Essential oils and their constituents part XLI. Identification of sesquiterpene hydrocarbons in oil of opoponax

NOTES

85

5 J, WEISS, C. H. &LINS,

J. SUCHER AND N. CARCIELLO, Ind. Eng. Chem. Prod. Res. DeveZo$., 3 (1964) 73a 6 P. W. SOLOMON, Anad. Chem., 36 (1964) 476. 7 P.S. HUDSON,W.M.HUTCXINSON,B. B. REGIER, A. J.MOPPATAND R.A.MENGELLAMP, ID0 Report No. 16830, O,vg. Reactor Techol. Quart. Re$t., July 1962. 8 L.,B. YEATTS, Jr.,D. N. HESS, H. F. MCDUFFIE AND W. T. RAINEY, Jr., US-AEC ORNL3602, TID-4500. g 13. VERSINO, I?.GEISS AND G. BARBERO;~. A,naZ.Chew, 201 (1964) 20. IO F. GEISS AND I-I. LAURENT, Nuclear Cojzgress, Vienna, May 1966. II J. M. VERGNAUD, J. Chromatog., 27 (1967) 54. 12 I?.ONUSICA, Tiresis, Univereits J. E. Purkyn$ Brno, 1967. 13 L. D. BBLYAKOVA, A.V. KISIZLEV AND N.V.KAVALEVA, Anal. Chem., 36 (1964) 1517. 14 A. V. KISELBV, I?.A. PASKONOVA, R. S. PETROVA AND I<. D. S&RBAKOVA, ZJt. Fiz. Khim., 38 (1964) 84.

7th, 1967

ReceivedNovember

J. Chomatog.,

3366

CHROM.

Essential oils and their Part

34 (1968) 81-85

XLI.

constituents

ldentificatio~

of s’esquiterpene

hydrocarbons

in oil of opoponax*

In a paper from this laboratory the occurrence of isomeric bisabolenes in oil of opoponax has been reportedz. A personal communication, received since, claiming the presence of only a-santalene and a-bisabolene in this oil3 prompted us to re-examine our samples following column and gas chromatographic purification. Fig. I shows the gas chromatogram of the sesquiterpene fraction as originally recorded employing the silicone nitrile XE-60 column3. Four fractions corresponding I

2

0

2..

4

6

TIME

Ii

8'

‘IO

I2

14

MlNlJ-iiS

Fig. I. Gas chrornstogram of the sesquiter@nc fractionof oil of opoponax. * For

tile previouspapcr,.seeref.I. J, C&romatog.,

34 (rg+)

Q5-SS

86

NOTES WAVELENGTH 5 I I

I

I

I

6 1

I

, MICRONS 1

.? I

I

I

8 I

I

I

IO

9

I

I

I

I3

I2

II I

I4

15

I1

I

0.1

0.6 0.6 I .o I .5

, w g

0. I 0.2

0” 0.3 s a 2

0.4 0.5 0.6 0,6 I .o I.5

O.,l W

z” 0.2 z 0.3 fs UJ 0.4 5 0.5 0.61

1-

I

I

I

II I

“H-r”-“---“---“-1

I \

Fraction N0.3:

P-~ISABOLENE

rl

II J

I

I

1

0.8

I .Ol

0. I t 0.2 0” 2

0.3

I _ \

i? 0.4 s 0.5 0.6

Fraction No. 4 ; It345 cm-1 uC=C 865

cm-l SCn

l-c_

1

1000

I

1900

I

I600

I

1700

I

1600

WAVENUMBER,

1500

1400

L

1300

1200

1100

1000 ,_aoo

800

34 (1965) 85-88

A

CM-’

Fig. 2. Infrared spectra of the gas chromatographic fractions. Instrument : Perlrin-Elmer Phase: fraction Nos. I and 2, liquid film’; fraction Nos. 3 and 4, Ccl, solution. ‘J. Chromatog.,

700

221.

NOTES

Fmclion

I:0

(a)

0.a

- SANTALENE

0,

1.00

( 1.63 (C) 11.05

fDl

Fraction

I.58

2:

P-

BlSAt3OLENE

(0)

(01 cc. I.61 (51 (Cl (d)

2.70 5.10 s.~)I

Froctlon

3:8_8tSABOLENE lb)

I?&. 3. NMR spectra of the gas chromatographic CDCl,. Internal Reference : TMS.

frractions. Instrument:

Varian

A-6oA.

Solvent :

J. Chromatog., 34 (1968)

85-88

88

NOTES

to the peaks so numbered were collected. The infrared and NMR spectra of fractions I and 2 (Figs. 2 and 3) agreed with those of c+santalene and c+bisabolene. The infrared spectrum of fraction 3 was identical to that reported for ,&bisabolene*. The NMR spectrum of the fraction was consistent with the structure of @-bisabolene and also agreed with that measured for this sesquiterpene by BATE@. Fraction 4 could not be re-examined due to polymerisation during storage. Its infrared spectrum as originally obtained (Fig. 2) was found to be identical with that of regenerated bisabolene”. We, therefore, conclude that oil of opoponax contains ct-santalene, oc-bisabolene and ,&bisabolene, as well as some other isomeric bisabolene. Reseakh Laboratories, Food artd Dmg Directorate, Defiartmetint of National HeaZth and Welfare, Ottawa

ISHWARC.NIGAM

(Carlzada)

GEORGEA. NEVILLE

I I. C. N~GAM,H. KOMAE, G. A. NEVILLE,~. RADECKA ANDS. KPAICNIKAR, Tetrahedron Letters, in press. 2 I. C. NIGAM AND L. LEVI,J. Ckromatog., 23 (IgG6) 217. 3 A. I?.REGAN AND R. R. ANDREWS, personal comnlunication andJ. Cbomatog., 31 (x967)209. 4 J, PLIVA,M. HORAK, V. HEROUT AND F. SORM, Die Terfiene.SammZun~ derspektven und Pkysikaliscken Konstanten. Teil I. Sespriter$ene, Akademie-Verlag, Berlin,rg60. 5 R.B, B~~~~,personalcorrespondt~~ce.

Received

December

J. Ckromatog.,

18th 1967

34 (1968) 85-88