WO2012064099A2 - Composition d'arômes reproduisant la fragrance du citrus unshiu de l'île de jeju, et composition la contenant pour application externe à la peau - Google Patents

Composition d'arômes reproduisant la fragrance du citrus unshiu de l'île de jeju, et composition la contenant pour application externe à la peau Download PDF

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Publication number
WO2012064099A2
WO2012064099A2 PCT/KR2011/008501 KR2011008501W WO2012064099A2 WO 2012064099 A2 WO2012064099 A2 WO 2012064099A2 KR 2011008501 W KR2011008501 W KR 2011008501W WO 2012064099 A2 WO2012064099 A2 WO 2012064099A2
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WIPO (PCT)
Prior art keywords
composition
fragrance
citrus
jeju island
weight
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Application number
PCT/KR2011/008501
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English (en)
Korean (ko)
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WO2012064099A3 (fr
Inventor
최지영
고승호
서형제
Original Assignee
주식회사 아모레퍼시픽
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.)
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Application filed by 주식회사 아모레퍼시픽 filed Critical 주식회사 아모레퍼시픽
Priority to CN201180054414.7A priority Critical patent/CN103260634B/zh
Priority to JP2013538637A priority patent/JP5972893B2/ja
Publication of WO2012064099A2 publication Critical patent/WO2012064099A2/fr
Publication of WO2012064099A3 publication Critical patent/WO2012064099A3/fr
Priority to HK14100166.2A priority patent/HK1186990A1/xx

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/75—Rutaceae (Rue family)
    • A61K36/752—Citrus, e.g. lime, orange or lemon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • C11B9/0007—Aliphatic compounds
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0092—Heterocyclic compounds containing only N as heteroatom

Definitions

  • the present invention relates to a fragrance composition reproducing the fragrance of citrus unshiu Jeju Island and a skin external composition containing the same, more specifically, methyl in the Jeju island citrus fragrance component analyzed by the SPME method (Solid Phase Micro Extraction)
  • the present invention relates to a fragrance composition prepared by adding anthranilate (Methyl anthranilate) to reproduce Jeju Island citrus fruit intact and having excellent palatability, and a composition for external preparation for skin containing the same.
  • citrus fruits refers to plants belonging to the citrus (Citrus), Fortunella (Poncirus) and the genus (Poncirus) of the Rutaceae Auranti- oideae.
  • Citrus plants are found in Southeast Asia and its surrounding islands, including India and China, in Australia and in Africa, and are not present in continental Europe or in the continents of North and South America. Korea is located in the northernmost part of the world's citrus cultivation area, and the southern coast of the Korean peninsula, including Jeju Island, Tongyeong, Geoje, and Namhae, is the main producing region.
  • Citrus tree is an evergreen broad-leaved small arbor, leaf is regenerated, lanceolate or broad lanceolate, blunt, basal, 5-7 cm long, 5 cm wide, with flat edges or wave-shaped serrates, with or without leafy wings.
  • Stems are straight, but branched, bark brown, finely divided, without thorns on branches.
  • Fruits are spherical, 3-4 cm in diameter, ripened in orange or yellow red in October, and the rind is well separated from the flesh, and the center is empty and divided into 9-10 threads.
  • the outer shell is smooth and glossy.
  • the fruit is edible, and the rind is called dermis in one shot and is used for colds. Flowers are white, bloomed and discharged from May to June, and they are single, and the flowers are 2cm long and have a characteristic dark fragrance.
  • the present inventors analyzed the fragrance components by the SPME method to reproduce the fragrance of the citrus flowers of Jeju Island, Myrcene, phenylacetaldehyde oxime and Indole are the main components Found.
  • the inventors of the present invention while the fragrance composition containing methyl anthranilate, the main component of the Jeju Island citrus scent and the characteristic fragrance component representing the Jeju citrus flowers, can reproduce the intrinsic scent of the Jeju citrus flowers as it is It discovered that palatability was excellent and completed this invention.
  • Another object of the present invention is to provide an external preparation for skin containing the perfume composition.
  • citrus Jeju citrus fruits containing 60 to 70% by weight of the odor component consisting of Myrcene, Phenylacetaldehyde oxime and Indole with respect to the total weight of the composition
  • the odor component consisting of Myrcene, Phenylacetaldehyde oxime and Indole with respect to the total weight of the composition
  • a perfume composition that reproduces the scent of flowers.
  • the fragrance composition according to the present invention contains the main component of the Jeju Island citrus scent analyzed by SPME method in a specific content, and by further adding methyl anslanylate to it, the inherent scent of the citrus flower of Jeju could be reproduced as it is, and the scent could also improve the palatability.
  • the SPME method Solid Phase Micro Extraction; SUPELCO international, Vol. 13, No. 4, p. 9-10
  • SUPELCO international, Vol. 13, No. 4, p. 9-10 was used to analyze the odor component of citrus flowers in Jeju Island.
  • the SPME method does not use a solvent and does not require pretreatment, so that the perfume component can be analyzed quickly and simply.
  • the SPME method analyzes the odor component of citrus flowers of Jeju Island, which has high volatility, 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.
  • a combination fragrance was formed, and the similarity with the citrus flowers of Jeju Island citrus flavor and palatability of the fragrance was performed through the olfactory sensory test.
  • the sensory test was conducted by a professional steward and a general public.
  • the similarity with the citrus scent of Jeju Island and the taste of scent were evaluated by questionnaire.
  • the present invention provides a fragrance composition reproducing the fragrance of the citrus flowers of Jeju island by containing the fragrance component and methyl anthranilate as an essential component of the Jeju citrus flowers.
  • the perfume composition according to the present invention preferably contains 22 to 42 wt% of myrcene, 11 to 31 wt% of phenylacetaldehyde oxime and 1 to 20 wt% of indole based on the total weight of the composition.
  • the fragrance composition according to the present invention may further enhance palatability by further adding methyl ansranilate, which is a characteristic fragrance component indicating that Jeju is a citrus fruit, to the main component of the citrus scent of Jeju island, wherein the methyl ansranilate is a total composition 5 to 25% by weight, more preferably 10 to 20% by weight based on the weight.
  • methyl ansranilate which is a characteristic fragrance component indicating that Jeju is a citrus fruit
  • the fragrance composition according to the present invention may further include secondary fragrance components representing the fragrance of Jeju island citrus flowers in addition to the main component, for example, 2 to 22% by weight of the total weight of the composition, 2-phenylethyl 1 to 10% by weight of alcohol, 0.5 to 13% by weight of linalol and 0.01 to 11% by weight of geraniol.
  • secondary fragrance components representing the fragrance of Jeju island citrus flowers in addition to the main component, for example, 2 to 22% by weight of the total weight of the composition, 2-phenylethyl 1 to 10% by weight of alcohol, 0.5 to 13% by weight of linalol and 0.01 to 11% by weight of geraniol.
  • these secondary ingredients are preferably used within the above range, since they do not significantly affect the odor of the citrus flowers of Jeju Island, they may be contained in an amount outside the above range unless they affect the reproduction of the Jeju odor citrus odor. Can be.
  • the present invention also relates to a skin external preparation composition containing a fragrance composition that reproduces the Jeju island citrus odor.
  • the external preparation composition for skin according to the present invention may contain the perfume composition in an amount of 0.01 to 20% by weight based on the total weight of the composition.
  • the user When included in the skin external preparation composition in the range specified above, the user can recognize the fragrance similar to Jeju citrus flowers, can exhibit high palatability, and can also increase the persistence of the fragrance.
  • the external preparation composition for skin containing the perfume composition according to the present invention may include, for example, an ointment, a lotion, a soluble burn, a suspension, an emulsion, a cream, a gel, a spray, a pape, a warning, a patch or a water paste.
  • the present invention is not limited thereto, and may be blended with any base known in the art.
  • Jeju citrus flowers with strong scent were picked and the scent components were collected by adsorbing the scent components on a fiber coated with 85 ⁇ m polyacrylate fiber for 2 hours. The collection took place for three hours in Seogwipo City, Jeju Island.
  • 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.
  • Jeju citrus flowers contain myrcene, phenylacetaldehyde oxime and indole as the main odor component, it was confirmed that these main components occupy 65.26% by weight of the whole odor.
  • Example B a combination perfume (Sample B) having the composition of Table 2 was prepared (unit: wt%).
  • Example B The following sensory evaluation was carried out to investigate the similarity of the flavors of the combination drug prepared in Example 2 (Sample B) and natural Jeju Island citrus flowers.
  • the sensory evaluation was performed on 20 general men and women aged 20 to 45 years.
  • the sample A of the citrus flower pollen in Jeju island and the sample B of the combination perfume reproduced by the SPME method were in charge of each.
  • the taste similarity (question 1) and taste preference (question 2) of sample A and sample B were examined, and the results are shown in Table 4 below.
  • the combination perfume composition composed of the components analyzed by the SPME method did not have a similar smell with natural Jeju citrus flowers. Therefore, the professional evaluation group composed of the steering company performed sensory evaluation on each flavor component of the citrus flowers of Jeju Island. As a result, among the scents of the citrus flowers of Jeju Island, Mirsen, which produces sweet scent of sweet balsam, scent similar to phenylacetaldehyde oxime and jasmine, which can feel fresh floral scent Nae confirmed that the three components of indole are the main ingredients that create the unique scent of citrus flowers.
  • Combination fragrances # 1 to # 4 were prepared in the composition of Table 5 by changing the content of the three fragrances to 50 to 80% by weight while maintaining a constant ratio of these three components (unit: wt%).
  • Example 3 For the four combination fragrances prepared in Example 3, the sensory evaluation on the similarity and palatability with citrus fruit scent was carried out in the same manner as in Test Example 1. On the other hand, after conducting a comparative sensory evaluation of the two flavors, a 5-minute rest period was given so that there was no post-sensory paralysis. Sensory evaluation results on the taste similarity and palatability of the new combination perfume and citrus flowers are shown in Table 6 below.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract

Cette invention concerne une composition d'arômes reproduisant la fragrance du Citrus unshiu de l'île de Jeju, et une composition la contenant pour application externe à la peau. Plus particulièrement, cette invention concerne une composition d'arômes caractérisée en ce qu'un anthranilate de méthyle est ajouté aux ingrédients de fragrance du Citrus unshiu de l'île de Jeju, et en ce que les ingrédients de fragrance sont analysés par une technique de micro-extraction sur phase solide (SPME) de manière à reproduire la fragrance unique du Citrus unshiu de l'île de Jeju et à obtenir une préférence supérieure de la part des utilisatrices. Cette invention concerne également une composition contenant la composition selon l'invention pour application externe à la peau.
PCT/KR2011/008501 2010-11-12 2011-11-09 Composition d'arômes reproduisant la fragrance du citrus unshiu de l'île de jeju, et composition la contenant pour application externe à la peau WO2012064099A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201180054414.7A CN103260634B (zh) 2010-11-12 2011-11-09 再现济州岛柑橘花的香味的香料组合物及含有该组合物的皮肤外用组合物
JP2013538637A JP5972893B2 (ja) 2010-11-12 2011-11-09 済州島みかんの花の香りを再現した香料組成物及びこれを含有する皮膚外用剤組成物
HK14100166.2A HK1186990A1 (en) 2010-11-12 2014-01-08 Aroma composition whereby the fragrance of citrus unshiu of jeju island is reproduced, and composition containing same for external application to the skin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2010-0112880 2010-11-12
KR1020100112880A KR101799027B1 (ko) 2010-11-12 2010-11-12 제주도 감귤꽃의 향취를 재현한 향료 조성물 및 이를 함유하는 피부 외용제 조성물

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WO2012064099A2 true WO2012064099A2 (fr) 2012-05-18
WO2012064099A3 WO2012064099A3 (fr) 2012-07-19

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PCT/KR2011/008501 WO2012064099A2 (fr) 2010-11-12 2011-11-09 Composition d'arômes reproduisant la fragrance du citrus unshiu de l'île de jeju, et composition la contenant pour application externe à la peau

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JP (1) JP5972893B2 (fr)
KR (1) KR101799027B1 (fr)
CN (1) CN103260634B (fr)
HK (1) HK1186990A1 (fr)
WO (1) WO2012064099A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160084761A (ko) * 2015-01-06 2016-07-14 한국콜마주식회사 톱풀의 향취를 재현한 향료 조성물 및 이를 함유한 피부외용제 조성물
KR101843166B1 (ko) 2016-08-12 2018-03-29 (주)셀트리온 제주도 감귤 재배지의 공간향을 재현한 향료 조성물
CN110129133A (zh) * 2015-02-06 2019-08-16 爱茉莉太平洋股份有限公司 再现柑橘花类香气的香料组合物

Families Citing this family (5)

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KR20160094777A (ko) * 2015-02-02 2016-08-10 (주)아모레퍼시픽 무화과의 향취를 재현한 향료 조성물
JP2016160200A (ja) * 2015-02-27 2016-09-05 馬路村農業協同組合 柚子花精油及び化粧料用香料並びに化粧料
WO2017142279A1 (fr) * 2016-02-15 2017-08-24 (주)셀트리온 Composition aromatique reproduisant des parfums locaux de diverses régions
KR102428986B1 (ko) * 2016-04-29 2022-08-04 (주)아모레퍼시픽 백련꽃의 향취를 재현한 향료 조성물
JP6974041B2 (ja) * 2017-06-06 2021-12-01 サッポロビール株式会社 飲料、飲料ベース、飲料の製造方法、飲料ベースの製造方法、及び、オレンジフラワー様の香気の付与方法

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EP0993302B1 (fr) * 1997-06-23 2006-11-02 Naturex Inc. Compositions aromatisees aux agrumes, stables en conservation, renfermant des extraits de plantes
JP2009203438A (ja) * 2008-02-29 2009-09-10 T Hasegawa Co Ltd 柑橘香味増強剤

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JP4711336B2 (ja) * 2005-09-06 2011-06-29 曽田香料株式会社 香粧品用香料組成物
KR100645879B1 (ko) * 2005-11-10 2006-11-14 (주)아모레퍼시픽 녹차꽃의 향취를 재현한 향료 조성물
KR101234024B1 (ko) * 2006-10-31 2013-02-19 (주)아모레퍼시픽 백매화의 향취를 재현한 향료 조성물
KR101438368B1 (ko) * 2007-11-19 2014-09-12 (주)아모레퍼시픽 인삼꽃의 향취를 재현한 향료 조성물

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EP0993302B1 (fr) * 1997-06-23 2006-11-02 Naturex Inc. Compositions aromatisees aux agrumes, stables en conservation, renfermant des extraits de plantes
JP2004168936A (ja) * 2002-11-21 2004-06-17 Kiyomitsu Kawasaki シトラス様香料組成物
JP2005075881A (ja) * 2003-08-29 2005-03-24 T Hasegawa Co Ltd 香料組成物
JP2009203438A (ja) * 2008-02-29 2009-09-10 T Hasegawa Co Ltd 柑橘香味増強剤

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160084761A (ko) * 2015-01-06 2016-07-14 한국콜마주식회사 톱풀의 향취를 재현한 향료 조성물 및 이를 함유한 피부외용제 조성물
KR101669664B1 (ko) 2015-01-06 2016-10-28 한국콜마주식회사 톱풀의 향취를 재현한 향료 조성물 및 이를 함유한 피부외용제 조성물
CN110129133A (zh) * 2015-02-06 2019-08-16 爱茉莉太平洋股份有限公司 再现柑橘花类香气的香料组合物
KR101843166B1 (ko) 2016-08-12 2018-03-29 (주)셀트리온 제주도 감귤 재배지의 공간향을 재현한 향료 조성물

Also Published As

Publication number Publication date
JP2013543863A (ja) 2013-12-09
JP5972893B2 (ja) 2016-08-17
WO2012064099A3 (fr) 2012-07-19
CN103260634A (zh) 2013-08-21
KR20120051443A (ko) 2012-05-22
CN103260634B (zh) 2015-08-19
HK1186990A1 (en) 2014-03-28
KR101799027B1 (ko) 2017-11-21

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