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Extraction Methods for Tuberose Oil and Their Chemical Components

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The objectives of the project were to compare essential oil extraction methods from the double-flower variety of tuberose (Polianthes tuberosa L.). The flowers were extracted by cold or hot enfleurage, or by solvent extraction with hexane or petroleum ether. The chemical composition of the tuberose absolutes was analyzed by gas chromatography-mass spectrometry (GC-MS). The results showed that percentage yields of tuberose oil from cold enfleurage, hot enfleurage, hexane and petroleum ether extractions were 0.3137%, 6.5808%, 0.0279% and 0.0182%, respectively. The main chemical component detected in both enfleurage absolutes was methyl benzoate, while benzyl benzoate and pentacosane were found to be the main chemical components in hexane and petroleum ether absolutes, respectively.
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Kasetsart J. (Nat. Sci.) 43 : 204 - 211 (2009)
1Herb and Biodiverstiy Technology Unit, KAPI, Kasetsart University, Bangkok 10900, Thailand.
2Department of Botany, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand.
3Department of Product Development, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand.
*Corresponding author, e-mail: aappsr@ku.ac.th
Extraction Methods for Tuberose Oil and
Their Chemical Components
Prapassorn Rakthaworn1*, Uraiwan Dilokkunanant1,
Udomlak Sukkatta1, Srunya Vajrodaya2, Vichai Haruethaitanasan3,
Potechaman Pitpiangchan1 and Putthita Punjee 1
ABSTRACT
The objectives of the project were to compare essential oil extraction methods from the double-
flower variety of tuberose (Polianthes tuberosa L.). The flowers were extracted by cold or hot enfleurage,
or by solvent extraction with hexane or petroleum ether. The chemical composition of the tuberose
absolutes was analyzed by gas chromatography-mass spectrometry (GC-MS). The results showed that
percentage yields of tuberose oil from cold enfleurage, hot enfleurage, hexane and petroleum ether
extractions were 0.3137%, 6.5808%, 0.0279% and 0.0182%, respectively. The main chemical component
detected in both enfleurage absolutes was methyl benzoate, while benzyl benzoate and pentacosane
were found to be the main chemical components in hexane and petroleum ether absolutes, respectively.
Key words: Polianthes tuberosa L., essential oil, absolute, distillation, enfleurage, solvent extraction,
chemical component
INTRODUCTION
The tuberose, Polianthes tuberosa L., is
a tuberous perennial plant with a waxy, luminous
white flower in the family Agavaceae. Its flower
odor is very sweet, floral and honey-like and can
help give emotional strength and center the mind.
It is known to improve an individual’s capacity
for emotional depth and can stimulate the right
side of the brain and bring serenity to the mind
and heart. It also contains anti-inflammatory and
antispasmodic properties (Maliga, 2003).
Tuberose flowers have long been used
in perfumery as a source of essential oils and aroma
compounds. These aromatics are synthesized in
various plant organelles and as plant protection
against herbivores and infection, as well as to
attract pollinators (Dudareva and Negre, 2005).
At present, the demand for volatile oil is
expanding. Essential oils can be extracted using a
variety of methods, such as hydro distillation and
solvent extraction, although some are not
commonly used today, such as cold and hot
enfleurage extraction (Maliga, 2003).
The objectives of this work were to use
tuberose flowers to compare the scent, percentage
oil yield and chemical component of tuberose
absolutes obtained by cold or hot enfleurage
extraction and by solvent extraction using hexane
or petroleum ether.
MATERIALS AND METHODS
Flower preparations
Tuberose panicles were cut-off and put
into a water tank to keep the flowers fresh. Freshly
opened blossoms were collected every day, and
weighed and subjected to extraction.
Extraction methods
Enfleurage: Cold and hot enfleurage
processes were used in the tuberose oil extraction.
In cold enfleurage, palm wax was heated to 80°C
for 2 h and poured into rectangular glass trays,
with 100 ml/tray. After the palm oil had cooled
down and turned to wax at room temperature,
tuberose flowers were put on the wax in each tray
and covered with another waxed tray. The flowers
were replaced with fresh flowers every 24 h. Six
pairs of the trays with 1,000, 1,500, 2,000, 2,500,
3,000 and 3,500 g of tuberose flowers were studied
as shown in Table 1. The floral scents in the wax
(pomade) were extracted by ethanol and the
ethanol was evaporated leaving the absolute de
enfleurage behind. In hot enfleurage, tuberose
flowers were put into 400 ml palm oil, which was
warmed at 60°C. The flowers were warmed for
30 min and cooled down at room temperature.
After leaving overnight at about 8-10°C, the palm
oil was warmed up to 60°C again and the previous
flowers were filtered out and replaced with new
flowers. The steps were repeated using 300, 400,
500, 600, 700 and 800 g of flower in each
treatment. The flower scent was extracted from
the pomade by the same method used for the
enfleurage extraction (Gupta, 1952).
Solvent Extraction: Hexane and
petroleum ether were used to extract the scents
from tuberose flowers because they are strongly
non-polar solvents and are frequently used in
solvents to extract oils. Six different weights of
100,150, 200, 250, 300 and 350 g of flowers were
soaked in 1 L of each solvent for 1 h. After
removing the debris, the solvents were evaporated
leaving the concrete behind. Tuberose absolute
was extracted from each concrete sample using
alcohol. Physical appearances, such as color, odor
and other characteristics were observed for all
extracts. Yields of extracts from each method were
assessed, compared, and used to determine the
saturation point of fat, oil and solvent to absorb
the scent from the tuberose flowers.
Chemical composition analysis
Absolutes in petroleum ether and in
hexane 100 ppm were analyzed for their main
chemical components by a Shimadzu QP5050A
gas chromatography mass spectrometer.
Table 1 Tuberose flowers used in enfleurage extractions.
Extraction method Tuberose flower weight (g)
Treatment 1 Treatment 2 Treatment 3 Treatment 4 Treatment 5 Treatment 6
Cold enfleurage 1,000 1,500 2,000 2,500 3,000 3,500
(200 ml wax / treatment)
Hot enfleurage 300 400 500 600 700 800
(400 ml oil / treatment)
Table 2 Tuberose flowers used in solvent extractions.
Extraction method Tuberose flower weight (g)
Treatment 1 Treatment 2 Treatment 3 Treatment 4 Treatment 5 Treatment 6
Hexane extraction 100 150 200 250 300 350
Petroleum ether extraction 100 150 200 250 300 350
Kasetsart J. (Nat. Sci.) 43(5) 205
206 Kasetsart J. (Nat. Sci.) 43(5)
RESULTS AND DISCUSSION
Extractions
Enfleurage: Tuberose absolutes of both
cold and hot processes were similar in appearance;
they were sticky, waxy orange-brown oils. The
absolute from the cold extraction was lighter in
color than from the hot extraction. The saturation
point of palm stearin (cold enfleurage) and palm
oil (hot enfleurage) for the absorption of essential
oil from tuberose flowers was 2,500 g flower/200
ml palm wax and 500 g flower/400 ml palm oil,
respectively and the yield varied from treatment
to treatment (Figure 1) with average yields of
0.3137% and 6.5808%, respectively. However, it
has been noted that the saturation point of fat
depends on the essential oil content in the flowers
and properties of the fat (Pensuk et al., 2007).
The absolute yields from cold enfleurage
were less than those from hot enfleurage in all
treatments. This was probably due to the heat used
in the extraction process, as the wax was able to
extract a greater yield from tuberose petals than
in the cold process (Alchemy Works, 2007).
Moreover, absolutes from both methods contained
palm wax and palm oil, which was extracted by
ethanol used in the process. The wax was more
easily removed from the ethanol than the palm oil
(Pensuk et al., 2007), which may have caused the
difference in yields. However, the cold enfleurage
scent was more similar to that of a fresh tuberose
flower than the hot enfleurage absolute, because
tuberose oil is extremely delicate and thus, heating
the petals would destroy the most delicate
components (Handa, 2005). Cold enfleurage
absolute gave the scent most strongly reminiscent
of natural tuberose flowers and was safe for use;
it was appropriate for use in high-grade perfume
materials, However, enfleurage had the
disadvantage of being very labor-intensive and
expensive.
Solvent extraction: The concretes and
absolutes obtained from hexane and petroleum
ether extractions appeared similar. Concretes were
a yellow solid with a tuberose odor and absolutes
were brownish yellow with a strong tuberose scent.
The scent of tuberose absolute extracted from
petroleum ether was closer to that of natural
flowers than from hexane. The optimum amount
of 150 g flower/l for hexane and petroleum ether
extraction produced yields of 0.0279% and
0.0192%, respectively (Figure 2). Solvent
extraction was more cost-efficient than the
enfleurage process, and so was appropriate for
Figure 1 Yield of tuberose oil from cold (a) and hot (b) enfleurage extractions.
(a) Treatment 1 = 1000 g flowers/200 ml wax (b) Treatment 1 = 300 g flowers/400 ml oil
Treatment 2 = 1500 g flowers/200 ml wax Treatment 2 = 400 g flowers/400 ml oil
Treatment 3 = 2000 g flowers/200 ml wax Treatment 3 = 500 g flowers/400 ml oil
Treatment 4 = 2500 g flowers/200 ml wax Treatment 4 = 600 g flowers/400 ml oil
Treatment 5 = 3000 g flowers/200 ml wax Treatment 5 = 700 g flowers/400 ml oil
Treatment 6 = 3500 g flowers/200 ml wax Treatment 6 = 800 g flowers/400 ml oil
Kasetsart J. (Nat. Sci.) 43(5) 207
producing absolute on a pilot scale, but, this was
not considered the best method for the extraction
of essential oils, as the solvent was harmful and
could leave a residue behind that could cause
allergies and effect the immune system (Handa,
2005).
Chemical composition
Enfleurage: The chromatogram of the
cold enfleurage absolute detected 10 chemicals
(Figure 3 and Table 3), with the major components
being methyl benzoate (30.17%), benzyl benzoate
(23.64%), 7-decen-5-olide (13.33%) and methyl
salicylate (12.11%).
Ten chemical constituents were also
detected in the hot enfleurage absolute, with
methyl benzoate being the main component again,
but with a higher percentage yield (44.85%) than
in the cold enfleurage absolute. Moreover, (Z)-3-
hexenyl 2-oxopropanoate was a major component
(27.38%) only in the hot enfleurage absolute.
There were some differences in the chemical
composition between the cold and hot enfleurage
absolutes. However, methyl benzoate, methyl
salicylate and benzyl benzoate were found in both
absolutes. Among these components, methyl
benzoate was considered the major characteristic
of tuberose absolute, which is known as oil of
niobe and tuberose. It possesses a pleasant smell,
strongly reminiscent of the fruit and is mostly used
in perfumery (Reverchon and Poletto, 1996). The
results showed that temperature and the method
of extraction affected not only the chemical
composition of the absolutes, but also the
percentage yield.
Solvent extraction: Fourteen chemicals
were detected in the tuberose hexane absolute.
Benzyl benzoate (24.25%), pentacosane (19.23%)
and 7-decen-5-olide (14.96%) were the major
chemical components (Figure 5 and Table 5).
There were 14 chemicals identified in the
petroleum ether absolute. The main components
were pentacosane (29.44%), 7-decen-5-olide
(18.13%) and heptacosane (12.53%). However,
benzyl benzoate represented only 10.28% (Figure
6 and Table 6). Petroleum ether extracted more
wax, e.g. pentacosane and heptacosane, from plant
cells than hexane. Plant wax was located in the
cuticle of the epidermis. Some flowers such as
jasmine and tuberose contained scent in the flower
wax, which could be dissolved with some solvents
(Alchemy-works, 2007). If the wax content were
high, it would be difficult to obtain the essential
oil by distillation. In this case, extraction by
solvents extracted more oil resulting in the
tuberose scent of the petroleum ether absolutes
Figure 2 Tuberose concretes and absolutes obtained from hexane (a) and petroleum ether (b) extraction.
Treatment 1 = 100 g flowers/1,000 ml solvent Treatment 4 = 250 g flowers/1,000 ml solvent
Treatment 2 = 150 g flowers/1,000 ml solvent Treatment 5 = 300 g flowers/1,000 ml solvent
Treatment 3 = 200 g flowers/1,000 ml solvent Treatment 6 = 350 g flowers/1,000 ml solvent
208 Kasetsart J. (Nat. Sci.) 43(5)
Table 3 Chemical compositions of cold enfleurage absolute.
Peak No. Retention time (min) % Relative peak area Possible compounds
110.996 30.17 methyl benzoate
212.896 12.11 methyl salicylate
3 14.567 1.78 indole
414.818 1.47 (E)-citral
515.297 4.45 methyl anthranilate
616.021 1.80 methyl eugenol
717.306 8.83 (E)-methyl isoeugenol
8 17.373 13.33 7-decen-5-olide
920.755 2.43 (z)-beta-farnesene
10 21.943 23.64 benzyl benzoate
Figure 3 Chromatogram of cold enfleurage absolute.
Table 4 Chemical compositions of hot enfleurage absolute.
Peak No. Retention time (min) % Relative peak area Possible compounds
110.987 44.85 methyl benzoate
212.904 7.18 methyl salicylate
314.740 2.91 2,4-decadien-1-al
414.815 27.38 (Z)-3-hexenyl 2-oxopropanoate
5 15.736 4.15 1-tetradecene
617.300 1.78 (E)-methyl isoeugenol
7 17.374 3.35 (Z)-nerolidol
818.460 3.39 1-hexadecene
921.922 3.75 benzyl benzoate
10 23.119 1.26 2-heptadecanone
Figure 4 Chromatogram of hot enfleurage absolute.
Kasetsart J. (Nat. Sci.) 43(5) 209
Table 5 Chemical compositions of tuberose absolutes obtained by hexane extraction.
Peak No. Retention time (min) %Relative peak area Possible compound
114.804 3.70 (Z)-3-hexenyl 2-oxopropanoate
216.009 1.07 methyl eugenol
316.744 2.32 methyl isoeugenol
417.294 1.89 (E)-methyl isoeugenol
5 17.364 14.96 7-decen-5-olide
617.494 8.36 2,4,-di-tert-butylphenol
718.449 8.85 1-hexadecene
820.736 1.94 alpha-farnesol
921.901 24.25 benzyl benzoate
10 24.198 1.39 benzyl salicylate
11 26.245 4.96 ecosanol
12 32.440 2.47 tricosane
13 36.972 19.23 pentacosane
14 43.542 4.60 heptacosane
Figure 5 Chromatogram of tuberose hexane absolute.
being closer to natural flowers than from hexane
absolute. In the current study, most of the
chemicals identified in from both solvent
extractions were similar. However, some
chemicals in the tuberose absolutes from both
solvents were different; methyl anthranilate, 1-
tetradecene and (Z)-methyl isoeugenol were
detected only in the petroleum ether absolute,
while (Z)-3-hexenyl 2-oxopropanoate, 2,4,-di-tert-
butylphenol and ecosanol were detected only in
the hexane absolute. Several studies have shown
that the tuberose absolute contained many
chemical constituents, such as: benzyl benzoate,
(Z)–5–decen–4-oilde, (Z,Z)–6,9–dodecadien–4–
oilde, (Z)–6–dodecadien–4–oilde, eugenol,
farnesol, geraniol, hecogenin, methyl benzoate,
methylvanillin, nerol, (Z)–6–nonen–4–olide,
(Z)–5–octen–4–oilde, piperonal, tuberoholoside
and tuberolide (Nuntavan, 1996). Reverchon and
Poletto (1996) reported the main chemical
components of tuberose absolute from super
critical fluid extraction were: 1,8-cineole, methyl
benzoate, methyl salicilate, trans-methyl eugenol
and benzyl benzoate. Moreover, Jumras and
Possom (2003) reported tuberose oil chemical as
follows: methyl benzoate, methyl anthranilate,
benzyl alcohol, butyric acid, eugenol, nerol,
farnesol and geraniol.
210 Kasetsart J. (Nat. Sci.) 43(5)
CONCLUSIONS
The percentage yield of absolutes
obtained from cold enfleurage, hot enfleurage,
hexane and petroleum ether extractions were
0.3137%, 6.5808%, 0.0279%, and 0.0182%,
respectively. The main chemical component
detected in absolutes extracted by enfleurage was
methyl benzoate, while benzyl benzoate and
pentacosane were found to be the main chemical
components in absolutes extracted by hexane and
petroleum ether, respectively. The main chemical
components of absolute extracted by petroleum
ether were pentacosane, 7-decen-5-olide and
heptacosane, respectively. The main components
in cold enfleurage absolute were: methyl benzoate,
benzyl benzoate, 7-decen-5-olide and methyl
salicylate, respectively.
ACKNOWLEDGEMENT
This work was financially supported by
Kasetsart University Research and Development
Institute (KURDI) and Kasetsart Agricultural and
Agro-Industrial Product Improvement Institute
(KAPI).
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Alchemy Works. 2007. Tuberose wax. High
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Dudareva, N. and F. Negre. 2005. Practical
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plant volatile emission. Curr. Opin. Plant
Biol. 8: 113-118.
Figure 6 Chromatogram of tuberose absolute obtained from petroleum ether extraction.
Table 6 Chemical compositions of tuberose absolute obtained from petroleum ether extraction.
Peak No. Retention time (min) %Relative peak area Possible compounds
115.297 4.15 methyl anthranilate
2 15.741 0.98 1-tetradecene
316.022 1.89 methyl eugenol
416.757 4.85 methyl isoeugenol
517.117 0.96 (Z)-methyl isoeugenol
617.311 6.05 (E)-methyl isoeugenol
7 17.385 18.13 7-decen-5-olide
818.463 1.69 1-hexadecene
920.754 4.06 alpha-farnesol
10 21.935 10.28 benzyl benzoate
11 24.217 1.34 benzyl salicylate
12 32.462 3.65 tricosane
13 37.013 29.44 pentacosane
14 43.597 12.53 heptacosane
Kasetsart J. (Nat. Sci.) 43(5) 211
Gupta, K.C. 1952. Manufacture of Perfumes
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Polianthes tuberosa (Linn.) is traditionally considered as an ornamental and medicinal plant worldwide. However, extensive studies on its phytochemical composition are very limited. Hence the present work aims at identifying the total phytochemical ingredients present in different crude extracts of tuberosa. Phytochemical analysis has been carried out for differential cold solvent extracts of various parts of tuberosa such as petals, stamens, and ovary by gas chromatography coupled with mass spectrometry, ultra‐performance liquid chromatography to quadrupole time‐of‐flight mass spectrometry, and evaporative light scattering detector analyzers for the identification of bioactive components. Among the various solvents used for the extraction, diethyl ether is found to be the most suitable and efficient solvent, as its total differential recovery from the crude extract is about 0.24% compared to 0.04% obtained by using n‐hexane or petroleum ether. Numerous phytochemicals have been identified by the chromatography and MS techniques, which demonstrate the presence of essential fatty acids along with other pharmacological importance phytoconstituents. Identification of additional phytochemicals present in the crude extract of tuberosa flower further enhances its biological and pharmacological significance. The present work lays a foundation for further research and development of phytoconstituents of tuberosa flower. This article is protected by copyright. All rights reserved
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In this work, an essential oil was extracted from from Sedap Malam (Tuberose) flower using n-hexane as the solvent. The extraction process was performed using simple soxhlet extraction method with the ratio between Sedap Malam flower and n-hexane solvent was 1:5. The physical properties, such as density and rendement values of the extracted essential oil were analyzed. The analysis results exhibited that the essential oil has average rendement value of 9.91 % and density value of 0.9275 g/mL. Additionally, organoleptic testing was also carried out to test the response of respondents toward the color and odor/fragrance of the extracted essential oil. The results showed that the responses of the respondents about the color and fragrance of the extracted essential oil were quite satisfactory. The highest responses for both color and the fragrance were belong to “Really Like” category. The extracted essential oil was also characterized using Gas Chromatography - Mass Spectrometry (GC-MS) apparatus and Fourier Transform Infra-Red (FT-IR) analysis.
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The objectives of this study are to obtain essential oil from Sedap Malam (Tuberose) flower via extraction method and to characterize the physical and chemical properties of the essential oil produced, such as density, rendement, and chemical composition. The extraction process was carried out by using methanol solvent. The ratio between Sedap Malam flower and the methanol solvent was 1:5. After the extraction process of the essential oil finished, the essential oil and the solvent were separated via a simple distillation process. The collected essential oil was then characterized using Gas Chromatography-Mass Spectrophotometry (GC-MS) apparatus and Fourier Transform Infra-Red (FT-IR) analysis to investigate the content of the essential oil extracted from Sedap Malam flower. The physical characterization results showed that the essential oil has average rendement value of 12.605 % and density value of 1.0905 g/mL. Additionally, organoleptic test was carried to test the response of respondents toward the color and odor/fragrance of the essential oil extracted from Sedap Malam flower. Most of the responses were included in categories of “Like” and “Really like”. Additionally, for the fragrance, most of response of the respondents for all the four samples of essential oil were in category of “Really like”.
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A Satisfying evening flower (Polianthes Tuberos) is done concurrently as cut flowers, so that many flowers are rotten and wasted as garbage, the other utilization as essential oil. The influence of adsorbent and texture type Polianthes Tuberos to essential oil yield. The results showed that each adsorbent gave the yield of a mixture of vegetable and animal fat with a water content of 0.21%, the amount of water content indicates the hardness degree of the adsorbent. The essential oil obtained clear yellow, smells typical a very strong of them, does not leave spots on the filter paper and the yield obtained 4.279%. Enfleuration technique is a good technique for the intake of essential oils from flowers
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White champaka (Michelia alba DC.) is a fragrant flower with a gentle scent that has long been utilized by Thai people; M. alba products remain widely popular in the Thai market. There are several methods for extracting aromatic oil from M. alba flowers and one of them is the enfleurage method which is believed to yield an aromatic oil with closely similar odor to fresh flowers. In this study, M. alba flower oil was extracted by a newly modified enfleurage method using developed buffalo fats along with other aromatic extraction methods; steam distillation and hexane extraction. The chemical composition of M. alba oil extracted from each technique was studied and compared using gas chromatography-mass spectrometry (GC-MS) data. Ac-cording to the comparison study of M. alba flower oil, the enfleurage method gave a light yellow oil with similar odor to fresh M. alba flowers and its main composition was indole (1H) (35.5%), whereas the steam distillation method gave a colorless oil with similar odor to boiled M. alba flowers rather than fresh ones. Its major component was linalool (66.92%). The hexane extraction method gave a transparent oil sample with similar but more pungent odor to that of fresh M. alba flowers and its major compounds were 2-methyl bu-tanoic acid and linolool (33.01% and 28.92%, respectively). Indole was also found as a minor component in M. alba flower oil extracted by the steam distillation technique, but was absent in oil extracted by hexane. With further comparison, linalool and 2-methyl butanoic acid were also found in oil extracted by the enfleurage method but in negligible amounts. With regard to perfumery, indole is the natural compound that increases the perceived odor strength and improves the stability of other aromatic compounds in volatile oils. The major components of indole in M. alba flower oil extracted by the enfleurage method could be an obvious benefit of this method. In conclusion, M. alba flower oil extracted by the enfleurage method, using developed buffalo fats, has a desirable quality of aromatic oil, which should meet the high demands of the aromatherapy market.
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A new process to obtain volatile oils by fractionation of flower concretes by supercritical fluid extraction was successfully tested for rose and tuberose. Chemical analysis indicated that the quality of the product obtained by means of this technique is superior to that of the corresponding product obtained by the traditional techniques. Microphotographs and extraction results allowed to make some hypotheses on the extraction mechanisms. A model that reproduced the major features of the extraction process of concretes was developed by integration of the solute balance on the concrete and the supercritical solvent. An equilibrium regime in the first part of the process and a variable external mass transfer resistance described the experimental results of the extraction of concretes at different flow rates fairly well.
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Throughout their life cycles, plants release diverse blends of volatile compounds that play crucial roles in pollinator attraction, defense and communication. The importance of plant volatiles, in addition to the general appeal of fragrances and flavors to humans, have made these secondary metabolites a target for metabolic engineering. In the past decade, significant discoveries in the plant volatile biosynthetic pathways have provided a starting point for their modification. Pioneering attempts to alter plant volatile profiles have uncovered the complexity of networks and their regulation, and have built new avenues for future successful metabolic engineering.
Spa and Aromatherapy. Amarin Printing Company Limited
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Jumras, S. and M. Passom. 2003. Spa and Aromatherapy. Amarin Printing Company Limited, Bangkok.. 148 pp.
Tantalizing tuberose. The Chamomile Times and Herbal News
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Handa, S.S. 2005. Traditional and Modern methods of extraction of essential oils from aromatic plants. Presentation at the training course on cultivation, post-harvesting and processing technologies of medicinal and aromatic plants in developing countries. ICSUNIDO organized at Bomako, Mali (West Africa), 25-29 July 2005.