessing fatty acid (FA) composition in relation to inflam- used to describe the adsorption equilibrium isotherm, and the
matory markers can shed light on the role of different FA and their equilibrium data were fitted best by the Langmuir model. The max-
metabolism in low-grade inflammation. Existing exploratory stud- imum adsorption capacity of acid-washed OPAC was found to be
ies in children are scarce, and findings inconsistent. We hence aim 36.23 mg/g by using the Langmuir model. The thermodynamic
to analyze associations of FA with common inflammatory mark- analysis indicated that the adsorption of PGE on acid-washed
ers, high-sensitivity C-reactive protein (hs-CRP), and interleu- OPAC was an endothermic and physical process in nature. The
kin-6 (IL-6), in 10-year-old children. Complete data were available experimental data were fitted by using pseudo-first-order, pseu-
for 958 participants from the 10-year follow-up of the LISAplus do-second-order, and intra-particle diffusion models. It was found
(Influence of Lifestyle-Related Factors on the Immune System that the kinetic of PGE adsorption onto acid-washed OPAC fol-
and the Development of Allergies in Childhood plus the Influence lowed well the pseudo-second-order model for various initial PGE
of Traffic Emissions and Genetics) birth cohort study. FA compo- concentrations and the adsorption process was controlled by both
sition was assessed in serum glycerophospholipids. Hs-CRP and film diffusion and intra-particle diffusion. The desorption test indi-
IL-6 were categorized into three levels. Associations of FA with cated the removal of GEs from palm oil was attributed to not only
inflammatory markers were assessed using multinomial logis- the adsorption of GEs on acid-washed OPAC, but also the deg-
tic regression, adjusting for potential confounders. Additionally, radation of GEs adsorbed at activated sites with acidic character.
sex-stratified analyses were carried out. FA exposures associated Furthermore, no significant difference between before and after
with significantly higher low-grade inflammation, as indicated by PGE adsorption in oil quality was observed.
higher hs-CRP or IL-6 levels, included: palmitic acid (PA) (IL-6:
P<0.001, 95% confidence interval: 1.30; 2.43), arachidonic acid
(AA) (hs-CRP: P=0.002, 1.07; 1.31), n-6 highly unsaturated FA Synthetic Biology
(HUFA) (hs-CRP: P=0.002, 1.06; 1.27), ratio of AA to linoleic
acid (AA/LA) (hs-CRP: P<0.001, 1.16; 1.62) and total saturated
FA (SFA) (IL-6: P<0.001, 1.77; 3.15). FA exposures associated with
Microbial and genetically engineered
reduced levels of inflammatory markers included LA (hs-CRP: oils as replacements for fish oil in
P=0.001, 0.84; 0.96; IL-6: P<0.001, 0.69; 0.90) and total polyun-
saturated FA (PUFA) (IL-6: P<0.001, 0.57; 0.78). These findings aquaculture feeds
suggest that higher SFA and minor n-6 HUFA, namely PA and AA, Sprague, M., et al., Biotechnol. Lett. 39: 1599, https://doi.
are associated with increased low-grade inflammation in children, org/10.1007/s10529-017-2402-6.
whereas the major dietary n-6 PUFA and total PUFA are associated As the global population grows, more of our fish and seafood
with reduced inflammation. Elevated desaturase activity, estimated are being farmed. Fish are the main dietary source of the omega-3
by the ratio AA/LA, may be associated with higher inflammation, (n-3) long-chain polyunsaturated fatty acids (LC-PUFA), eicos-
particularly in boys. apentaenoic (EPA) and docosahexaenoic (DHA) acids, but these
cannot be produced in sufficient quantities as are now required for
Adsorption removal of glycidyl esters human health. Farmed fish have traditionally been fed a diet con-
sisting of fishmeal and fish oil, rich in n-3 LC-PUFA. However, the
from palm oil and oil model solution increase in global aquaculture production has resulted in these
finite and limited marine ingredients being replaced with sus-
by using acid-washed oil palm wood- tainable alternatives of terrestrial origin that are devoid of n-3
based activated carbon: kinetic and LC-PUFA. Consequently, the nutritional value of the final product
has been partially compromised with EPA and DHA levels both
mechanism study falling. Recent calls from the salmon industry for new sources of
Cheng, W., et al., J. Agric. Food Chem. 65: 9753–9762, https://doi. n-3 LC-PUFA have received significant commercial interest. Thus,
org/10.1021/acs.jafc.7b03121. this review explores the technologies being applied to produce de
Acid-washed oil palm wood-based activated carbon (OPAC) novo n-3 LC-PUFA sources, namely microalgae and genetically
has been investigated for its potential application as a promising engineered oilseed crops, and how they may be used in aquafeeds
adsorbent in the removal of glycidyl esters (GEs) from both palm to ensure that farmed fish remain a healthy component of the
oil and oil model (hexadecane) solution. It was observed that the human diet.
Remain
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Agglutinin in Soybean Grain technical and scientific information is presented in a
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Setting the Standard | Since the 1920s, the global fats and oils industry has relied on the analytical integrity of the Official Methods and
Recommended Practices of the AOCS. AOCS has set the standard for analytical methods critical to processing, trading, utilizing, and evaluating
fats, oils, and lipid products. Worldwide acceptance has made the AOCS Methods a requirement wherever fats and oils are analyzed.
Recent developments on genetic produced competitively from carbohydrates if theoretical yields are
approached and if processing is efficient. Instead of carbohydrate
engineering of microalgae for biofuels fermentation, hypothetical photochemical production from CO2
was also considered. Using again a simple model, the same com-
and bio-based chemicals modity chemicals remained the most attractive ones.
Ng, I.-S., et al., Biotechnol. J. 12, October 2017, https://doi.
org/10.1002/biot.201600644.
Microalgae serve as a promising source for the production of Industrial Applications
biofuels and bio-based chemicals. They are superior to terrestrial
plants as feedstock in many aspects and their biomass is naturally
rich in lipids, carbohydrates, proteins, pigments, and other valuable
Review of vegetable seeds oils as
compounds. Due to the relatively slow growth rate and high culti- biolubricants
vation cost of microalgae, to screen efficient and robust microalgal
Kumar, D., et al., Energy Environ. Focus, 6: 103–113, 2017,
strains as well as genetic modifications of the available strains for
https://doi.org/10.1166/eef.2017.1251.
further improvement are of urgent demand in the development of
Vegetable oils are the best alternative source of lubricating
microalgae-based biorefinery. In genetic engineering of microalgae,
oils used in automotive and industrial applications. Their high-
transformation and selection methods are the key steps to accom-
oleic contents make vegetable oils environmentally friendly and
plish the target gene modification. However, determination of the
cheaper than petroleum oils. The seeds of non-edible vegetable
preferable type and dosage of antibiotics used for transformant
plants contain larger amounts of oils that can be converted into
selection is usually time-consuming and microalgal-strain-depen-
bio-lubricants and further used in engines and industrial applica-
dent. Therefore, more powerful and efficient techniques should
tions. Bio-lubricants are renewable, nontoxic, and biodegradable.
be developed to meet this need. In this review, the conventional
This research article reviews the fatty acid contents and friction
and emerging genome-editing tools (e.g., CRISPR-Cas9, TALEN,
behaviors of mahua, coconut, palm, sal, neem, olive, castor, canola,
and ZFN) used in editing the genomes of nuclear, mitochondria,
cashew nut, and jatropha oils.
and chloroplast of microalgae are thoroughly surveyed. Although
all the techniques mentioned above demonstrate their abilities to
perform gene editing and desired phenotype screening, there still
need to overcome higher production cost and lower biomass pro- Alternative oil extraction methods
ductivity, to achieve efficient production of the desired products in
microalgal biorefineries. from Echium plantagineum L. seeds
using advanced techniques and green
Potential of commodity chemicals solvents
to become bio-based according to Castejón, N., et al., Food Chem. 244: 75-82, 2018, https://doi.
maximum yields and petrochemical org/10.1016/j.foodchem.2017.10.014.
The edible oil processing industry involves large losses of
prices organic solvent into the atmosphere and long extraction times.
In this work, fast and environmentally friendly alternatives for
Straathof, A.J.J. and A. Bampouli, Biofuel., Bioprod., Biorefin. 11:
the production of echium oil using green solvents are proposed.
798–810, 2017,
Advanced extraction techniques such as Pressurized Liquid
https://doi.org/10.1002/bbb.1786
Extraction (PLE), Microwave Assisted Extraction (MAE) and
Carbohydrates are the prevailing biomass components avail-
Ultrasound Assisted Extraction (UAE) were evaluated to effi-
able for bio-based production. The most direct way to convert car-
ciently extract omega-3 rich oil from Echium plantagineum seeds.
bohydrates into commodity chemicals is by one-step conversion
Extractions were performed with ethyl acetate, ethanol, water
at maximum theoretical yield, such as by anaerobic fermentation
and ethanol:water to develop a hexane-free processing method.
without side product formation. Considering these hypothetical
Optimal PLE conditions with ethanol at 150 °C during 10 min
yields and petrochemical prices in Europe in 2010–2014, a ranking
produced a very similar oil yield (31.2%) to Soxhlet using hexane
of 58 commodity chemicals was made using a simple model with
for 8 h (31.3%). UAE optimized method with ethanol at mild con-
ethanol as a base case. It was concluded that base chemicals such as
ditions (55 °C) produced a high oil yield (29.1%). Consequently,
lower olefins and benzene-toluene-xylene (BTX) are too cheap and
advanced extraction techniques showed good lipid yields and fur-
require too much carbohydrate to be produced competitively com-
thermore, the produced echium oil had the same omega-3 fatty acid
pared to bioethanol. However, more oxidized products that require
composition than traditionally extracted oil.
multiple conversion steps in petrochemical production, such as
adipic acid, acrylic acid, acrylate esters, and 1,4-butanediol, can be
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inform January 2018 Volume 29 (1)

THE “SHEAR” MAGIC OF

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10 Unraveling the fusty/musty off-flavor in native cold-pressed

18 From laboratory to full-scale degumming: a new efficient

22 Extraction of proteins and active substances from microalgae

26 Tall oil, its chemistries and applications

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FIG. 3. Process layout for enzymatic degumming using Quara LowP

ugation for optimum separation and to deactivate the enzyme.

The simplest analytical tools are required: FFA-analysis to

FIG. 3. Phycocyanin and protein separation by precipitation at

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