WO2008054067A1 - Perfume composition for expressing the fragrance of ume flowers - Google Patents

Perfume composition for expressing the fragrance of ume flowers Download PDF

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Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
fragrance
japanese apricot
flowers
apricot flowers
perfume composition
Prior art date
Application number
PCT/KR2007/004745
Other languages
English (en)
French (fr)
Inventor
Yeon Ju Hong
Eun Ju Lee
Hyung Jye Seo
Byeong Bae Jeon
Original Assignee
Amorepacific Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020060106240A external-priority patent/KR101234023B1/ko
Priority claimed from KR1020060106238A external-priority patent/KR101234024B1/ko
Application filed by Amorepacific Corporation filed Critical Amorepacific Corporation
Priority to JP2009534475A priority Critical patent/JP5452228B2/ja
Priority to CN2007800400619A priority patent/CN101528273B/zh
Publication of WO2008054067A1 publication Critical patent/WO2008054067A1/en

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Classifications

    • 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

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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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
PCT/KR2007/004745 2006-10-31 2007-09-28 Perfume composition for expressing the fragrance of ume flowers WO2008054067A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2009534475A JP5452228B2 (ja) 2006-10-31 2007-09-28 梅の香臭を再現した香料組成物
CN2007800400619A CN101528273B (zh) 2006-10-31 2007-09-28 一种散发梅花香气的香料组合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR1020060106240A KR101234023B1 (ko) 2006-10-31 2006-10-31 홍매화의 향취를 재현한 향료 조성물
KR1020060106238A KR101234024B1 (ko) 2006-10-31 2006-10-31 백매화의 향취를 재현한 향료 조성물
KR10-2006-0106238 2006-10-31
KR10-2006-0106240 2006-10-31

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009099890A2 (en) * 2008-02-01 2009-08-13 Mary Kay Inc. Methods of treating skin with aromatic skin-active ingredients
FR2952530A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante anhydre sans alcool comprenant au moins un alcane lineaire volatil ; procede de parfumage
FR2952529A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante anhydre comprenant au moins un alcool volatil et au moins un alcane lineaire volatil ; procede de parfumage
FR2952531A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante aqueuse comprenant au moins un alcane lineaire volatil ; procede de parfumage
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 (zh) * 2013-11-08 2016-06-15 弗门尼舍有限公司 具有花香气味的醇

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JP2001213750A (ja) * 2000-01-28 2001-08-07 Ichimaru Pharcos Co Ltd バラ科植物水蒸気蒸留水含有化粧料組成物
KR20030050279A (ko) * 2001-12-18 2003-06-25 주식회사 태평양 천연송이버섯의 향을 재현한 향료조성물
KR20050045428A (ko) * 2003-11-11 2005-05-17 주식회사 생그린 항산화 활성을 갖는 매화추출물을 포함하는 화장료 조성물
WO2005053151A1 (en) * 2003-11-20 2005-06-09 Northrop Grumman Corporation Variable supply amplifier system

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JP3821222B2 (ja) * 2002-04-05 2006-09-13 ライオン株式会社 ロスマリン酸含有組成物
JP2005015686A (ja) * 2003-06-27 2005-01-20 Kiyomitsu Kawasaki フルーツ様香料組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001213750A (ja) * 2000-01-28 2001-08-07 Ichimaru Pharcos Co Ltd バラ科植物水蒸気蒸留水含有化粧料組成物
KR20030050279A (ko) * 2001-12-18 2003-06-25 주식회사 태평양 천연송이버섯의 향을 재현한 향료조성물
KR20050045428A (ko) * 2003-11-11 2005-05-17 주식회사 생그린 항산화 활성을 갖는 매화추출물을 포함하는 화장료 조성물
WO2005053151A1 (en) * 2003-11-20 2005-06-09 Northrop Grumman Corporation Variable supply amplifier system

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2009099890A2 (en) * 2008-02-01 2009-08-13 Mary Kay Inc. Methods of treating skin with aromatic skin-active ingredients
EA020293B1 (ru) * 2008-02-01 2014-10-30 Мэри Кэй Инк. Применение композиции, содержащей этил-линалул, для ухода за кожей
EP2324816A3 (fr) * 2009-11-19 2015-03-04 L'Oréal Composition parfumante aqueuse comprenant au moins un alcane lineaire volatil ; procede de parfumage
FR2952531A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante aqueuse comprenant au moins un alcane lineaire volatil ; procede de parfumage
FR2952529A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante anhydre comprenant au moins un alcool volatil et au moins un alcane lineaire volatil ; procede de parfumage
FR2952530A1 (fr) * 2009-11-19 2011-05-20 Oreal Composition parfumante anhydre sans alcool comprenant au moins un alcane lineaire volatil ; procede de parfumage
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
FR2960148A1 (fr) * 2010-05-20 2011-11-25 Oreal Dispositifs de pulverisation d'une composition parfumante comprenant au moins un alcane lineaire liquide volatil ; procedes de parfumage
CN105683347A (zh) * 2013-11-08 2016-06-15 弗门尼舍有限公司 具有花香气味的醇
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 (zh) * 2013-11-08 2023-01-31 弗门尼舍有限公司 具有花香气味的醇

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