WO2009066904A1 - Perfume composition for expressing the fragrance of ginseng flower (panax ginseng c.a.meyer) - Google Patents

Perfume composition for expressing the fragrance of ginseng flower (panax ginseng c.a.meyer) Download PDF

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Publication number
WO2009066904A1
WO2009066904A1 PCT/KR2008/006710 KR2008006710W WO2009066904A1 WO 2009066904 A1 WO2009066904 A1 WO 2009066904A1 KR 2008006710 W KR2008006710 W KR 2008006710W WO 2009066904 A1 WO2009066904 A1 WO 2009066904A1
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Prior art keywords
fragrance
ginseng
perfume composition
flowers
ginseng flowers
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PCT/KR2008/006710
Other languages
French (fr)
Inventor
Chang Sik Woo
Byeong Bae Jeon
Hyung Jye Seo
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Amorepacific Corporation
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Priority to JP2010533966A priority Critical patent/JP5616792B2/en
Priority to CN2008801165358A priority patent/CN101861137B/en
Publication of WO2009066904A1 publication Critical patent/WO2009066904A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • C11B9/0007Aliphatic compounds
    • C11B9/0015Aliphatic compounds containing oxygen as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • C11B9/0026Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • C11B9/0026Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • C11B9/0069Heterocyclic compounds
    • C11B9/0092Heterocyclic compounds containing only N as heteroatom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures

Abstract

Disclosed is a perfume composition, which contains hedione that is an artificial synthetic substance having a delicate flower fragrance, and methylionone that is an artificial synthetic substance having a soft and freesia-like flower fragrance, in addition to decanal, nonanal, 2-methylpyrrole, benzaldehyde, acetophenone and the like, analyzed as the fragrant components of ginseng flowers by an SPME method. Thus, the perfume composition has a fragrance like the characteristic fragrance of ginseng flowers while having high preference.

Description

[DESCRIPTION]
[invention Title]
Perfume composition for expressing the fragrance of Ginseng flower (Panax ginseng C. A. Meyer) [Technical Field]
The present invention relates to a perfume composition, which contains hedione that is an artificial synthetic substance having a delicate flower fragrance, and methylionone that is an artificial synthetic substance having a soft and freesia-like flower fragrance, in addition to decanal, nonanal, 2-methylpyrrole, benzaldehyde, acetophenone and the like, analyzed as the fragrant components of ginseng flowers by an SPME method, and thus has a fragrance like the characteristic fragrance of ginseng flowers while having high preference. [Background Art]
Panax ginseng C. A. Meyer which is a dicotyledonous plant belonging to the family Araliaceae is classified as a perennial plant. It grows in remote mountain forests and is cultivated as a medicinal plant. It is 60 cm in height, a new stem grows each year, and 3-4 leaves sprout from the tip of the stem. In the summer, a thin flower stalk comes out, and 4-40 small flowers having a light yellowish color come out from the tip of the stalk. The flowers have five leaves and stamens and one pistil. The fruit thereof is drupe, has an elliptic shape, is 5-9 mm in diameter, becomes bright red when being ripe, and has two semicircular kernels in the central portion thereof. The root thereof is used for medicinal purposes and has the shape of the human body. Ginseng has been considered as an elixir of life long. The root of ginseng which is cultivated in Korea is a fleshy root which consists of a main root and 2- 5 lateral roots and is light yellowish white in color. Although the number of the lateral roots varies depending on soil, a transplanting method, a fertilizer, water content, etc., ginseng is a plant having strong branching habits, and the shape of the root thereof varies depending on the age thereof . The root of ginseng is harvested when the age thereof is 4 -6-year-old. The flower of ginseng emits a luxurious fragrance, which entirely differs from that of the root and is similar to that of freesia, and for this reason, the fragrant components of ginseng flowers were collected from a ginseng field located at Chohyeon-ri, Namil-myeon, Geumsan-gun, Chungcheongnam-do, Korea, and were analyzed and then expressed.
To prepare products having a fragrance like that of such ginseng flowers, various conventional methods may be used. Examples of these conventional methods include a solvent extraction method of making absolute oils using the fragrant components of flowers, and a steam distillation method of making essential oils using the fragrant components. However, in these methods, high heat should be applied during the extraction process, complicated treatment processes are used so as to require a long period of time, and the fragrance of the product can greatly differ from the characteristic fragrance of flowers.
In order to overcome such shortcomings, an SPME method (Solid Phase Micro Extraction; SUPELCO international, Vol.13, No.4, p.9-10) was developed. The SPME method can analyze fragrant components in a rapid and convenient manner without the need to use a solvent and to pretreat samples .
[Disclosure] [Technical Problem]
Accordingly, the present inventors have made efforts to develop a product having a fragrance like that of ginseng flowers, using the SPME method effective in analyzing the fragrant components of living natural materials. As a result, the present inventors have found that decanal, nonanal, 2-methylpyrrole, benzaldehyde, acetophenone and the like are the main fragrant components of ginseng flowers, and have attempted to develop a product having a fragrance like that of ginseng flowers, using these components. However, the results of sensory tests conducted by the present inventors showed that the fragrance of ginseng flowers could not be expressed only with these components.
Accordingly, the present inventors have continued to study to develop a product having a fragrance like that of ginseng flowers and, as a result, found that a perfume composition, which contains, as essential components, hedione that is an artificial synthetic substance, and methylionone that is an artificial synthetic substance having a soft and freesia-like flower fragrance, in addition to the fragrant components of ginseng flowers, including decanal, nonanal, 2- 2-methylpyrrole, benzaldehyde and acetophenone, can emit a fragrance like the characteristic fragrance of ginseng flowers while having high preference, thereby completing the present invention.
Therefore, it is an object of the present invention to provide a perfume composition, which can emit a fragrance like the characteristic fragrance of ginseng flowers and has high preference.
Another object of the present invention is to provide a skin external composition containing said perfume composition as a constituent component. [Technical Solution]
The perfume composition of the present invention contains, as essential components, hedione and methylionone which are artificial synthetic substances, in addition to the main fragrant components of ginseng flowers, including decanal, nonanal, 2-methylpyrrole, benzaldehyde and acetophenone, and the secondary fragrant components of ginseng flowers, including methyl vinyl ketone, hexanal, methyl heptenone, cis-3-hexenol and methyl salicylate.
The perfume composition of the present invention contains, based on 100 wt% of the composition, 18-25 wt% of decanal, 13-18 wt% of nonanal, 10-14 wt% of 2-methylpyrrole, 10-14 wt% of benzaldehyde and 2.7-3.7 wt% of acetophenone, which are the main fragrant components of ginseng flowers, 5.8-10.5 wt% of methyl vinyl ketone, 3.6-6.5 wt% of hexanal, 2.8-5.2 wt% of methyl heptenone, 2.5-3.6 wt% of cis-3- hexenol and 2.8-5.0 wt% of methyl salicylate, which are the secondary fragrant components of ginseng flowers, and 3-5 wt% of hedione and 5-10 wt% of methylionone, which are artificial synthetic substances. If decanal, nonanal, 2- methylpyrrole, benzaldehyde, acetophenone and artificial synthetic substances hedione and methylionone, which are main components for producing a fragrance like that of ginseng flowers, are used in amounts deviating from the above-specified ranges, the similarity of fragrance to the fragrance of ginseng flowers will be decreased, and the preference of fragrance will also be decreased. However, although the other components are preferably used in the above-specified content ranges, such components can also be used in amounts deviating from the above-specified ranges, as long as they have no effect on the production of the fragrance of ginseng flowers, because they have no great effect on the fragrance of ginseng flowers.
The composition according to the present invention, having the components and contents as described above, can be added to skin external preparations, such as perfume and cosmetic products, and the amount of composition added can be suitably selected according to any conventional technique known in the art so as to achieve the desired effects.
Examples of such external preparations include ointments, lotions, solubilized phases, suspensions, emulsions, creams, gels, sprays, pastas, plasters, patches and liquid plasters. However, the scope of the present invention is not limited only thereto, and the inventive composition may be added to any base known in the art.
Meanwhile, in the present invention, the SPME method was used to analyze the fragrant components of ginseng flowers. The SPME method is advantageous for analyzing the highly volatile fragrant components of ginseng flowers, because the fragrant components adsorbed to a fiber material can be desorbed at the inlet of a GC-MS column without any special pretreatment and can be rapidly injected into the column so as to greatly reduce the analysis time. In the present invention, perfume compositions were prepared based on the fragrant components of ginseng flowers, analyzed by the SPME method. These compositions were subjected to olfactory sensory tests in a ginseng field located at Chohyeon-ri, Namil-myeon, Geumsan- gun, Chungcheongnam-do, Korea in order to examine the similarity of fragrance thereof to the fragrances of ginseng flowers and the preference of fragrance thereof. The sensory tests were conducted by professional flavorists and general persons, and the similarity of fragrance of the compositions to the fragrance of ginseng flowers and the preference of fragrance thereof were evaluated through questionnaire survey. [Advantageous Effects]
As described above, the compositions according to the present invention contain hedione that is an artificial synthetic substance having a delicate flower fragrance, and methylionone that is an artificial synthetic substance having a soft and freesia-like flower fragrance, in addition to decanal, nonanal, 2-methylpyrrole, benzaldehyde, acetophenone and the like. Thus, the perfume composition of the present invention can emit a fragrance like the fragrance of ginseng flowers and can also improve the preference of fragrance . [Best Mode] Hereinafter, the present invention will be described in further detail with reference to the following examples. It is to be understood, however, that the scope of the present invention is not limited these examples, and other applications and modifications of the present invention will be obvious to those skilled in the art.
Examples
Reference Example 1: Analysis of fragrance of ginseng flowers using SPME method Ginseng flower branches having strong fragrance were selected and maintained on a 85-μm polyacrylate fiber, and the fragrant components were collected for 2 hours. The collection of the fragrant components was conducted a ginseng field located at Chohyeon-ri, Namil-myeon, Geumsan- gun, Chungcheongnam-do, Korea.
After the fragrant components were collected, the fiber having the fragrant components collected thereon was sealed. The sealed fiber was put into the inlet of a GC-MS column, and then desorbed for 2 minutes and subjected to GC-MS analysis. The GC-MS analysis was carried out in the following conditions.
Analysis conditions
Analysis instrument: HP 5890 II GC Detector: HP 5972 MSD Column: DB-I (60 m X 0.25 mm X 0.25 urn) Carrier gas : He Inlet temperature: 250 °C Detection temperature: 280 °C Oven temperature: 70-220 °C (3 °C/min) Ionization voltage: 70 eV Desorption time: 2 min
As a result, the fragrant components of ginseng flowers, analyzed by the SPME method, are shown in Table 1 below. [Table l]
Figure imgf000009_0001
As can be seen in Table 1 above, ginseng flowers contained, as main fragrant components, decanal, nonanal, 2-methylpyrrole, benzaldehyde, acetophenone and the like, and these main components accounted for 72.03 wt% of the total weight of the fragrant components.
Reference Example 2 : Comparative sensory evaluation of fragrance between perfume composition, prepared based on analysis results, and ginseng flowers
Based on the above analysis results, a perfume composition (sample B) shown in Table 2 below was prepared, and the similarity of fragrance between the perfume composition and ginseng flowers was examined through sensory evaluation.
[Table 2]
Figure imgf000010_0001
The sensory evaluation was conducted on twenty 20-45- year-old general men and women, and the similarity of fragrance (question 1) between ginseng flowers (sample A) and the perfume composition (sample B) obtained using the SPME method, and the preference of fragrance (question 2) , were examined by causing the evaluation panels to smell the fragrance of each of the samples A and B and answering a questionnaire shown in Table 3 below. The evaluation results are shown in Table 4 below. [Table 3]
Questionnaire
(1) Question 1: how the fragrance of the sample A is similar to the fragrance of sample B? 1) completely dissimilar
2) not particularly similar
3) so-so
4) somewhat similar
5) significantly similar
(2) Question 2: how you like the fragrance of the sample B?
1) completely disliking
2) not particularly liking
3) so-so
4) slightly liking
5) significantly liking
[Table 4 ]
Figure imgf000011_0001
Figure imgf000012_0001
As can be seen in Table 4, the perfume composition (sample B) had a fragrance greatly different from the fragrance of ginseng flowers, and showed low preference. Reference Example 3 : Analysis of fragrance and comparison of fragrance with ginseng flowers, conducted by professional evaluation group
As can be seen in Reference Example 1, the perfume composition comprising the components analyzed by the SMPE method had no similarity to the fragrance of ginseng flowers. Thus, each of the fragrant components of ginseng flowers was subjected to sensory evaluation by a professional evaluation group consisting of flavorists. As a result, it was found that, among the fragrant components of ginseng flowers, decanal, nonanal, 2-methylpyrrole, benzaldehyde and acetophenone were major components making the characteristic fragrance of ginseng flowers.
Example 1: Preparation of new perfume compositions having varying contents of main components of ginseng flowers
From the results of Reference Example 3, it could be seen that the main components of the characteristic fragrance of ginseng flowers were decanal, nonanal, 2- methylpyrrole, benzaldehyde and acetophenone. Thus, in order to provide a perfume composition, which contains these five components to emit the fragrance of ginseng flowers and, at the same time, has high preference, the present inventors prepared new perfume compositions #1 to #7.
The perfume compositions #1 to #7 were prepared such that the ratio between these three components was maintained constant while the total content of these three components were changed in the range of 50-80 wt% (see Table 5) . [Table 5]
Figure imgf000013_0001
Example 2 : Sensory evaluation of perfume compositions prepared in Example 1
The seven new perfume compositions, prepared in Example 1, were examined with respect to the similarity of fragrance to the fragrance of ginseng flowers and the preference of fragrance using sensory evaluation in the same manner as described in Reference Example 2. Meanwhile, after the comparative sensory evaluation of two perfume compositions was conducted, a breathing time of 5 minutes was given to eliminate olfactory paralysis. Sensory evaluation results for the similarity of fragrance between the new perfume compositions and ginseng flowers, and the preference of fragrance, are shown in Table 6 below. [Table 6]
Figure imgf000014_0001
As shown in Table 6 above, the perfume composition #5, in which the content of the three main components was 70 wt%, showed the highest similarity and preference among the seven perfume compositions, but all the similarity and preference of the perfume composition #5 were lower than the expected values .
Example 3 : Preparation of perfume compositions having improved fragrance based on analysis conducted by professional evaluation group
To improve the similarity and preference of the perfume composition #5, which was shown to be most similar to the fragrance of ginseng flowers in Table 6 above, new perfume compositions were prepared by adding hedione that is an artificial synthetic substance, and methylionone that is an artificial synthetic substance having a soft and freesia-like flower fragrance, to the perfume composition #5 in which the total content of decanal, nonanal, 2- methylpyrrole, benzaldehyde and acetophenone was 75%. The hedione was added at varying concentrations of 3-10 wt%, the methylionon was added at varying concentrations of 0-10 wt%, and the other components were added so as to make a total content of 100%. These perfume compositions are shown in Table 7 below. [Table 7]
Figure imgf000015_0001
Figure imgf000016_0001
Example 4 : Sensory evaluation of perfume compositions prepared in Example 3
The seven perfume compositions #A, #B, #C, #D, #E, #F and #G prepared in Example 3 were examined with respect to the similarity of fragrance to the fragrance of ginseng flowers and the preference of fragrance by performing sensory evaluation in the same manner as described in Reference Example 2 above. Meanwhile, after the comparative sensory evaluation of two perfume combinations was conducted, a breathing time of 5 minutes was given to eliminate olfactory paralysis. Sensory evaluation results for the similarity of fragrance between the new perfume compositions and ginseng, and the preference of fragrance, are shown in Table 8 below. [Table 8]
Figure imgf000016_0002
Figure imgf000017_0001
As can be seen in Table 8 above, when 7-10 wt% of hedione and 5-10 wt% of methylionone were added to the main fragrant components of ginseng flowers, including decanal, nonanal, 2-methylpyrrole, benzaldehyde and acetophenone, the resulting compositions could have a fragrance like that of ginseng flowers and could show high preference (average of more than 3.5) .
Preparation Example 1
A perfume shown in Table 9 below was prepared using the above-described perfume composition having similarity to the fragrance of ginseng flowers. [Table 9]
Perfume containing perfume composition having fragrance like that of ginseng flowers
(content: wt%)
Perfume composition having fragrance like that of ginseng flowers 15
Alcohol To IOO
Water 5
Pigment q.s.
UV-blocking agent q.s.

Claims

[CLAIMS]
[Claim l]
A perfume composition having a fragrance having a like that of ginseng flowers, the composition containing, as active ingredient, fragrant components of ginseng flowers, hedione and methylionone . [Claim 2]
The perfume composition of Claim 1, wherein the fragrant components of ginseng flowers are decanal, nonanal, 2-methylpyrrole, benzaldehyde and acetophenone . [Claim 3]
The perfume composition of Claim 2, wherein the perfume composition additionally contains methyl vinyl ketone, hexanal, methyl heptenone, cis-3 -hexenol and methyl salicylate. [Claim 4]
The perfume composition of Claim 3, wherein the perfume composition contains, based on 100 wt% of the composition, 18-25 wt% of decanal, 13-18 wt% of nonanal, 10-14 wt% of 2-methylpyrrole, 10-14 wt% of benzaldehyde,
2.7-3.7 wt% of acetophenone, 5.8-10.5 wt% of methyl vinyl ketone, 3.6-6.5 wt% of hexanal, 2.8-5.2 wt% of methyl heptenone, 2.5-3.6 wt% of cis-3 -hexenol, 2.8-5.0 wt% of methyl salicylate, 3-5 wt% of hedione and 5-10 wt% of methylionone.
[Claim 5]
A skin external composition containing the perfume composition of any one of Claims 1 to 4.
PCT/KR2008/006710 2007-11-19 2008-11-14 Perfume composition for expressing the fragrance of ginseng flower (panax ginseng c.a.meyer) WO2009066904A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2010533966A JP5616792B2 (en) 2007-11-19 2008-11-14 A fragrance composition that reproduces the scent of ginseng flowers
CN2008801165358A CN101861137B (en) 2007-11-19 2008-11-14 Perfume composition for expressing the fragrance of ginseng flower (Panax ginseng C.A.Meyer)

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KR10-2007-0118077 2007-11-19
KR1020070118077A KR101438368B1 (en) 2007-11-19 2007-11-19 Perfume composition for expressing the fragrance of Ginseng flower(Panax ginseng C.A.Meyer)

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KR101438368B1 (en) 2014-09-12
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CN101861137A (en) 2010-10-13
JP5616792B2 (en) 2014-10-29
KR20090051607A (en) 2009-05-22

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