https://doi.org/10.

34101/actaagrar/150/1702
Essential oil extraction… Cs. D. András et al.

Essential oil extraction from herbs and their use in

the food industry

CSABA DEZSŐ ANDRÁS – BERNADETTE SALAMON – ÉVA GYÖRGY –

EMŐKE (DOBRI) MIHOK – ALEXANDRU SZÉP
Sapientia Hungarian University of Transylvania, Department of Food Science,
Csíkszereda, Romania
alszep@uni.sapientia.ro

Summary

Essential oil extraction of wild caraway and thyme was performed using a
classical (HD) and microwave hydro-distillation (MWHD) and a laboratory
supercritical fluid extraction (SFE) with a carbon dioxide as solvent. Our
experiments demonstrated that the extraction yield of the essential oil performed
in same conditions was influenced by the location of growth area; the maximum
extraction yield of 10 ml 100 g-1 caraway was obtained from dried seeds collected
from Csíkmadaras. This quantity far exceeded the yield of the Újtusnád samples.
In the case of wild caraway (Carum carvi L.), the extraction method influenced the
composition of the essential oil (carvone/limonene ratio), the highest limonene
content being achieved by classical hydro-distillation. In the case of thyme, this
effect was not detected, the thymol/carvacrol ratio was independent from the
given extraction method. The obtained thyme essential oil possesses high
antimicrobial activity demonstrated by agar diffusion test. The thyme extract
provides a good protection against microorganisms collected on the surface of
fresh vegetables following bacterial stains: Citrobacter portucalensis, Pseudomonas
hunanensis, Pseudomonas baetica, Pseudomonas parafulva, Bacillus mojavensis and
Enterobacter cloacae. Protective effect was also detected on the vegetable surface of
by chitosan-based edible film coating during a 6-day-long storage period at a
temperature of 4 °C. The caraway essential oil used as soft cheese seasoning with
a direct, dilution-free method, proved to be unsuitable because the uneven
distribution and confer a strong, unpleasant taste to the product in comparison
with the ground wild caraway seed-dressed cheese.

Keywords: essential oil, caraway, thyme, carvone, limonene, antimicrobial effect,

edible coating, growth area

Introduction

The use of plant-based compound in human nutrition as nutraceuticals is

becoming increasingly widespread (Gupta, 2016). Of the approximately
3000 known essential oils in 2004, 300 were used in industrial quantities
(Burt, 2004). Their use in the food industry, in addition to the
characteristic aroma, is mainly due to the antimicrobial effect of some of
their components (Preedy, 2015; Shojaee-Aliabadi et al., 2018). The

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growing market led to an increase in the number of researches aimed at

modernizing the extraction methods. At present, many laboratory and
industrial processes are known for extracting essential oils, starting from
classical to modern energy input (microwave, pulse, oral, ohmic)
methods (Mandal et al., 2015). For the extraction of essential oil, classical
water vapor distillation is used (both at the laboratory and in the small
scale); in industrial-scale production, percolation, solid-fluid extraction
and, last but not least, the supercritical fluid extraction method is
extended (Roohinejad et al., 2018).
In the European Pharmacopoeia (Ph. Eur.) the vapor distillation (VD)
is presented in both known methods: hydro-distillation–HD (vapor
evolves from the herb suspension in the cooking bowl) and classic water
steam distillation–SD (the steam generated in the steam generator flows
through the plant cartridge). Direct heating can be achieved by boiling
water under pressure, water vapor, electrical resistance (heating basket).
More modern versions of microwave heating (Kapás et al., 2011;
Navarrete et al., 2011; Chemat et al., 2013) can be used for steam
development, distillation or pretreatment. In pretreatment it is possible to
use enzymatic digestion, where different fiber destruction (cellulase,
hemicellulase, xylanase), pectin degradation (pectinase) or other enzymes
(such as protease) are used (Bhat, 2000; Kashyap et al., 2001). Microwave
assisted hydro-distillation (MHD) usually involves the use of freshly
harvested parts of plants, whereby the required water vapor is provided
by moisture. In case of solid-fluid extraction, it is necessary to form the
appropriate dried particle size (grinding or crushing) as the internal
diffusion is the rate determining step of the extraction process. Different
energy inputs methods are used to increase the extraction yield, such as
intense mixing–Turbo HD–(Manayer et al., 2015), ultrasound (Deng et al.,
2014; Gavahian et al., 2015; Roselló-Soto et al., 2015; Koubaa et al., 2016),
or pulsating electric field (Dobreva et al., 2013). A high pressure-high
temperature fast extraction method has been developed, giving good
results. The short-time high pressure steam treatment is followed by a
sudden drop in pressure, and the formed vapors breaks the cell walls
explosively, and subsequently they are separated from gas phase by
condensation (Chemat et al., 2017).
For determination of essential oil yield, weighing or volume
measurement is used. The water-essential oil mixture is a hetero-
azeotropic system, the condensate separates in two phase (water and
essential oil) as the two compounds are very low mutual solubility. The
most suitable laboratory apparatus for essential oil obtaining is the
Clevenger-head, where the position of the backflow connection is
adjusted the essential oil/water density ratio (Clevenger, 1928; Hornok,
1990). The following of the position change of the separation meniscus (in

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the graduated collecting capillary) in time is effective for measuring the

kinetic of the hydro-distillation (Kapás et al., 2011). The extraction yield is
influenced by a number of factors, as the growing zone, harvesting time,
pre-treatment parameters and the extraction techniques (Bailer et al.,
2001; Calin-Sanchez et al., 2013; Roohinejad et al., 2018).
The anticonvulsant effect of caraway tee used in folk medicine is
acknowledged by modern medicine. Also it has been demonstrated that
the essential oil inhibits the proliferation of Escherichia coli, Streptococcus
faecalis, Staphylococcus aureus and other pathogenic microorganism living
in the colon. The antimicrobial effect is attributed to D-limonene and
carvone content (Zhang et al., 2014), as the antimicrobial activity of this
components is confirmed experimentally (Shojaee-Aliabadi et al., 2018).
In addition to its beneficial effect on digestion, it also improves liver
function and has proven antioxidant potential (Samojlik et al., 2010).
The folk cuisine uses caraway seeds (in ground or intact form) as a
spice, also is used as herb for the preservation and flavoring of edible
fatty oils, as olive oil (for salad dressing), where the product it also
enriched in aroma (Farag et al., 1989, 1990). Essential oil of wild caraway
give a pleasant aroma and flavor to foods and provide also microbial
protection, given by carvone and limonene content (Lopez et al., 2005;
Čvek et al., 2010; György and György 2010; Jeong et al., 2014). Analyzing
of antimicrobial effects it was demonstrated (Mohinger et al., 2013) that
caraway essential oil has a good inhibitory effect on several microbial
strains (Listeria monocytogenes, S. aureus, B. cereus, E. coli O157:H7 and
Salmonella typhimurium) without decreasing the growth of lactic acid
bacteria (L. delbrueckii ssp. bulgaricus and S. thermophilus). It is claimed
that 0.3 to 0.5% of caraway essential oil caused a 1.3 log to 4 log decrease
of E-coli O157:H7 in soft yoghurt cheese (Mohamed et al., 2013) in 7 and
14 days. The antimicrobial effect of other essential oils, including thyme,
oregano, etc. has been largely studied, positive results being reported for
many foods (Khorshidian et al., 2018). As our previous experiments
shown, the obtaining method, the extraction time, the pretreatment and
the plant vegetation stage and influenced the both the distillation kinetics
as well as the major components ratio (András et al., 2014, 2015ab). Since
the location of the growing field may have influence, we studied the
effect of harvesting location on essential oil yield and composition.

Material and method

The wild caraway samples were collected from Csík (Ciuc) Depression
(Csíkmadaras/Mădăraş, Hargitafürdő/Băile Harghita, Zsögöd/Jigodin
and Újtusád/Tuşnadu Nou), thyme samples from Szelterszfürdő/Băile
Selters (Harghita County) mountain pastures. The plant material was

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first classified (the green and ripe shoots was separated) then dried,
sieved and finally elutriated in air current. The selected grains were
stored in a dry place until analysis. The after-dried seeds (to equilibrium
moisture) were grounded in Retsch Grindomix GM 200 laboratory mill.
The extraction was carried out by hydro-distillation method, using a
laboratory vapor distillation apparatus (Figure 1), with 1.5 ml (0.01 ml
divisions) volume Clevenger collector, a 125 W electrically heated round-
bottom flask, corresponding to the Pharmacopoeia. Also, microwave
hydro-distillation was performed (Kapás et al., 2011) in a modified
microwave apparatus (Figure 2). The sample amount was 10 g of dried,
grounded seeds, suspended in 200 ml distilled water.
The supercritical fluid extraction (SFE) was performed with
Supercritical Fluid Technology SFT 100 System (András et al., 2015a),
where in a 10 ml volumetric tube extractor operated at 40 °C temperature
and above 10 MPa pressure. The essential oil from the ground seeds was
extracted with supercritical carbon dioxide. Sampling was performed by
opening the isothermal valve heated to 42 °C; the condensed essential oil
was collected in a collector.

Figure 1. Schematic representation of the hydro-distillation equipment with

Clevenger collector

Note: 1. Round-bottom flask, 2. Steam tube, 3. Vapor condenser, 4. Scaled capillary for
volume measure, 5. Stopcock, 6. Electric heater (125 W)

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Figure 2. Schematic representation of the microwave hydro-distillation equipment

with Clevenger collector

Note: 1. Round-bottom flask, 2. Heating circuit of a microwave furnace 3. Shielding tube, 4.

Vapour outlet tube, 5. Clevenger collector, 6. Sample collector, 7. Timer, 8. Power regulator,
9. On/off switch, 10. Teflon round bottom bracket.

Gas chromatography method was used to determine the quality and

relative chromatographic percentages of essential oil components. Gas
chromatography (GC-FID) conditions for each sample was the same:
Varian CP 3380 apparatus, 100×0.25 mm quartz-capillary column CP-
Sil88 (FAME), flame ionization detector (FID) at 270 °C detector and
injector temperature, carrier gas hydrogen (235 kPa). The temperature
program: heating to 50 °C for 1 min, then heating with gradient of 5 °C
min-1 to the final temperature (210 ... 270 °C). Anhydrous sodium sulfate
was used to remove the water residue from the samples. The injected
sample (V=1 µL) with volatile oil/n-hexane ratio equal to 1:15. Reference
chromatogram (Kubeczka and Formácek, 2002) was used to evaluate the
results.

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At the laboratory level, two practical utilization experiments of the

essential oil were carried out. In the first, we investigated the
antimicrobial effect of the thyme extract and some of the commercially
available essential oils (cinnamon, oregano, juniper, mint and
lemongrass); while in the second experiment we measured the flavoring
effect of the wild-caraway essential oil in cheese. The effect thyme
essential oil on Citrobacter portucalensis, Pseudomonas hunanensis,
Pseudomonas baetica, Pseudomonas parafulva, Bacillus mojavensis and
Enterobacter cloacae microbes, isolated from fresh vegetable, was
estimated by measuring the inhibition zone diameter. After the
solidification of the sterile nutrient media filled in the Petri dish, the test
bacteria were plated by plating and a 10 mm diameter hole was prepared
in the center of the cup to which 0.1 ml of essential oil was pipetted.
After the incubation time has elapsed, the diameter of the inhibition
zone was measured. Based on the results, the most efficient antimicrobial
oil was chosen. Essential oil additivated chitosan-based edible coating
was prepared and applied on tomato surface, to perform storage
experiments (6 days at 4 °C), than deterioration inhibition was evaluated
(compared with the control sample).
In the second experiment we flavored soft cheese with ground non-
ground wild caraway seeds and their essential oil, produced in the
laboratory. For the qualification of the final product a sensory test with
questionnaire was performed. Flavoring was done after the curd
breaking by added the seeds or extract. In each experiment we followed
the same cheese-making procedure (65 °C pasteurization temperature, 15
min holding time, cooling to 32 °C, inoculation with propionic acid-
producing bacteria (0.8 g per 2.3 l) and enzyme (0.09 g per 2.3 l),
coagulation process at 32 °C temperature and 3 hour duration, curd
cutting uniformly, partial elimination the whey, flavoring by mixing (12.5
g of wild caraway per 2.3 l, 15 g grounded wild caraway per 2.3 l and 1
ml of essential oil per 2.3 l), whey elimination at 4 °C temperature, chilled
maturation in cylinder form with daily flip of product, sensory
qualification).
The mixture for chitosan-based antimicrobial edible coating film was
prepared as follows: 1 g of acetic acid was diluted with 100 ml distilled
water, and then 2 g of chitosan was added. The mixture was
homogenized for 4 hours with magnetic stirrer, isothermal at 25 °C. Then
2 g of glycerol, Tween 20 solution and 0.3 g of essential oil were mixed
and agitated to the former. After 10 minutes stirring was homogenized
and degassed for 30 minutes in an ultrasonic bath for obtaining the
coating mixture). The formed viscous gel was used to coating the
vegetable, the film on vegetable surface was formed by immersion. The
edible film-coated vegetable was stored at 4 °C for 6 days before analysis.

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Results and discussion

Essential oil yield variation of samples from different growth field

The data analysis of the experimental results shown, that the obtained
quantity of essential oil was influenced by the growth location in both
case (for green and ripe wild caraway). As shown in Figure 3, parallel
measurements of two samples from the same location are situated almost
on the same curve. This indicate the homogeneity of the samples.

Figure 3. Kinetic curves of hydro-distillation yield of green seeds collected from

different growing location

Furthermore, it can be observed that for samples from different

growth locations the yields show quite large variations. The highest
essential oils yield from green caraway is provided from Újtusnád
samples. The essential oil yields for ripe wild caraway are shown in
Figure 4. The ripe samples from Csíkmadaras the highest essential oil
content, much more than the samples of Zsögöd and Hargitafürdő.
The linearization method was used to determine the parameters of
hydrodistillation kinetics (Milojević et al., 2008; Kapás et al., 2011). Figure
5 shows that for green caraway the model describes with a medium
accuracy change of extracted quantity in time (R2=0.87–0.94), but for ripe
(mature) caraway (where the two phases separated in Clevenger-head)
more accurate results were obtained (R2=0.93–0.99).
Comparing the values of maximum yields (Figure 6), we find that
these are different for different growth location. The highest yield was
observed for mature caraway from Csíkmadaras. Analyzing the
composition of the essential oil it can be observed that, although the
number of components varies, the two main constituents – limonene and
carvone – represent more than 85% of the mixture, for both, green and
mature seeds of wild caraway evenly.

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Figure 4. Kinetic curves of hydro-distillation yield of mature wild caraway collected

from different growing location

Figure 5. The linearized kinetics for model parameters determination

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 Essential oil extraction… Cs. D. András et al.

Figure 6. Variation of the maximum essential oil yield in function of

harvesting location and year

Analyzing the relative amount (weight percentage) of the two main

components (Figure 7) shown that the ratio of D-limonene in the
Csíkmadaras sample extract is higher than in other samples (for green
and mature samples both). It can also be observed, that in case of hydro-
distillation obtained essential oils, the proportion of limonene is higher
than for supercritical extract. It has been demonstrated that supercritical
extraction is more selective than other extraction methods (András et al.,
2002), but in this case (batch experiments) the observed increase of
carvone proportion may attributable to the most volatile component loss
(limonene) in sample collection step. No major difference in the essential
oil quality thyme of wild obtained by HD and SFE can be observed. The
chromatograms of the thyme essential oils obtained by different methods
are represented on Figure 8. Regardless of the obtaining method, the
retention time of the main components are the same for all three
chromatograms. The similar relative amount of the main compounds
(thyme and carvone) shows that the extraction method did not affect the
composition of the obtained product.

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Essential oil extraction… Cs. D. András et al.

Figure 7. The relative amount (percentage by weight) of the two main components for
hydro-distillation and supercritical fluid extraction of essential oils of
wild caraway collected from different growth area
a) green wild caraway seeds; b) ripe wild caraway seeds

100%
90%
80%
70%
60%
50%
40%
30%
20%
10%
0%
HD SFE HD SFE HD
Újtusnád Csíkmadaras Hargitafürdő

Limonene Carvone

b
100%
90%
80%
70%
60%
50%
40%
30%
20%
10%
0%
HD SFE HD SFE HD SFE
Csíkmadaras Hargitafürdő Zsögöd

Limonene Carvone

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 Essential oil extraction… Cs. D. András et al.

Figure 8. The chromatograms of the thyme extracts (SFE 9/1 supercritical extraction,
HD hydro-distillation, MWHD-microwave assisted hydro-distillation)

The antimicrobial effect of the thyme extract

The result presented in Table 1 refer to the magnitude of inhibition zones
(in millimeters) generated by the antimicrobial effect of the essential oils.

Table 1. Antimicrobial effect of the analyzed essential oils

Tested Cinnamon Oregano Thyme Lemon- Mint Juniper

microorganism oil oil oil grass oil oil oil
Enterobacter No No No
7.2±0.75 13.8±1.94 8.2±0.4
cloacae inhibition inhibition inhibition
Pseudomonas No No No
7.6±0.8 9.0±1.41 3.4±1.02
parafulva inhibition inhibition inhibition
Pseudomonas
7.4±0.49 27.6±3.2 27±3.95 12±1.1 8.0±1.1 18±3.03
baetica
Bacillus
5.8±0.75 16.8±0.75 35.4±1.36 7.0±1.26 1.8±0.75 16±2.61
mojavensis
Pseudomonas No No
2.4±0.49 5.8±1.94 5.6±0.49 5.8±0.75
hunanensis inhibition inhibition
Citrobacter No
8.8±0.75 30.6±0.8 9.8±1.47 3.0±1.26 4.2±0.75
portucalensis inhibition

This results show that the strongest inhibitor was the thyme essential
oil, which proved to be the most effective for all studied bacteria, only the

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oregano oil compete with it. This result is in a good agreement with
recent literature data (Memar et al., 2017). In contrast, mint, lemongrass,
and especially juniper essential oil were ineffective against several
bacteria.
The effect of the thyme extract on surface microbe development was
tested by film coating. After storage, the difference between the film-
coated (left) and uncoated cocktail tomato (right) was well-displayed
(Table 2). Untreated cocktail tomato started to deteriorate, on the surface
patches of brown and softs spots appeared, changes in consistency, and
molding began. In contrast, the coated cocktail tomato remained in good
condition, in terms of its appearance and its texture.

Table 2. The antimicrobial effectiveness of the thyme extract-containing coating film on

the cocktail tomato after short time storage

Microbe quantity on Uncoated Coated

surface (CFU g-1) surface surface

Total number of
131 20
mesophilic aerobic bacteria
Staphylococcus aureus 60 0

Characterization of the wild caraway-flavored soft cheese

Our laboratory experiments have demonstrated that in the case of soft
cheese, only the seeds (in ground and ungrounded form) could be use
after the curd thickening, otherwise it is very difficult to ensure uniform
distribution in the mixture. The addition of essential oil of wild caraway
in curd was difficult, due by the important changes in cheese texture
caused by even small quantities of dispersed essential oil. The uneven
distribution causes great displeasure in the sensorial analysis, each of the
10 persons highlighted the strong aroma of some cheese pieces, which
could be prevented only by a more efficient dispersion method.

Conclusions

Our experiments demonstrate that the growing field has great influence
on the essential oils yield but less on the of the two main components
(carvone and limonene) ratio. The highest yield was obtained from the
Csíkmadaras harvested samples, while the highest carvone/limonene
ratio was provided by the supercritical extraction. For wild caraway
samples the essential oil extraction composition was influenced by the
extraction method, but for extraction of thyme samples, for essential oil
with lower volatility this behavior was not observed. In case of thyme

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essential oil the ratio of relative amount (mass %) of the main

components (thymol and carvacrol) remained the same for all three
obtaining methods. The laboratory test have proven that the thyme
essential oil possess inhibition effect on the microorganisms growth
collected from the surface of fresh vegetables. The inhibitory effect of
thyme was comparable with oregano. The edible chitosan coating
contained thyme extract on tomato surface possess positive effect in
storage for six days, protecting its consistency from bacterial
deterioration processes. Industrial applicability requires the acquisition
of more laboratory information regarding the molds growth and the
synergistic effects of essential oils. Regarding the use of wild caraway
essential oil as a flavoring agent of cheese it can be concluded, that
without uniform distribution of even a small quantity of EO-s, the
product did not win the appreciation of the sensorial evaluators.

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