WO2008054067A1 - Perfume composition for expressing the fragrance of ume flowers - Google Patents
Perfume composition for expressing the fragrance of ume flowers Download PDFInfo
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- WO2008054067A1 WO2008054067A1 PCT/KR2007/004745 KR2007004745W WO2008054067A1 WO 2008054067 A1 WO2008054067 A1 WO 2008054067A1 KR 2007004745 W KR2007004745 W KR 2007004745W WO 2008054067 A1 WO2008054067 A1 WO 2008054067A1
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- fragrance
- japanese apricot
- flowers
- apricot flowers
- perfume composition
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, 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
- C11B9/00—Essential oils; Perfumes
Definitions
- the present invention relates to a perfume composition having a fragrance like the characteristic fragrance of Japanese apricot flowers (also called as “ume flowers”, hereinafter we call “Japanese apricot flowers”). More particularly, the present invention relates to a perfume composition, which contains an artificial synthetic substance, in addition to the fragrant components of Japanese apricot flowers (also called as “ume flowers”, hereinafter we call “Japanese apricot flowers”). More particularly, the present invention relates to a perfume composition, which contains an artificial synthetic substance, in addition to the fragrant components of Japanese apricot flowers (also called as “ume flowers”, hereinafter we call “Japanese apricot flowers”). More particularly, the present invention relates to a perfume composition, which contains an artificial synthetic substance, in addition to the fragrant components of Japanese apricot flowers (also called as “ume flowers”, hereinafter we call “Japanese apricot flowers”). More particularly, the present invention relates to a perfume composition, which contains an artificial synthetic substance, in addition
- Japanese apricot flowers determined by analyzing the fragrant components of white Japanese apricot flowers or red Japanese apricot flowers, and thus has a fragrance like the characteristic fragrance of Japanese apricot flowers and, at the same time, has high preference.
- Japanese apricot trees, Prunus mume Siebold & Zucc are deciduous small trees belonging to the family Rosaceae, the order Rosaceae, and are native to China and distributed in Japan, China and Korea.
- Japanese apricot trees come in many varieties depending on the intended use thereof or the color of flowers or the shape of petals, and are classified, according to the color of petals, into white Japanese apricot trees having white flowers, and red Japanese apricot trees having red flowers.
- the present inventors have made efforts to develop a product having a fragrance like that of Japanese apricot flowers, using the SPME method effective in analyzing the fragrant components of living natural materials. As a result, the present inventors have found out the fragrant components of white Japanese apricot flowers and red Japanese apricot flowers, but have found that a product having a fragrance like the fragrance of natural Japanese apricot flowers cannot be obtained only with a combination of the fragrant components .
- the present inventors have continued to study in order to a product having a fragrance like that of white Japanese apricot flowers or red Japanese apricot flowers and, as a result, a perfume composition, which contains, active ingredients, an artificial synthetic substance, in addition to the main fragrant components of
- Japanese apricot flowers can emit a fragrance like the characteristic fragrance of white Japanese apricot flowers or red Japanese apricot flowers and has high preference, thereby completing the present invention.
- Another object of the present invention is to provide a skin external composition containing said perfume composition as a constituent component.
- the present invention provides a perfume composition having a fragrance like that of white Japanese apricot flowers, the perfume composition containing, as active ingredients, fragrant components of white Japanese apricot flowers, and florol.
- the perfume composition having a fragrance like that of white Japanese apricot flowers contains, as essential components, artificial synthetic substance florol, in addition to the main fragrant components of white Japanese apricot flowers, including benzaldehyde , benzyl acetate and benzyl alcohol .
- the present invention provides a perfume composition having a fragrance like that of red
- Japanese apricot flowers which contains, as active ingredient, fragrant components of red Japanese apricot flowers, and phenylisohexanol.
- the perfume composition having a fragrance like that of red Japanese apricot flowers contains, as essential components, artificial synthetic substance phenylisohexanol, in addition to the main fragrant components of red Japanese apricot flowers, including benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol and cinnamyl acetate.
- compositions according to the present invention emit a fragrance like that of white Japanese apricot flowers or red Japanese apricot flowers and have high preference.
- the inventive composition having a fragrance like that of white Japanese apricot flowers contains, as active ingredients, artificial synthetic substance florol in addition to the fragrant components of white Japanese apricot flowers.
- Japanese apricot flowers contains, as essential components, benzaldehyde, benzyl acetate, benzyl alcohol and artificial synthetic substance florol, and may further contain, as secondary components, acetophenone , decanal, nonanal, 2 , 2 , 6-trimethyl-5-cyclohexene-l, 4-dione, iso-butyl alcohol, butyl alcohol, dodecane, eugenol, tridecane, camphor, hexanal and the like.
- the perfume composition of the present invention contains, based on the total weight of the composition, 40-52 wt% of benzaldehyde, 18-24 wt% of benzyl acetate, 6-8 wt% of benzyl alcohol, 5.8-6.8 wt% of acetophenone, 1.5-2.6 wt% of decanal, 1.0-1.5 wt% of nonanal, 0.8-2.1 wt% of 2, 2 , ⁇ -trimethyl-S-cyclohexene-l, 4- dione, 2.0-6.0 wt% of iso-butyl alcohol, 1.0-4.1 wt% of butyl alcohol, 1.0-2.5 wt% of dodecane, 0.1-0.4 wt% of eugenol, 0.1-0.3 wt% of camphor, 1.0-2.6 wt% of tridecane, 0.1-0.3 wt% of hexanal, and 4-8 wt% of artificial synthetic substance florol.
- benzaldehyde, benzyl acetate, benzyl alcohol and artificial synthetic substance florol which are main components for producing a fragrance like that of white Japanese apricot flowers, are used in amounts deviating from the above-specified ranges, the similarity of fragrance to the fragrance of natural white Japanese apricot flowers will be decreased, and the preference of fragrance will also be decreased.
- the other components are preferably used in the above-specified content ranges, such components may also be used in amounts deviating from the above ranges, as long as they have no effect on the production of a fragrance like that of white Japanese apricot flowers, because they have no great effect on the fragrance of white Japanese apricot flowers.
- the inventive perfume composition having a fragrance like that of red Japanese apricot flowers contains, as essential components, the fragrant components of red Japanese apricot flowers, and artificial synthetic substance phenylisohexanol.
- the composition having a fragrance like that of red Japanese apricot flowers contains, as main components, benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol, cinnamyl acetate and artificial synthetic substance phenylisohexanol, and may further contain, as secondary components, acetophenone, ethyl alcohol, ethyl ether, pentane and the like.
- the perfume composition of the present invention contains, based on the total weight of the composition, 48-52 wt% of benzaldehyde, 24-26 wt% of benzyl acetate, 7-9 wt% of benzyl alcohol, 0.1-3 wt% of cinnamaldehyde, 1.5-2 wt% of cinnamyl alcohol, 0.5-0.7 wt% of cinnamyl acetate, 4-6 wt% of acetophenone, 1.3-1.6 wt% of ethyl alcohol, 0.9-1.2 wt% of ethyl ether, 0.6-0.8 wt% of pentane and 4-6 wt% of artificial synthetic substance phenylisohexanol.
- benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol, cinnamyl acetate and artificial synthetic substance phenylisohexanol which are main components for producing a fragrance like that of red Japanese apricot flowers, are used in amounts deviating from the above-specified ranges, the similarity of fragrance to the fragrance of natural red Japanese apricot flowers will be decreased, and the preference of fragrance will also be decreased.
- the other components are preferably used in the above-specified content ranges, such components may also be used in amounts deviating from the above ranges, as long as they have no effect on the production of a fragrance like that of red Japanese apricot flowers, because they have no great effect on the fragrance of red Japanese apricot flowers.
- 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 .
- external preparations include ointments, lotions, solubilized phases, suspensions, emulsions, creams, gels, sprays, pastas, plasters, patches and liquid plasters.
- 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.
- the SPME method was used to analyze the fragrant components of white Japanese apricot flowers and red Japanese apricot flowers.
- the SPME method is advantageous for analyzing the highly volatile fragrant components of white Japanese apricot flowers and red Japanese apricot 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.
- perfume compositions were prepared based on the fragrant components of white Japanese apricot flowers and red Japanese apricot flowers, analyzed by the SPME method.
- compositions were subjected to olfactory sensory tests in order to examine the similarity of fragrance thereof to the fragrances of white Japanese apricot flowers and red Japanese apricot flowers and the preference of fragrance thereof .
- the sensory tests were conducted by professional perfumers and general persons, and the similarity of fragrance of the compositions to the fragrance of Japanese apricot flowers and the preference of fragrance thereof were evaluated through questionnaire survey.
- compositions according to the present invention contain the fragrant components of white Japanese apricot flowers or red Japanese apricot flowers, analyzed by the SPME method, and an artificial synthetic substance, and thus can emit a fragrance like the fragrance of natural Japanese apricot flowers and can also improve the preference of fragrance.
- the collection of the fragrant components was conducted in a wild Japanese apricot tree grove, located at Daap-myeon, Gwangyang-si, Jeollanam-do, Korea.
- the fiber having the fragrant components collected thereon was sealed so as to prevent the volatilization of the fragrant components.
- 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
- white Japanese apricot flowers contained, as main fragrant components, benzaldehyde, benzyl acetate, benzyl alcohol, acetophenone, decanal, nonanal, 2, 2, 6-trimethyl-5-cyclohexene-l, 4-dione and the like, and these main components accounted for 90.22% of the total weight of the fragrant components.
- the perfume composition (sample B) had a fragrance greatly different from the fragrance of wild white Japanese apricot flowers, and showed preference lower than the average value.
- the perfume composition comprising the components analyzed by the SMPE method had no similarity to the fragrance of wild white Japanese apricot flowers.
- each of the fragrant components of wild white Japanese apricot flowers was subjected to sensory evaluation by a professional evaluation group consisting of perfumers.
- Red Japanese apricot flower branches having strong fragrance were selected and maintained on a 85- ⁇ m polyacrylate fiber for SPME analysis, and the fragrant components were collected for 2 hours.
- the collection of the fragrant components was conducted in a wild Japanese apricot tree grove, located at Okryong-myeon, Gwangyang-si,
- the fiber having the fragrant components collected thereon was sealed so as to prevent the volatilization of the fragrant components.
- the sealed fiber was put into the inlet of a
- red Japanese apricot flowers contained, as fragrant components, benzaldehyde, benzyl acetate, benzyl alcohol, cinnamyl alcohol, cinnamyl acetate, cinnamylaldehyde and the like, and these main fragrant components accounted for 92.392% of the total weight of the fragrant components .
- the perfume composition (sample B) had a fragrance greatly different from the fragrance of natural red Japanese apricot flowers (sample B) , and showed preference lower than the average value .
- red Japanese apricot flowers six components, including benzaldehyde, which is the major fragrant component of fruits, such as cherries and almonds, benzyl acetate, which has sweet fruit fragrance and makes jasmine fragrance, benzyl alcohol, which has a light aromatic fragrance and is used to produce a fragrance like that of jasmine, gardenia or lilac, and cynnamaldehyde , cinnamyl alcohol and cinnamyl acetate, which are the main components of cinnamon fragrance, were major components making the characteristic fragrance of red Japanese apricot flowers.
- benzaldehyde which is the major fragrant component of fruits, such as cherries and almonds
- benzyl acetate which has sweet fruit fragrance and makes jasmine fragrance
- benzyl alcohol which has a light aromatic fragrance and is used to produce a fragrance like that of jasmine, gardenia or lilac
- cynnamaldehyde cinnamyl alcohol and cinnamy
- Example 1 Preparation of new perfume compositions having varying contents of main components of white Japanese apricot flowers
- the perfume compositions #1-6 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 65-90t% (see Table 9) . [Table 9]
- Example 2 Sensory evaluation of perfume compositions prepared in Example 1
- the perfume composition #3 in which the content of the three main components was 75%, showed the highest similarity and preference among the six perfume compositions, but all the similarity and preference of the perfume composition #3 were lower than the average values (so-so) .
- Example 3 Preparation of perfume compositions having improved fragrance of white Japanese apricot flowers, based on analysis conducted by professional evaluation group
- new perfume compositions were prepared by adding florol (tetrahydro-4-methyl-2- (2-methyl propyl) -2H-pyran-4- ol) , having a clean and soft floral fragrance, to the perfume composition #3 in which the total content of benzaldehyde , benzyl acetate and benzyl alcohol was 75%.
- the florol was added at concentrations of 2%, 4%, 6%, 8% and 10%, and the other components were added so as to make a total content of 100%.
- These perfume compositions are shown in Table 11 below.
- Example 4 Sensory evaluation of perfume compositions prepared in Example 3
- Example 3 The five perfume compositions #A, #B, #C, #1D and #1E, prepared in Example 3 , were examined with respect to the similarity of fragrance to the fragrance of white Japanese apricot flowers and the preference of fragrance by performing sensory evaluation in the same manner as described in Reference Example 1 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 white Japanese apricot flowers, and the preference of fragrance, are shown in Table 12 below. [Table 12]
- Example 5 Preparation of new perfume compositions having varying contents of main components of red Japanese apricot flowers
- the perfume compositions #7-12 were prepared such that the ratio between these six components was maintained constant while the total content of these six components were changed in the range of 65-90t% (see Table 13) . [Table 13]
- Example 6 Sensory evaluation of perfume compositions prepared in Example 5
- the perfume composition #8 in which the content of the six main components was 85%, showed the highest similarity and preference among the six perfume compositions, but all the similarity and preference of the perfume composition #8 were lower than the average values (so-so) .
- Example 7 Preparation of perfume compositions having improved fragrance, based on analysis conducted by professional evaluation group
- new perfume compositions were prepared by adding phenylisohexanol, having a delicate and attractive fragrance, to the perfume composition #8 in which the total content of benzaldehyde , benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl acetate and cinnamyl alcohol was
- Example 8 Sensory evaluation of perfume compositions prepared in Example 7
- a perfume composition which can emit a fragrance like that of natural Japanese apricot flowers and has high preference, can be provided by adding an artificial synthetic substance to the main fragrant components of natural white Japanese apricot flowers or red Japanese apricot flowers, analyzed by the SPME method.
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Abstract
Disclosed herein are perfume compositions having a fragrance like that of Japanese apricot flowers. More specifically, disclosed is a perfume composition having a fragrance like that of white Japanese apricot flowers, which contains artificial synthetic substance florol, in addition to the main fragrant components of white Japanese apricot flowers, including benzaldehyde, benzyl acetate and benzyl alcohol, analyzed by an SPME method. Also disclosed is a perfume composition having a fragrance like that of red Japanese apricot flowers, which contains artificial synthetic substance phenylisohexanol, in addition to the main fragrant components of red Japanese apricot flowers, including benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol and cinnamyl acetate, analyzed by the SPME method. The perfume compositions emit a fragrance like the characteristic fragrance of natural Japanese apricot flowers and, at the same time, has high preference.
Description
[DESCRIPTION] [invention Title]
PERFUME COMPOSITION FOR EXPRESSING THE FRAGRANCE OF UME FLOWERS [Technical Field]
The present invention relates to a perfume composition having a fragrance like the characteristic fragrance of Japanese apricot flowers (also called as "ume flowers", hereinafter we call "Japanese apricot flowers"). More particularly, the present invention relates to a perfume composition, which contains an artificial synthetic substance, in addition to the fragrant components of
Japanese apricot flowers, determined by analyzing the fragrant components of white Japanese apricot flowers or red Japanese apricot flowers, and thus has a fragrance like the characteristic fragrance of Japanese apricot flowers and, at the same time, has high preference.
[Background Art]
Japanese apricot trees, Prunus mume Siebold & Zucc, are deciduous small trees belonging to the family Rosaceae, the order Rosaceae, and are native to China and distributed in Japan, China and Korea. Japanese apricot trees come in many varieties depending on the intended use thereof or the color of flowers or the shape of petals, and are classified, according to the color of petals, into white Japanese apricot trees having white flowers, and red Japanese apricot trees having red flowers.
To prepare products having a fragrance like that of Japanese apricot flowers, various methods can be
conventionally 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 is required, and the fragrance of the product can be greatly different from the characteristic fragrance of flowers.
Recently, in order to overcome such shortcomings, a head space method and an SPME method were developed. Among them, the SPME (Solid Phase Micro Extraction; SUPELCO international, Vol.13, No.4, p.9-10) method is considered to be an excellent technology, which can analyze the fragrant components in a rapid and convenient manner without needing the use of solvent and the pretreatment of samples . [Disclosure] [Technical Problem]
The present inventors have made efforts to develop a product having a fragrance like that of Japanese apricot flowers, using the SPME method effective in analyzing the fragrant components of living natural materials. As a result, the present inventors have found out the fragrant components of white Japanese apricot flowers and red Japanese apricot flowers, but have found that a product having a fragrance like the fragrance of natural Japanese apricot flowers cannot be obtained only with a combination
of the fragrant components .
Accordingly, the present inventors have continued to study in order to a product having a fragrance like that of white Japanese apricot flowers or red Japanese apricot flowers and, as a result, a perfume composition, which contains, active ingredients, an artificial synthetic substance, in addition to the main fragrant components of
Japanese apricot flowers, can emit a fragrance like the characteristic fragrance of white Japanese apricot flowers or red Japanese apricot flowers and has 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 white Japanese apricot flowers or red Japanese apricot 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]
To achieve the above objects, in one aspect, the present invention provides a perfume composition having a fragrance like that of white Japanese apricot flowers, the perfume composition containing, as active ingredients, fragrant components of white Japanese apricot flowers, and florol.
The perfume composition having a fragrance like that of white Japanese apricot flowers contains, as essential components, artificial synthetic substance florol, in
addition to the main fragrant components of white Japanese apricot flowers, including benzaldehyde , benzyl acetate and benzyl alcohol .
In another aspect, the present invention provides a perfume composition having a fragrance like that of red
Japanese apricot flowers, which contains, as active ingredient, fragrant components of red Japanese apricot flowers, and phenylisohexanol.
The perfume composition having a fragrance like that of red Japanese apricot flowers contains, as essential components, artificial synthetic substance phenylisohexanol, in addition to the main fragrant components of red Japanese apricot flowers, including benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol and cinnamyl acetate.
Hereinafter, the present invention will be described in further detail.
The compositions according to the present invention emit a fragrance like that of white Japanese apricot flowers or red Japanese apricot flowers and have high preference.
The inventive composition having a fragrance like that of white Japanese apricot flowers contains, as active ingredients, artificial synthetic substance florol in addition to the fragrant components of white Japanese apricot flowers.
The composition having a fragrance like that of white
Japanese apricot flowers contains, as essential components, benzaldehyde, benzyl acetate, benzyl alcohol and artificial synthetic substance florol, and may further contain, as
secondary components, acetophenone , decanal, nonanal, 2 , 2 , 6-trimethyl-5-cyclohexene-l, 4-dione, iso-butyl alcohol, butyl alcohol, dodecane, eugenol, tridecane, camphor, hexanal and the like. The perfume composition of the present invention contains, based on the total weight of the composition, 40-52 wt% of benzaldehyde, 18-24 wt% of benzyl acetate, 6-8 wt% of benzyl alcohol, 5.8-6.8 wt% of acetophenone, 1.5-2.6 wt% of decanal, 1.0-1.5 wt% of nonanal, 0.8-2.1 wt% of 2, 2 , δ-trimethyl-S-cyclohexene-l, 4- dione, 2.0-6.0 wt% of iso-butyl alcohol, 1.0-4.1 wt% of butyl alcohol, 1.0-2.5 wt% of dodecane, 0.1-0.4 wt% of eugenol, 0.1-0.3 wt% of camphor, 1.0-2.6 wt% of tridecane, 0.1-0.3 wt% of hexanal, and 4-8 wt% of artificial synthetic substance florol. If benzaldehyde, benzyl acetate, benzyl alcohol and artificial synthetic substance florol, which are main components for producing a fragrance like that of white Japanese apricot flowers, are used in amounts deviating from the above-specified ranges, the similarity of fragrance to the fragrance of natural white Japanese apricot flowers will be decreased, and the preference of fragrance will also be decreased. Although the other components are preferably used in the above-specified content ranges, such components may also be used in amounts deviating from the above ranges, as long as they have no effect on the production of a fragrance like that of white Japanese apricot flowers, because they have no great effect on the fragrance of white Japanese apricot flowers.
The inventive perfume composition having a fragrance like that of red Japanese apricot flowers contains, as essential components, the fragrant components of red
Japanese apricot flowers, and artificial synthetic substance phenylisohexanol.
The composition having a fragrance like that of red Japanese apricot flowers contains, as main components, benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol, cinnamyl acetate and artificial synthetic substance phenylisohexanol, and may further contain, as secondary components, acetophenone, ethyl alcohol, ethyl ether, pentane and the like. The perfume composition of the present invention contains, based on the total weight of the composition, 48-52 wt% of benzaldehyde, 24-26 wt% of benzyl acetate, 7-9 wt% of benzyl alcohol, 0.1-3 wt% of cinnamaldehyde, 1.5-2 wt% of cinnamyl alcohol, 0.5-0.7 wt% of cinnamyl acetate, 4-6 wt% of acetophenone, 1.3-1.6 wt% of ethyl alcohol, 0.9-1.2 wt% of ethyl ether, 0.6-0.8 wt% of pentane and 4-6 wt% of artificial synthetic substance phenylisohexanol. If benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl alcohol, cinnamyl acetate and artificial synthetic substance phenylisohexanol, which are main components for producing a fragrance like that of red Japanese apricot flowers, are used in amounts deviating from the above-specified ranges, the similarity of fragrance to the fragrance of natural red Japanese apricot flowers will be decreased, and the preference of fragrance will also be decreased. Although the other components are preferably used in the above-specified content ranges, such components may also be used in amounts deviating from the above ranges, as long as they have no effect on the production of a fragrance like that of red Japanese apricot
flowers, because they have no great effect on the fragrance of red Japanese apricot 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 white Japanese apricot flowers and red Japanese apricot flowers. The SPME method is advantageous for analyzing the highly volatile fragrant components of white Japanese apricot flowers and red Japanese apricot 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 white Japanese apricot flowers and red Japanese apricot flowers, analyzed by the SPME method. These compositions were subjected to olfactory sensory tests in order to examine the similarity of fragrance
thereof to the fragrances of white Japanese apricot flowers and red Japanese apricot flowers and the preference of fragrance thereof . The sensory tests were conducted by professional perfumers and general persons, and the similarity of fragrance of the compositions to the fragrance of Japanese apricot 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 the fragrant components of white Japanese apricot flowers or red Japanese apricot flowers, analyzed by the SPME method, and an artificial synthetic substance, and thus can emit a fragrance like the fragrance of natural Japanese apricot flowers and can also improve the preference of fragrance. [Mode for Invention]
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.
Reference Example 1: Analysis of fragrance of white Japanese apricot flowers
1. Analysis of fragrance of white Japanese apricot flowers using SPME method
White Japanese apricot flower branches having strong fragrance were selected and the fragrant components were
adsorbed to polyacrylate fiber coated with 85-jMii polyacrylate for SPME analysis and collected for 2 hours.
The collection of the fragrant components was conducted in a wild Japanese apricot tree grove, located at Daap-myeon, Gwangyang-si, Jeollanam-do, Korea.
After the fragrant components were collected, the fiber having the fragrant components collected thereon was sealed so as to prevent the volatilization of the fragrant components. 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 (6O m X 0.25 mm X 0.25 um)
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 white
Japanese apricot flowers, analyzed by the SPME method, are shown in Table 1 below. [Table l]
As can be seen in Table 1 above, white Japanese apricot flowers contained, as main fragrant components, benzaldehyde, benzyl acetate, benzyl alcohol, acetophenone, decanal, nonanal, 2, 2, 6-trimethyl-5-cyclohexene-l, 4-dione and the like, and these main components accounted for 90.22% of the total weight of the fragrant components.
2. Comparative sensory evaluation of fragrance between perfume composition, prepared based on analysis results, and wild white Japanese apricot 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 wild white Japanese apricot flowers was examined through sensory evaluation. [Table 2]
The sensory evaluation was conducted on twenty 20-45- year-old general men and women, and the similarity of fragrance (question 1) between wild white Japanese apricot 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 ]
As can be seen in Table 4, the perfume composition (sample B) had a fragrance greatly different from the fragrance of wild white Japanese apricot flowers, and showed preference lower than the average value.
1-3: Analysis of fragrance and comparison of fragrance with white Japanese apricot 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 wild white Japanese apricot flowers. Thus, each of the fragrant components of wild white Japanese apricot flowers was subjected to sensory evaluation by a professional evaluation group consisting of perfumers. As a result, it was found that, among the fragrant components of white Japanese apricot flowers, three components, including benzaldehyde, which is the major fragrant component of fruits, such as cherries and almonds, benzyl acetate, which has sweet fruit fragrance and makes jasmine fragrance, and benzyl alcohol, which has a light aromatic fragrance and is used to produce a fragrance like that of jasmine, gardenia or lilac, were major components making the characteristic fragrance of white Japanese apricot flowers. Reference Example 2 : Analysis of red Japanese apricot flowers
1. Analysis of fragrance of red Japanese apricot flowers using SPME method
Red Japanese apricot flower branches having strong fragrance were selected and maintained on a 85-μm polyacrylate fiber for SPME analysis, and the fragrant components were collected for 2 hours. The collection of the fragrant components was conducted in a wild Japanese apricot tree grove, located at Okryong-myeon, Gwangyang-si,
Jeollanam-do, Korea. After the fragrant components were collected, the fiber having the fragrant components collected thereon was sealed so as to prevent the volatilization of the fragrant components. 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 (6O 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) Ionizaton voltage: 70 eV
Desorption time: 2 min
As a result, the fragrant components of white
Japanese apricot flowers, analyzed by the SPME method, are shown in Table 5 below.
[Table 5]
As can be seen in Table 5 above, red Japanese apricot flowers contained, as fragrant components, benzaldehyde, benzyl acetate, benzyl alcohol, cinnamyl alcohol, cinnamyl acetate, cinnamylaldehyde and the like, and these main fragrant components accounted for 92.392% of the total weight of the fragrant components .
2. Comparative sensory evaluation of fragrance between perfume composition, prepared based on analysis results, and red Japanese apricot flowers
Based on the above analysis results, a perfume composition (sample B) shown in Table 6 below was prepared, and the similarity of fragrance between the perfume composition and red Japanese apricot flowers was examined through sensory evaluation. [Table 6]
The sensory evaluation was conducted on twenty 20-45- year-old general men and women, and the similarity of fragrance (question 1) between wild red Japanese apricot 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 7 below. The evaluation results are shown in Table 8 below. [Table 7]
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 8 ]
As can be seen in Table 8 above, the perfume composition (sample B) had a fragrance greatly different from the fragrance of natural red Japanese apricot flowers (sample B) , and showed preference lower than the average value .
1-3: Analysis of fragrance and comparison of fragrance with red Japanese apricot flowers, conducted by professional evaluation group As can be seen in Reference Example 2, the perfume composition comprising the components analyzed by the SMPE method had no similarity to the fragrance of natural red Japanese apricot flowers. Thus, each of the fragrant components of red Japanese apricot flowers was subjected to sensory evaluation by a professional evaluation group consisting of perfumers. As a result, it was found that, among the fragrant components of red Japanese apricot flowers, six components, including benzaldehyde, which is the major fragrant component of fruits, such as cherries and almonds, benzyl acetate, which has sweet fruit fragrance and makes jasmine fragrance, benzyl alcohol, which has a light aromatic fragrance and is used to produce a fragrance like that of jasmine, gardenia or lilac, and cynnamaldehyde , cinnamyl alcohol and cinnamyl acetate,
which are the main components of cinnamon fragrance, were major components making the characteristic fragrance of red Japanese apricot flowers.
Example 1: Preparation of new perfume compositions having varying contents of main components of white Japanese apricot flowers
From the results of Reference Example 1, it could be seen that the main components of the characteristic fragrance of white Japanese apricot flowers were benzaldehyde, benzyl acetate and benzyl alcohol. Thus, in order to provide a perfume composition, which contains these three components to emit the fragrance of white Japanese apricot flowers and, at the same time, has high preference, the present inventors prepared new perfume compositions #1-6.
The perfume compositions #1-6 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 65-90t% (see Table 9) . [Table 9]
Example 2 : Sensory evaluation of perfume compositions prepared in Example 1
The six new perfume compositions, prepared in Example 1, were examined with respect to the similarity of fragrance to the fragrance of white Japanese apricot flowers and the preference of fragrance using sensory evaluation in the same manner as described in Reference Example 1. 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 white Japanese apricot flowers, and the preference of fragrance, are shown in Table 10 below. [Table 10]
As shown in Table 10 above, the perfume composition #3 , in which the content of the three main components was 75%, showed the highest similarity and preference among the six perfume compositions, but all the similarity and preference of the perfume composition #3 were lower than the average values (so-so) .
Example 3 : Preparation of perfume compositions having improved fragrance of white Japanese apricot flowers, based on analysis conducted by professional evaluation group
To improve the similarity and preference of the perfume composition #3, which was shown to be most similar
to the fragrance of white Japanese apricot flowers in Table
6 above, new perfume compositions were prepared by adding florol (tetrahydro-4-methyl-2- (2-methyl propyl) -2H-pyran-4- ol) , having a clean and soft floral fragrance, to the perfume composition #3 in which the total content of benzaldehyde , benzyl acetate and benzyl alcohol was 75%.
The florol was added at concentrations of 2%, 4%, 6%, 8% and 10%, and the other components were added so as to make a total content of 100%. These perfume compositions are shown in Table 11 below.
[Table ll]
The five perfume compositions #A, #B, #C, #1D and #1E, prepared in Example 3 , were examined with respect to the similarity of fragrance to the fragrance of white Japanese apricot flowers and the preference of fragrance by performing sensory evaluation in the same manner as described in Reference Example 1 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 white Japanese apricot flowers, and the preference of fragrance, are shown in Table 12 below. [Table 12]
As can be seen in Table 12 above, 4-8 wt% florol was added to the main fragrant components of white Japanese apricot flowers, including benzaldehyde, benzyl acetate and benzyl alcohol, the resulting compositions could have a fragrance like that of white Japanese apricot flowers and show high preference (average of more than 3.5) .
Meanwhile, it could be seen that, when florol was added in amounts of less than 4 wt% or more than 8 wt%, the fragrance similarity and preference of the resulting perfume compositions were slightly higher than or not substantially different from those of the perfume compositions containing no florol (see #4 in Table 10) .
Example 5 : Preparation of new perfume compositions having varying contents of main components of red Japanese apricot flowers
From the results of Reference Example 2, it could be seen that the main components of the characteristic fragrance of red Japanese apricot flowers were benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl
alcohol and cinnamyl acetate. Thus, in order to provide a perfume composition, which contains these six components to emit the fragrance of red Japanese apricot flowers and, at the same time, has high preference, the present inventors prepared new perfume compositions #7-12.
The perfume compositions #7-12 were prepared such that the ratio between these six components was maintained constant while the total content of these six components were changed in the range of 65-90t% (see Table 13) . [Table 13]
Example 6 : Sensory evaluation of perfume compositions prepared in Example 5
The six new perfume compositions #7-#12, prepared in Example 5, were examined with respect to the similarity of fragrance to the fragrance of red Japanese apricot flowers
and the preference of fragrance by performing 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 red Japanese apricot flowers, and the preference of fragrance, are shown in Table 14 below. [Table 14]
As shown in Table 14 above, the perfume composition #8, in which the content of the six main components was 85%, showed the highest similarity and preference among the six perfume compositions, but all the similarity and preference of the perfume composition #8 were lower than the average values (so-so) .
Example 7 : 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 #8, which was shown to be most similar to the fragrance of red Japanese apricot flowers in Table
14 above, new perfume compositions were prepared by adding phenylisohexanol, having a delicate and attractive fragrance, to the perfume composition #8 in which the total content of benzaldehyde , benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl acetate and cinnamyl alcohol was
85%. The phenylisohexanol was added at concentrations of 2%, 4%, 6%, 8% and 10%, and other components were added so as to make a total content of 100%. These perfume compositions are shown in Table 15 below.
[Table 15]
Example 8 : Sensory evaluation of perfume compositions prepared in Example 7
The five perfume compositions #F, #G, #H, #11 and #1J, prepared in Example 7, were examined with respect to the similarity of fragrance to the fragrance of red Japanese apricot 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 red Japanese apricot flowers, and the preference of fragrance, are shown in Table 16 below.
[Table 16]
As can be seen in Table 16 above, 4-6 wt% of
phenylisohexanol was added to the main fragrant components of red Japanese apricot flowers, including benzaldehyde , benzyl acetate and benzyl alcohol, the resulting compositions could have a fragrance like that of red Japanese apricot flowers and show high preference (average of more than 3.5).
Meanwhile, it could be seen that, when phenylisohexanol was added in amounts of less than 4 wt% or more than 6 wt%, the fragrance similarity and preference of the resulting perfume compositions were slightly higher than or not substantially different from those of the perfume compositions containing no phenylisohexanol (see Table 14) .
Preparation Example 1
A perfume shown in Table 17 below was prepared using the above-described perfume composition having similarity to the fragrance of white Japanese apricot flowers. [Table 17]
Perfume containing perfume composition having fragrance like that of white Japanese apricot flowers
Perfume composition having fragrance like
15 wt% that of white Japanese apricot flowers 80 wt%
Alcohol 5 wt%
Water q.s.
Pigment q.s.
UV-blocking agent
Preparation Example 2
A perfume shown in Table 18 below was prepared using
the above-described perfume composition having similarity to the fragrance of red Japanese apricot flowers. [Table 18]
Perfume containing perfume composition having fragrance like that of red Japanese apricot flowers
Perfume composition having fragrance like
18 wt% that of red Japanese apricot flowers 80 wt%
Alcohol 2 wt%
Water q.s.
Pigment q.s.
UV-blocking agent
[industrial Applicability]
As described above, according to the present invention, a perfume composition, which can emit a fragrance like that of natural Japanese apricot flowers and has high preference, can be provided by adding an artificial synthetic substance to the main fragrant components of natural white Japanese apricot flowers or red Japanese apricot flowers, analyzed by the SPME method.
Claims
[CLAIMS] [Claim l]
A perfume composition having a fragrance like that of white Japanese apricot flowers, the composition containing, as active ingredients, fragrant components of white Japanese apricot flowers, and florol.
[Claim 2]
The perfume composition of Claim 1, wherein the fragrant components of white Japanese apricot flowers are benzaldehyde, benzyl acetate and benzyl alcohol.
[Claim 3]
The perfume composition of Claim 2, further containing acetophenone, decanal, nonanal, 2 , 2 , δ-trimethyl- 5-cyclohexene-l, 4-dione, isobutyl alcohol, butyl alcohol, dodecane, eugenol, camphor, tridecane and hexanal . [Claim 4]
The perfume composition of Claim 3, wherein the perfume composition contains, based on the total weight of the composition, 40-52 wt% of benzaldehyde, 18-24 wt% of benzyl acetate, 6-8 wt% of benzyl alcohol, 5.8-6.8 wt% of acetophenone, 1.5-2.6 wt% of decanal, 1.0-1.5 wt% of nonanal, 0.8-2.1 wt% of 2 , 2 , 6-trimethyl-5-cyclohexene-l, 4- dione, 2.0-6.0 wt% of iso-butyl alcohol, 1.0-4.1 wt% of butyl alcohol, 1.0-2.5 wt% of dodecane, 0.1-0.
4 wt% of eugenol, 0.1-0.3 wt% of camphor, 1.0-2.6 wt% of tridecane,
0.1-0.3 wt% of hexanal, and 4-8 wt% of florol.
[Claim 5]
A perfume composition having a fragrance like that of red Japanese apricot flowers, the composition containing, as active ingredients, fragrant components of red Japanese apricot flowers, and phenylisohexanol . [Claim δ]
The perfume composition of Claim 5, wherein the fragrant components are benzaldehyde, benzyl acetate, benzyl alcohol, cinnamaldehyde, cinnamyl acetate and cinnamyl acetate. [Claim 7]
The perfume composition of Claim 6, further containing acetophenone, ethyl alcohol, ethyl ether and pentane . [Claim 8]
The perfume composition of Claim 7, wherein the perfume composition contains, based on the total weight of the composition, 48-52 wt% of benzaldehyde, 24-26 wt% of benzyl acetate, 7-9 wt% of benzyl alcohol, 0.1-3 wt% of cinnamaldehyde, 1.5-2 wt% of cinnamyl alcohol, 0.5-0.7 wt% of cinnamyl acetate, 4-6 wt% of acetophenone, 1.3-1.6 wt% of ethyl alcohol, 0.9-1.2 wt% of ethyl ether, 0.6-0.8 wt% of pentane and 4-6 wt% of phenylisohexanol . [Claim 9]
A skin external composition containing the perfume composition of any one of Claims 1 to 8.
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| JP2009534475A JP5452228B2 (en) | 2006-10-31 | 2007-09-28 | A fragrance composition that reproduces the odor of plum |
| CN2007800400619A CN101528273B (en) | 2006-10-31 | 2007-09-28 | Perfume composition for expressing the fragrance of ume flowers |
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| KR1020060106240A KR101234023B1 (en) | 2006-10-31 | 2006-10-31 | Perfume composition for expressing the fragrance of Prunus mume Siebold ＆ Zucc |
| KR1020060106238A KR101234024B1 (en) | 2006-10-31 | 2006-10-31 | Perfume composition for expressing the fragrance of White Maehwa(Prunus mume Sieb. et Zucc.) |
| KR10-2006-0106238 | 2006-10-31 | ||
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| WO2009099890A2 (en) * | 2008-02-01 | 2009-08-13 | Mary Kay Inc. | Methods of treating skin with aromatic skin-active ingredients |
| FR2952530A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | Anhydrous composition, useful in e.g. fresh water and eau de toilette and for perfuming keratin material or garments, comprises at least one perfuming substance, and volatile linear alkane e.g. n-nonane |
| FR2952531A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | AQUEOUS SCENSE COMPOSITION COMPRISING AT LEAST ONE VOLATILE LINEAR ALKANE; PERFUMING PROCESS |
| FR2952529A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | Anhydrous composition, useful in the form of e.g. fresh water and for perfuming keratin material or garments, comprises a perfuming substance, a volatile alcohol e.g. ethanol, and a volatile liquid linear alkane e.g. n-nonane |
| WO2011144519A1 (en) * | 2010-05-20 | 2011-11-24 | L'oreal | Devices for spraying a fragrancing composition comprising at least one volatile liquid linear alkane; fragrancing processes |
| CN105683347A (en) * | 2013-11-08 | 2016-06-15 | 弗门尼舍有限公司 | Alcohol with flower odor |
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| US8399521B2 (en) | 2008-02-01 | 2013-03-19 | Mary Kay Inc. | Methods of treating skin with aromatic skin-active ingredients |
| WO2009099890A3 (en) * | 2008-02-01 | 2009-11-05 | Mary Kay Inc. | Methods of treating skin with aromatic skin-active ingredients |
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| EP2324816A3 (en) * | 2009-11-19 | 2015-03-04 | L'Oréal | Aqueous flavouring composition including at least one volatile linear alkane; flavouring method |
| FR2952529A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | Anhydrous composition, useful in the form of e.g. fresh water and for perfuming keratin material or garments, comprises a perfuming substance, a volatile alcohol e.g. ethanol, and a volatile liquid linear alkane e.g. n-nonane |
| FR2952531A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | AQUEOUS SCENSE COMPOSITION COMPRISING AT LEAST ONE VOLATILE LINEAR ALKANE; PERFUMING PROCESS |
| FR2952530A1 (en) * | 2009-11-19 | 2011-05-20 | Oreal | Anhydrous composition, useful in e.g. fresh water and eau de toilette and for perfuming keratin material or garments, comprises at least one perfuming substance, and volatile linear alkane e.g. n-nonane |
| WO2011144519A1 (en) * | 2010-05-20 | 2011-11-24 | L'oreal | Devices for spraying a fragrancing composition comprising at least one volatile liquid linear alkane; fragrancing processes |
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| CN105683347A (en) * | 2013-11-08 | 2016-06-15 | 弗门尼舍有限公司 | Alcohol with flower odor |
| US20160264910A1 (en) * | 2013-11-08 | 2016-09-15 | Firmenich Sa | Alcohol with floral odor |
| US9982218B2 (en) * | 2013-11-08 | 2018-05-29 | Firmenich Sa | Alcohol with floral odor |
| US10370616B2 (en) | 2013-11-08 | 2019-08-06 | Firmenich Sa | Alcohol with floral odor |
| CN115651762A (en) * | 2013-11-08 | 2023-01-31 | 弗门尼舍有限公司 | Alcohol with floral scent |
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| JP5452228B2 (en) | 2014-03-26 |
| JP2010508385A (en) | 2010-03-18 |
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