Analytical Chemistry Letters

ISSN: 2229-7928 (Print) 2230-7532 (Online) Journal homepage: http://www.tandfonline.com/loi/tacl20

Chemical Studies of Fatty Oil of Terminalia chebula

Seeds Kernels

Praveen Onial, M.S.M. Rawat & Rameshwar Dayal

To cite this article: Praveen Onial, M.S.M. Rawat & Rameshwar Dayal (2014) Chemical Studies
of Fatty Oil of Terminalia chebula Seeds Kernels, Analytical Chemistry Letters, 4:5-6, 359-363,
DOI: 10.1080/22297928.2014.990405

To link to this article: http://dx.doi.org/10.1080/22297928.2014.990405

Published online: 12 Mar 2015.

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 TACL 4 (5 & 6) 2014 pp 359 - 363 359
ISSN Print: 2229-7928
ISSN Online: 2230-7532

Chemical Studies of Fatty Oil of Terminalia chebula Seeds Kernels

Praveen Onial 1*, M.S.M. Rawat 2, Rameshwar Dayal 1

Chemistry Division, Forest Research Institute, Dehradun, India

1

2
Chemistry Department, H.N.B. Garhwal University, Srinagar Garhwal, India
Received 07 April 2014; accepted in revised form 18 August 2014
Downloaded by [New York University] at 09:45 09 September 2015

Abstract: The Terminalia chebula fruit kernel oil, constituents of methyl ester derivatives of fatty
acids were analyzed using gas chromatography. The results obtained contain saturated (04), as well as unsaturated
(02) fatty acids of T. chebula oils. The fatty oil content obtained from the seeds kernels of T. chebula was found
to be (37.37-44.91 %) averaging (41.14 %) on moisture free basis. GLC analysis of methyl esters of the fatty acids
obtained from the fatty oil after its hydrolysis followed by esterification with methanol/sulphuric acid indicated
the presence of eight compounds of which six were identified. The fatty acid composition Table 2 indicated that
linoleic acid (39.2 %) is the major constituent of the oil followed by oleic acid (38.5 %), palmitic acid (18.4 %),
stearic acid (2.7 %), arachidic acid (0.7 %), behenic acid (0.2 %), and lipids. Due to the presence of a high
percentage of valuable analytes in T. chebula, there is an increased importance in its use in pharmaceuticals, as
well as its applications in the new formulations for various skin diseases to prevent and cure different infections.

Key words: Terminalia chebula, seeds kernel, fatty oil, GLC, linoleic acid.

Introduction room temperature, is called an oil. The two terms

Fats and oils are one of the oldest classes of
chemical compounds used by humans. Animal fats
were prized for edibility, candles, lamp oils, and
conversion to soap. Fats and oils are composed
primarily of triglycerides, esters of glycerol and
fatty acids 1. A fatty acid is a carboxylic acid often
with a long unbranched aliphatic tail (chain), which
is either saturated or unsaturated. The most
abundant natural fatty acids have an even number
of carbon atoms because their biosynthesis
involves acetyl-CoA, a coenzyme carrying a two-
carbon-atom group 2. Palmitic acid (16.0 %) is
probably the commonest saturated fatty acid 3-5.
Stearic acid (18.0 %) is also relatively common
and may on occasions be more abundant than
palmitic acid. The natural stuff consisting of
glycerol esters which is soild at room temperature,
is commonly called a fat and one that is liquid at
are purely conventional since the same substance
may be a fat in one climate and oil in another.
Chemically, the so called fats contain relatively
large proporation of combined stearic acid (m.p.
69oC) and palmitic acid (m.p. 64oC) and therefore
melt at a higher temperature than oils which
contain a large proportion of oleic acid (m.p.
14oC). Physical properties of natural fats and oils
vary widely even though they are composed of
the same or similar fatty acids. These differences
result from differences in the proportion of fatty
acids and the structure of individual triglycerides.
Most of the carboxylic acids of biological origin
are found as esters of glycerol that is as,
triacylglycerols. Triacylglycerols are the oils of
plants and the fats of animal origin. They include
such common substances as peanut oil, soybean
oil, corn oil, sunflower oil, butter, lard and tallow.

*Corresponding author (Praveen Onial )

E-mail: < Onialp@icfre.org > © 2014, Har Krishan Bhalla & Sons
 Praveen Onial et al., / TACL 4 (5 & 6) 2014 359 - 363
Triacylglycerols that are liquids at room
temperature are generally called oils; those that
are solid are called fats. Hydrolysis of a fat or oil
produces a mixture of fatty acids. Most natural
fatty acids have unbranched chains and, because
they are synthesized from two carbon units, they
have an even number of carbon atoms.
Triacylglycerols with a high proportion of unsatu-
rated and polyunsaturated fatty acids have lower
melting points, they are oil.
Terminalia chebula (Combretaceae) is among
the major forest species and its fruits pericarp is
utilized for medicinal (Trifla) and various other
purposes ie. Tanneries (leather), dyeing etc. but
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360
65 7/3/2008) was deposited in the Herbarium of
Systematic Botany Branch, Botany Division,
Forest Research Institute, New Forest, Dehradun
and the plant were confirmed & authenticated by
them. The seeds were broken to get the kernels.
Kernels were powdered and used for the
extraction of fatty oil.
Isolation of fatty oil
The crushed seeds kernels (47.215 g) were
taken into soxhlet apparatus and extracted with
petroleum ether (60-80oC), figure 1. The extract
was filtered and evaporated in Rota vapor bath
at reduced pressure on a gently heated water

the seeds and the kernels were discarded. There
was no systematic study on seed kernel oil of T.
chebula, some studies on the isolation and
characterization of fatty oil of T. chebula from
other countries have been reported 6-8. Therefore,
it was thought worthwhile to carry out the isolation
and characterization of fatty oil from the seeds
kernels of T. chebula of the region. The studies
on the fatty oil and its methyl ester may bring
some new possibilities on the utilization of the
abundantly available un-used/waste seed kernels
of the fruits of T. chebula.
Experimental
Collection of seeds
The mature fruits of T. chebula were collected
from Forest Research Institute campus plantation
Dehradun, Uttarakhand (India) in the month of
October, 2008 and air dried in shade, crushed to
get the seeds. A voucher specimen (No. 156864-
Table 1. Physico-Chemical Characteristics of Seeds kernel oil from T. chebula 9-12
bath. The extracted oil was dried over anhydrous
sodium sulphate. Yellow (light) colored fatty oil
(21.205 g) was obtained. The average yield of
the oil was found to be 41.14 % on moisture
free basis. Physico-chemical characterization
of the oil was determined by using standard
methods 10 and the results obtained are given
in Table 1.
Separation of mixed fatty acids and unsaponi-
fiable matter of the oil
Fatty oil (4.0 g) was saponified by refluxing for
two hours with 40 ml of 0.5N alcoholic potassium
hydroxide. The alcohol was distilled off comp-
letely. The soap was diluted with 80 ml of water
and the unsaponifiable matter extracted with
diethyl ether (3 x 80 ml) in a separating funnel.
The etheral extract was washed with distilled
water to neutral and dried over anhydrous sodium
sulphate. Removal of the solvent on a gently

S. No. Characteristic Value

1 Average yield of oil (%) 41.14

2 Specific gravity (at 25°C) 0.8576
3 [α]D 27.2°C ( in petroleum ether) 00.06
4 Refractive index (at 25°C) 1.463
5 Acid value 2.2
6 Saponification value 202.5
7 Iodine value 105.1
8 Methyl ester of mixed fatty acid 70.22 %
9 Unsaponifiable matter of oil 5.50 %
10 Mixed fatty acid of oil 80.14 %
 Praveen Onial et al., / TACL 4 (5 & 6) 2014 359 - 363 361
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Here: (1) Terminalia chebula seeds, (2) Kernels of seeds, (3) powder kernels (yellow), (4) Soxhlet
Extraction of powder seeds kernels, (5) Extracted fatty oil, (6) Volume measurement of fatty oil, (7)
purified fatty oil, (8) Specific gravity analysis of oil, (9) separation of Saponified/Unsaponified oil,
(10) Methyl ester, (11) Unsaponificable matter, (12) Kernels powder after extraction (light cream).
Figure 1. Extraction of fatty oil from the seed kernels of Terminalia chebula
fruit and preparation of methyl ester from the oil
heated water bath yielded the unsaponifiable Preparation of methyl esters
matter (0.220 g). The unsaponifiable matter was The mixed fatty acids (2.5 g) were esterified
found to be 5.50 % by weight of the oil. The with methanol (30 ml) in presence of concentrated
aqueous soap solution was acidified with dilute sulphuric acid (2 ml) for four hours 13. Most of
hydrochloric acid (10 %) and warmed on water MeOH evaporated with addition of distil water
bath to regenerate the mixed fatty acids. The (50 ml). The methyl esters so formed were
solution was cooled and liberated acids were extracted with diethyl ether and the etheral solution
extracted with diethyl ether (3 x 80 ml). The etheral washed three times with 25 ml portions of
extract was washed with distilled water and dried potassium carbonate solution (5 %) and then with
over anhydrous sodium sulphate. Removal of the distilled water.
solvent on a gently heated water bath from the After dehydrating with anhydrous sodium
dried ethereal extract on a gently heated water sulphate and filtration, the solvent was removed
bath yielded a mixture of mixed fatty acids (3.2059 completely and 0.7150 g of methyl ester was
g). The mixed fatty acid was found to be 80.14 % obtained. The moisture free yield of the methyl
of weight of the oil. ester was 70.22 %.
 Praveen Onial et al., / TACL 4 (5 & 6) 2014 359 - 363
Gas-Chromatography analysis
Fatty acids methyl esters was determined using
Chemito series gas chromatography (GC) equip-
ped with flame ionization detector and SILAR
column (3.0 m x 0.25 mm x 0.25 mm). The FID
detector temperature was programmed at 240oC
with flow rate 0.8 ml/min. The column temperature
was programmed from 150-230oC (with increase
in temperature 3oC/min. followed by a final hold
up time 20 minutes. Nitrogen at 4 Kg/cm2 pressure
was used as the carrier gas. The peaks were
identified by comparison with the retention times
of the reference compounds, under the same
conditions and by peak enhancement methods.
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The peak area percentage was considered as
weight percentage. Eight peaks were obtained in
the chromatogram, showing the presence of same
number of methyl esters of fatty acids present in
the mixture. The percentage composition of
different fatty acids is being given in Table 2. All
measurements were performed in triplicate, and
the mean values of the analysis were taken using
one-way analysis of variance (ANOVA).
Results
The fatty oil content obtained from the seeds
kernels of T. chebula was found to be (37.37-
44.91 %) averaging (41.14 %) on moisture free
basis and its physico-chemical characteristics
were determined using standard methods and are
given in Table 1. GLC analysis of methyl esters
of the fatty acids obtained from the fatty oil after
its hydrolysis followed by esterification with
methanol/sulphuric acid indicated the presence of
eight compounds of which six were identified. The
fatty acid composition (Table 2.) indicated that
Table 2. Chemical composition of fatty oil from Terminalia chebula seeds kernels
Fatty acid Type
composition (wt %) C:N* (fatty acids)
Palmitic acid 18.4 C16:0 Saturated
Stearic acid 2.7 C18:0 Saturated
Oleic acid 38.5 C20:0 Unsaturated
Linoleic acid 39.2 C18:1 Unsaturated
Arachidic acid 0.7 C18:2 Saturated
Behenic acid 0.2 C22:0 Saturated
362
linoleic acid (39.2 %) is the major constituent of
the oil followed by oleic acid (38.5 %), palmitic
acid (18.4 %), stearic acid (2.7 %), arachidic acid
(0.7 %), behenic acid (0.2 %), and lipids. The
weight percentage of unsaturated fatty acid (77.6
%) is found greater than the saturated fatty acids
(22.9 %).
Conclusion
The T. chebula fruit kernel oil, constituents of
methyl ester derivatives of fatty acids were
analyzed using gas chromatography. GLC analysis
of methyl esters of the fatty acids obtained from
the fatty oil after its hydrolysis followed by
esterification with methanol/sulphuric acid
indicated the presence of eight compounds of
which six were identified. The yield of the fatty
oil from the seeds kernel was found 41.14 %
whereas on review of data on fatty oil in T.
chebula was found to be 30- 37.9 % 6-8. Hence,
our study reveals the better yield of the fatty oil
from the seeds kernel from Uttarakhand region,
and it is the first report on the fatty oil of the seeds
kernel from T. chebula. These fatty acids have
commercial application and can be very well
utilizes i.e. Linoleic acid can be used in making
quick drying oils which are useful in oil and
varnishes, beauty products because of its bene-
ficial properties on the skin (anti-inflammatory,
acne reductive & moisture reduction properties).
Oleic acid, palmitic acid, stearic acid and arachidic
acid as its sodium salt is a major component of
soap, detergent as an emulsifying agent. Behenic
acid is used as hair conditioners and moisturizers
because of their smoothing properties. Due to the
presence of a high percentage of valuable analytes
Sturicture
CH3 (CH 2)14COOH
CH3 (CH 2)16COOH
CH3 (CH2)7CH5CH (CH2)7COOH
CH3 (CH2)4CH5CH CH2CH5CH (CH2)7COOH
CH3 (CH 2)18COOH
CH3 (CH 2)20COOH
 Praveen Onial et al., / TACL 4 (5 & 6) 2014 359 - 363 363
in T. chebula, there is an increased importance Acknowledgements
in its use in pharmaceuticals, as well as its The Authors are thankful to the Director, Forest
applications in the new formulations for various Research Institute, Dehradun for encouragement
skin diseases to prevent and cure different and providing facilities to carry out this work.
infections. Thanks are also due to Head Chemistry Division.
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