Journul of Chromurogrupl~~.

503 ( 1990) I-24

Elsevier Science Publishers B.V.. Amsterdam
CHROM

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

P.O. Box 252C, Hobart,

Tasmaniu

7001 (Austruliu)

3rd. 1989)

CONTENTS
I. Introduction
.............................................
2. Kovlits retention indices
.......................................
3. Acknowledgements
.........................................
4. Summary
...............................................
References
................................................

I
2
23
23
23

INTRODUCTION

The separation and identification

of monoterpenes
and sesquiterpenes
in plant
essential oils and other natural and synthetic sources relies heavily on gas chromatography. In some cases gas chromatography
may be the sole means of identification,
in
which case at least two columns of substantially
different polarity are required for any
confidence
in assignments
based on direct comparison
of retention
times with
standards or precise knowledge of Kovits retention indices. Even where combined
gas chromatographyymass
spectrometry
is used for the analysis, assignments
often
cannot be made on the basis of mass spectrometric
data only. As has been noted by
Jennings and Shibamoto,
many terpenes have essentially identical mass spectra. This
can be due to the initial similarity of structures, or due to various fragmentations
and
rearrangements
after ionization.
Hence some knowledge of retention characteristics
is
often required to complement
mass spectral data.
Much of the relevant literature is concerned with retention data on the many
different types of stationary
phase that have been used for terpene separations.
However, most work now is carried out on capillary columns with standard
dimethyl polysiloxane
(methyl silicone) non-polar
and Carbowax 20M polar phases.
Indices on these phases have been reported in the literature over many years, but no
single source to data has provided
a comprehensive
summary.
Jennings
and
Shibamoto2
have published
a substantial
set of retention
indices for flavour and
fragrance compounds
on these phases, including some 150 terpenes. Andersen and
002l-9673/90/$03.50

((1 1990 Elsevier Science Publishers

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

are listed in Tables

1-3.

RETENTION
TABLE

INDICES

OF MONOTERPENES

AND SESQUITERPENES

ALPHABETICAL
QUITERPENES

LIST OF REPORTED
KOVATS INDICES
OF MONOTERPENES
ON CW20M AND METHYL
SILICONE
PHASES

I = Kovats index; T = isothermal temperature

(C) at which the index was determined,
index was determined
using temperature
programming.
Compound

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

Carveyl acetate cisCarveyl acetate tr~uwCarvomenthone

Carvomenthyl
acetate
Carvone

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.

Cadinol rCadinol 6Cadinol TCalacorene

zCalamenene

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(-

Copaene BCubebene rCubebene

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-

Farnesol rrans,tran.sFarnesyl acetate

Fenchene aFenchene [jFenchol
Fenchone
Fenchyl
Geranial

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)

Linalool oxide 1 (pyran)

Linalool oxide II (pyran)
Linalyl acetate
Linalyl

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-

Ocimenol cisOcimenol trctnsPdtchoulene

/IPerilla aldehyde
Perillyl acetate
Perillyl alcohol
Phellandrene
a-

Phellandrene

I{-

Phellandrol
Pinane cis-

Pinane

OF MONOTERPENES

irww

Pinene a-

Pinene oxide rPinene /G

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

Selinene 6Selinene 7-epi-aSelinene IO-@-ccSesquiphellandrene

Seychellene
Shisool
Sibirene
Sinuene
Spathulenol
Tagetone cisTagetone transTerpinene CC
Terpinene

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

Terpinyl acetate cis-flTerpinyl butyrate

Terpinyl formate
Terpinyl isobutyrate
Terpinyl isopentanoate
Terpinyl pentanoate
Terpinyl propionate
Tetrahydrogeraniol
Tetrahydrogeranyl
Tetrahydrohumulene
Tetrahydrolavandulol
Tetrahydrolinalool
Tetrahydrolinalyl
Tetrahydromyrcenol

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

a Indices reported from this laboratory

were determined on a 50 m x 0.33 mm I.D. BP20 column
with a 0.5-nm film thickness (S.G.E.), temperature
programmed
from 100 to 220C at 3C/min with helium
as carrier gas.
b Refs. 2 and 30 have conflicting orders of elution for cis- and trans-linalool
oxides.
Refs. 21 and 38 have conflicting orders of elution for cis- and trans-p-menth-2-en-1-01s.

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

Bulnesene aGuaiene 6Selinene r*Geranial

Muurolene aVerbenone
Borneo1
Farnesene trans.trans-ccNeryl acetate
Himachalene
[jMenth-3-en-9-01
pChamigrene
pDihydroagarofuran
[jAlaskene /jBicyclogermacrene
Citronellyl propionate
Zingiberene
Citronellyl isobutyratc
Piperitone
Bisabolene cis-aBicyclogermacrene
Bisabolene pTerpinyl propionate
Terpinyl isobutyrate
Selinene aValencene
Muurolene G(Geranyl acetate
Curcumene /IFarnesene trurzs,tranwxSelinene flNero1
Carveyl acetate transDihydrogeraniol
Selinene w
Bornyl butyrate
Citronellol c(Valencene
Cadinene 6Alaskene aNeryl isobutyrate
Chamigrene
G(Citronellol (p-)
Linalyl pentanoate
Bisabolene
Cadinene ySelinene pBicyclogermacrene
Neryl propionate
Bornyl isopentanoate
Selinene 7-epi-ccSesquiphellandrene
pCurcumene
c(- (ar-)

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

Sabinyl acetate (cis-)

Neryl formate
Cymene-7-01 pThymol
Lavandulyl
acetate
Cymenene
Ascaridole
Bornyl acetate
Isobornyl acetate
Menthyl acetate
Myrtenol
Perillyl alcohol
Dihydroterpinyl
acetate
Geranyl formate
Terpinene-4-yl
acetate
Isomenthyl acetate
Carvacrol
Neoisomenthyl
acetate
Citronellic acid
Piperitenone
Nerolic acid
Dihydrocarvyl
acetate
Linalyl propionate
Myrcenyl propionate
Terpinyl acetate
Terpinyl formate
Citronellyl acetate
Citronellyl acetate
Citronellyl acetate
Terpinyl acetate
Neryl acetate
Neryl acetate
Geranic acid
Longipinene
aCubebene w
Geranyl acetate
Linalyl isobutyrate
Ylangene aCopaene tlLongicyclene
lsobornyl propionate
Copaene cxPatchoulene
fiCubebene c(Cubebene pElemene 6Bourbonene
/jAnastreptene
Y langene aCopaene aCyperene
Cyperene
Longifolene

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

Drs. J. Brophy and M. Ridd are thanked

some of the references.

for their comments

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.
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C. R. Costin,

C. M. Kramer

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S. J. Terhune

fhytoch~wristry,

I2 (1973)

and J. W. Hogg, Phytochcmistry,

I2 (1973)

9 T. Shibamoto,

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Mookherjee and B. J. Willis (Editors), F1uvor.s und Fragrunccs: A World Pcr.vpwtiw
(Proceeding.~ of/he
Anu/ysi.v,

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,

in Food S~~icnce, Vol. 18). Elsevier,

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.
Analytical Methods Committee,
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,
Anul. Chem.. 42 (1970) 403.
T. Sakai, H. Maarse. R. E. Kepner, W. G. Jennings and W. M. Longhurst,
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(1967) 1070.
R. Ter Heide, Z. Anul. Chrm., 236 (1968) 215.
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
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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.
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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.