WO2018097524A1 - Composition aromatique reproduisant la fragrance de syringa velutina var. kamibayashii - Google Patents

Composition aromatique reproduisant la fragrance de syringa velutina var. kamibayashii Download PDF

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Publication number
WO2018097524A1
WO2018097524A1 PCT/KR2017/012722 KR2017012722W WO2018097524A1 WO 2018097524 A1 WO2018097524 A1 WO 2018097524A1 KR 2017012722 W KR2017012722 W KR 2017012722W WO 2018097524 A1 WO2018097524 A1 WO 2018097524A1
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Prior art keywords
fragrance
weight
benzyl
composition
round
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PCT/KR2017/012722
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English (en)
Korean (ko)
Inventor
임소연
고승호
함대영
Original Assignee
주식회사 아모레퍼시픽
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Priority claimed from KR1020170148788A external-priority patent/KR102213993B1/ko
Application filed by 주식회사 아모레퍼시픽 filed Critical 주식회사 아모레퍼시픽
Publication of WO2018097524A1 publication Critical patent/WO2018097524A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations

Definitions

  • the present invention is a round clove flower ( Syringa) velutina var. It relates to a perfume composition that reproduces the smell of kamibayashii , more specifically benzaldehyde (benzaldehyde), indol (phenol), phenethyl alcohol, Benzyl alcohol, methyl palmitate, alpha-bergamotene and methyl anthranilate are added to benzyl acetate to improve the taste of round clove. It relates to a fragrance composition which reproduces the smell of flowers.
  • Round cloves are deciduous broad-leaved shrubs that grow in the mountains of some parts of Korea.
  • the growing environment grows on the slopes of the foothills where the sun is well and the water is good and the height is about 1 ⁇ 1.5m.
  • the root is medicinal to help get rid of bloating or warm the abdomen. When one flower is seen from the side, it is seen as a ' ⁇ ' and is called a clove because the flower has a fragrance.
  • head space methods including SPME methods (Solid Phase Micro Extraction); SUPELCO international, Vol. 13, No. 4, p. 9-10) have been developed. It became. Unlike the conventional extraction method, the head space method does not use a solvent and does not require pretreatment, and thus, there is an advantage in that the perfume component can be analyzed quickly and simply. On the other hand, volatile flavor components are easy to analyze, but volatile components with low volatility or high molecular weight have disadvantages that are not easy to analyze with this method.
  • GC Gas Chromatography
  • GC-O is a method that analyzes the odor component through the peak of the chromatogram and at the same time smells directly, but does not appear as a peak, but actually identifies the odor component.
  • the present inventors attempted to reproduce the scent of the round clove flower by using the SPME method which is effective in analyzing the odorant substances of living natural products.
  • the main component of the fragrance analyzed by the SPME method could not reproduce the fragrance of the round clove, but when benzyl acetate is used together, it can reproduce the unique fragrance of the round clove. It was found that the present invention was completed.
  • Another object of the present invention is to provide an external composition for skin containing the perfume composition.
  • Still another object of the present invention is the use of a perfume composition which reproduces the scent of a rounded clove according to the present invention in the manufacture of an external preparation for skin, for example, a cosmetic composition, a perfume composition, a detergent composition, and the like.
  • a perfume composition which reproduces the scent of a rounded clove according to the present invention in the manufacture of an external preparation for skin, for example, a cosmetic composition, a perfume composition, a detergent composition, and the like.
  • the use as an effective odor component is provided.
  • a fragrance composition that reproduces the fragrance of the round clove flower containing the fragrance component of the round clove flower and benzyl acetate.
  • the present invention also provides an external composition for skin containing the perfume composition.
  • the fragrance composition according to the present invention contains benzyl acetate together with the main components of the round clove flower scent, such as benzaldehyde, indole, phenethyl alcohol, benzyl alcohol, methyl palmitate, alpha-bergamothene and methyl anthranilate,
  • the scent of the round clove flower can be reproduced, and the palatability of the scent can be improved.
  • benzaldehyde (benzaldehyde), indole (indol), phenethyl alcohol, benzyl alcohol, methyl palmitate, alpha-bergamomten (benzaldehyde) that is a odor component of the round clove flower
  • benzaldehyde benzaldehyde
  • indole indol
  • phenethyl alcohol benzyl alcohol
  • methyl palmitate alpha-bergamomten
  • alpha-bergamomten (benzaldehyde) that is a odor component of the round clove flower
  • the present invention relates to a fragrance composition which reproduces the fragrance of a rounded clove flower containing ⁇ -bergamotene), methyl anthranilate, and benzyl acetate as active ingredients.
  • the fragrance composition reproducing the scent of the round clove according to the present invention benzophenone, methyl salicylate, phenylacetaldehyde, benzyl benzoate, isopropyl myri It may be characterized by further containing an isopropyl myristate, benzyl salicylate, methyl benzoate and geraniol as an auxiliary odor component.
  • composition according to the present invention contains benzyl acetate, which is an artificial synthetic material, as an essential ingredient together with the main odor component of the round clove flower, thereby reproducing the inherent odor of the round clove flower. It can increase the smell similarity and exhibit excellent palatability.
  • benzaldehyde indole, phenethyl alcohol, benzyl alcohol, methyl palmitate, alpha-bergamothene, methyl anthranilate, etc. may be used.
  • benzophenone methyl salicylate, phenylacetaldehyde, benzyl benzoate, isopropyl myristate, benzyl salicylate, methyl benzoate, geraniol and the like can be used.
  • the fragrance composition according to the present invention is 43 to 53% by weight, preferably 45 to 50% by weight, 7 to 9.5% by weight of indole, preferably 7.5 to 9% by weight, and phenethyl, based on the total weight of the composition 8 to 13% by weight of alcohol, preferably 11 to 12% by weight, 10 to 16% by weight of benzyl alcohol, preferably 11 to 15% by weight, 2 to 4% by weight of methyl palmitate, preferably 2.5 to 3.5% by weight, alpha-bergamothene 2 to 4.5% by weight, preferably 2.5 to 4% by weight, methyl anthranilate in the range of 1.5 to 3.5% by weight, preferably 2 to 3% by weight,
  • benzyl benzoate 0.5-1.2 wt% of isopropyl myristate Benzyl salicylate, 0.5-0.8 wt%, methyl benzoate 0.25-0.55 wt%, geraniol 0.2-0.45 wt%, benzyl acetate 0.5-3.5 wt%, preferably 1.5-3.0 wt%, More preferably, it can contain in 2.0 to 3.0weight% of a range.
  • Benzaldehyde, indole, phenethyl alcohol, benzyl alcohol, methyl palmitate, alpha-vergamothene and methyl anthranilate and benzyl acetate which are the main components for reproducing the scent of rounded clove flowers. It is not preferable because the smell similarity with the round clove flower is lowered, and the palatability of the smell is lowered.
  • other secondary components such as benzophenone, methyl salicylate, phenylacetaldehyde, benzyl benzoate, isopropyl myristate, benzyl salicylate, methyl benzoate and geraniol are recommended to be used within the above range.
  • it may be contained in an amount outside the range as long as it does not affect the reproduction of the round clove flower fragrance.
  • this invention relates to the external composition for skin containing the said fragrance composition.
  • the fragrance composition according to the present invention can be formulated into external skin bases such as perfumes, cosmetics, fragrances, and the like, and the blending amount can be appropriately selected and blended in order to achieve a desired effect in accordance with techniques conventional in the art.
  • Examples of the external preparations according to the present invention include, but are not limited to, ointments, lotions, soluble burns, suspensions, emulsions, creams, gels, sprays, powders, warning agents, patches or water pastes. It can be blended into any external agent well known in the art.
  • the SPME method can be used as an analysis method for the odor component of the round clove flower in the present invention.
  • the SPME method analyzes the odor component of the highly volatile rounded clove flower because the odor components adsorbed on the fiber can be quickly desorbed and injected into the GS-MS column without special pretreatment. It is advantageous to In addition, the SPME method is simpler and easier to concentrate than the conventional pretreatment method, and can reduce the incidence of sample contamination and by-products because the organic solvent is not used regardless of the form of the matrix. There is an advantage that can increase the reliability.
  • a combination fragrance was prepared based on the fragrance component of the round clove flower analyzed by the SPME method, and similarity with the round clove flower fragrance and palatability were performed through olfactory sensory test.
  • the sensory test was conducted by professional stewards and the general public, and the similarity with the scent of rounded clove flowers and palatability were evaluated by questionnaire.
  • the fragrance was collected by adsorbing the fragrance component on the fiber (Polyacrylate Fiber) coated with 85 ⁇ m polyacrylate for 2 hours. Collection took place for 3 hours.
  • the fiber After collecting the odor component, the fiber (Fiber) was sealed, it was transferred to the inlet of GC-MS, and then desorbed for 2 minutes, and GC-MS analysis was performed.
  • GC-MS analysis conditions are as follows.
  • benzaldehyde, benzyl alcohol, phenethyl alcohol, indole, methyl palmitate, alpha-bergamothene and methyl anthranilate are the main odorants, and these main ingredients are 69.05 weight in total. It was confirmed that it occupies%.
  • Example B a newly prepared combination fragrance having the composition of Table 2 was prepared, and the fragrance similarity between the fragrance and natural round clove flower pot (sample A) was verified through sensory evaluation. .
  • Sample B a combination fragrance, was found to have a lot of difference with the scent of the round clove flower pot, and it was confirmed that the palatability was low.
  • the fragrance composition artificially formulated with the components analyzed by the SPME method was very similar to the odor collected directly from the round clove flower pot.
  • the expert evaluation group composed of steering yarns performed sensory evaluation on the respective flavor components of the round clove flower.
  • benzaldehyde which produces fruity scent among the scents of round clove flowers
  • benzyl alcohol which produces fruity floral scent
  • pale which produces rose floral scent.
  • Netyl alcohol indole to create an animalic scent
  • methyl palmitate to produce a waxy scent
  • alpha-bergamomten to produce a woody scent
  • sweet fruity scent The seven components of methyl anthranilate to produce the main ingredient was confirmed to produce the unique odor of the round clove flower.
  • the main component of the original flavor of the round clove flower is composed of benzaldehyde, benzyl alcohol, phenethyl alcohol, indole, methyl palmitate, alpha- bergamoten and methyl anthranilate. Therefore, the present inventors prepared the new combination fragrances of # 1 to # 4, as shown in Table 5, in order to prepare a fragrance with good palatability while containing the seven components of the round clove flower as it is.
  • Combination fragrances # 1 to # 4 were prepared by varying the total content of these seven main components to 80-95 wt% (unit: wt%). Specific compositions are shown in Table 5 below.
  • Example 2 The four fragrances (# 1 to # 4) of Example 1, which were newly combined, were subjected to sensory evaluation in the same manner as in Test Example 1 in order to examine the similarity and palatability with the round clove aroma. On the other hand, after conducting the comparative sensory evaluation of the two combination flavors, a 5-minute rest period was given so that there was no post-sensory paralysis. The results of sensory evaluation on the smell similarity and palatability of the new combination fragrance and round clove flower are shown in Table 6 below.
  • the content standard of benzyl acetate was set at the discretion of the expert group of the steering company, and the content of benzyl acetate was 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%
  • the other ingredients were adjusted to adjust the total content 100 according to the change in the content of benzyl acetate.
  • the composition of these recombinant flavors is shown in Table 7 below.
  • Example 2 For the seven kinds of combination fragrances of Example 2 (# ga ⁇ # company), the sensory evaluation was carried out in the same manner as in Test Example 1 in order to find the taste similarity with the round clove flower and palatability. . On the other hand, after performing the comparative sensory evaluation of the two combination flavors, a 5 minute rest period was given, so that there was no post-sensory paralysis. The results of sensory evaluation on odor similarity and odor preference between the new combination perfume and the round clove flower are shown in Tables 9 and 10 below.
  • the fragrance similarity to the round clove flowers and the fragrance palatability are excellent, so the fragrance of the round clove flowers is reproduced well It could be confirmed (average 7.5 or more).
  • the perfume composition (sample #bar of Table 7) having similarity with the odor of the round clove flower was combined with an alcohol, water, a pigment, and a sunscreen to prepare a perfume of Table 12 below.
  • Perfume containing fragrance composition which reproduces fragrance of round clove flower Round Clove Flower Fragrance Reproduction Combination Fragrance 15 wt% Alcohol 81 wt% water 2 wt% Pigment Quantity Sunscreen Quantity

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition aromatique reproduisant la fragrance de Syringa velutina var. kamibayashii et, plus spécifiquement, une composition aromatique reproduisant la fragrance de Syringa velutina var. kamibayashii, la composition aromatique ayant une excellente palatabilité par ajout d'acétate de benzyle à benzaldéhyde, indole, alcool phénéthylique (également connu sous le nom 2-phényléthanol), alcool benzylique, palmitate de méthyle, alpha-bergamotène et anthranilate de méthyle, qui sont analysés en tant que composants de fragrance de Syringa velutina var. Kamibayashii au moyen d'un procédé de microextraction sur phase solide (SPME). La composition aromatique selon la présente invention peut reproduire la fragrance de Syringa velutina var. kamibayashii et améliorer la palatabilité au parfum, en contenant, conjointement avec de l'acétate de benzyle, des composants principaux pour la fragrance de Syringa velutina var. kamibayashii, tel que benzaldéhyde, indole, alcool phénéthylique, alcool benzylique, palmitate de méthyle, alpha-bergamotène, et anthranilate de méthyle.
PCT/KR2017/012722 2016-11-24 2017-11-10 Composition aromatique reproduisant la fragrance de syringa velutina var. kamibayashii WO2018097524A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2016-0157245 2016-11-24
KR20160157245 2016-11-24
KR1020170148788A KR102213993B1 (ko) 2016-11-24 2017-11-09 둥근정향나무꽃의 향취를 재현한 향료 조성물
KR10-2017-0148788 2017-11-09

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112226280A (zh) * 2020-10-09 2021-01-15 湖北中烟工业有限责任公司 一种基于桂花关键香气成分的香料及其在卷烟中的应用
CN115524435A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种市售公丁香中印尼公丁香含量的检测方法
CN115524437A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种基于gc-ms对国内外公丁香进行产地判定的方法
CN115524438A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种基于hs-spme-gc-ms分析市售丁香中公丁香含量的方法
CN115968258A (zh) * 2020-08-25 2023-04-14 高砂香料工业株式会社 碳酸饮料、香料组合物的制备方法、碳酸饮料的起泡抑制方法
CN115524437B (zh) * 2022-10-11 2024-07-05 云南中烟工业有限责任公司 一种基于gc-ms对国内外公丁香进行产地判定的方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19980075750A (ko) * 1997-04-01 1998-11-16 서경배 섬개회나무꽃 추출물을 함유하는 방향제 조성물
KR20090044112A (ko) * 2007-10-31 2009-05-07 주식회사 코리아나화장품 천연 백합향을 이용하여 백합의 향취를 재현한 향료 조성물
KR20150056185A (ko) * 2013-11-15 2015-05-26 (주)아모레퍼시픽 풍란의 향취를 재현한 향료 조성물
KR20160028775A (ko) * 2014-09-04 2016-03-14 주식회사 엘지생활건강 향료 조성물
KR20160097767A (ko) * 2015-02-10 2016-08-18 주식회사 엘지생활건강 향료 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19980075750A (ko) * 1997-04-01 1998-11-16 서경배 섬개회나무꽃 추출물을 함유하는 방향제 조성물
KR20090044112A (ko) * 2007-10-31 2009-05-07 주식회사 코리아나화장품 천연 백합향을 이용하여 백합의 향취를 재현한 향료 조성물
KR20150056185A (ko) * 2013-11-15 2015-05-26 (주)아모레퍼시픽 풍란의 향취를 재현한 향료 조성물
KR20160028775A (ko) * 2014-09-04 2016-03-14 주식회사 엘지생활건강 향료 조성물
KR20160097767A (ko) * 2015-02-10 2016-08-18 주식회사 엘지생활건강 향료 조성물

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115968258A (zh) * 2020-08-25 2023-04-14 高砂香料工业株式会社 碳酸饮料、香料组合物的制备方法、碳酸饮料的起泡抑制方法
CN112226280A (zh) * 2020-10-09 2021-01-15 湖北中烟工业有限责任公司 一种基于桂花关键香气成分的香料及其在卷烟中的应用
CN115524435A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种市售公丁香中印尼公丁香含量的检测方法
CN115524437A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种基于gc-ms对国内外公丁香进行产地判定的方法
CN115524438A (zh) * 2022-10-11 2022-12-27 云南中烟工业有限责任公司 一种基于hs-spme-gc-ms分析市售丁香中公丁香含量的方法
CN115524437B (zh) * 2022-10-11 2024-07-05 云南中烟工业有限责任公司 一种基于gc-ms对国内外公丁香进行产地判定的方法

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