IJPCBS 2015, 5(1), 315-320 Worawan Saingam et al.

ISSN: 2249-9504

INTERNATIONAL JOURNAL OF PHARMACEUTICAL, CHEMICAL AND BIOLOGICAL SCIENCES

Available online at www.ijpcbs.com Research Article

HYDRODISTILLATION AND VOLATILE COMPOUNDS

IDENTIFIED FROM DRIED POWDER JASMINE
(JasminumsambacL.) BY GC-MS
Worawan Saingam*, Laksana Charoenchai, Chaowalit Monton
and Jirapornchai Suksaeree
Sino-Thai Traditional Medicine Research Center, Faculty of Pharmacy,
Rangsit University, PathumThani, Thailand-120 00, Bangkok.

ABSTRACT
Jasmine (JasminumsambacL.) is one of scented Thai flower have been used for Thai traditional
medicine. It has therapeutic properties and can be used as a cardiotonic agent, antidizziness,
antidepressant, anti-inflammatory and antiseptic. In the present study, hydrodistillation, the most
common method was exploited to extract volatile oil from jasmine dried powder. Theyield of the
extracts was 0.05% v/w. Chemical composition of the volatile oil were analysed by GC-MS, a
process that integrated the features of gas chromatography and mass spectrometry to improve
efficacy of volatile oil analysis. Volatile oil is complex mixture, constituted by terpenoid
hydrocarbons, oxygenated terpenes. It was found that the main constituents of the volatile oil was
(E,E)-7,11,15-Trimethyl-3-methylene-hexadeca-1,6,10,14-tetraene.Low yield of the jasmine
volatile oils can be improved in future study by considered sample preparation and extraction
process. GC-MS is selective, rapid and efficient for both the identification volatile oil components
and composition variations.

Keywords: JasminumsambacL., Hydrodistillation, GC-MS.

INTRODUCTION use of these aromatic flowers as natural

Jasmine (JasminumsambacL.), an aromatic flavoring agent in Thai foods and Thai desserts.
flower is a major part of Thai traditional Nowadays, jasmine is developed to commercial
medicine (TTM)in many recipies such as Ya-hom productby extract with volatile organic solvent
(Teppajit, Nawakot, Tip-osod and Inthajak)1. such as petroleum ether, hexane and liquid
Thai people believed that jasmine has been use carbondioxide. This product called concreteused
forcardiotonic agent andantidizziness. in perfume, cosmetic, spa business and aroma
Pharmacoloigcal studies have shown coronary therapy4. Moreover, distillation is the common
vasodilator effect, cardiotropicactivities, method for extracted volatile oil from aromatic
stimulate nervours system, anti-bacterial plants. Hydrodistillation is commonly used to
(Streptococcus sanguinis and Pseudomonas determine volatile oil for quality control in raw
aeruginosa) and anti-fungal (Aspergillusniger). In material of herbal medicine.
clinical studies, (R)-(-)-linalool, an active There are several methods for extracting
compound in jasmine has sedative effect in volatile oil from plant materials.
patients and present unique aroma from Hydrodistillation is the most common method
flowers2. Moreover, other chemical composition for volatile oil extraction. There are three types
in volatile oil from jasmine are benzyl alcohol, of hydrodistillation including water distillation,
benzyl acetate3, jasmine lactone, methyl water and steam distillation and direct steam
jasmonte, geraniol, jasmine, jasmone, methyl distillation5. Many volatile oils from flowers,
benzoate, caryophyllene, cadinene, hexenyl such as rose, jasmine, lavender, camomile,
benzoate, etc2. During last centuries, Thai people ylangylang, clove can be prepared by these

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IJPCBS 2015, 5(1), 315-320 Worawan Saingam et al. ISSN: 2249-9504

method. Although distillation is a simple ground and screened through a 40-mesh sieve.
method, there are many factors affecting on the The obtained jasmine dried powders packed in
amount of volatile oil such as extracting method, zipped-lock plastic bags and store at room
duration time of distillation, distilled temperature (25-30°C) for further experiments.
temperature. In case of plants which are
unstable at high temperature, distillation must METHODS
be done at low temperature with preferable Hydrodistillation
solvent extraction. After the solvent has been Jasmine dried powder (50 g) were accurately
evaporated, the wax residue called concrete was weigh and distilled in 500 mL of water in a 1000
left. The commercial volatile oils are then mL round bottomed flask using Clevenger-type
separated from the insoluble waxes by apparatus as described in Thai Herbal
dissolving in alcohol. Moreover, enfleurage is a Pharmacopoeia, 2004. The distillation processes
method for extracting volatile oil from flowers were performed in triplicate. Hydrodistillated
by put petals of flower on a layer of animal fat. condition set at the temperature of 130-150 °C
The fat saturated with volatile oil was extracted and distillation rate 2-3 mL/min for 5 hours9.
later6. Open the stopper of the apparatus until the
Gas Chromatography-Mass Spectrometry (GC- volatile oil in the preparation line.Then stand for
MS) is a process that integrated the features of more than 1 hour at room temperature, the
gas chromatography and mass spectrometry to water and volatile oil were separated. The
improve efficacy of qualitative and quantitative volume of the volatile oil was collected in
analysis within a test sample. The gas millimeter and calculated percentage of the
chromatograph applies which depend on the volatile oil content in sample using the
column (type, material, length, diameter, film expression:
thickness) as well as the phase properties. The
mass spectrometer does this by breaking each
molecule into ionized fragments and detecting
these fragments using their mass to charge
ratio7. Applications of GC-MS include drug
detection, plasma detection, fire investigation,
where V = the volume in mL of volatile oil
environmental analysis, explosives W = the weight in g of dried powder
investigation, and identification of unknown
samples. Additionally, it can identify trace
Volatile compound analysis using GC-MS
elements in materials that were previously
The components of the volatile oil were
thought to have disintegrated beyond
identified by GC-MS. The volatile oil from
identification8.
jasmine dried powder was dissolved in hexane
The purposes of this study were to distill and
and directly injected into the injection port of
identify the volatile compounds released from gas chromatograph (Agilent Technologies
jasmine (JasminumsambacL.). Since jasmine
7890A GC system) coupled with a mass
dried powder is a composition in many Thai
spectrometer (Agilent Technologies 5975C inert
traditional formulas, it is characterized to
XL EI/CI MSD with Triple-Axis Detector).The GC
control the quality of raw material which active
was operated on an Agilent J&W GC column HP-
compound in volatile oil related to therapeutic
5 column (30 m x 0.32 mm, id. with 0.52μm film
effect. In addition, this study used for quality
thickness) and helium was used as the carrier
control of jasmine dried powder before apply to
gas. The temperature program was started with
other formulation.
an initial temperature of 150°C and held for 4
min at this temperature, then heated up to
MATERAILS AND METHODS
170°C with a heating rate of 0.8°C/min and held
MATERIALS
for 1 min, heated up to 220°C with a heating rate
Distilled water for distillation from Puris® RO
of 3.0°C/min and held for 1 min, heated up to
water system, model Expe-RO Ele 10-M, Korea.
240°C with a heating rate of 1.0°C/min and held
Hexane (Labscan) was purchased from TTK
for 1 min and heated up to 250°C with a heating
science, Bangkok, Thailand.
rate of 5.0°C/min and held for 5 min as shown in
Table1 at a flow rate of 0.7 mL/min. The
Preparation of flower samples
obtained mass spectra were preliminarily
The dried flowers of Jasmine
interpreted by comparing with those of Enhance
(JasminumsambacL.) were purchased from
Chemstation Version D00.00.38 (Agilent
CharoensukOsot, NakhonPathom province, Technologies), the Mass Spectral Search Library
Thailand. Flowers were separated the
of the National Institute of Standards and
contaminant such as gravel, insect, etc. Then
Technology (NIST, Gaithersburg, USA).

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IJPCBS 2015, 5(1), 315-320 Worawan Saingam et al. ISSN: 2249-9504

RESULTS AND DISCUSSION The volatileoil contained a mixture of acyclic

Hydrodistillation diterpenes (alcohols and hydrocarbons) and
Hydrodistillation is commonly used for volatile various straight-chain fatty acid derivates
oil extraction. This method is applied for the (alcohols, esters, and both saturated and
extraction of volatile oil from jasmine dried unsaturated hydrocarbons inchain length
powder in this study. The physical appearances carbon atoms) as shown in Figure2. The
of the extracted oils were found to be yellow to majority compounds were(E,E)-7,11,15-
brownish viscous solution to wax. The scent of Trimethyl-3-methylene-hexadeca-1,6,10,14-
the extracted oil obtained is similar to fresh tetraene(42.203 %). Geraniol is one of chemical
jasmine flowers. The %yield of the extracts was constituents in jasmine11 was also detected in
very low (0.05% v/w). Since this method was low abundance (1.105 %). While linalool, an
indicated the dried powder being boiled in active compound in jasmine2,4,12 and present
water, using heating mantle for 5 hoursand unique aroma from flowers was not detected
relatively high temperature (130-150 °C), the since raw material, jasmine was dried by hot air
compound can be destroyed during the process. oven in 50-60 °C for 6 hours as a results, linalool
Moreover, raw material (jasmine) was dried may be lost from this process.
from oven before distillation process that
affected to some volatile oil was lost. In case of CONCLUSIONS
jasmine dried powder, oils are difficult to Hydrodistillation have been demonstrated for
extract from the surface of the powder unless the extraction of volatile oil from jasmine dried
the powder is wetted sufficiently enough for powder. The %yield of the extracts was very low
diffusion to take place10. In this experiment used (0.05% v/w).The chemical compositions of the
50 g of jasmine dried powder per 500 mL of volatile oils from these flowers were identified
distilled water, this ratio is enough for wetted by GC-MS, there were found to be 12 volatile
powder. Although hydrodistillation is an compounds. The volatile oil contained many
appropriate for extract volatile oil from many chemical groups, but they were mostly terpenes.
plants but this method has many disadvantage It is difficult to distill volatile oil from dried
such as oil component like esters are sensitive powder as many factors can affect the quantity
to hydrolysis, tends to be a small operation of the volatile oils. The quantity of volatile oil
(operated by one or two persons), it takes a long depended on raw material (jasmine dried
time to accumulate much oil, so good quality oil powder) and method for extractionthat affected
is often mixed with bad quality oil and slower to chemical composition in volatile oil.
process. Therefore, it will becontinue this study,
especially process to prepare raw material and
Volatile compound analysis using GC-MS method of extraction in order to increase quality
Analysis of volatile oil obtained hydrodistillation and quantity of volatile oil. GC-MS is a good
was done using gas chromatography couple method, due to its simplicity, rapidity and
with mass spectrometer method. The efficiency, for both the identification volatile oil
chromatogram generated by gas components and composition variations.
chromatography shows the composition of the
volatile oil from jasmine dried powder is shown ACKNOWLEDGEMENTS
in Figure1. For mass spectrometer presents the The authors would like to acknowledge the
percentage (%) of each component. There were Sino-Thai Traditional Medicine Research Center,
found to be 12 volatile compounds identified Faculty of Pharmacy, Rangsit University,
from jasmine dried powder. The detected Thailand for supports.
compounds are presented in Table2.

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Fig. 1: The GC chromatogram of volatiles oil of jasmine dried powder

OH O
geraniol 2(1H)-Azulenone,4,5,6,7,8,8a-hexahydro-8a-methyl-, (s)-

O
O

O
hexadecanoic acid, ethyl ester hexadecanoic acid, methyl ester

(E,E)-7,11,15-trimethyl-3-methylene-hexadeca-1,6,10,14-tetraene 9,12-Octadecadienoic acid (Z,Z)-, methyl ester

O
O

O O

9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)- 9,12,15-Octadecatrienoic acid, ethyl ester, (Z,Z,Z)-

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Linoleic acid ethyl ester 9-Tricosene, (Z)-

Heneicosane Hexacosane

Fig. 2: Chemical structure of volatile oils from jasmine dried powder

Table 1: Working condition

for GC-MS analysis
Rate (°C/min) Temp. (°C) Hold (min)
- 150 4
0.8 170 1
3.0 220 1
1.0 240 1
5.0 250 5

Table 2: Volatile oil composition in jasmine dried powder

RT Constituent Rate %
5.707 Geraniol 1.105
18.759 2(1H)-Azulenone,4,5,6,7,8,8a-hexahydro-8a-methyl-, (s)- 2.579
38.011 Hexadecanoic acid, methyl ester 3.925
42.284 Hexadecanoic acid, ethyl ester 4.004
43.998 (E,E)-7,11,15-Trimethyl-3-methylene-hexadeca-1,6,10,14-tetraene 42.203
47.065 9,12-Octadecadienoic acid (Z,Z)-, methyl ester 2.770
47.341 9,12,15-Octadecatrienoic acid, methyl ester (Z,Z,Z)- 10.323
49.842 Linoleic acid ethyl ester 2.231
50.091 9,12,15-Octadecatrienoic acid, ethyl ester (Z,Z,Z)- 7.645
54.127 9-Tricosene, (Z)- 15.487
55.096 Heneicosane 4.379
63.842 Hexacosane 3.348

REFERENCES 5. Handa SS, Khanuja SPS, Longo G and

1. National Drug System Development Rakesh DD. Extraction Technologies for
committee, Ministry of public health. Medicinal and Aromatic Plants.
National List of Essential Medicines. International Center for Science and
2013. High Technology Trieste. 2008;115-21.
2. Ito Y, Sugimoto A, Kakuda T and Kubota 6. Pensuk W, PadumanondaT and
K. Identification of potent odorants in Pichaehsoonthon C. Comparison of the
Chinese jasmine green tea scented with chemical constituents in Micheliaalba
flowers of Jasminumsambac. J Agric flower oil extract by steam distillation,
Food Chem. 2002;50:4878-84. hexane extraction and enfleurage
3. Thanapad S and Charoenpuchitnun S. method. J Thai Tradit Altern Med.
The study of volatile Oils from 2007;5:30–9.
ThaiFlowers. Faculty of Pharmacy, 7. Bramer SEV. An Introduction to Mass
Mahidol University. Bangkok 1981. Spectrometry. Widener University.
4. Paibon W, Yimnoi CA, Tembab N, Department of Chemistry. 1998;26.
Boonlue W, Jampachaisri K and 8. Sahil K, Prashant B, Akanksha M,
Nuengchamnong N. Comparison and Premjeet S and Devashish R. Gas
evaluation of volatile oils from three Chromatography-Mass Spectrometry:
different extraction methods for some Applications. International Journal of
Thai fragrant flowers. International Pharmaceutical & Biological Archives.
Journal of Cosmetic Science. 2011;150– 2011; 2(6):1544-60.
6. 9. Ministry of public health, Thailand .Thai
Herbal Pharmacopoeia. 2004;3:159-60.

319
IJPCBS 2015, 5(1), 315-320 Worawan Saingam et al. ISSN: 2249-9504

10. Ozek T. Distillation Parameters for Pilot University College of Engineering&

Plant Production of Technology Malaysia. 2006;17.
LaurusnobilisEssential oil. Rec Nat 12. Samakradhamrongthai R, Utama-Ang N
Prod. 2012;6(2):135-43. and Thakeow P. Identification of
11. Rashid MFSA. Extraction of Essential volatile compounds released from dry
Oils from Jasmine Flower Using Solvent scented Thai flowers and their potential
Extraction Method. Faculty of Chemical application in flower-mixed tea. As. J
& Natural Resources Engineering Food Ag-Ind. 2009;2(04):525-34.

320