Professional Documents
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Printed
in The Netherlands
22 I51
Review
Gas chromatographic retention indices of monoterpenes and
sesquiterpenes on methyl silicone and Carbowax 20M phases
N. W. DAVIES
Central
Science Laboratory.
(Received
November
University
qf Tusmania
Tasmaniu
7001 (Austruliu)
3rd. 1989)
CONTENTS
I. Introduction
.............................................
2. Kovlits retention indices
.......................................
3. Acknowledgements
.........................................
4. Summary
...............................................
References
................................................
I
2
23
23
23
INTRODUCTION
B.V.
N.W. DAVIES
co-workers3-8
have provided a significant amount of information
on sesquiterpene
hydrocarbons.
A general discussion on the use of retention indices in essential oil
analyses has been presented by Shibamoto.
The following tables list Kovats retention indices for some 400 monoterpenes
and sesquiterpenes
(including some hydrogenation
products) on either or both of these
two types of stationary
phase from various literature
sources. Carbowax
20M
(CW20M) phases include DB-Wax, BP20, PEG 20M and HP20, while methyl silicone
phases include SE-30, SF-96, OV-I, OV-101, BPl, CPSILSCB, SP2100, DBl and HPl.
There will be slight differences between the McReynolds
constants on these various
equivalent
phases. The age of a column and amount of use it has had also have
a slight influence on polarity of the liquid phase.
The dependence
of retention
index on temperature
has been extensively
described,
including
specific reference to terpenes-r3.
In the temperature
programmed mode variables such as carrier gas flow-rate and programme rate affect the
measurement,
since they determine the temperature range that the sample is exposed to
prior to elution. Several articles have described the relationships
between isothermal
and temperature
programmed
retention indices14-18.
Temperature
has a relatively small effect on Kovats indices of terpenes on
methyl silicone phases, but can have quite marked effects on the indices on CW20M.
Differences of over 50 units can readily occur in indices determined
under widely
different conditions
on CW20M.
Multiple entries occur in the tables for many
compounds
to enable comparisons
between different
references and to give an
indication of the dependence of the retention index on temperature.
Some indices have
been specifically excluded from the tables where there is a clear discrepancy between
different sources.
This summary is primarily intended as a guide to aid the analysis of essential oils
and related natural and synthetic products by gas chromatography
combined with
mass spectrometry
or other spectroscopic
detection.
Data on the majority
of
commonly occurring monoterpenes
and sesquiterpenes
are listed here, as well as data
on some that are relatively obscure. The tables are listed in alphabetical order, and also
in order of reported Kovats indices on CW20M and methyl silicone phases. These
naturally do not represent elution sequences since the data include indices obtained
under various isothermal and temperature programmed
conditions, as well as multiple
entries. Where possible generally accepted common names have been used. Isomer
identification
symbols (a, /?, y, 6, E, cis, tram, p, rpi, etc.) have been added at the end of
the parent compound
name.
2. KOVATS
RETENTION
The Kovats
INDICES
retention
indices
1-3.
RETENTION
TABLE
INDICES
OF MONOTERPENES
AND SESQUITERPENES
ALPHABETICAL
QUITERPENES
LIST OF REPORTED
KOVATS INDICES
OF MONOTERPENES
ON CW20M AND METHYL
SILICONE
PHASES
Aequilobene
Agarofuran
XAlaskene aAlaskene pAlloaromadendrene
Allo-ocimene
cisAllo-ocimene
trtmsAmorphene
G(Anastreptene
Aromadendrene
Ascaridole
Ascaridole epoxide
Barbatene xBarbatene BBergamotene
G(Bergamotene
trcms-fiBicycloelemene
Bicyclogermacrene
Bisabolane a
Bisabolane b
Bisabolene r*Bisabolene cis-ccBisabolene [jBisabolol LYBisabolol /?Borneo1
Bornyl
acetate
Bornyl benzoate
Bornyl butyrate
Bornyl formate
Bornyl isopentanoate
Bourbonene
/%
Bulnesene t(Cadalene
Cadina- 1.4-diene
C WZOM
AND
SES-
or prog
if the
Methyl silicone
R<f
1702
1907
1763
1738
1660
1662
1683
1373
1392
1691
1724
1568
1650
150
prog
165
165
130
prog
prog
70
70
prog
165
150
prog
4
19
5
5
20
2
21
13
13
22
3
4
21
1483
170
1475
1478
150
prog
20
2
1132
1120
1451
1492
1391
110
110
prog
170
170
13
13
22
3
4
1278
1215
I440
1473
1436
1427
110
110
170
170
prog
prog
23
23
4
4
24
22
1490
prog
22
1448
1458
1505
1496
1496
1595
1666
1164
1154
1177
1278
150
150
170
prog
130
175
175
prog
110
175
135
25
25
3
22
3
26
27
2
23
27
28
1749
1473
1239
1512
1386
1406
prog
prog
prog
prog
130
prog
2
2
2
2
3
2
1502
1646
1518
prog
prog
prog
22
22
22
1627
1690
1590
1586
1482
1744
1738
176X
1492
1510
1766
1740
1745
2022
150
150
prog
prog
prog
prog
130
prog
130
130
165
prog
165
160
4
4
24
22
24
22
20
21
25
25
3
22
3
26
1698
1735
prog
prog
2
21
1599
1615
135
150
28
29
1760
1610
1774
1586
1546
1526
1729
2203
1786
prog
prog
prog
165
prog
prog
prog
prog
prog
2
2
2
3
2
22
22
30
22
Rc$
(Continued on p. 4)
N.W. DAVIES
1 (continued)
TABLE
Cmpound
c W20M
I
Ref:
1784
1761
1785
1792
1766
2224
2150
2136
1926
1916
1837
1839
1842
1021
1066
1078
1083
1518
I65
prog
prog
I65
prog
prog
prog
prog
I65
prog
prog
I50
prog
65
75
75
prog
prog
3
2
21
3
2
24
31
31
6
22
22
4
2
32
5
28
2
2
1504
1524
130
prog
3
2
1507
1227
I30
prog
3
2
Carvacrol
Carveol cis-
1064
II41
1156
2159
1820
65
75
75
prog
prog
32
5
28
2
2
Carveol
/w7.r-
1790
prog
1502
1524
1518
953
952
956
954
I 136
II26
986
1009
1013
1297
1215
1222
1209
1200
prog
170
prog
100
100
100
prog
prog
II0
100
100
IO0
prog
120
prog
prog
120
22
4
2
32
5
28
2
2
23
32
5
2X
2
23
2
2
23
1795
1759
IS0
I50
29
29
1181
II0
23
1641
1715
I50
prog
29
2
Carvone oxide
Carvyl propionate
Caryolan- I-01
Caryophyllane
(I
Caryophyllane
h
Caryophyllane
(
Caryophyllane
d
Caryophyllene
1805
1833
2019
1522
1533
1555
1562
1617
1618
1655
2033
2000
1966
1617
1627
1961
1640
1578
1600
prog
prog
prog
130
130
130
130
prog
130
I65
prog
prog
prog
130
130
prog
I65
prog
prog
2
2
31
25
25
25
25
2
20
3
31
24
31
25
25
2
3
22
2
1228
1223
1261
1440
prog
I25
prog
prog
1425
1432
1450
1450
1428
1436
1417
1559
1576
I50
I50
150
I50
prog
I50
130
prog
prog
25
25
25
25
2
20
3
24
24
1458
1465
1585
1414
I411
1436
I50
I50
prog
130
prog
prog
25
25
2
3
22
2
Cadinene
(5-
Cadinene
7.
Camphane
Camphene
Camphor
Carane
Carene
ci.c3.
Caryophyllene
Caryophyllene
Cedrane
Cedrane
Cedrene
Cedrene
8/jH8aHepoxide
z-
alcohol
oxide
z-
RETENTION
INDICES
OF MONOTERPENES
AND
SESQUITERPENES
1 (continued)
TABLE
Compound
Cedrene
CWZUM
jj-
Cedrol
Rqf:
1670
1633
1605
2100
165
prog
prog
prog
3
2
22
2
1421
I446
prog
1765
1737
150
150
4
4
1185
prog
Cineole
1223
1228
1465
1491
70
prog
prog
135
20
2
2
28
Citronella1
Citronellic
Citronellol
acid
p-
Citronellol
Citronellyl
d(acetate
Citronehyl
butyrate
Citronellyl
Citronellyl
ethyl ace&l
formate
Citronehyi
isobutyrdte
Citronellyl
Citronellyl
pentanoate
propionate
Clovane
Clovene
Copaene
G(-
p-
Cubenol epjCuparene
Curcumene
a- (ar-)
Curcumene
/G
silicone
Chdmigrene
xChamigrene
/IChrysanthenone
Cineole I ,41.8-
Methyl
1722
1765
prog
150
2
34
1760
1645
1662
1671
1786
1811
1626
1600
1638
1705
1739
1880
1700
1738
1621
1601
1551
1493
1519
1626
1481
1458
1560
1541
2037
1811
1838
1831
1777
1787
1756
150
prog
135
150
prog
150
prog
prog
150
prog
150
prog
prog
150
175
175
165
prog
prog
prog
130
prog
130
prog
prog
130
150
prog
prog
165
165
34
2
28
29
2
29
2
2
29
2
29
2
2
29
35
35
3
22
2
2
20
22
20
22
30
20
4
22
22
3
3
130
Rcf:
3
2
1609
1616
1523
1550
1100
1010
1000
1025
1017
1137
1143
1146
1300
1215
1216
1224
prog
1335
1335
1335
1511
prog
prog
1423
1261
prwz
prw
2
2
1469
pro6
1608
1427
prog
prog
2
2
130
prog
3
22
2
2
20
22
20
22
1506
1516
150
170
20
4
1475
1510
130
170
3
3
1378
1369
1398
1445
1362
1381
1400
1381
175
170
170
100
2
27
4
4
23
prog
80
100
prog
prog
135
160
125
prog
100
175
135
140
prog
prog
prog
150
prog
150
33
23
2
23
27
2
28
23
2
(Continwd
on p. 6)
N.W. DAVIES
6
TABLE
1 (continued)
Compound
Methyl silicone
c W2UM
T
I
Cyclocitral
aCyclocitral
/I&
Cyclosativene
Cymene p-
Cymene-7-ol
Cymene-R-o1
Cymenene
Cyperene
pp-
Damascenone
Dihydrocurcumene
Dihydroagarofuran
bDihydrocarveol
Dihydrocarvone
Dihydrocarvyl
acetate
Dihydrogeraniol
Dihydrohumulene
Dihydrolinalool
I ,2-
Dihydrolinalool
Dihydromyrcenol
6,76. IO-
Dihydromyrcenyl
acetate
Dihydronerol
Dihydroterpinyl
acetate
Dimethyl-l.6-octadiene
3.7
Dimethyloctane
2,6Dimethyl-2-octene
2,6Drimenol
Elemane
Elemene flElemene 6Elemene .,IElemol
Eudesmane 4aH,SaHEudesmane 4/~H,5ctHEudesmol w
Eudesmol
/I-
Eudesmol
Eudesmol
Eudesmol
Farnesene
Farnesene
Farnesene
27-epi-ccIO-epi-ycis,ci.wcis,trans-r/ran,r,cis-a-
Rqf.
1549
1250
1272
1275
165
75
prog
70
3
5
2
20
1846
prog
24
1606
1535
1801
1696
1737
1713
1600
1670
1700
1759
1655
1512
1537
1449
1438
1473
1431
1725
1561
165
prog
prog
130
prog
prog
prog
prog
150
150
175
prog
150
150
prog
150
prog
150
prog
3
22
31
25
I9
2
2
2
29
34
35
2
34
34
2
34
2
34
2
922
65
32
2525
1460
1608
1591
1469
1642
2078
1636
1582
2237
2249
2248
2258
2182
2244
2121
1697
1727
1722
prog
130
130
prog
prog
prog
prog
130
130
prog
prog
prog
prog
prog
prog
prog
prog
prog
prog
I9
25
20
22
22
22
24
25
25
I9
21
I9
21
I9
19
19
22
22
22
R<fI
1100
1200
1400
1016
1020
1018
1270
1167
1277
1398
1398
II0
125
170
100
prog
100
115
115
100
130
prog
23
23
3
5
2
20
23
23
23
3
22
1448
I50
25
1188
1183
1319
prog
prog
prog
2
2
2
1122
prog
1063
1056
1202
prog
80
prog
2
23
2
1282
946
938
966
prog
90
100
80
2
23
32
23
1403
1400
150
150
25
20
1381
1425
1540
1497
1405
prog
prog
prog
150
150
22
22
24
25
25
RETENTION
TABLE
INDICES
OF MONOTERPENES
1 (continued)
Methyl silicone
C W20M
Farnesene
trun.~,trun.~-ct-
Farnesene
Farnesene
cis-firrans-p-
AND SESQUITERPENES
acetate
Gerdnic acid
Geraniol
Geranyl
Geranyl
acetate
butyrate
Geranyl
formate
Geranyl
isobutyrate
Geranyl isopentanoate
Geranyl pentanoate
Geranyl propionate
Germacrane
h
Germacrane
c
Germacrane
d
Germacrene
D
Globulol
Grandisol
Guaiene cxGuaiene /jGuaiene 6Gurjunene
aGurjunene
fi- (calarene)
Helmiscapene
Helmiscapene
Himachalene
Himachalene
Iflara-
Himachalene
/&
R<f:
R</lf:
1756
1735
1636
1671
1668
1668
130
prog
prog
130
165
prog
20
22
22
20
3
22
1501
1494
150
prog
20
22
2225
1071
1057
1574
1580
1410
200
70
70
prog
135
prog
28
13
13
2
28
2
1473
1730
prog
prog
2
2
1842
1797
150
prog
34
2
1754
1872
1904
1684
1717
1795
1821
1895
1960
1834
1572
1585
1593
1712
1718
2104
135
prog
150
prog
150
prog
150
prog
prog
150
130
130
130
prog
130
prog
28
2
29
2
29
2
29
2
2
29
25
25
25
22
20
21
1426
1449
1448
1745
1787
957
949
1110
1125
1080
1077
1220
1252
1260
1347
1234
1243
1237
1363
1532
150
170
prog
175
200
110
110
prog
135
prog
105
prog
prog
120
140
175
prog
120
135
prog
20
4
36
27
28
13
13
2
2X
2
23
2
2
23
23
27
2
23
28
2
1282
prog
1493
prog
1593
1632
prog
prog
2
2
1477
1482
1489
1468
1488
150
150
150
prog
150
25
25
25
22
20
1651
1667
1729
1591
1529
1656
1593
1683
1686
1873
1704
1649
1736
1718
prog
prog
prog
165
prog
165
prog
150
150
150
165
prog
150
prog
22
22
22
3
22
3
22
4
4
4
3
22
4
22
1200
1454
1482
1502
1413
1400
1435
110
prog
prog
prog
130
prog
130
23
22
22
22
3
22
3
1467
1466
1542
1444
1442
1517
1494
170
170
170
130
prog
170
prog
4
4
4
3
22
4
22
(Continued
on p. 8 )
N.W. DAVIES
8
TABLE
I (continued)
C W20M
Himachalene
*rHop ether
Humuladienone
Humulane
Humulene
Humulene epoxide
Humulene epoxide
Humulenol
II
Humulol
Ipsdienol
Ipsenol
Iridomyrmecin
Isoborneol
Isobornyl
I
II
acetate
Isobornyl formate
Isobornyl propionate
Isocamphane
www
Isocamphane
ci.sIsogeraniol
ci.sIsogeraniol
1rww
Isogeraniol ;Isogeranyl acetate ;Isoiridomyrmecin
Isomenthol
Isomenthone
Isomenthyl
acetate
Isopinocampheol
Isopinocamphone
Isopulegol
Isopulegyl
acetate
Isosativene
Junenol
Karahana
ether
Lavandulol
Lavandulyl
acetate
Limonene
Limonene
Limonene
epoxide
epoxide
cktrans-
Methyl
silicone
R<jI
1723
1360
1952
1609
1672
1707
1719
1972
2011
2234
2124
I50
prog
prog
I75
prog
prog
I65
prog
prog
prog
prog
4
31
31
35
22
21
3
31
31
31
31
1499
170
1437
1465
1447
prog
prog
130
22
2
3
1128
1087
1400
1157
1149
1279
100
90
I35
prog
110
prog
23
23
23
2
23
2
1228
1376
975
980
prog
prog
100
100
2
2
32
32
1422
1182
II74
II56
II51
1283
150
130
100
130
prog
130
23
20
23
20
39
20
II70
II57
II45
II33
1258
II5
II0
prog
II0
prog
23
23
2
23
2
1441
170
1154
1153
1274
prog
II0
prog
2
23
2
1025
1030
1024
III9
1122
100
prog
100
100
100
5
2
20
23
23
1660
prog
1584
1623
1596
1676
1056
1065
1812
1812
1800
1726
prog
150
prog
prog
65
65
I50
I50
I50
I50
2
29
2
2
32
32
2
2
2
29
1667
130
20
1528
1468
1579
1599
130
prog
130
I50
20
39
20
29
1574
prog
1585
1608
1639
2028
1368
1662
1707
1597
1609
II87
1206
1210
prog
I50
I65
prog
prog
prog
I50
prog
I50
75
prog
70
2
29
3
31
31
2
34
2
29
5
2
20
Rgf:
RETENTION
TABLE
INDICES
OF MONOTERPENES
AND SESQUITERPENES
1 (continued)
CW2UM
Compound
(furdn)
Linalooi
oxide cis-
Linalool
oxide trms-
(furan)
butyrate
Linalyl
Linalyl
formate
isobutyrate
Linalyl
Linalyl
Linalyl
Linalyl
isopentanoate
2-methylbutyrate
pentanoate
propionate
Longicyclene
Longifolane
Longifolane
Longifolene
7ctH7[IH-
Longipinene
rLongipinene
sMentha-Z,X-dienl-01 c&-pMenthane
IKI~.Y-~IMenthane c,i.s-p
Menthan- l-01 pMenthan-2-01
pMenthan-7-01
cis-pMenthan-7-01
truns-pMenthan-X-01 pMenthan-9-01
c&-pMenthan-9-01
rmns-pMenthan-R-yl
acetate c&pMenthan-X-yl
acetate ~runs-pMenth-I-ene
pMenth-4(R)-ene
pMenth- I -en-9-01 pMenth- I (7)-en-9-01 pMenth-2-en-l-01
cis-pMenth-2-en-
l-01 truns-p-
Menth-2-en-7-01
Menth-2-en-7-01
Menth-3-en-9-01
cis-ptrans-pp-
silicona
R<f
RPf.
1506
1533
1555
1423
1461
1451
1432
prog
I35
150
prog
prog
prog
prog
2
28
34
2h
30
2b
30b
1092
1097
1086
1068
prog
I35
90
prog
2
28
23
2h
1082
prog
1063
1077
1246
1240
1420
100
100
prog
130
prog
23
23
2
23
2
1206
1366
prog
prog
2
2
1461
1450
1500
1324
prog
prog
prog
prog
2
2
2
2
1371
1460
1467
1398
1404
1359
1432
II20
981
995
II56
1205
130
I50
I50
prog
130
I30
170
95
100
100
160
160
3
25
25
22
3
3
4
23
32
32
33
33
1162
160
33
985
998
160
160
33
33
Ill1
prog
38
I I28
prog
38
Linalool
Methyl
1538
1569
1680
1698
1570
1597
1622
1698
1695
1765
1596
1624
1554
1627
1633
1574
1643
1541
1612
prog
I50
prog
150
prog
prog
150
prog
prog
prog
prog
I50
I65
130
130
prog
I65
I65
I50
2
29
2
29
2
2
29
2
2
2
2
29
3
25
25
22
3
37
4
1022
1045
65
65
32
32
1823
1800
120
120
I2
I2
1806
1777
1598
1623
120
120
I50
I50
I2
12
29
29
1904
1881
1560
1662
1628
1597
1839
1842
1736
120
120
prog
prog
prog
prog
120
120
120
I2
I2
38
2l,
38
21,
I2
12
I2
(Continued
on p. IO)
10
TABLE
N.W. DAVIES
1 (continued)
I
Menth-g-en-l-01
Menth-8-en-2-01
Menthofuran
Menthone
acetate
Muurolene
a-
Muurolene
y-
Muurolene
Myrcene
E-
Myrcene-R-01
Myrcenol
Myrcenyl
acetate
Myrcenyl propionate
Myrtanol cisMyrtenal
Myrtenol
Myrtenyl acetate
Neocarvomenthyl
acetate
Neoisocarvomenthyl
acetate
Neoisomenthol
Neoisomenthyl
acetate
Neomenthol
Neomenthyl
Neral
acetate
Nero1
Nerolic acid
Nerolidol cisNerolidol
trans-
Neryl acetate
Reb
pp-
Menthol
Mcnthyl
Methyl silicone
c WZOM
Compound
1503
1460
1612
1640
1600
1478
1518
1444
1600
1541
1753
1727
1730
1695
1725
1692
1714
II56
II66
II68
1919
1585
1631
1574
1595
1625
130
prog
prog
130
prog
prog
130
prog
150
prog
165
prog
prog
130
165
prog
165
prog
75
70
150
prog
150
prog
150
prog
20
39
2
20
39
2
20
39
29
39
3
22
2
20
3
22
3
2
28
20
34
2
34
2
29
2
1720
1604
1672
1634
1602
1623
1559
I50
150
150
130
130
I50
prog
29
29
29
20
20
29
39
1569
1680
150
prog
29
2
1757
1808
prog
150
2
34
1961
prog
2000
2044
1699
1735
prog
prog
prog
150
2
I9
2
29
R<J
II56
1208
II47
II55
1171
II68
1171
1143
1158
II42
160
160
130
prog
prog
130
prog
prog
130
prog
33
33
20
39
2
20
39
2
20
39
1281
1495
prog
130
39
3
1500
1486
1486
prog
150
150
2
20
20
1445
986
988
984
130
prog
100
100
3
2
28
20
II03
prog
1247
prog
1327
1245
II73
1281
prog
120
120
120
2
23
23
23
II80
1297
130
130
20
20
II59
1159
prog
120
39
23
1227
1220
1218
1218
1316
1524
1540
1553
prog
120
prog
120
140
prog
175
prog
2
23
2
23
23
2
27
2
1345
1343
prog
135
2
23
RETENTION
TABLE
INDICES
AND
11
SESQUITERPENES
1 (continued)
Neryl butyrate
Neryl formate
Neryl isobutyrate
Neryl isopentanoate
Neryl propionate
Nootkatone
Norbornyl
acetate
Ocimene ci.Q-
Ocimene
Methyl silicone
C W2OM
Compound
trams-/I-
Phellandrene
I{-
Phellandrol
Pinane cis-
Pinane
OF MONOTERPENES
irww
Pinene a-
Pinocdmphone
Pinocarveol
trunxPinocarveyl
acetate
Pinonic acid cisPiperitenone
Piperitenone
oxide
Piperitone
Pulegone
Pyrovetivene
rRose oxide cis-
iruns-
Ref.
1868
1663
1700
1764
1790
1864
1771
1794
2250
1476
1238
1228
150
prog
150
prog
150
prog
prog
150
prog
prog
70
prog
29
2
29
2
29
2
2
29
2
2
20
2
1257
1250
1660
1685
1488
70
prog
150
150
prog
20
2
34
34
22
1791
150
29
1177
1173
prog
70
2
13
1216
1213
1896
1075
1061
prog
70
120
prog
65
2
I3
I2
2
32
1062
1049
1036
1038
prog
65
75
70
2
32
28
20
1120
II20
1124
70
75
prog
20
28
2
1682
150
29
1997
1739
1662
1817
1354
prog
prog
prog
165
prog
21
2
2
3
2
1267
prog
1474
prog
1574
1436
pm2
2
2
1802
1112
1027
1025
1027
1042
1038
prog
prog
1378
1253
1281
1002
1007
pw
100
pw
90
100
prog
prog
120
115
prog
1000
II0
90
1025
1032
prog
110
9x7
977
1002
981
973
942
939
942
1100
978
983
981
II52
1132
prog
R4
2
2
20
2
23
20
2
22
23
23
2
I3
23
2
13
prog
110
I IO
2
23
33
2
32
28
20
2
23
20
28
2
23
23
1427
1315
165
125
23
23
1247
1231
1230
1522
1087
1100
prog
2
23
2
3
2
23
80
160
prog
100
100
100
prog
I12
100
100
125
prog
170
prog
95
(Continued
on p. 12)
12
TABLE
N.W. DAVIES
1 (continued)
Compound
C W20M
trm-
Rose oxide
Sabinene
Sabinene hydrate
Sabinene hydrate
Sabinol (cis-)
Sabinyl
acetate
c,iswum-
(cis-)
Safranal
Santalene epi-[G
Santalene YSantalene [ISantalol USativene
Scapanene
Selina-3.7( I I)-diene
Selina-4( l4), 7( I I)-diene
Selina-4( 14). 7-diene
Selina-4, I I -diene
Selinene x-
Selinene /C
p-
y-
Terpinene- l-01
Terpinene-4-01
Terpinene-4-yl
Terpineol a-
Terpineol
Terpineol
/I6-
acetate
Methyl silicone
1370
prog
1130
1130
70
prog
20
2
1463
1683
prog
prog
38
2
1651
1677
prog
I50
2
29
1638
1574
I653
prog
prog
prog
22
22
22
1595
1664
1791
1816
1694
1702
1751
1729
1759
1767
1727
1756
1728
1775
1803
1776
1669
165
150
prog
I65
I65
I50
150
prog
prog
I65
prog
prog
165
prog
I65
prog
prog
3
4
I9
3
3
4
4
22
21
3
22
21
3
19
37
22
22
1594
1646
2153
I50
150
prog
4
4
21
Ref.
1189
1188
1247
1251
1576
1601
1628
1637
70
70
75
prog
prog
135
prog
prog
20
I3
28
2
24
28
2
21
1640
1731
1685
150
prog
I35
29
21
28
1616
1655
prog
prog
2
2
ReJ
II00
II14
972
976
1092
1060
II35
II30
1262
prog
95
100
prog
prog
prog
prog
II5
prog
2
23
20
2
38
38
2
23
2
1167
1437
1412
1450
1660
1421
1465
120
prog
prog
prog
I75
170
170
23
22
22
22
27
3
4
1476
170
1513
1484
170
prog
3
22
1506
1477
170
prog
3
22
1512
prog
22
1248
1427
1451
130
170
170
23
4
4
1136
1125
1016
1018
1056
1057
II0
II0
100
II0
100
prog
23
23
20
13
28
2
1129
1175
1170
1160
1282
1185
1178
1205
1137
II60
I35
prog
115
I75
120
prog
I35
160
prog
prog
28
2
23
27
23
2
28
33
2
2
RETENTION
TABLE
INDICES
OF MONOTERPENES
13
I (continued)
Compound
Methyl silicone
CWZOM
T
I
~______
Terpinolene
Terpinyl
AND SESQUITERPENES
acetate
acetate
acetate
Tetrahydrothujopsane
Tetrahydrothujopsane
Thuj-2-en-Co1
cisThuj-2-en-4-01
transThujene G(-
Thujone c+
Thujopsene
Thujyl acetate
Thymol
Tricyclene
IJndulatene
Valencane (nootkatane)
Valencene
Valerianol
Verbenol cisVerbenol transVerbenone
Vetivenene
Viridiflorene
Viridiflorol
b-
a
b
Rej
Rt$
1074
1081
100
100
28
20
1333
1337
prog
140
2
23
1514
1333
1467
1565
1614
1426
II85
prog
prog
prog
prog
prog
prog
pog
2
2
2
2
2
2
2
1087
1088
prog
90
2
23
1090
prog
34
1496
1508
1053
1035
931
935
938
II00
1425
1451
1430
150
150
140
140
100
110
prog
II0
prog
prog
130
25
25
40
40
20
13
2
23
22
2
3
1270
928
1557
1493
1482
1487
1457
130
100
170
150
prog
prog
130
23
5
4
25
22
2
3
1165
1140
1195
1185
1563
1544
1484
1588
100
120
prog
I10
170
prog
prog
150
23
23
2
23
3
22
22
20
1279
1289
1287
1687
1722
1622
1828
1666
1748
1858
1928
1747
1626
1675
1582
1653
1600
1397
1431
1422
1414
1449
1668
1678
1551
1468
1038
1023
75
70
prog
prog
150
150
prog
prog
prog
prog
prog
prog
prog
150
150
175
150
prog
150
150
prog
150
130
130
too
100
70
70
28
20
2
2
29
29
2
2
2
2
2
2
2
34
29
35
34
2
34
29
2
34
25
25
40
40
20
I3
1626
1660
1684
1626
prog
prog
165
150
22
2
3
29
1009
1812
1624
1722
1751
1760
2231
75
150
130
prog
prog
165
prog
5
4
25
22
34
3
19
1733
prog
1885
1868
1697
2103
2112
165
prog
prog
180
prog
3
22
22
20
21
(Continued on p. 14)
14
TABLE
N.W. DAVIES
1 (continued)
Compound
Ylangene
C WZOM
a-
Zingiberene
Zizaene
Zonarene
Methyl silicone
Rej
Ref:
1539
1491
1728
1738
1706
1781
165
prog
prog
165
165
165
3
22
22
3
3
8
1396
1368
1486
1480
1482
170
prog
prog
170
170
3
22
22
3
3
TABLE 2
KOVATS INDICES
Column
headings
LISTED
IN ORDER
and footnotes
ON CW20M
as for Table
I.
Compound
R<f
Compound
R<f
Dimethyloctane
2,6Tricyclene
Camphane
Menthane trans-pThujene c(Pinene d(Pinene G(Thujene aMenthane cis-pPinane transIsocamphane
transFenchene bPinane cisPinane transCarane cisIsocamphane
cisCamphene
Fenchene aPinane cisCamphene
Camphene
Pinene /IPinene /G
Pinene /ISabinene
Sabinene
Carene 3Carene 3-
922
1009
1021
1022
1023
1036
1038
1038
1045
1049
1056
1057
1061
1062
1064
1065
1066
1071
1075
1078
1083
1120
1120
1124
1130
1130
1141
1156
65
75
65
65
70
75
70
70
65
65
65
70
65
prog
65
65
75
70
prog
75
prog
70
75
prog
70
prog
75
75
32
5
32
32
13
28
20
20
32
32
32
13
32
2
32
32
5
13
2
28
2
20
28
2
20
2
5
28
Myrcene
Myrcene
Myrcene
Phellandrene
c(Phellandrene
G(Cineole I ,4Limonene
Terpinene aTerpinene CILimonene
Limonene
Phellandrene
/IPhellandrene
/ICineole 1,8Cineole 1,8Ocimene c&/3Ocimene &-/ITerpinene yCymene pOcimene Iruns-pTerpinene yOcimene trans-pCymene pCymene pTerpinolene
Terpinolene
Terpinolene
Rose oxide cis-
1156
1166
1168
1173
1177
1185
1187
1188
1189
1206
1210
1213
1216
1223
1228
1228
1238
1247
1250
1250
1251
1257
1272
1275
1279
1287
1289
1354
prog
75
70
70
prog
prog
75
70
70
prog
70
70
prog
70
prog
prog
70
75
75
prog
prog
70
prog
70
75
prog
70
prog
2
28
20
13
2
2
5
13
20
2
20
13
2
20
2
2
20
28
5
2
2
20
2
20
28
2
20
2
RETENTION
TABLE
INDICES
OF MONOTERPENES
AND
SESQUITERPENES
15
2 (continued)
Compound
RqJ:
Hop ether
Karahana
ether
Rose oxide frun.~Aho-ocimene
ci.rAllo-ocimene
/raw
Tetrahydrolinalool
Fenchone
Tetrahydromyrcenol
Tetrahydrolinalyl
acetate
Linalool oxide cis- (furan)
Dihydromyrcenyl
acetate
Tetrahydrohnalool
Linalool oxide wun.s- (furan)
Dihydromyrcenol
6,10Menthone
Dihydrolinalool
6,7Tetrahydromyrcenol
Linalool oxide truns- (furan)
Cubebene w
Elemane
Menthofuran
Linalool oxide cis- (furan)
Sabinene hydrate trunsCitronella1
Isomenthone
Thuj-2-en-4-01
transElemene &
Dihydromyrcenol
6,10Fenchyl acetate
Norbornyl
acetate
Menthone
Cubebene GIBicycloelemene
Pdtchoulene
/ICitronella]
Y langene aBisabolane a
Copaene aMenthofuran
Linalool
Bisabolane h
Dihydrolinalool
1,2Camphor
Menthone
Copaene c(Caryophyllane
a
Bourbonene
/IIsomenthone
Gurjunene
aCaryophyllane
h
Linalool
Cyperene
Dihydrolinalool
1,2-
1360
1368
1370
1373
I392
1397
1410
1414
1422
1423
1431
1431
1432
1438
1444
1449
1449
1451
1458
1460
1460
1461
1463
1465
1468
1468
1469
1473
1473
1476
1478
1481
1482
1488
1491
1491
1492
1493
1503
1506
1510
1512
1518
1518
1519
1522
1526
1528
1529
1533
1533
1535
1537
prog
prog
31
31
prog
70
70
2
13
13
prog
prog
prog
150
prog
2
2
2
29
2h
prog
150
prog
2
34
30
prog
prog
150
150
prog
prog
130
prog
prog
prog
prog
prog
100
prog
150
prog
prog
prog
130
prog
prog
135
prog
130
prog
130
prog
130
prog
prog
130
prog
130
prog
130
prog
130
135
prog
150
2
39
34
34
2h
22
25
39
30
38
2
39
40
22
34
2
2
2
20
24
22
28
22
25
22
20
2
25
2
2
20
2
25
22
20
22
25
28
22
34
Compound
Linalyl acetate
Ylangene w
Cubebene /ILongipinene
w
Menthyl acetate
Bourbonene
BCyclosativene
Copaene G(Thuj-2-en-4-01
ci~Longicyclene
Caryophyllane
c
Linalool
Neomenthol
Cubebene [IMenth-2-en-l-01
cis-pDihydroterpinyl
acetate
Caryophyllane
d
Anastreptene
Linalyl acetate
Neomenthyl
acetate
Linalyl formate
Germacrane
b
Fenchol
Isopulegol
Longifolene
Myrcenyl acetate
Santalene c(Terpinene- l-01
Cedrene aIsomenthyl acetate
Fenchol
Eudesmane 4fiH, 5olHTetrahydrogeranyl
acetate
Isobornyl acetate
Germacrane
c
Isopulegyl acetate
Myrcenol
Bergamotene
truns-pBourbonene
bBergamotene
aElemene /?Gurjunene aGermacrane
d
Gurjunene B- (calarene)
Sibirene
Myrcenyl acetate
Sativene
Isobornyl formate
Linalyl propionate
Lavandulyl
acetate
Linalyl isobutyrate
Menth-2-en-l-01
trans-pMenthan-8-yl
acetate cis-p-
1538
1539
1541
1541
1541
1546
1549
1551
1551
1554
1555
1555
1559
1560
1560
1561
1562
1568
1569
1569
1570
1572
1574
1574
1574
1574
1574
1576
1578
1579
1580
1582
1582
1584
1585
1585
1585
1586
1586
1590
1591
1591
1593
1593
1594
1595
1595
1596
1596
1597
1597
1597
1598
Ret
prog
165
prog
165
prog
prog
165
165
100
165
130
150
prog
130
prog
prog
130
150
150
150
prog
130
prog
prog
prog
prog
prog
prog
prog
130
135
130
150
prog
130
prog
prog
prog
165
prog
prog
165
130
prog
150
150
165
prog
prog
prog
prog
prog
150
2
3
22
37
39
2
3
3
40
3
25
34
39
20
38
2
25
4
29
29
2
25
2
2
22
2
22
24
22
20
28
25
29
2
25
2
2
22
3
24
22
3
25
22
4
29
3
2
2
2
2
21,
29
(Continued on p. 16)
16
TABLE
N.W. DAVIES
2 (continued)
Compound
R<J:
Bornyl acetate
Isomenthyl acetate
Cedrene c(Citronellyl formate
Dihydrocarvone
Menthol
Menthyl acetate
Tetrahydrolavandulol
Clovene
Terpinene-4-01
Neoisomenthyl
acetate
Neocarvomenthyl
acetate
Cedrene bCyperene
Elemene /IIsopulegyl acetate
Humulane
Lavandulyl
acetate
Bornyl formate
Longipinene
/IMenthol
Bornyl acetate
Terpineol flCaryophyl!ene
Cedrane 8pHCaryophyllene
Clovane
Linalyl isobutyrate
Terpinyl acetate cis-fiIsobornyl acetate
Menthan-X-yl acetate
rmns-pNeoisomenthyl
acetate
Linalyl propionate
Valencane (nootkatane)
Myrcenyl propionate
Citronellyl ethyl acetal
Copaene /%
Tetrahydrogeraniol
Thujopsene
Thujyl acetate
Barbatene r*Cedrane 8aHLongifolane
7aHMenth-2-en-l-01
trans-pTerpinene-4-01
Myrcenol
Cedrene pLongifolane
7/IHNeoisomenthol
Eudesmane 4ctH, 5aHFarnesene h-pCitronellyl formate
1599
1599
1600
1600
1600
1600
1600
1600
1601
1601
1602
1604
1605
1606
1608
1608
1609
1609
1610
1612
1612
1615
1616
1617
1617
1618
1621
1622
1622
1623
I35
I50
prog
prog
prog
I50
I50
I75
I35
130
150
prog
165
130
I50
I75
I50
prog
I50
prog
I50
prog
prog
130
130
I75
I50
I50
I50
28
29
2
2
2
39
29
34
35
28
20
29
22
3
20
29
35
29
2
4
2
29
2
2
25
20
35
29
29
29
1623
1623
1624
1624
1625
1626
1626
1626
1626
1626
1627
1627
1627
1628
1628
1631
1633
1633
1634
1636
1636
1638
I50
150
I50
130
prog
prog
prog
prog
prog
I50
I50
130
130
prog
prog
I50
prog
130
130
130
prog
I50
29
29
29
25
2
2
2
2
22
29
4
25
25
38
2
34
2
25
20
25
22
29
prog
Compound
Santalene epi-BIsosativene
Cedrene c+
Menthol
Terpinene-4-yl
acetate
Carvomenthyl
acetate
Elemene yLongifolene
Citronellyl acetate
Sinuene
Himachalene
aAromadendrene
Guaiene CISabinyl acetate (cis-)
Santalene BTetrahydrohumulene
Caryophyllene
Dihydrohumulene
Terpineol 6Gurjunene
b- (calarene)
Alloaromadendrene
Isoborneol
Ocimenol cisThujopsene
Alloaromadendrene
Citronellyl acetate
Lavandulol
Menth-2-en-l-01
cb-pPulegone
Neryl formate
Scapanene
Terpinyl formate
Guaiene [jIsomenthol
Farnesene trrms-pFarnesene tram-/lTetrahydrothujopsane
(I
Seychellene
Cedrene /IDihydrocarvyl
acetate
Citronellyl acetate
Farnesene frans-flHumulene
Neoisocarvomenthyl
acetate
Tetrahydrogeraniol
Isobornyl propionate
Sabinyl acetate (cis-)
Tetrahydrothujopsane
h
Linalyl butyrate
Neral
Pinocarveyl acetate IronsAlloaromadendrene
Helmiscapene
c(-
R<f
1638
1639
1640
1640
1640
1641
1642
1643
1645
1646
1649
1650
1651
1651
1653
1653
1655
1655
1655
1656
1660
1660
1660
1660
1662
1662
1662
1662
1662
1663
1664
1666
1667
1667
1668
1668
1668
1669
1670
1670
1671
1671
1672
1672
1675
1676
1677
1678
1680
1680
I682
1683
1683
prog
I65
I65
130
I50
I50
prog
I65
prog
I50
prog
prog
prog
I50
prog
prog
130
I65
prog
130
prog
I65
prog
I50
130
prog
I50
I50
22
3
3
20
29
29
22
3
2
4
22
21
22
2
22
35
3
35
2
3
20
2
34
2
2
28
2
21,
2
2
4
2
22
20
3
22
25
22
3
2
29
20
22
29
34
prog
I50
130
2
29
25
prog
prog
I50
prog
I50
2
2
29
21
4
prog
prog
prog
prog
prog
I75
I65
I75
prog
I65
130
prog
I50
prog
prog
I35
prog
RETENTION
TABLE
INDICES
OF MONOTERPENES
17
2 (continued)
Compound
Sabinol
1683
1684
1684
1685
1685
1686
1687
1690
1691
1692
1694
1695
1695
1696
1697
1697
1698
1698
1698
1699
1700
1700
1700
1702
1702
1704
1705
1706
1707
1707
1712
1713
1714
1715
I717
1718
1718
1719
1720
1722
1722
1722
1722
1723
1724
1725
1725
1726
1727
1727
1727
1728
1728
(ci,v-)
formate
Thujopsene
Ocimenol trunsTerpineol aHelmiscapene
/jTerpinyl acetate
Barbatene /IAmorphene
c(Muurolene ySelina-4( l4), 7-diene
Linalyl 2-methylbutyrate
Muurolene yDihydrocurcumene
Farnesene cis,cis-rViridiflorene
Borneo1
Linalyl butyrate
Linalyl isopentanoate
Neryl acetate
Citronellyl propionate
Dihydrocarvyl
acetate
Neryl formate
Aequilobene
Selina-4-,I I-diene
Himachalene
aCitronellyl isobutyrate
Zizaene
Humulene
Lavandulol
Germacrene
D
Dihydrocarveol
Muurolene sCarvone
Geranyl formate
Germacrene
D
Himachalene
pHumulene
Myrtenyl acetate
Citronellol (fi-)
Farnesene trans,cis-aTerpinyl acetate
Valencene
Himachalene
yAmorphene
w
Dihydronerol
Muurolene yIsogeranyl acetate yFarnesene cis,trans-aMuurolene c(Selinene pSelinene 6Zingiberene
Geranyl
AND SESQUITERPENES
T
prog
prog
165
I50
135
150
prog
150
prog
prog
165
prog
130
130
prog
prog
prog
150
prog
prog
prog
I50
150
150
I50
I65
prog
165
prog
I50
prog
prog
165
prog
I50
130
prog
165
I50
prog
prog
150
prog
150
165
I50
165
I50
prog
prog
prog
165
prog
Ref
2
2
3
34
28
4
2
4
22
22
3
2
20
25
22
22
2
29
2
2
2
29
29
4
4
3
2
3
21
34
22
2
3
2
29
20
22
3
29
2
22
29
22
4
3
34
3
29
22
22
22
3
22
Compound
1729
1729
1729
1730
1730
1733
1735
1735
1735
1736
1736
1737
1737
1738
1738
1738
1738
1739
1739
1740
1744
1745
1747
1748
1751
1751
1753
1754
1756
1756
1756
1757
1759
1759
1759
1760
1760
1760
1761
1763
1764
1765
1765
1765
1766
1766
1767
1768
1771
1774
1775
1776
1777
&fi
prog
prog
prog
prog
prog
prog
prog
prog
I50
I50
120
150
prog
165
130
150
165
I50
prog
prog
prog
I65
prog
prog
I50
prog
165
135
I65
130
prog
prog
I50
I50
prog
prog
150
I65
prog
I65
prog
I50
I50
prog
165
prog
165
prog
prog
prog
prog
prog
prog
22
22
22
2
2
2
21
22
29
4
I2
4
I9
5
20
29
3
29
2
22
22
3
2
2
4
34
3
28
3
20
21
2
29
34
21
2
34
3
2
5
2
4
34
2
3
2
3
21
2
2
I9
22
22
(Continued
on p. IS)
I8
TABLE
N.W. DAVIES
2 (continued)
C0WtpWld
Menthan-9-01
trans-pZonarene
Cadinene 6Cadinene 6Cadina- 1,Cdiene
Citronellyl butyrate
Curcumene
c(- (ar-)
Carve01 transNeryl isobutyrate
Perillyl acetate
Selina-3,7( I I)-diene
Cadinene yNeryl propionate
Carveyl acetate cisGeranyl isobutyrate
Geraniol
Isogeraniol yMenthan-7-01
trans-pDamascenone
Selinene IO-epi-ccCarvone oxide
Menthan-Y-01 cis-pNero1
Citronellyl butyrate
Cuparene
Isogeraniol
cisIsogeraniol
transUndulatene
Selina-4( 14),7( I I)-diene
Pyrovetivene
w
Carve01 cisGerdnyl isobutyrate
Menthan-7-01
k-pTerpinyl butyrate
Cuparene
Carvyl propionate
Geranyl propionate
Calamenene
Cuparene
Calamenene
Menth-2-en-7-01
cis-pCalamenene
Geraniol
Menth-2-en-7-01
tram-pCymene-8-01 pTerpinyl isopentanoate
Neryl isopentanoate
Neryl butyrate
Vetivenene [IGeranyl butyrate
Himachalene
ar-
1777
1781
1784
1785
1786
1786
1787
1790
1790
1791
1791
1792
1794
1795
1795
1797
1800
1800
1801
1803
1805
1806
1808
1811
1811
1812
1812
1812
1816
1817
1820
1821
1823
1828
1831
1833
1834
1837
1838
1839
1839
1842
1842
1842
1846
1858
1864
1868
1868
1872
1873
120
I65
165
prog
prog
prog
165
prog
I50
150
prog
I65
150
I50
prog
prog
I50
120
prog
I65
prog
120
I50
I50
130
I50
I50
150
I65
I65
prog
I50
120
prog
prog
prog
I50
prog
150
I50
120
prog
I50
120
prog
prog
prog
I50
prog
prog
I50
I2
8
3
21
22
2
3
2
29
29
I9
3
29
29
2
2
2
I2
31
37
2
I2
34
29
20
2
2
4
3
3
2
29
I2
2
22
2
29
22
4
4
12
2
34
12
24
2
2
29
22
2
4
Compound
Citronellyl pentanoate
Menth-l(7)-en-9-01
pVetivenene /IGeranyl isopentanoate
Phellandrol
Geranyl butyrate
Menth-I-en-9-01
pAgarofuran
aCalacorene
c(Myrcene-8-01
Calacorene
aTerpinyl pentanoate
Humuladienone
Geranyl pentanoate
Cedrene epoxide c(Nerolidol ci.rCaryophyllene
oxide
Humulene epoxide I
Caryophyllene
oxide
Nerolidol frunsHumulene epoxide II
Cdryolan- I-01
Bisabolol aJunenol
Caryophyllene
alcohol
Cubenol @piNerolidol transElemol
Cedrol
Viridiflorol
Globulol
Viridiflorol
Eudesmol IO-up&yHumulol
Cadinol TCadinol 6.
Spathulenol
Carvacrol
Eudesmol yCadalene
Cadinol OLFarnesyl acetate
Valerianol
Humulenol
II
Eudesmol c(Eudesmol I-epi-aEudesmol w
Eudesmol w
Nootkatone
Eudesmol /jDrimenol
I
1880
1881
1885
1895
1896
1904
1904
1907
1916
1919
1926
1928
1952
1960
1961
1961
1966
1972
2000
2000
201 I
2019
2022
2028
2033
2037
2044
2078
2100
2103
2104
2112
2121
2124
2136
2150
2153
2159
2182
2203
2224
2225
2231
2234
2237
2244
2248
2249
2250
2258
2525
T
prog
120
165
prog
120
150
120
prog
prog
150
165
prog
prog
prog
prog
prog
prog
prog
prog
prog
prog
prog
160
prog
prog
prog
prog
prog
prog
180
prog
prog
prog
prog
prog
prog
prog
prog
prog
prog
prog
200
prog
prog
prog
prog
prog
prog
prog
prog
prog
R<f:
2
I2
3
2
12
29
12
I9
22
34
6
2
31
2
2
2
31
31
24
2
31
31
26
31
31
30
I9
24
2
20
21
21
I9
31
31
31
21
2
19
30
24
28
19
31
I9
I9
19
21
2
21
19
RETENTION
TABLE
OF MONOTERPENES
AND
SESQUITERPENES
19
KOVATS
Column
INDICES
INDICES
headings
LISTED
IN ORDER
Compound
Tricyclene
Thujene aThujene aDimethyloctane
2,6Thujene aPinene aPinene aPinene aDimethyl- 1,6-octadiene
3 .7Fenchene pCamphene
Camphane
Camphene
Camphene
Fenchene c(Dimethyl-2-octene
2,6Sabinene
Pinane trunslsocamphane
~ransSabinene
Pinane cisPinene /Ilsocamphane
cisMenthane trans-pPinane trunsPinene bPinene /JMyrcene
Menth- I -ene pCanine cisMyrcene
Pinane cisMyrcene
Menthane cis-p
Menth-4(8)-ene-pCineole 1,4Phellandrene
aPhellandrene
aPinane cisPhellandrene
w
Carene 3Cineole 1,4Carene 3Cymene pTerpinene w
Cineole 1,8Cymene pTerpinene aCymene pLimonene
ON METHYL
as for Table
1.
Rclf
928
931
935
938
938
939
942
942
946
949
952
953
954
956
957
966
972
973
975
976
977
978
980
981
981
981
983
984
985
986
986
987
988
995
998
1000
1000
1002
1002
1007
1009
1010
1013
1016
1016
1017
1018
1018
1020
1024
100
100
110
100
5
20
13
32
prog
100
100
2
20
28
prog
90
110
100
100
prog
100
110
80
100
100
100
prog
80
100
100
100
prog
prog
100
100
160
100
prog
prog
100
100
160
80
90
prog
160
110
100
prog
100
100
100
prog
100
110
prog
100
2
23
13
5
32
2
28
13
23
20
32
32
2
23
20
32
32
2
2
28
20
33
32
2
2
28
32
33
23
23
2
33
13
5
2
28
5
20
2
20
13
2
20
and footnotes
SILICONE
Compound
Cineole 1,8Limonene
Ocimene cis-pPhellandrene
pOcimene c&/IOcimene c&/ILimonene
Phellandrene
bThuj-2-en-4-01
transOcimene truns-/IOcimene truns-pThuj-2-en-Co1
cisDihydromyrcenol
6,10Terpinene yTerpinene ySabinene hydrate trunsDihydromyrcenol
6,10Linalool oxide 1 (pyran)
Linalool oxide cis- (furan)
Terpinolene
Fenchone
Linalool oxide II (pyran)
Fenchone
Terpinolene
Linalool oxide trans- (furan)
Linalool
Ipsenol
Rose oxide cisTetrahydrolinalool
Tetrahydrolinalool
Tetrahydromyrcenol
Linalool
Sabinene hydrate cisLinalool
Chrysanthenone
Cyclocitral aPinene oxide aRose oxide cisRose oxide transThujone LYMyrcenol
Fenchol
Menth-2-en-l-01
cis-pNorbornyl
acetate
Rose oxide transLimonene epoxide cisAllo-ocimene
transMentha-2,8-dienI-01 c&pDihydrolinalool
1,2Limonene epoxide truns-
I
1025
1025
1025
1025
1027
1027
1030
1032
1035
1038
1042
1053
1056
1056
1057
1060
1063
1063
1068
1074
1077
1077
1080
1081
1082
1086
1087
1087
1087
1088
1090
1092
1092
1097
1100
1100
1100
1100
1100
1100
1103
1110
1111
1112
1114
1119
1120
I 120
1122
1122
Ref.
100
100
prog
prog
100
90
prog
110
140
prog
100
140
80
100
prog
prog
prog
100
20
5
2
2
20
23
2
13
40
2
20
40
23
28
2
38
2
23
2b
28
23
23
prog
100
105
100
pw
100
pw
90
90
prog
prog
90
prog
prog
prog
135
100
110
112
95
prog
110
prog
prog
prog
prog
95
100
110
95
prog
100
2:
2b
23
23
2
2
23
34
2
38
28
23
23
23
23
2
23
2
2
38
2
23
23
13
23
2
23
(Coniinued on p. 20)
N.W. DAVIES
20
TABLE
3 (continued)
Compound
Ret
Fenchol
Tagetone trunsCamphor
Ipsdienol
Menth-2-en- l-01 /runs-pTerpinene-4-01
Sabinol (cis-)
Allo-ocimene
cisPinocarveol
fransIsopulegol
Sabinol (cis-)
Camphor
Tagetone cisCitronella1
Terpineol /iVerbenol wansMenthone
Citronella1
Menthone
lsopulegol
Citronella1
Menthofuran
lsoborneol
lsomenthone
Pinocamphone
Lavandulol
Borneo1
Lavandulol
Menthofuran
Isomenthone
Menth-8-en- l-01pMenthan-l-01
plsoborneol
Isopinocamphone
Menthone
Neomenthol
Neomenthol
Terpinene-4-01
Terpineol 6Menthan-8-01 pBorneo1
Verbenol cisCymene-8-01 pSafranal
Menthol
Isopinocampheol
Terpinene-Cot
Menthol
Menthol
Menthol
Myrtenal
lsomenthol
Terpinene-4-01
1125
1125
1126
1128
I 128
1129
1130
1132
1132
1133
1135
1136
1136
1137
1137
1140
1142
1143
1143
1145
1146
1147
1149
1151
1152
1153
1154
1154
I 155
1156
1156
1156
1157
1157
1158
1159
1159
1160
1160
1162
1164
1165
1167
1167
1168
1170
1170
1171
1171
1173
1173
1174
1175
135
110
110
100
prog
135
115
110
110
110
prog
prog
110
prog
prog
120
prog
135
prog
prog
160
130
110
prog
110
110
110
prog
prog
130
160
160
prog
110
130
prog
120
175
prog
160
prog
100
115
120
130
115
115
prog
prog
175
120
100
prog
28
23
23
23
38
28
23
13
23
23
2
2
23
2
2
23
39
28
2
2
33
20
23
39
23
23
23
2
39
20
33
33
2
23
20
39
23
27
2
33
2
23
23
23
20
23
23
2
39
27
23
23
2
Compound
Borneo1
Terpineol IXNeoisomenthol
Carvomenthone
Isomenthol
Dihydrocarvone
Terpineol aTetrahydrogeraniol
Verbenone
Dihydrocarveol
Verbenone
Carve01 trunsCyclocitral /?Grandisol
Dihydromyrcenyl
acetate
Menthan-2-01
pTerpineol c(Linalyl formate
Menth-8-en-2-01
pCarve01 lrunsAscaridole epoxide
Carve01 cisCitronellol (B-)
Citronehol
([I-)
Nero1
Nero1
Fenchyl acetate
Neral
Carve01 cisCarvone
Citronellol (b-)
Cadinene yNeral
Carvone
lsobornyl formate
Pulegone
Piperitone
Geraniol
Gerdniol
Bornyl formate
Linalyl acetate
Geraniol
Myrtanol cisLinalyl acetate
Myrcenyl acetate
Piperitone
Shisool
Geranial
Perilla aldehyde
Isopulegyl acetate
Geranial
Carvone oxide
Citronellyl formate
1177
1178
1180
1181
1182
1183
1185
1185
1185
1188
1195
1200
1200
1200
1202
1205
1205
1206
1208
1209
1215
1215
1215
1216
1218
1218
1220
1220
1222
I223
1224
1227
1227
1228
1228
1230
1231
1234
1237
1239
1240
1243
1245
1246
1247
1247
1248
1252
1253
1258
1260
1261
1261
175
135
130
110
130
27
28
20
23
20
prog
prog
prog
110
2
2
2
23
prog
prog
120
125
110
2
2
23
23
23
prog
160
160
2
33
33
prog
160
2
33
prog
110
120
2
23
23
prog
100
2
23
prog
120
2
23
prog
120
prog
125
175
2
23
2
23
27
prog
prog
prog
prog
prog
125
175
120
2
2
2
2
2
23
27
23
prog
130
23
prog
120
2
23
prog
prog
prog
2
2
2
130
23
prog
120
2
23
prog
120
2
23
prog
prog
2
2
RETENTION
TABLE
INDICES
OF MONOTERPENES
AND SESQUITERPENES
21
3 (continued)
Compound
ReC
Compound
1262
1267
1270
1270
1274
1277
1278
1278
1279
1281
1281
1281
1282
1282
1282
1283
1297
1297
1300
1315
1316
1319
1324
1327
1333
1333
1335
1335
1335
1337
1343
1345
1347
1359
1362
1363
1366
1368
1369
1371
1376
1378
1378
1381
1381
1381
1386
1391
1396
1398
1398
1398
1398
prog
prog
115
130
prog
100
110
135
prog
prog
120
115
prog
prog
120
130
prog
130
125
125
140
prog
prog
prog
prog
prog
prog
135
140
140
135
prog
140
130
150
135
prog
prog
prog
130
prog
130
prog
prog
prog
prog
130
170
170
prog
130
prog
prog
2
2
23
23
2
23
23
28
2
39
23
23
2
2
23
20
2
20
23
23
23
2
2
2
2
2
2
28
23
23
23
2
23
3
20
28
2
22
22
3
2
3
22
22
22
22
3
4
3
2
3
22
22
Cubebene pCyclosativene
Elemene bGurjenene c(lridomyrmecin
Elemane
Longifolene
Eudesmane 4/?H,5czHBourbonene
pCedrene G(Santalene aGurjunene c(Cedrene aCaryophyllene
Linalyl butyrate
Cedrene [jSativene
Isoiridomyrmecin
Citronellyl ethyl acetal
Caryophyllane
LI
Elemene yThujopsene
Farnesene truns-pTerpinyl propionate
Bergamotene
trans-pCitronellyl propionate
Pinonic acid cisSibirene
Caryophyllene
Thujopsene
Caryophyllane
h
Longipinene
bGurjunene
[j- (calarene)
Bergamotene
c(Caryophyllene
Cedrene c(Neryl propionate
Humulene
Santalene epi-bBarbatene c(Carvyl propionate
Isosativene
Himachalene
c(Himachalene
nCopaene BMuurolene ECedrene /&
Humulene
Bisabolane a
Dihydrocurcumene
Farnesene trans-BFarnesene trans-,&
Caryophyhane
(
1400
1400
1400
1400
1400
1403
1404
1405
1406
1411
1412
1413
1414
1417
1420
1421
1421
1422
1423
1425
1425
1425
1426
1426
1427
1427
1427
1427
1428
1430
1432
1432
1435
1436
1436
1436
1436
1437
1437
1440
1440
1441
1442
1444
1445
1445
1446
1447
1448
1448
1448
1449
1450
T
150
170
150
prog
135
150
130
150
prog
prog
prog
130
130
130
prog
130
170
150
prog
150
prog
prog
150
prog
prog
prog
165
170
prog
130
150
170
130
prog
150
prog
prog
prog
prog
170
prog
170
prog
130
prog
130
prog
130
150
150
prog
170
150
(Continued
Rejl
20
3
20
22
23
25
3
25
2
22
22
3
3
3
2
3
3
23
2
25
22
22
20
2
22
2
23
4
2
3
25
4
3
24
20
2
2
22
22
4
2
3
22
3
2
3
2
3
25
25
36
4
25
on p. 22)
22
TABLE
N.W. DAVIES
3 (continued)
Compound
Caryophyllane
d
Linalyl 2-methylbutyrate
Santalene /?Amorphene
uSinuene
Thujopsene
Guaiene aValencene
Bisabolane b
Cedrane SBHLongifolane
7aHLinalyl isopentanoate
Cedrane SaHHumulene
Scapanene
Helmiscapene
pHelmiscapene
aLongifolane
7/HTerpinyl isobutyrate
Germacrene
D
Citronellyl isobutyrate
Barbatene /IBornyl butyrate
Neryl isobutyrate
Alloaromadendrene
Curcumene
G(-(ar-)
Selina-4(14),7-diene
Germacrane
b
Selinene ,&
Alloaromadendrene
Zingiberene
Germacrane
c
Guaiene /?Valencene
Zizaene
Aequilobene
Selinene d(Viridiflorene
Muurolene yZingiberene
Valencene
Germacrene
D
Germacrane
d
Bicyclogermacrene
Amorphene
aGeranyl isobutyrate
Valencane (nootkatane)
Farnesene trans,trans-ccHimachalene
pMuurolene aBisabolene cis-aBisabolene pTetrahydrothujopsane
(I
Eudesmane 4ctH,SaHHimachalene
y-
I
1450
1450
1450
1451
1451
1451
1454
1457
1458
1458
1460
1461
1465
1465
1465
1466
1467
1467
1467
1468
1469
1473
1473
1474
1475
1475
1476
1477
1477
1478
1480
1482
1482
1482
1482
1483
1484
1484
1486
1486
1487
1488
1489
1490
1492
1493
1493
1494
1494
1495
1496
1496
1496
1497
1499
T
150
prog
prog
prog
170
prog
prog
130
150
150
150
prog
150
prog
170
170
170
150
prog
prog
prog
170
prog
prog
I50
130
170
150
prog
prog
170
150
prog
prog
170
170
prog
prog
150
prog
prog
150
150
prog
170
prog
150
prog
prog
130
prog
130
150
150
170
ReJ
25
2
22
22
4
2
22
3
25
25
25
2
25
2
4
4
4
25
2
22
2
4
2
2
20
3
3
25
22
2
3
25
22
22
3
4
22
22
20
22
2
20
25
22
3
2
25
22
22
3
22
3
25
25
4
Compound
Linalyl pentanoate
Muurolene GCFarnesene tran.s,trans-aBulnesene aCalamenene
Guaiene 6Cadinene 6Bisabolene
Cuparene
Selinene /?Cadinene yTetrahydrothujopsane
b
Curcumene /ICitronellyl butyrate
Bornyl isopentanoate
Sesquiphellandrene
BSelinene c(Terpinyl butyrate
Cuparene
Himachalene
/?Cadina- 1,Cdiene
Calamenene
Pyrovetivene
c(Chamigrene
G(
Cadinene 6Calamenene
Nerolidol cisGeranyl butyrate
Elemol
Nerolidol cisHimachalene
arVetivenene /IChamigrene
/INerolidol transUndulatene
Caryophyllene
alcohol
Vetivenene /ITerpinyl isopentanoate
Neryl isopentanoate
Caryophyllene
oxide
Cedrene epoxide c(Viridiflorol
Geranyl isopentanoate
Citronellyl pentanoate
Cedrol
Terpinyl pentanoate
Cedrol
Geranyl pentanoate
Cadalene
Santa101 c(Bisabolol pFarnesol trans,transBornyl benzoate
Farnesyl acetate
Nootkatone
I
1500
1500
1501
1502
1502
1502
1504
1505
1506
1506
1507
1508
1510
I511
1512
1512
1513
1514
1516
1517
1518
1518
1522
1523
1524
1524
1524
1532
1540
1540
1542
1544
1550
1553
1557
1559
1563
1565
1574
1576
1585
1588
1593
1608
1609
1614
1616
1632
1646
1660
1666
1745
1749
1787
1802
T
prog
prog
150
prog
prog
prog
130
170
150
170
130
150
170
prog
prog
prog
170
prog
170
170
prog
prog
170
170
prog
170
prog
prog
prog
175
170
prog
170
prog
170
prog
170
prog
prog
prog
prog
150
prog
prog
prog
prog
175
prog
prog
175
175
175
prog
200
prog
Ref
2
2
20
22
22
22
3
3
20
3
3
25
3
2
2
22
3
2
4
4
22
2
3
4
2
4
2
2
24
27
4
22
4
2
4
24
3
2
2
24
2
20
2
2
2
2
27
2
22
27
27
27
2
28
2
RETENTION
INDICES
OF MONOTERPENES
AND
23
SESQUITERPENES
3. ACKNOWLEDGEMENTS
and provision
of
4. SUMMARY
Gas chromatographic
retention indices (Kovats indices) are a valuable aid in the
identification
of monoterpenes
and sesquiterpenes
in essential oils and related natural
and synthetic products. Some 900 Kovats indices of 400 individual compounds
on
methyl silicone (dimethyl polysiloxane)
and/or Carbowax
20M liquid phases are
summarized
from the general literature.
REFERENCES
I E. sz. Kovlits, Hclv. Chim. At/u, 41 (1958) 1915.
2 W. Jennings and T. Shibamoto,
Qurrlitutive Anulysis ofFluvar und Frqgruncr Volutiks by Ciu.s.~ Cupi1iur.v
Column Gus Chromutogruphy,
Academic Press, New York, 1980.
3 N. H. Andersen and M. S. Falcone, J. Chromutogr.,
44 (1969) 52.
4 N. H. Andersen, P. Bissonette, C.-B. Liu, B. Shunk, Y. Ohta, C.-L. W. Tseng, B. Moore and S. Huneck,
Ph~tochmzi.str~~, I6 ( 1977) I73 I
5 N. H. Andersen and D. D. Syrdal, Phy/ochcmi.vtr>,. 9 (1970) 1325.
6 N. H. Andersen,
Y. Ohta, C-B. Liu, C. M. Kramer, K. Allison and S. Huneck. Phy/ochcmi.stry.
16
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7 N. H. Andersen,
2709.
8 N. H. Andersen,
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C. R. Costin,
C. M. Kramer
D. D. Syrdal, B. M. Lawrence,
fhytoch~wristry,
I2 (1973)
I2 (1973)
9 T. Shibamoto,
IO
II
I2
I3
I4
I5
I6
I7
I8
I9
20
21
22
IO/h
ln/rrnutionrrl
f Dcwkpments
23
24
25
26
27
28
29
30
Congress
of Exwniirrl
Oils,
Flavors
und
Fragrunw,s,
WushinR/on,
DC,
19&j),
Amsterdam,
1988, p, 951.
A. A. Swigar and R. M. Silverstein, Monorrrpmc~s. Aldrich, Milwaukee, WI, 1981.
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Anu/~s/ (London),
IO9 (I 984) 1343.
H. Maarse, J. Chromutogr..
106 (1975) 369.
P. A. Hedin, A. C. Thompson
and R. C. Gueldner.
Phy/ochemi,wy.
IO (1971) 1693.
P. A. Hedin, R. C. Gueldner and A. C. Thompson,
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R. Tressl, L. Friese, F. Fendesack and H. Kiippler, .I. Aqic. Food Chew.. 26 (1978) 1426.
24
31
32
33
34
35
36
37
38
39
40
N.W. DAVIES
R. Tressl. L. Friese, F. Fendesack and H. Koppler, J. Agric. Food Chem.. 26 (1978) 1422.
R. E. Kepner and H. Maarse, J. Chromuto~r., 66 (1972) 229.
P. A. Hedin, A. C. Thompson
and R. C. Gueldner, And. Chem., 44 (1972) 1254.
R. Ter Heide. J. Chromutogr.,
129 (1976) 143.
R. U. Luisetti and R. A. Yunes. J. Chromatogr.
Sci., 9 (1971) 624.
L. Schreyen, P. Dirinck. P. Sandra and N. Schamp, J. Agric. Food Chem., 27 (1979) 872.
Y. Ohta, T~truhedron.
33 (1977) 617.
Analytical
Methods Committee,
Anulyst (London),
I13 (1988) 1125.
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Marcel Dekker, New York, 198 I.
M. Novak, Phytochcmistry,
24 (1985) 858.