WO1996018710A1 - Composition de parfum - Google Patents

Composition de parfum Download PDF

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Publication number
WO1996018710A1
WO1996018710A1 PCT/JP1995/002478 JP9502478W WO9618710A1 WO 1996018710 A1 WO1996018710 A1 WO 1996018710A1 JP 9502478 W JP9502478 W JP 9502478W WO 9618710 A1 WO9618710 A1 WO 9618710A1
Authority
WO
WIPO (PCT)
Prior art keywords
menthol
dimethyl
composition
perfume composition
methyl
Prior art date
Application number
PCT/JP1995/002478
Other languages
English (en)
Japanese (ja)
Inventor
Toshiya Shimada
Kiyohiko Imaoka
Tetsuo Gomi
Original Assignee
Lion 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
Application filed by Lion Corporation filed Critical Lion Corporation
Publication of WO1996018710A1 publication Critical patent/WO1996018710A1/fr

Links

Classifications

    • 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
    • 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
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

Definitions

  • the present invention enhances the refreshing sensation of 1-menthol by using a combination of I-menthol and a compound for enhancing the refreshing sensation, and enhances the refreshing sensation.
  • the present invention relates to a fragrance composition which imparts expression and diffusion properties and further enhances the fragrance and taste.
  • 1-menthol can provide a certain degree of refreshing sensation, but is added in a large amount to enhance the refreshing sensation and improve the expression On the contrary, there was a problem of causing bitterness and irritation.
  • the present invention has been made in view of the above circumstances, and is intended to be used in an oral composition containing 1-menthol, for example, to provide a refreshing ⁇ RCO feeling with 1-menthol.
  • the purpose of the present invention is to provide a fragrance composition that can enhance the sensation and diffusion of the refreshing sensation and improve the flavor and taste, etc. .
  • the present inventors have conducted intensive studies in order to achieve the above-mentioned object, to enhance the cooling sensation of 1-menthol, and to improve the expression of the cooling sensation.
  • the compounds represented by 1) to (4) are used in combination with 1-menthol, the cooling sensation of 1-menthol is enhanced, the expression and diffusibility are improved, and the fragrance is further improved. It has been found that an unexpected effect of enhancing the overall flavor and taste is produced, and the present invention has been accomplished.
  • R ′ is a carbon number
  • R 2 and R 3 are Each represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 3 carbon atoms.
  • the fragrance composition according to the present invention includes, for example, oral compositions such as dentifrices, mouthwashes, mouth fresheners, foods and drinks such as chewing gum, candies, troches and the like. Or shampoos, rinses, hair tonics, stones, cosmetics, and other perfumes or fragrances that provide a refreshing feeling to the scalp It is a combination of 11-menthol and the above-mentioned enhancing compound.
  • the I-menthol used in the present invention may be one isolated from an essential oil of a plant or the like, or one synthesized, and
  • Essential oils containing 1-menthol such as mint oil
  • mint oil can be used as they are. It is a mini down bets oil, Japanese species Tsu force, oil (J apanese M int O il) , Bae Nono 0 seemingly emissions preparative oil (P eppermint 0 i 1, M itcham P eppermint O il, E nglish B lack Mint Oil and English White Mint 0 i 1).
  • the above mint oil may be used singly or in combination of two or more, and may be used in combination with isolated or synthetic 1-methyl. Good.
  • the amount of 1-menthol should be 1 to 60% (% by weight, hereinafter the same), especially 10 to 50% of the whole fragrance composition. Is preferred. If the 1-menthol is less than 1%, a sufficient refreshing feeling may not be obtained, and if it is more than 60%, 1-menthol may be introduced into the oral cavity. May cause bitterness and irritation.
  • the potentiating compounds used in the present invention are ketones, alcohols, furans and pinenes represented by the following formulas (1) to (4): One of these can be used alone, or two or more can be used in combination.
  • R ′ is a monovalent hydrocarbon group having 1 to 5 carbon atoms, particularly a methyl group, an ethyl group, and an n-propyl group.
  • R 2 and R 3 are preferably a hydrogen atom or a monovalent hydrocarbon group having 1 to 3 carbon atoms, particularly a methyl group, An ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group and the like are preferably used.
  • the amount of the enhancing compound used in the present invention is not necessarily limited, but the mixing ratio of 1-methyl to the enhancing compound is 1: 0.00 by weight ratio. It is preferred that they are blended so as to be in the range of 1 to 1: 0.1, particularly 1: 0.05 to 1: 0.05. If the compounding ratio is less than 1: 0.0001, the effect of improving the refreshing feeling may not be sufficiently obtained, and if the mixing ratio is larger than 1: 0.1, the refreshing feeling may be sufficiently obtained. May cause unpleasant odor and smell.
  • the perfume composition of the present invention enhances the cooling sensation of I-menthol by using 1-menthol in combination with the above-mentioned compound for enhancing the cooling sensation. It enhances the diffusibility and the diffusivity, and enhances the flavor and overall taste of the perfume composition.
  • the perfume composition of the present invention further includes other essential oils and perfume materials, for example, Spare Mint, Avies, Anise, Nose, Bey, Fan , Caraway, Card, Power, Damon, Katsushia, Shinnamon, Clove, Corianda, and Stragon, Eucalyptus, Fennennole, Fair's Needle, Grape Fenole, Lorenole, Lemon, Lemon Glass, Mandolin, Majoram, Mace, Melissa, Orange, Origanum, Pigment, No.
  • Spare Mint Spare Mint, Avies, Anise, Nose, Bey, Fan , Caraway, Card, Power, Damon, Katsushia, Shinnamon, Clove, Corianda, and Stragon
  • Eucalyptus Fennennole
  • Fair's Needle Grape Fenole, Lorenole, Lemon, Lemon Glass, Mandolin, Majoram, Mace, Melissa, Orange, Origanum, Pigment, No.
  • the fragrance composition of the present invention is suitably used for oral compositions such as dentifrices, mouthwashes, mouth fresheners, foods and drinks, and cosmetics.
  • oral compositions such as dentifrices, mouthwashes, mouth fresheners, foods and drinks, and cosmetics.
  • it imparts an excellent refreshing sensation, its expression and diffusibility, and also has an excellent effect of enhancing the overall aroma and taste.
  • the compound for enhancing 3-methyl-2-butanone was added to the peppermint oil (1-menthol content of 50% by weight) at various compounding levels in the compounding amounts shown in Table 1. And a five-point evaluation method. Sensory evaluation was performed. The results are shown in Table 2.
  • Fragrance compositions 1 and 2 having the following composition were prepared and blended with an oral composition (toothpaste) having the composition shown below.
  • Peppermint oil (1-Menthol content 40% by weight)
  • E 3 — Methyl 1-Pen No. 0.3
  • F 2,4-Dimethyl 1 3—Pentano 0.3
  • G 2, 5—Dimethyl ⁇ ⁇ 5 ⁇ 5 ⁇ ⁇ ⁇
  • each oral composition perfume composition 1 (including the enhancing compounds A to I) and perfume composition 2 (without the enhancing compound)) (100% by weight) was added.
  • 10 toothpastes were used to evaluate the refreshing sensation, the refreshing sensation, the diffusivity, and the intensity of the flavor by a panel of 10 experts. Table 3 shows the results.
  • Perfume composition 1 is better 10 9 What to use 8
  • fragrance composition 1 It is assumed that there is no difference between them 3 2 2 2 It is better to use fragrance composition 1
  • the oral composition containing the fragrance composition combined with the enhancing compound of the present invention is compared with the composition without the enhancing compound.
  • a significant difference was observed in the sensory test, and it was confirmed that the sensory substance gave an excellent refreshing feeling.
  • the following describes the fragrance composition of the present invention with various oral compositions,
  • Mint oil 0 3 Spare mint oil 0 0 5 Fan oil 0 0 2 Strobery free 0 0 1

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)

Abstract

L'invention concerne une composition de parfum comprenant une combinaison de l-menthol avec un ou plusieurs potentialisateurs ayant les formules générales (1) à (4). Dans ces formules, R1 représente un groupe hydrocarboné monovalent en C¿1?-C5, et R?2 et R3¿ représentent chacun un hydrogène ou un groupe hydrocarboné monovalent en C¿1?-C3. La composition convient à des préparations destinées à l'hygiène buccale telles que les dentifrices, les collutoires et les solutions rafraîchissantes, ainsi qu'à des aliments, des boissons, des cosmétiques, etc. Elles confèrent une excellente fraîcheur, elles ont la propriété de développer et de diffuser la fraîcheur et elles se comportent également comme des potentialisateurs de l'arôme et du goût.
PCT/JP1995/002478 1994-12-12 1995-12-05 Composition de parfum WO1996018710A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6/332147 1994-12-12
JP33214794A JP3417106B2 (ja) 1994-12-12 1994-12-12 香料組成物

Publications (1)

Publication Number Publication Date
WO1996018710A1 true WO1996018710A1 (fr) 1996-06-20

Family

ID=18251676

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/002478 WO1996018710A1 (fr) 1994-12-12 1995-12-05 Composition de parfum

Country Status (4)

Country Link
JP (1) JP3417106B2 (fr)
CN (1) CN1062301C (fr)
MY (1) MY121554A (fr)
WO (1) WO1996018710A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7632790B2 (en) 2004-03-15 2009-12-15 Givaudan S.A. Trisubstituted furans suitable for the preparation of fragrance compositions
AU2013274406B2 (en) * 2012-06-11 2017-02-02 The Cleveland Clinic Foundation Treatment and prevention of cardiovascular disease and thrombosis

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1202982B1 (fr) * 1999-07-22 2003-11-26 Firmenich Sa Preparation d'une lactone beta,gamma-insaturee et son utilisation a titre d'ingredient aromatisant et parfumant
JP4916103B2 (ja) * 2004-09-30 2012-04-11 小川香料株式会社 冷感増強剤
JP4996048B2 (ja) * 2004-09-30 2012-08-08 小川香料株式会社 感覚刺激増強剤
JP4679132B2 (ja) * 2004-12-20 2011-04-27 小川香料株式会社 炭酸飲料用添加剤
JP5171104B2 (ja) * 2007-05-07 2013-03-27 花王株式会社 口腔用組成物
CN104704093B (zh) * 2012-10-08 2017-09-01 帝斯曼知识产权资产管理有限公司 香味和芳香配制物(v)
EP3658109B1 (fr) * 2017-12-21 2022-12-07 Firmenich SA Compositions de refroidissement et d'amplification d'arôme

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS509863B1 (fr) * 1970-07-27 1975-04-16
JPS63267253A (ja) * 1987-04-27 1988-11-04 Taiyo Koryo Kk 香料組成物
JPH01261327A (ja) * 1988-04-13 1989-10-18 Taiyo Koryo Kk 香料組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS509863B1 (fr) * 1970-07-27 1975-04-16
JPS63267253A (ja) * 1987-04-27 1988-11-04 Taiyo Koryo Kk 香料組成物
JPH01261327A (ja) * 1988-04-13 1989-10-18 Taiyo Koryo Kk 香料組成物

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7632790B2 (en) 2004-03-15 2009-12-15 Givaudan S.A. Trisubstituted furans suitable for the preparation of fragrance compositions
AU2013274406B2 (en) * 2012-06-11 2017-02-02 The Cleveland Clinic Foundation Treatment and prevention of cardiovascular disease and thrombosis
US10064830B2 (en) 2012-06-11 2018-09-04 The Cleveland Clinic Foundation Treatment and prevention of cardiovascular disease and thrombosis

Also Published As

Publication number Publication date
MY121554A (en) 2006-02-28
CN1062301C (zh) 2001-02-21
JPH08157862A (ja) 1996-06-18
CN1169748A (zh) 1998-01-07
JP3417106B2 (ja) 2003-06-16

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