FLAVOUR AND FRAGRANCE JOURNAL, VOL. 2.

99-102 (1987)

A Fresh Look at the Constituents of Indian Olibanum Oil

J. Verghese* and M. T. Joy
Synthite Industrial Chemicals Private Ltd. Synthite Valley, Kolenchery-68231I , Kerala, India

J. A. Retamar and Griselda G. Malinskas

IPNA YS (CONICET-UNL),Santiago del Estero 2829. (-3000)Sonia Fe. Argenrinu

C. A. N. Catalan
Instituto de Quimica Organics. Facultad de Bioquimica, Quimica y Farmacia, Universidad Nacional de Tucuman. Ayacucho 491,
(4000) S. M . de Tucuman, Argentina

E. G . Gros
Departamenlo de Quimica Orgdnica, Facultad de Ciencias Exactas y Narurales, Universidad de Buenos Aires, Ciudad
Universitaria, (1428) Buenos Aires, Argentina

Indian olibanum oil obtained by steam distillation of Boswellia serrata Roxb. gum-oleoresin has been analysed by
a combination of GC, GC-MS and ‘H-NMR. GC revealed 40 components of which 26 have been identified. With
its high content of a-thujene, the Indian oil differs from olibanum oils from other sources.
KEY WORDS Boswellia serrata Roxb. Indian olibanum oil a-Thujene

INTRODUCTION formed the bulk of the oil along with minor

Indian olibanum is derived from Boswellia serrata
Roxb. (Fam. Burseraceae).’.’ When the bark of
the tree is incised a milky liquid oozes out and it
congeals slowly into a gum-oleoresin. The total
availability of this exudate is quite
The steam distillation of Indian olibanum
affords an oil of pale yellow or greenish tinge and
sweet agreeable odourM with properties quite
similar to those obtained from olibanum of
African origin.2h
Solely based ‘on boiling point of the oil and by
analogy with other “turpentines”’,’ it was inferred
originally that the Inidan olibanum oil consisted
mainly of (+)-a-pinene admixed probably with
P - ~ i n e n e .Further
~ examination of the oil re-
vealed that (+)-a-thujene was the prime consti-
tituent, with small amounts of 0-pinene and
(+ )-a-phellandrene.’* see x.y.Io (+)-Limonene,
p-cymene, linalol, geraniol, terpineol, elemol,
terpinyl acetate, cadinene, anisic aldehyde and
estragol were later Recently, by
gas chromatography, it was found that, in
conformity with the earlier conclusion, a-pinene
amounts of f3-pinene; limonene, dipentene and
phellandrene were also detected, and possibly
terpinolene. I The variations reported in the
composition of the oil may be due not only to the
existence of chemical races’ but also to seasonal
fluctuations, and the period and the time of
collection of the gum-oleoresin.” In view of the
conflicting reports of these earlier investigations,
it was considered desirable to undertake further
studies into the composion of Indian olibanum
oil.
EXPERIMENTAL
Volatile oil
Boswellia serrafa Roxb. gum-oleoresin Grade I
(200 g) was submitted to exhaustive hydrodistilla-
tion in a Clevenger-type apparatus and yielded
8% w/w pale yellow fragrant oil with n:’ 1.4683;
(a):’ + 20.8”; djO 0.8460; €.I. 5.2; E.I. after
acetylation 43.6; A.I. 0.5.

“Author to whom correspondence should be addressed

0882-5734/87/03OO99-04$05 .OO Receit.ed 27 April 1987

0 1987 by John Wiley & Sons, Ltd. Accepted 31 July I987
100 J . VERGHESE E T A L .

Analysis ture programme: 60°C (15 min) + 190°C at 3°C

The isolate obtained above was analysed by
GC. GC-MS and 'H-NMR. Quantitative deter-
mination was realized on a Varian Model 3300 gas
chromatograph equipped with an electronic integ-
rator 4290 and a 2 m x 118" stainless steel column
packed with 10% Carbowax 20M on Gas Chrom
Q 11, 80-100 mesh; carrier gas 30ml nitrogen
min- I ; injection temperature: 200°C; detector
temperature: 220°C (flame ionization); tempera-
min-I.
GC-MS analysis was carried out with a Varian
Aerograph 1400 gas chromatograph (1.2m x
2 m m stainless steel column packed with 10%
Carbowax 20M on Chromosorb W-YP. 80-100
mesh; carrier gas 20ml helium min- ; tempera-
ture programme: 60°C + 225°C at 4°C min-')
interfaced with a Varian-MAT CH7-A Mass
Spectrometer and data processing system Varian-
M A T 166. Other instruments and columns

Table I . Constituents of Boswellia serralu (Indian olibanum) oit

Identification

Peakt Cornpo ti ntl ci MS CCI-GC 'H-NMR

I 'Tricyclcne 0.02 +
2 n-Pincne 7.73 + + +
3 n-Thujene 61.36 + + +
4 'Camphene (1.04 +
5 13-Pinene 0.21 + +
6 "Sahinene 5.07 -k + +
7 "3-Carene 1.15 + +
x n-Phellandrene 2.22 + +
9 .'n-Terpincne 0.41 + +
10 Unidentified 0.33
II Limonene I .55 + +
12 *P-Phellandrene 0.03 +
13 'y-Terpinene 0. I5 + +
I4 Unidentified 0.36
15 P-Cyrnene 4.2X + + +
I6 Unidentified 0.ox
17 'Fenchone traces +
IX 'a-Thujone I .7h + + 1
19 *V-Thujone 1.40 + + +
20 'Menthone traces +
21 Unidentified 0.71
22 'lsornent hone traces +
23 *+Bourhoncne I .4Y +
24 'Camphor 0.04 +
2s Linalol 0. 19 + +
26 *Terpincn-J-ol 0.45 + +
27 Unidentified 0.48
28 'Zingiberene I .01 +
9' Unidentified (1,OY
30 Sesquitcrpene MW 204 0.22
31 Estragol 2.73 + +
32 a-Terpineol 0.ss + +
33 Unidentified 0.26
34 Unidentified 0.08
35 *Citronellol? 0.01 +
36 Unidentified MW 202 2. I7
37 unidentified 0.0.5
38 * Meth yleugenol 0.33 + +
39 *Elernicin or asarone 0.37 +
40 Sesquiterpene MW 218 0.60

+Peaks numbered according to the elution order from the Carbowax 20M column.
 INDIAN OLIBANUM OIL 101

employed were: Perkin-Elmer preparative gas 4-01 with sabinene fits in well with the generaliza-
chromatograph Model Fzl and Varian 3300 gas tion of Koedam et a1.I’
chromatograph; 2 m X 1 / 8 stainless steel column Previous work had not reported any ketonic
packed with 15% FFAP on Chromosorb W-AW, constituents of the Indian oil. We find that it
80-100 mesh; 4 m x 118” stainless steel column contains fenchone, a- and P-thujones, menthone,
packed with 5% Carbowax 20M on Chromosorb isomenthone and camphor, totalling to < 4%.
W-AW, 80-100 mesh. The absence of verbenone, a consituent of other
The major components of the oil were isolated olibanum oils, is of special
by preparative GC using a 2.7m X 6.7mm The Indian oil is devoid of esters and aldehy-
column packed with 5% Carbowax 20M on des. Terpinyl acetate earlier reported in the oil
Chromosorb G , 80-100 mesh and their identities was not detected.““’ ‘H-NMR spectrum of the oil
established by ‘H-NMR. did not display any visible signal in the 9-l0ppm
a-Pinene and a-thujene were not resolved on region, thus ruling out the presence of aldehydes.
the Carbowax 20M or FFAP column but a Turning to peak 39, it seems to originate from
baseline separation was obtained with a SF 96 elemicin rather than from asarone. The mass
column (10% Silicone Fluid SF 96 (methyl) on spectra of these compounds are very similar and
Chromosorb W-AW, 80-100 mesh; 4 m X 1/8” are not of much diagnostic value. However,
stainless steel column; oven temperature: SOT) asarone occurs rarely in nature. Another point in
which permitted an estimation of the relative favour of elemicin is that it is related to estragol
percentages of these monoterpenes. and methyleugenol which are found in the oil.
Of the 27 sesquiterpenes established as consti-
tuents of a commercial sample of olibanum oil,”
RESULTS AND DISCUSSION f3-bourbonene is the only one found in the Indian
oil. Additionally, the oil contains zingiberene.
GC monitoring of the oil revealed 40 components Currently, Indian olibanum oil enjoys ‘a wide
(Table 1). Of the constituents reported we found and varied use in perfumery’.’’ With the
in the sample: a-pinene, a-thujene, f3-pinene, appropriate chemistry and the potential availabil-
a-phellandrene, limonene, p-cymene, linalol, ity in technical quantity and purity from Indian
a-terpineol and estragol. Asterisked compounds olibanum oil, a-thujene could become a valuable
were identified for the first time. raw material for the terpene industry.3 The
It is interesting to note that the composition of exploitation of this hydrocarbon will ensure a new
Boswellia serratu oil is different from the oils of status for Indian olibanum oil in the field of
African and Arabian olibanums. 12-16 Unquestion- essential oils.
ably the Indian oil is unique by its abundance of
a-thujene which in other olibanum oils is either
not detected or present in low To our Acknowledgements-We wish to express our thanks to R.
Carri6, M. Appendino and B. Guzman for analytical gas
knowledge the Indian oil is thus the most chromatography. One of the referees is thanked for suggesting
attractive source of a-thujene. the approach favouring the presence of elemicin in the oil.
~

Dominance of a-thujene in the Boswellia

serrata oil is in conformity with the finding of
Simonsen.’ O n the other hand, significant
amounts of a-pinene and octyl acetate are
characteristic of olibanum oils from Aden and
Eritrean sources respectively. 12. see 14*15 Keeping
in mind the recommendation of Klein and
Obermann,I2 we now propose that the essential
oils from Indian, Aden and Eritrean gum-
oleoresin are best differentiated by GC evalua-
tion of the respective key consituents, viz.
a-thujene, a-pinene and octyl acetate.
Linalol, terpinene-4-01, a-terpineol and prob-
ably citronellol amounting to 1.2% comprise the
alcohols of the oil. The co-existence of terpinene-
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