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Composition of blackcurrant aroma isolated from leaves, buds, and berries of Ribes nigrum L/Mustsostra (Ribes nigrum L.) lehtede, pungade ja marjade aroomi keemiline koostis.

INTRODUCTION

Blackcurrant blackcurrant
Noun

a very small blackish edible fruit that grows in bunches on a bush

blackcurrant ngrosella negra

blackcurrant black n
 (Ribes nigrum L. (Saxifragacea)) is cultivated extensively in central and northern Europe. Its buds, berries, and also leaves have a very characteristic odour. Blackcurrant berries are used in many flavour applications of food and beverages, for jamming, and juice production. Blackcurrant buds are applied as a starting material for the preparation of the essential oil and absolutes, which are used as flavouring in cosmetics and food products. Leaves are used in canning some vegetables (cucumbers, tomatoes).

Numerous studies of the blackcurrant aroma were carried out by Anderson & von Sydow [1-4], Nursten & Williams [5], Latrasse and co-workers [6-9], Nijssen & Maarse [10], Kerslake & Menary [11], Marriott [12], Nishimura & Mihara [13], and Piry et al. [14]. A large number of components, of which the terpenoic hydrocarbons are quantitatively the most important, have been identified in the blackcurrant aroma. The compounds found in significant amounts are [alpha]- and [beta]-pinene, sabinene, 3-carene, [beta]-phellandrene, and terpinolene.

Different constituents, responsible for the characteristic "catty cat·ty 1  
adj. cat·ti·er, cat·ti·est
1. Subtly cruel or malicious; spiteful: a catty remark.

2. Catlike; stealthy.
 note" of black-currant, have been identified. Nishimura & Mihara [13] reported isolation of 3-hydroxy-2-methyl-butyronitriles and (Z)- and (E)-2-hydroxymethyl-2-butenenitriles from blackcurrant bud absolute as odour compounds. Latrasse and coworkers [6-8] identified 4-methoxy-2-methyl-2-butanethiol as a component with the characteristic catty note in blackcurrant buds. Non-sulphur containing aroma chemicals with blackcurrant odour (spiro-ethers) were studied by Van der Weerdt [15].

The aroma from R. nigrum growing in Estonia has not been studied earlier by capillary GC and we did not find any literature data about the use of the chiral chi·ral
adj.
Of or relating to the structural characteristic of a molecule that makes it impossible to superimpose it on its mirror image.



chi·ral
 capillary column for blackcurrant aroma analysis.

The aim of this work was to compare the composition of blackcurrant aroma extracts isolated by the simultaneous distillation/extraction (SDE SDE - Software Development Environment: equivalent to SEE. ) micromethod from berries, leaves, and buds of R. nigrum using nonpolar nonpolar

not having poles; not exhibiting dipole characteristics.
 (OV-101), polar (PEG 20M), and chiral (CYDEX B) capillary columns and the GC/MS GC/MS Gas Chromatograph/Mass Spectrometer
GC/MS Gas Chromatograph/Mass Spectrometry
GC/MS Gas Chromatograph/Mass Spectrograph
 method. The blackcurrant oil yields from different materials and changes in the concentrations of aroma compounds during the ripening process were studied, and the enantiomeric ratio of some monoterpenoic compounds was determined.

EXPERIMENTAL

Materials

Buds, leaves, and berries were harvested from one blackcurrant bush growing in Estonia (near Rapla). A total of five samples were collected on different dates (Table 1).

Sample preparation

Aroma compounds were isolated from fresh blackcurrant material. SDE was performed in the micro-apparatus of Marcusson's type during 2 h using n-hexane as the solvent and n-tetradecane as the internal standard for yield determination. For the isolation procedure 100-140 g of fruits and about 20 g of leaves and buds were used.

Capillary gas chromatography gas chromatography (GC)

Type of chromatography with a gas mixture as the mobile phase. In a packed column, the packing or solid support (held in a tube) serves as the stationary phase (vapour-phase chromatography, or VPC) or is coated with a liquid stationary phase
 

GC analyses were performed on a Chrom-5 gas chromatograph gas chromatograph
n.
An instrument used in gas chromatography to separate a sample of a volatile substance into its components.
 equipped with a flame ionization detector A flame ionization detector (FID) is a type of detector used in gas chromatography. Principle
The Flame Ionization Detector (FID) is one of the many methods by which to analyze materials coming off of gas chromatography column.
. Helium was used as the carrier gas with a splitting ratio 1 : 150. Fused silica fused silica
n.
See quartz glass.
 capillary columns with stationary phases of different polarity were used. Table 2 specifies the columns used and the conditions of the analysis.

A Hewlett-Packard Model 3390A integrator was applied for data processing data processing or information processing, operations (e.g., handling, merging, sorting, and computing) performed upon data in accordance with strictly defined procedures, such as recording and summarizing the financial transactions of a . Quantitation of peaks was expressed as a percentage of the total peak area. The yields (%) of aroma compounds were determined using the internal standard according to according to
prep.
1. As stated or indicated by; on the authority of: according to historians.

2. In keeping with: according to instructions.

3.
 the formula

X = [K.sub.st]([A.sub.x]/[A.sub.st])%,

where [A.sub.x], [A.sub.st]--the total peak area of the aroma substances and the peak area of the internal standard, respectively

[K.sub.st]--% of the internal standard in the sample material

Component identification was based on the comparison of the temperature programming retention indices (RI) determined on different columns with authentic RI data either from our data bank or obtained from the literature [16-19]. The results obtained were confirmed by GC/MS.

Gas chromatography/mass spectrometry spectrometry /spec·trom·e·try/ (spek-trom´e-tre) determination of the wavelengths or frequencies of the lines in a spectrum.

spec·trom·e·try
n.
 

Mass spectrometric analyses were carried out on a Hitachi M-80B gas chromatograph double-focusing mass spectrometer spectrometer

Device for detecting and analyzing wavelengths of electromagnetic radiation, commonly used for molecular spectroscopy; more broadly, any of various instruments in which an emission (as of electromagnetic radiation or particles) is spread out according to some
 using a SPB-1 (30 m x 0.32 mm) fused silica capillary column. The temperature program was 3 min at 50[degrees]C, then 50-120[degrees]C at 5[degrees]C/min and 120-290[degrees]C at 8[degrees]C/min.

RESULTS AND DISCUSSION

The recoveries of essential oils from different fresh blackcurrant materials obtained applying the SDE micromethod with n-hexane as the solvent varied in the range 0.001-0.21% (Table 1). The yields of oil from blackcurrant berries from the three samples of different ripening stage were quite similar (0.001-0.003%) being the highest for fully ripe berries. A much higher yield of oil was obtained from blackcurrant leaves (0.04%) and especially from blackcurrant buds (0.21%). According to the literature data the oil yield from blackcurrant leaves is 0.08-0.74 mg/g [12] depending on the isolation method (distillation or extraction), from buds 2-5 mg/g [8], and from berries 10-13 ppm [3].

The complex nature of the blackcurrant aroma is demonstrated in the chromatogram chromatogram /chro·mato·gram/ (kro-mat´o-gram) the record produced by chromatography.

chro·mat·o·gram
n.
The pattern of separated substances obtained by chromatography.
 (Fig. 1). Table 3 lists the compounds identified in the blackcurrant oils and their relative amounts (%) in the oils isolated from berries, buds, and leaves. The RI data in three stationary phases are also reported.

Altogether 63 compounds were identified in the blackcurrant oils studied. Perillaldehyde, decanoic acid decanoic acid

one of the saturated fatty acids found in the endosperm of the coconut (Cocos nucifera), in coconut oil and in other seed oils. Used in diets for patients with fat malabsorption syndromes. Called also n-capric acid.
, and palmitic acid palmitic acid /pal·mit·ic ac·id/ (pal-mit´ik) a 16-carbon saturated fatty acid found in most fats and oils, particularly associated with stearic acid; one of the most prevalent saturated fatty acids in body lipids.  have not been found in blackcurrant oil before. The monoterpenoic hydrocarbon fraction was the main part of the oil for all the parts of blackcurrant with its relative amounts varying from 55% to 67% of the oils (Table 3). The composition of the major monoterpenes was found to be in good agreement with the previous studies [1-14]. 3-Carene, [beta]-phellandrene, (Z)- and (E)-[beta]-ocimene, limonene lim·o·nene  
n.
A liquid, C10H16, with a characteristic lemonlike fragrance, used as a solvent, wetting agent, and dispersing agent and in the manufacture of resins.
, and terpinolene were identified in high quantities (0.9-26.9%).

Sesquiterpenes made up 7.5-15.7% of the blackcurrant oils. The major sesquiterpene sesquiterpene (sesˑ·kw·terˑ·pēn),
n
 in the oils was (E)-[beta]-caryophyllene (4.6-9.3%). The other sesquiterpenes made up less than 4.1% in all samples. Oxygenated terpenes terpenes (terˑ·pēnz),
n.pl a large-sized group of unsaturated hydrocarbons with the empirical formula (C5H8)n.
 were found in quantities 5.7-14.2% of oils. From the 20 oxygenated monoterpenes identified in the blackcurrant oils only [alpha]-terpineol and citronellyl acetate were found to form over 1%. The main oxygenated sesquiterpene was caryophyllene oxide (0.5-9.8%). The other groups of compounds in the oils were aromatic compounds, aliphatic aliphatic /al·i·phat·ic/ (al?i-fat´ik) pertaining to any member of one of the two major groups of organic compounds, those with a straight or branched chain structure.

al·i·phat·ic
adj.
 aldehydes, alcohols and acids, and n-alkanes [C.sub.16]-[C.sub.21].

Generally the same substances although with quantitative differences were present in the oils of the different blackcurrant materials. Camphene cam·phene  
n.
A colorless crystalline terpene, C10H16, used in the manufacture of synthetic camphor and insecticides.



[camph(or) + -ene.]
 and linalool linalool

a natural insecticidal compound found in oil extracted from citrus peel. Similar in activity to d-limonene.
 were found in leaves and buds but not in berries. Some aliphatic oxygenated compounds (heptanal, decanal Dec´a`nal

a. 1. Pertaining to a dean or deanery.
His rectorial as well as decanal residence.
- Churton.

Decanal side
the side of the choir on which the dean's tall is placed.
, 2-decanol, ethyl ethyl (ĕth`əl), CH3CH2, organic free radical or alkyl group derived from ethane by removing one hydrogen atom.  decanoate, palmitic acid, but also 1,8-cineole, myrtenal, 1-p-menthen-9-al, and perillaldehyde), not found in leaves, were identified in small quantities in buds and in the highest quantities in blackcurrant berries. The aromatic hydrocarbon Noun 1. aromatic hydrocarbon - a hydrocarbon that contains one or more benzene rings that are characteristic of the benzene series of organic compounds
benzene, benzine, benzol - a colorless liquid hydrocarbon; highly inflammable; carcinogenic; the simplest of the
 p-cymenene was also found in small quantities in buds and leaves, but occurred in quantities up to 5% in berries. Compared with the other parts the blackcurrant buds contained more monoterpenes ([beta]-phellandrene, terpinolene, [alpha]-pinene, limonene) and n-alkanes. The aroma from blackcurrant leaves contained more [beta]-ocimene isomers isomers (ī´sōmurz),
n.pl 1. organic compounds having the same empirical formula–i.e.
 and caryophyllene oxide than the oils from the other parts. The blackcurrant aroma isolated from berries was rich in aromatic and aliphatic compounds and oxygenated monoterpenes.

[FIGURE 1 OMITTED]

The aroma from fully ripe blackcurrant berries showed a higher yield and contained more monoterpenoic hydrocarbons and less oxygenated terpenes than the aroma of unripe and overripe o·ver·ripe  
adj.
1. Too ripe.

2. Marked by decay or decline.



over·ripe
 berries.

The enantiomer enantiomer /en·an·tio·mer/ (en-an´te-o?mer) one of a pair of compounds having a mirror image relationship.  ratios (the amount of one enantiomer expressed as percentage of the total amount of the pair of compounds) of some monoterpenoic compounds in the blackcurrant aroma samples are presented in Table 4. It was found that in the enantiomeric composition of the compounds studied the aroma from different blackcurrant parts and from berries of different ripening stage was quite similar.

In most cases a significant (+)-enantiomer excess was observed for the monoterpenes [alpha]- and [beta]-pinene (65-82%), but (-)-enantiomer excess (57-67%) was observed for oxygenated compounds (linalool, terpinen-4-ol, [alpha]-terpineol). In the case the content of linalool and [alpha]-terpineol in the oil of blackcurrant leaves was very low (< 0.1%), the enantiomeric distribution was not considerable. (-)-Limonene and (-)-[beta]-phellandrene were eluted with (Z)-[beta]-ocimene and (E)-[beta]-ocimene (Table 3) and therefore the enantiomeric distribution of their enantiomers enantiomers (i·nanˑ·tē··merz),
n.
 could not be determined.

ACKNOWLEDGEMENT

Financial support for the work reported here was provided by the Estonian Science Foundation (grant No. 4028).

Received 10 July 2002, in revised form 8 October 2002

REFERENCES

[1.] Andersson, J. & von Sydow, E. The aroma of black currants I. Higher boiling compounds. Acta Chem. Scand., 1964, 18, 1105-1114.

[2.] Andersson, J. & von Sydow, E. The aroma of black currants II. Lower boiling compounds. Acta Chem. Scand., 1966, 20, 522-528.

[3.] Andersson, J. & von Sydow, E. The aroma of black currants III. Chemical characterization of different varieties and stages of ripneness by gas chromatography. Acta Chem. Scand., 1966, 20, 529-535.

[4.] Andersson, J., Bosvik, R. & von Sydow, E. The composition of the essential oil of the black currant currant, northern shrub of the family Saxifragaceae (saxifrage family), of the same genus (Ribes) as the gooseberry bush. The tart berries of the currant may be black, white, or red; the white gooseberry becomes purple when mature.  leaves (Ribes nigrum L.). J. Sci. Food Agric., 1963, 14, 834-840.

[5.] Nursten, H. E. & Williams, A. A. Volatile constituents of the black currant (Ribes nigrum L.). II. The fresh fruit. J. Sci. Food Agric., 1969, 20, 613-619.

[6.] Latrasse, A., Rigaud, J. & Sarris, J. L'arome du cassis (Ribes nigrum L.) odeur principale et notes secondaries. Sci. Aliments ALIMENTS. In the Roman and French law this word signifies the food and other things necessary to the support of life, as clothing and the like. The same name is given to the money allowed for aliments. Dig. 50, 16, 43.
     2.
, 1982, 2, 145-162.

[7.] Rigaud, J., Etievant, P., Henry, R. & Latrasse, A. 4-Methoxy-2-methyl-2-mercapto-butane, a major constituent of the aroma of the blackcurrant bud (Ribes nigrum L.). Sci. Aliments, 1986, 6, 213-220.

[8.] Le Quere, J.-L. & Latrasse, A. Composition of the essential oils of blackcurrant buds (Ribes nigrum L.). J. Agric. Food Chem., 1990, 38, 3-10.

[9.] Le Quere, J.-L. & Latrasse, A. Identification of (+)spathylenol in the essential oil of blackcurrant buds (Ribes nigrum L.). Sci. Aliments, 1986, 6, 47-59.

[10.] Nijssen, L. M. & Maarse, H. Volatile compounds in black currant products. An additional factor in authenticity control of fruit juices. Flav. Fragr. J., 1986, 1, 143-148.

[11.] Kerslake, M. F. & Menary, R. C. Aroma constituents of black currant buds (Ribes nigrum L.). Perfum. Flavor., 1985, 9, 13-24.

[12.] Marriott, R. J. Isolation and analysis of blackcurrant (Ribes nigrum L.) leaf oil. In Flavors and Fragrances: A World Perspective (Lawrence, B. M., Mookherjee, B. D. & Willis, B. J., eds.). Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Washington, DC, U.S.A., 16-20 November 1986. Elsivier Science Publishers B.V., Amsterdam, 1988, 387-403.

[13.] Nishimura, O. & Mihara, S. Aroma constituents of blackcurrant buds (Ribes nigrum L.). In Flavors and Fragrances: A World Perspective (Lawrence, B. M., Mookherjee, B. D. & Willis, B. J., eds.). Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Washington, DC, U.S.A., 16-20 November 1986. Elsevier Science Publishers B.V., Amsterdam, 1988, 375-386.

[14.] Piry, J., Pribela, A., Durcanska, J. & Farkas, P. Fractionation fractionation /frac·tion·a·tion/ (frak?shun-a´shun)
1. in radiology, division of the total dose of radiation into small doses administered at intervals.

2.
 of volatiles from blackcurrant (Ribes nigrum L.) by different extractive extractive /ex·trac·tive/ (-tiv) any substance present in an organized tissue, or in a mixture in a small quantity, and requiring extraction by a special method.

ex·trac·tive
adj.
1.
 methods. Food Chem., 1995, 54, 73-77.

[15.] Van der Weerdt, A. J. A. Non-sulphur containing aroma chemicals with blackcurrant odor. In Flavors and Fragrances: A World Perspective (Lawrence, B. M., Mookherjee, B. D. & Willis, B. J., eds.). Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Washington, DC, U.S.A., 16-20 November 1986. Elsevier Science Publishers B.V., Amsterdam, 1988, 405-423.

[16.] Davies, N. W. Gas chromatographic chro·mat·o·graph  
n.
An instrument that produces a chromatogram.

tr.v. chro·mat·o·graphed, chro·mat·o·graph·ing, chro·mat·o·graphs
To separate and analyze by chromatography.
 retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J. Chromatogr., 1990, 503, 1-24.

[17.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC/MS identification. Mono- and sesquiterpenic hydrocarbons. Rastit. resur., 1996, 32, 48-58 (in Russian).

[18.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC/MS identification. Oxygen containing derivatives of mono- and sesquiterpenic hydrocarbons. Rastit. resur., 1997, 33, 16-28 (in Russian).

[19.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC/MS identification. Acetates of terpenic alcohols. Rastit. resur., 1999, 35, 30-37 (in Russian).

Anne Orav *, Tiiu Kailas, and Mati Muurisepp

Institute of Chemistry, Tallinn Technical University, Akadeemia tee 15, 12618 Tallinn, Estonia

* Corresponding author, aorav@chemnet.ee
Table 1. Time of collection and characterization of blackcurrant
samples

Sample   Material   Date of harvest   Ripening stage   Oil yield,
 No.                                                       %

1        Buds       May 2000                           0.21
2        Berries    4 July 2000       Unripe           0.002
3        Berries    17 July 2000      Fully ripe       0.003
4        Berries    16 August 2000    Overripe         0.001
5        Leaves     August 2000                        0.04

Table 2. Capillary columns and operating conditions

          Parameter                       Stationary phase

                                    OV-101      SW-10      CYDEX B

Column length, m                      50          60         50
Column internal diameter, mm         0.20        0.32       0.22
Stationary phase film                0.50        0.25       0.25
  thickness, [micro]m
Plate number for n-decane          145 000     300 000     170 000
  at 90[degrees]C
Helium flow rate, cm/sec            17-25       17-25       30-35
Injector temperature, [degrees]C     160         260         160
Column temperature, [degrees]C      50-250      70-220     60-220
Programming rate, [degrees]C/min      2           2           2

Table 3. Retention indices (RI) and composition of the essential
oils of blackcurrant buds, berries, and leaves. The components
identified in the highest yields are in bold

          Compound                       RI

                               OV-101   SW-10   CYDEX B

[alpha]-Thujene (MS)             923     1029     954
(-)-[alpha]-Pinene (MS)          930     1029     985
(+)-[alpha]-Pinene (MS)          930     1029     990
n-Heptanal                       879             1000
(+)-Camphene                     940     1074    1010
Sabinene (MS)                    963     1125    1024
Myrcene (MS)                     980     1161    1026
(+)-[beta]-Pinene (MS)           967     1116    1035
(-)-[beta]-Pinene (MS)           967     1116    1039
(+)(-)-3-Carene (MS)            1002     1148    1045
[alpha]-Phellandrene (MS)        993     1167    1046
[alpha]-Terpinene (MS)          1007     1180    1055
(Z)-[beta]-Ocimene (MS)         1026     1232    1069
(-)-Limonene (MS)               1020     1204    1069
(+)-Limonene (MS)               1020     1204    1072
p-Cymene (MS)                   1010     1273    1079
(E)-[beta]-Ocimene (MS)         1037     1250    1083
(-)-[beta]-Phellandrene         1019     1213    1083
(+)-[beta]-Phellandrene (MS)    1019     1213    1086
[gamma]-Terpinene (MS)          1047     1246    1100
1,8-Cineole (MS)                1020     1211    1114
Terpinolene (MS)                1078     1282    1124
p-Cymenene (MS)                 1072     1428    1157
1-Octen-3-ol (MS)                970     1450    1142
Oxygenated mono-                1055     1431    1167
  terpene [C.sub.10]
  [H.sub.18]O
(-)-Fenchone                    1066     1397    1205
Methyl benzoate                 1068             1205
trans-Linalool oxide            1072     1451    1210
(-)-Linalool (MS)               1085     1547    1238
(+)-Linalool (MS)               1085     1547    1240
Methyl chavicol                 1175     1660    1300
n-Decanal                       1185             1311
(-)-Terpinen-4-ol (MS)          1160     1593    1321
(+)-Terpinen-4-ol (MS)          1160     1593    1324
2-Decanol                       1197             1335
(+)-Myrtenal                    1166             1348
1-p-Menthen-9-al (MS)           1166             1352
(+)-[alpha]-Terpineol (MS)      1172     1690    1360
(-)-[alpha]-Terpineol (MS)      1172     1690    1363
Isoborneol                      1146             1370
Borneol                         1150     1693    1376
Bornyl acetate                  1268     1574    1381
Nerol                           1213     1800    1389
Citronellyl acetate (MS)        1334     1671    1432
(-)-Perillaldehyde a a          1243     1774    1441
Ethyl decanoate                 1375             1457
Geranyl acetate (MS)            1365     1755    1474
(+)(-)-(E)-[betaa]-Caryo-       1412     1586    1476
  phyllene (MS)
[gamma]-Elemene (MS)            1423             1494
[alpha]-Humulene (MS)           1443     1653    1511
Germacrene D                    1470     1690    1541
Bicyclogermacrene (MS)          1482     1716    1563
[delta]-Cadinene (MS)           1509     1749    1572
n-Hexadecane                    1600     1600    1600
Germacrene B (MS)               1547     1805    1615
Decanoic acid                   1368     2270    1652
n-Heptadecane                   1700     1700    1700
(+)(-)-Caryophyllene            1564     1960    1728
  oxide (MS)
n-Octadecane                    1800     1800    1800
n-Butyl cinnamate (MS)                           1850
n-Nonadecane                    1900     1900    1900
n-Eicosane (MS)                 2000     2000    2000
n-Heneicosane (MS)              2100     2100    2100
Palmitic acid                   1945             2217

COMPONENT GROUPS:
  Monoterpenes
  Oxygenated
    monoterpenes
  Sesquiterpenes
  Oxygenated
    sesquiterpenes
  Aliphatic
    compounds

    Total %

          Compound                       Concentration *, %

                               Buds          Berries          Leaves

                                1      2        3       4       5

[alpha]-Thujene (MS)            0.2   tr.       0.1    tr.      0.1
(-)-[alpha]-Pinene (MS)         0.6    0.3      0.4     0.4     0.3
(+)-[alpha]-Pinene (MS)         2.3    1.2      1.8     1.6     1.2
n-Heptanal                     tr.     0.3      0.4     0.7     --
(+)-Camphene                    0.2    --      --       --      0.1
Sabinene (MS)                   2.4    1.3      1.6     1.3     1.9
Myrcene (MS)                    0.8    0.3      0.4     0.4     0.6
(+)-[beta]-Pinene (MS)          0.3    0.3      0.4     0.2     0.8
(-)-[beta]-Pinene (MS)          0.1    0.1      0.2     0.1     0.2
(+)(-)-3-Carene (MS)           20.2   21.2     26.9    20.2    25.4
[alpha]-Phellandrene (MS)       0.7    0.7      0.8     0.8     0.3
[alpha]-Terpinene (MS)          1.1    2.2      2.5     1.9     0.7
(Z)-[beta]-Ocimene (MS)         6.7    2.7      5.5     2.1    11.3
(-)-Limonene (MS)              {
(+)-Limonene (MS)               4.9    3.4      3.2     3.9     2.3
p-Cymene (MS)                   0.1    0.9      0.8     0.4     0.6
(E)-[beta]-Ocimene (MS)         2.4    2.0      1.5     0.9     7.7
(-)-[beta]-Phellandrene        {
(+)-[beta]-Phellandrene (MS)   11.3    5.4      6.7     6.1     2.6
[gamma]-Terpinene (MS)          0.3    0.8      0.7     0.4     0.3
1,8-Cineole (MS)               tr.     0.6      0.3     0.4     --
Terpinolene (MS)               10.2    8.7      8.7     6.8     7.7
p-Cymenene (MS)                 0.2    3.5      4.8     4.0     0.3
1-Octen-3-ol (MS)               0.1    0.2      0.5     0.1     0.2
Oxygenated mono-                0.1    0.4      0.5     1.0     --
  terpene [C.sub.10]
  [H.sub.18]O
(-)-Fenchone                    0.1    0.4      0.3     0.4     0.2
Methyl benzoate
trans-Linalool oxide            0.1    0.3      0.3     0.2     --
(-)-Linalool (MS)               0.1    --      --       --      0.3
(+)-Linalool (MS)               0.1    --      --       --      0.3
Methyl chavicol                 --     0.7      0.3     1.2     --
n-Decanal                       --     0.3      0.4     0.3     0.1
(-)-Terpinen-4-ol (MS)          0.2    0.5      0.2     0.6     0.2
(+)-Terpinen-4-ol (MS)          0.1    0.2      0.2     0.4     0.1
2-Decanol                       0.1    0.4      0.4     0.6     --
(+)-Myrtenal                   tr.     0.5      0.4     0.3     --
1-p-Menthen-9-al (MS)           0.1    1.4      0.7     0.6     --
(+)-[alpha]-Terpineol (MS)      0.1    1.0      0.7     1.0     0.3
(-)-[alpha]-Terpineol (MS)      0.1    1.6      1.1     1.6     0.3
Isoborneol                      0.1    0.6      0.8     0.6     0.2
Borneol                         0.2    0.2      0.4     0.4     0.3
Bornyl acetate                  0.4    0.2      0.2     0.3     0.5
Nerol                           0.1    0.6      0.7     0.9     0.3
Citronellyl acetate (MS)        0.7    1.0      1.1     0.8     0.4
(-)-Perillaldehyde a a          0.1    0.5      0.5     0.4     --
Ethyl decanoate                 0.2    0.7      0.4     0.6     --
Geranyl acetate (MS)            0.4    0.5      0.7     0.7     0.3
(+)(-)-(E)-[betaa]-Caryo-       8.3    9.3      5.2     4.6     4.7
  phyllene (MS)
[gamma]-Elemene (MS)            0.2    1.4      1.1     3.8     0.4
[alpha]-Humulene (MS)           0.7    0.8      0.3       1     0.8
Germacrene D                    0.2    0.2      0.2     0.2     0.2
Bicyclogermacrene (MS)          0.1    0.8      0.4       2     0.1
[delta]-Cadinene (MS)           0.2    0.2      0.2     0.1     0.5
n-Hexadecane                   0.1    0.5      0.2     0.7     0.1
Germacrene B (MS)               4.1    3.0      1.6     1.6     0.8
Decanoic acid                   0.2    0.5      0.3     0.2     0.1
n-Heptadecane                   0.2    1.0      0.5     1.9     0.3
(+)(-)-Caryophyllene            2.4    1.0      0.5     0.6     9.8
  oxide (MS)
n-Octadecane                    0.2    0.8      0.5    tr.      0.2
n-Butyl cinnamate (MS)          0.2    1.0      0.8     0.9     0.7
n-Nonadecane                    0.3    1.0      0.8     1.1     0.5
n-Eicosane (MS)                tr.     0.4     tr.      0.3     0.1
n-Heneicosane (MS)              --     0.5      0.2     1.8     --
Palmitic acid                   0.1    2.1      2.2     2.9     0.4

COMPONENT GROUPS:
  Monoterpenes                 65.0   55.0     67.0    51.4    64.4
  Oxygenated                    3.3   12.2     10.3    12.7     4.4
    monoterpenes
  Sesquiterpenes               13.8   15.7      9.0    13.3     7.5
  Oxygenated                    2.4    1.0      0.5     0.6     9.8
    sesquiterpenes
  Aliphatic                     1.5    8.7      6.8    11.2     1.8
    compounds

    Total %                    86.0   92.6     93.6    89.2    87.9

MS--determined on GC/MS

*--determined on CYDEX B

tr.--traces (< 0.05%)

Table 4. Enantiomeric distribution of some monoterpenoic
Compounds in blackcurrant aroma

Compound                   Enantiomeric distribution, %

                        Buds        Berries         Leaves

                         1      2      3      4       5

(-)-[alpha]-Pinene      19.9   20.3   19.1   18.8    22.5
(+)-[alpha]-Pinene      80.1   79.7   80.9   81.2    77.5

(+)-[beta]-Pinene       75.0   65.1   67.3   69.7    81.7
(-)-[beta]-Pinene       25.0   34.9   32.6   30.3    18.3

(-)-Linalool            61.5    --     --     --     54.8
(+)-Linalool            38.5    --     --     --     45.2

(-)-Terpinen-4-ol       61.3   67.2   58.8   60.0    57.6
(+)-Terpinen-4-ol       38.7   32.8   41.2   40.0    42.4

(+)-[alpha]-Terpineol   42.8   39.5   37.2   39.0    48.3
(-)-[alpha]-Terpineol   57.1   60.5   62.8   61.0    51.7

--not detected
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Author:Orav, Anne; Kailas, Tiiu; Muurisepp, Mati
Publication:Estonian Academy of Sciences: Chemistry
Date:Dec 1, 2002
Words:3429
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