V. TE[EVI] et al.: Volatile Components of Plum Brandies, Food Technol. Biotechnol.

43 (4) 367–372 (2005) 367

ISSN 1330-9862 original scientific paper

(FTB-1474)

Volatile Components from Old Plum Brandies

Vele Te{evi}1*, Ninoslav Niki}evi}2, Anka Jovanovi}3, Dejan Djokovi}1,

Ljubodrag Vujisi}4, Ivan Vu~kovi}4 and Mirjana Boni}5
1
Faculty of Chemistry, University of Belgrade, Studentski trg 16, SCG-11000 Belgrade,
Serbia and Montenegro
2
Faculty of Agriculture, University of Belgrade, Nemanjina 6, SCG-11080 Zemun,
Serbia and Montenegro
3
Institute of Public Health, 29 Novembra 54a, SCG-11000 Belgrade, Serbia and Montenegro
4
Institute for Chemistry, Technology and Metallurgy, University of Belgrade, Njego{eva 12,
SCG-11000 Belgrade, Serbia and Montenegro
5
Institute of Public Health, Zmaj Jovina 30, SCG-2400 Subotica, Serbia and Montenegro
Received: January 25, 2005
Accepted: May 25, 2005

Summary
Gas chromatography and GC/MS methods were used to detect volatile components
of three home-made natural old plum brandy samples and one sample of industrially-pro-
duced plum brandy. Gas chromatography and gas chromatography-mass spectrometric
analysis of this extracts led to the identification of 99 components, including 46 esters, 7
hydrocarbons (alkanes and alkenes), 3 aldehydes, 9 alcohols, 1 lactone, 1 ketone, 8 acetals,
14 terpenes, 8 acids and 2 phenols. Ethyl esters of C8–C18 acids were the most abundant in
all samples. In addition, the content of methanol, ethanol and higher alcohols (C3–C5) was
determined.

Key words: plum brandy, aroma, GC/MS, ethyl esters

Aromatic compounds are very important for the

Introduction
quality and aroma of alcoholic beverages. These com-
Plum brandy, as a distillate of Prunus crop plum pounds can be classified into four groups: primary aro-
fermented must, apart from the main elements, ethanol matic compounds (whose entire aroma appears exactly
and water, contains numerous ingredients, the concen- as in the fruit during ripening); secondary aromatic
tration of which varies within an average of 0.5–1.0 % components (formed during alcoholic fermentation); ter-
depending on the raw material content, the way in tiary aromatic compounds (formed during the distilla-
which alcohol fermentation is carried out and the man- tion process); and quaternary aromatic compounds
ner in which distillation is conducted. Apart from nu- (formed during the maturation process). In a rich mix-
merous valued components it contains, plum brandy ture of alcoholic beverages aromatic compounds are
can also contain some undesirable ingredients. This re- present in a small percentage.
fers, first of all, to HCN, ethyl-carbamate and methanol. Chemical compounds that give a beverage its char-
However, certain amounts of methanol must be present acteristic flavour and aroma can be determined and
in fermented plum must distillates, in respect to the fact used to classify the beverage as to the type and country
that its presence in them is considered to be a proof and of origin. Such analysis has important applications in
indicator of authentic, natural, fruit origin. product control and prevention of brand fraud. No sin-

*Corresponding author; Phone: ++381 11 630 474; Fax: ++381 11 636 061; E-mail: vtesevic@chem.bg.ac.yu
368 V. TE[EVI] et al.: Volatile Components of Plum Brandies, Food Technol. Biotechnol. 43 (4) 367–372 (2005)

gle chemical in an alcoholic beverage is sufficient to dis- -H2O vapours in order to get a distillate with optimum
tinguish one brand from another or to determine its amounts of ingredients. Sokolova, Valjevka and Karan-
quality. Various components found in beverages such as ka were distilled in 1992, 1997 and 1993, respectively, in
whisky, rum and plum brandy originate from the fer- Charente type apparatus for simple distillation with the
mentation, distillation or ageing stages. Brandy, whisky volume of 100–150 L. The apparatus for Sokolova and
and rum contain similar volatile fermentation alcohols. Karanka did not have a column, only covers. Valjevka
The concentrations of these components depend on their apparatus was suplied with air dephlegmator above the
substrate of origin and on the yeasts used for fermenta- cover.
tion (1). During the ageing process, volatile and nonvol- All distillates were maturated in oak barrels: Mana-
atile phenolic compounds may be extracted from oak stirka, 495 L, casks type Quercus petreae L. (Quercus sessi-
ageing barrels. The extent of the extraction depends on liflora); Sokolova, 700 L, casks type Quercus pedunculata
the age, type and size of the barrel (2). Some of the com- (Quercus robur); Valjevka, 505 L, casks type Quercus pe-
pounds found in alcoholic beverages may react with one treae L. (Quercus sessiliflora); and Karanka, 1000 L, casks
another, dissociate, evaporate, or be absorbed, whereby type Quercus pedunculata (Quercus robur).
their concentrations change during the ageing process
(3). GC and GC/MS analysis of volatile compounds
Higher aliphatic aldehydes (nonanal and some oth- For a typical experiment, a 100-mL aliquot of each
ers), 2-undecanone, benzaldehyde, damascenone, benzyl beverage was mixed with 50 mL of dichloromethane
acetate, ethyl phenyl acetate, phenyl ethyl acetate, ethyl- and continuously extracted (2 h). The extract was dried
-3-phenylpropionate, methyl cinnamate, ethyl cinnama- (2 h) over anhydrous sodium sulfate, and concentrated
tes, and several other compounds were the most signifi- to 1.0 mL under nitrogen.
cant contributors to the typical plum brandy-like flavour
Gas chromatographic analysis was performed using
(4).
a gas chromatograph HP 5890 equipped with a flame
During the alcoholic fermentation of plum juice ma- ionization detector (FID) and a split/splitless injector.
ny esters can be formed, but the most significant ones The separation was achieved using a HP-5 (5 % diphen-
are acetate esters of higher alcohols (ethyl acetate, isoa- yl and 95 % dimethylpolysiloxane) fused silica capillary
myl acetate, isobutyl acetate and 2-phenyl ethyl acetate) column, 30 m x 0.25 mm i.d., 0.25 mm film thickness. GC
and ethyl esters of fatty acids (ethyl butyrate, ethyl lac- oven temperature was programmed from 50 °C (6 min)
tate, ethyl caprinate, ethyl caprylate and ethyl caprona- to 285 °C at a rate of 4.3 °C/min. Hydrogen was used as
te) (5). carrier gas; flow rate was 1.6 mL/min at 45 °C. Injector
Various extraction methods have been widely used temperature was 250 °C, detector temperature 280 °C,
for the analysis of volatile components of fruit brandies, and injection mode splitless. An injection volume of 1.0
such as distillation techniques, solvent extraction, solid mL was used for the beverage extract.
phase extraction (SPE), solid phase microextraction Gas chromatographic-mass spectrometric (GC/MS)
(SPME), and stir bar sorptive extraction (SBSE) (6–8). analysis was performed using an Agilent 6890 gas chro-
Gas chromatography (GC) is a powerful tool in the anal- matograph coupled with an Agilent 5973 Network mass
ysis of alcoholic beverage products. Minimal sample selective detector (MSD), in positive ion electron impact
preparation, in general, is required, since the samples (EI) mode. The separation was achieved using an Agi-
are in the liquid state in an alcohol or alcohol/water lent 19091S-433 HP-5MS fused silica capillary column,
matrix. The flavour compounds tend to be volatile in 30 m x 0.25 mm i.d., 0.25 µm film thickness. GC oven
nature, which fulfills one of the main requirements of temperature was programmed from 60 to 285 °C at a
GC. General detectors, such as the flame ionization de- rate of 4.3 °C/min. Helium was used as carrier gas, inlet
tector (FID), or more information-rich detectors, such as pressure was 25 kPa, linear velocity was 1 mL/min at
the mass selective detector (MSD), can be used. 210 °C. Injector temperature was 250 °C, and injection
The aim of this study was to compare the contents mode splitless. MS scan conditions: source temperature,
of volatile compounds in different plum brandies. 200 °C; interface temperature, 250 °C; E energy, 70 eV;
mass scan range, 40–350 amu (atomic mass units). Iden-
tification of the components was done on the basis of re-
Materials and Methods tention index and the comparison with reference spectra
(Wiley and NIST databases). Percentage (relative) of the
Four Serbian old plum brandy samples were ana-
identified compounds was computed from GC peak
lyzed: (i) plum brandy Manastirka 45 % (sample I), in-
area.
dustrially produced from Belgrade region, (ii) plum
brandy Sokolova rakija 45 % (sample II), home-made
from U`ice region, (iii) plum brandy Valjevka 45 %
GC analysis of alcohols
(sample III), home-made from Valjevo region, and (iv) Determination of methanol, ethanol and higher al-
plum brandy Karanka 45 % (sample IV), home-made cohols (C3–C5) in the old plum brandies was carried out
from U`ice region. by adding 2.5 mL of n-butanol (1 %) as an internal stan-
Manastirka was distilled in 1990 in modified Cha- dard to 2.5 mL of brandy. Prior to evaluation of ethanol
rente type apparatus for simple distillation with the vol- content each brandy was diluted tenfold with water.
ume of 300 L. Above the apparatus body and cover was A CE INSTRUMENTS Model 8000Top gas chromato-
a short rectification column with 4 floors. The purpose graph equipped with a headspace autosampler and fla-
of the column was to concentrate and purify alcohol- me ionisation detector (FID) was used. The separation
V. TE[EVI] et al.: Volatile Components of Plum Brandies, Food Technol. Biotechnol. 43 (4) 367–372 (2005) 369

was achieved using a J&W Scientific DB – WAX fused rated by maximum 20 points. The samples of plum
silica capillary column, 30 m x 0.32 mm i.d., 0.25 mm brandies were subjected to sensory evaluation by a
film thickness. GC oven temperature was programmed panel comprising 5 qualified testers, all of them highly
from 30 °C (6 min) to 220 °C at the rate of 4.3 °C/min. experienced in sensory testing.
Nitrogen was used as carrier gas; flow rate was 1 mL/
min at 210 °C. Injector temperature was 220 °C, while
detector temperature was 250 °C. The samples were in- Results and Discussion
jected with a 1:64.3 splitting.
The volatile compounds identified in the four spirits
are presented in Table 1. A total of 71, 71, 81 and 76 free
Sensory analysis
aroma compounds were identified in the plum brandy
Sensory assessment of plum brandy samples was samples I, II, III and IV, respectively, including alcohols,
performed using modified Buxbaum model of positive esters, monoterpene, carbonyl compounds, lactones, ac-
ranking. This model is based on 5 sensorial experiences ids, volatile phenols and acetal compounds.

Table 1. Aroma composition of the plum brandies I–IV (%)

Compound I II III IV RIa

Isoamyl acetate 0.72 0.21 0.11 0.13 876
2-methyl butyl acetate 0.32 0.05 0.07 880
Ethyl pentanoate 0.21 0.07 0.09 898
1,1-diethoxybutane 0.05 0.04
1,1-diethoxy-2-methyl propane 0.12
Methyl hexanoate 0.02 927
a-pinene 0.14 939
1,1-diethoxy-3-methyl butane 0.19 0.15 0.15 0.11
Benzaldehyde 1.33 0.97 0.60 0.65 961
Heptanol 0.20 0.07 0.02 969
b-myrcene 0.15 991
Ethyl hexanoate 3.08 1.62 1.36 1.33 996
p-cymene 0.21 0.03 0.04 1026
Limonene 0.02 0.01 1031
Benzyl alcohol 0.36 0.06 0.05 0.07 1060
g-terpinene 0.26 0.03 1062
Pentyl cyclopropane 0.17 0.02
c-linalool oxide 0.11 0.05 0.02 0.08 1074
1,1,3-triethoxypropane 0.20 0.04 0.05
t-linalool oxide 0.04 0.08 1088
1,1-diethoxyhexane 0.08 0.34 0.32 0.42
Ethyl heptanoate 0.03 0.04 0.02 1095
Linalool 0.12 0.03 0.05 1098
Nonanal 0.30 0.93 0.53 0.51 1098
b-phenyl ethyl alcohol 0.37 0.09 0.05 0.10 1110
Methyl octanoate 0.13 0.11 0.11 0.09 1125
Benzyl acetate 0.03 0.01 1163
Ethyl benzoate 13.46 4.35 2.32 4.10 1170
1,1-diethoxyheptane 0.08 0.14 0.08 0.06
a-terpineol 0.20 0.06 0.05 1189
Ethyl octanoate 9.99 6.36 6.34 6.23 1195
Decanal 0.03 0.03 0.03 1204
Methyl nonanoate 0.03 0.03 1225
Citronellol 0.03 0.03 1228
t-geraniol 0.04 0.04 0.01 0.01 1255
Ethyl salicylate 2.37 1.19 0.74 1.20 1267
1,1-diethoxyoctane 0.05 0.14
Ethyl nonanoate 1.61 1.66 1.62 2.23
Methyl decanoate 0.18 0.26 0.35 0.35 1326
2-methyl propyl benzoate 0.09 0.03
Isobutyl octanoate 0.01 0.01
Ethyl-3-phenylpropionate 0.60 0.29 0.13 0.65
370 V. TE[EVI] et al.: Volatile Components of Plum Brandies, Food Technol. Biotechnol. 43 (4) 367–372 (2005)

Compound I II III IV RIa

Eugenol 0.58 0.78 0.49 0.72 1356
2-methoxy-4-propylphenol 0.03 0.09
Decanoic acid 1.26 0.12 0.91
1,1-diethoxynonane 3.13 0.49
Ethyl-9-decanoate 0.13 0.11
Ethyl decanoate 14.03 14.89 15.25 19.88 1394
Methyl eugenol 0.15 1401
3-methyl butyl benzoate 0.20 0.10 0.07 0.18 1430
Isoamyl octanoate 0.04 0.10 0.10 0.14 1446
Dihydro-b-ionol 0.11 0.02 0.08
4-methoxy ethyl benzoate 0.05 0.01
Undecanoic acid 0.01
Ethyl cinnamate 1.27 0.72 0.46 0.87 1462
1-dodecanol 0.08 0.08 0.02 0.05 1473
Propyl decanoate 0.06 0.05 0.05 0.06
Ethyl undecanoate 0.14 0.15 0.24 1496
Ethyl-2,2-decadienoate 0.08
a-muurolene 0.06 0.08 1499
Pentadecane 0.09 0.01 0.05 1500
Methyl dodecanoate 0.14 0.25 0.31 1525
Isobutyl decanoate 0.10 0.09 0.09
Dodecanoic acid 3.32 0.83 1.79 3.73 1568
Hexyl benzoate 0.02 1576
Ethyl dodecanoate 5.63 12.06 13.42 17.03 1576
Anisyl-isobutyrate 0.25 0.05 0.03 0.04
Nerolidol 0.01 1564
3-methyl butyl decanoate 0.06 0.26 0.27 0.35
6,9-pentadecadien-1-ol 0.14
1,13-tetradecadiene 0.10 0.09 0.03
Bisabolol oxide 0.09 0.05 1635
Cyclotetradecane 0.11 0.10 0.12 0.19
g-dodecalactone 0.26 0.14 0.10 0.11 1647
Ethyl tridecanoate 0.09 0.13 0.11 0.09
2-pentadecanone 0.04 0.05
Heptadecane 0.02 0.04 1700
Methyl tetradecanoate 0.14 0.13 0.14 0.20 1727
Tetradecanoic acid 0.21 1.64 1.90 1.82
Cyclotetradecane 0.04 0.04
9-hexadecenoic acid 0.15 0.19 0.13
Ethyl tetradecanoate 1.29 3.90 4.35 3.99 1793
3-methyl butyl dodecanoate 0.10 0.53 0.42 0.27
2-phenyl ethyl octanoate 0.01 0.01 0.02
1-nonadecanol 0.07 0.14 0.12 0.10
Ethyl pentadecanoate 0.11 0.23 0.33 0.24
Methyl 9-hexadecenoate 0.05 0.05 0.03
Methyl hexadecanoate 0.14 0.27 0.41 0.23 1927
Hexadecanoic acid 0.66 0.24 0.55 0.39 1968
Ethyl-9-hexadecenoate 0.75 2.22 2.18
Eicosane 0.05 0.02 2000
Ethyl hexadecenoate 4.59 10.37 13.87 6.93 1993
2-phenyl ethyl octanoate 0.04 0.03 0.02
9,12-octadecadienoic acid 0.09 0.25 0.32 0.13 2092
9,12,15-octadecatrienoic acid 0.03 0.10 0.13 0.19
Hexadecane-1,2-diol 0.20 0.25 0.37
Ethyl linoleate 4.48 6.30 9.72 5.16 2177
Ethyl oleate 4.56 2180
Ethyl stearate 0.39 0.55 1.35 0.29 2194
a
Retention index on DB-5 and according to n-paraffins
V. TE[EVI] et al.: Volatile Components of Plum Brandies, Food Technol. Biotechnol. 43 (4) 367–372 (2005) 371

General composition of plum brandies was in accor- Table 2. Content of ethanol, methanol and high alcohols in
dance with previous studies carried out on Yugoslavian plum brandies (I–IV)
plum brandy (9).
b
Ethyl esters of C8–C18 fatty acids were the most j(ethanol) j(methanol) j(higher alcohols (C3–C5))
Sample
abundant in all samples. Fatty acid esters contribute to % % %
the flavour of the destillates with a pleasant fruity and I 38.64 0.22 0.14
flowery smell (10), indicative of the quality of the spirit II 38.50 0.13 0.09
(11). Among these, ethyl decanoate is the most abun-
III 44.95 0.54 0.16
dant of all esters. The ethyl esters, which are produced
during the fermentation of raw materials, are transfer- IV 45.56 0.44 0.19
red to the spirits and their content increases during ag- b
Total content of n-propanol, isobutanol, isoamyl alcohol and
ing (12). Isoamyl acetate, 2-methyl butyl acetate and ben- n-pentanol

Table 3. Sensory analyses of the old plum brandies

Assessment characteristics
Plum brandy
samples Colour Clearness Distinction Odour Taste Total
(max 1 pts) (max 1 pts) (max 2 pts) (max 6 pts) (max 10 pts) (max 20 pts)
Manastirka 1 1 2 5.6 9.0 18.6
Sokolova rakija 1 1 2 5.3 8.8 18.1
Valjevka 1 1 2 5.4 8.9 18.3
Karanka 1 1 2 5.3 8.8 18.1

zyl acetate constitute the acetic acid ester group, which sults of the performed sensory ranking, the best rated
are mostly responsible for the flowery and fruity aroma brandy is sample I, which was rated with very high sco-
of the distillates (13). Table 1 shows that isoamyl acetate re by 5 examiners (total sensory characteristics 18.60).
is present in the highest concentration among these These diferences between apparatus style and heteroge-
three acetates. neous maturation conditions cause different sensorial
Long chain fatty acids, decanoic, dodecanoic, tetra- evaluations of brandies.
decanoic, and hexadecanoic acid have less strong effect
on the flavour of the distillates (11,14). Table 1 shows Conclusions
that hexanoic acid has the highest mean value of all
these acids, followed by dodecanoic acid, decanoic acid The obtained results have shown that the produc-
and tetradecanoic acid. tion of plum brandies has significant influence on the
The oldest plum brandy (sample I) contained higher aroma constituents and the quality of brandies. Changes
concentration of some ingredients than other two (sam- in the distillation system and aging time induce consid-
ple II and III), such as: benzaldehyde, ethyl benzoate, erable modifications to the volatile composition of plum
ethyl salicylate and ethyl cinamate. Also, benzyl alcohol brandies. Besides the esters, fatty acids, and fusel alco-
and b-phenyl ethyl alcohol, which are known aromatic hols already identified in many types of spirits, other
alcohols, were found at higher concentrations in the volatile compounds have been identified. Some terpene
sample I. b-phenyl ethyl alcohol introduces a pleasant compounds, such as limonene, b-myrcene, a-pinene,
aroma to distillates, resembling to rose (15). a-terpineol, g-terpinene, cis/trans linalool oxide, linalool,
The aromatic terpene compounds, a-pinene and t-geraniol, citronellol, a-muurolene and nerolidol, were
identified for the first time in this type of spirit. These
b-myrcene, were detected only in sample I. Eugenol,
compounds may originate from the plum.
with an aroma of cloves, was detected in all samples
and therefore is very important for the aroma of these
spirits. Significant differences were not found for the References
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Hlapljivi sastojci {ljivovice

Sa`etak
Metode plinske kromatografije i kombinacija plinske kromatografije i masene spektro-
metrije upotrijebljene su za detekciju hlapljivih komponenti u tri uzorka doma}e {ljivovice
i jednom industrijski proizvedenom uzorku. Plinskokromatografskom metodom i kombi-
nacijom plinskokromatografske i masene spektrometrijske analize ekstrakata identificirano
je 99 komponenata, od ~ega su 46 esteri, 7 ugljikovodici (alkani i alkeni), 3 aldehidi, 9 al-
koholi, 1 lakton, 1 keton, 8 acetali, 14 terpeni, 8 kiseline i 2 fenoli. U svim uzorcima domi-
nantni su bili etil esteri C8-C18 kiselina. Osim toga odre|en je udjel metanola, etanola i
vi{ih alkohola (C3-C5).