JP2002114990A - Perfume composition and cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a perfume composition which excels in a liking to be reminded of the sea and a method for utilizing the composition. SOLUTION: The perfume composition comprises at least one selected from the group consisting of 3-octanone, 5-propyl-5-hydroxy-3,4-dimethyl-2(5H)- furanone, methanes containing two or more bromine atoms, and the compounds to be represented by the general formula (wherein R1 is a hydrogen atom or a methyl group; and R2, R3, and R4 are each independently hydrogen or bromine).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to 3-octanone,
5-propyl-5-hydroxy-3,4-dimethyl-2
(5H) -furanone, methanes containing two or more bromine atoms, and the following general formula (1)

[0002]

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(Wherein R ¹ represents a hydrogen atom or a methyl group,
R ² , R ³ and R ⁴ each independently represent a hydrogen atom or a bromine atom, and at least one is a bromine atom. The present invention relates to a marine-like perfume composition containing at least one selected from the group consisting of the compounds represented by the formula (1) and a cosmetic containing the perfume composition.

[0004]

2. Description of the Related Art With the recent diversification of the taste of fragrances, there has been an increasing tendency to seek softness, freshness, and naturalness, rather than seeking strong fragrances from fragrances. In particular, recently, people's desire for nature has increased, and demands for fragrances having high palatability, which characteristically image the natural environment, have increased, and development of fragrances having unprecedented new fragrances has been demanded.

Among them, in particular, since fragrances having a fragrance reminiscent of the sea have come to be touted, it is extremely important and important for the fragrance industry to develop and provide a fragrance material reminiscent of the sea. .

[0006] In Japanese Patent Publication No. 5-17960, 5,8,11-tetradecatrien-2-one has a fragrant flavor of seaweeds and fishware, is persistent, and has various flavor compositions. It is described that it is also useful as a modulating agent when incorporated in a product, and JP-A-61-53238 describes that 2-inals have a seaweed-like marine green aroma.

However, since 5,8,11-tetradecatrien-2-one and 2-inals are both expensive and difficult to obtain, they are inexpensive, easily obtainable, and practically valuable. A perfume composition is desired.

[0008]

SUMMARY OF THE INVENTION An object of the present invention is to provide a fragrance composition excellent in palatability reminiscent of the sea. Another object of the present invention is to provide a method for using such a fragrance composition.

[0009]

Means for Solving the Problems The present inventors have analyzed and studied the aroma of various things on the shore in order to meet the above-mentioned problems, and as a result, have found that 3-octanone, 5-propyl-5-
Hydroxy-3,4-dimethyl-2 (5H) -furanone, methanes containing two or more bromine atoms, and the following general formula (1)

[0010]

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(Wherein R ¹ represents a hydrogen atom or a methyl group;
R ² , R ³ and R ⁴ each independently represent a hydrogen atom or a bromine atom, and at least one is a bromine atom. The inventors have found that the compound represented by the formula (1) has an aroma reminiscent of the sea and is excellent in palatability, and has completed the invention.

The present invention includes the following inventions. (1) 3-octanone, 5-propyl-5-hydroxy-3,4-dimethyl-2 (5H) -furanone, methanes containing two or more bromine atoms, and the following general formula (1)

[0013]

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(Wherein R ¹ represents a hydrogen atom or a methyl group;
R ² , R ³ and R ⁴ each independently represent a hydrogen atom or a bromine atom, and at least one is a bromine atom. A fragrance composition, particularly a marine-like fragrance composition, comprising at least one member selected from the group consisting of compounds represented by the formula (1):

(2) The fragrance composition according to the above (1), further comprising at least one component selected from the group consisting of an air-dispersed aroma substance of seaweed and an organic solvent extracted from seaweed. Particularly marine-like perfume compositions.

(3) A cosmetic comprising the fragrance composition according to the above item (1) or (2), particularly a marine-like fragrance composition.

(4) The above-mentioned cosmetics include aromatic cosmetics such as perfume, eau de toilette, and colons, cosmetics for hair such as shampoos, rinses, treatments, hair tonics, hair creams, pomades, creams and emulsions. (Milk), basic cosmetics such as lotion, facial cleansers, packs, makeup cosmetics such as white powder, foundation, lipstick, cosmetics such as body shampoo, soap, bath additive, fragrance, aromatic deodorant, deodorant, etc. The cosmetic according to the above (3), which is one selected from the group consisting of:

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION The marine-like fragrance composition referred to in the present invention refers to a fragrance composition having an aroma reminiscent of the sea.

The compounds used in the present invention are all known compounds and can be purchased or synthesized by known methods. For example, 3-octanone is sold by Aldrich Chemical Co., and disclosed in Japanese Patent Application Laid-Open No. 9-20646, hinokitiol, cedren, santalol, tuyopsen, terpineol, pinene, 1,8-cineole,
Bath fragrance compositions comprising one or more essential oil components of linalyl acetate are described, but no marine-like odor is described.

3,4-dimethyl-5-hydroxy-5-
Propyl-2 (5H) -furanone is synthesized from 2,3-dimethylmaleic anhydride (2) commercially available from Aldrich Chemical Co., for example, by applying the method disclosed in German Patent No. 1072629 as follows. it can.

[0021]

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[0022] DE-A-1072629 states that:
The fragrances of the compound (3) and the compound (4) are only described as butter-like and celery-like, and there is no description about the fragrance reminiscent of the sea. Further, J. Boldingh et al. (RECUEIL Magazine, 85
Vol. 43, 1966), German Patent No. 10
The substance described in 72629 is a mixture of compound (3) and compound (4), wherein the component relating to odor is compound (4), and compound (3) is described as being odorless;
There is no description about the flavor of the compound (3) of the present invention.

Methanes containing two or more bromine atoms or the following general formula (1)

[0024]

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(Wherein R ¹ represents a hydrogen atom or a methyl group;
R ² , R ³ and R ⁴ each independently represent a hydrogen atom or a bromine atom, and at least one is a bromine atom. ) Are also sold, and although there are many documents, they describe environmental substances and the like, and there is no report suggesting that the compound is used as a fragrance material or flavor characteristics.

Specific examples of the methane containing two or more bromine atoms used in the present invention include dibromomethane, tribromomethane, and tetrabromomethane. Tribromomethane is preferred in that it is available.

Specific examples of the compounds represented by the general formula (1) in the present invention of the above (1) to (3) include 2
-Bromoanisole, 3-bromoanisole, 4-bromoanisole, 2-bromophenol, 3-bromophenol, 4-bromophenol, 2,3-dibromophenol, 2,4-dibromoanisole, 2,5-dibromophenol, 2,6-dibromoanisole, 3,4-
Dibromophenol, 3,5-dibromoanisole,
2,3,4-tribromophenol, 2,3,5-tribromoanisole, 2,3,6-tribromoanisole, 2,4,5-tribromophenol, 2,4,6-
Tribromoanisole, 3,4,5-tribromophenol, and the like.

Among the compounds represented by the general formula (1) exemplified above, 2-bromophenol, 2-bromoanisole, , 4-dibromoanisole, or 2,
4,6-Tribromoanisole is preferred.

3-octanone, 5-propyl-5-hydroxy-3,4-dimethyl-2 (5H) -furanone, methanes containing two or more bromine atoms and the following general formula (1)

[0030]

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(Wherein R ¹ represents a hydrogen atom or a methyl group;
R ² , R ³ and R ⁴ each independently represent a hydrogen atom or a bromine atom, and at least one is a bromine atom. At least one or more components selected from the group consisting of the compounds represented by the following formulas (hereinafter, also collectively referred to as “components such as 3-octanone”) may be used by being added to various flavor compositions. it can.

The amount of 3-octanone is preferably in the range of 0.01 to 2.0% by mass based on the total amount of the fragrance composition. 5-propyl-5-hydroxy-3,4-dimethyl-2 (5
H) -Furanone is 0.01% based on the total amount of the fragrance composition
The range of -2.0 mass% is preferable. Methanes containing two or more bromine atoms are present in a proportion of 0.00
The range of 1 to 1.0% by mass is preferred. 2-bromophenol, 2-bromoanisole, 2,4-dibromoanisole, 2,4,6-tribromoanisole, other 3
The component such as -octanone is preferably in the range of 0.001 to 2.0% by mass based on the total amount of the fragrance composition. Further, these may be used in combination.

The fragrance composition of the present invention containing a component such as 3-octanone can be further added with a marine algae air-dispersed aroma substance component and a seaweed organic solvent extraction component to give a nuance reminiscent of the sea. In the present invention, the air-emitted odorant component of seaweed is an odorant emitted into the atmosphere from wet seaweed, and among the detected components, particularly limonene, camphene, elemol, p-cymene, Hexanal, heptanal, octanal, benzaldehyde, (E) -2-undecenal, indole, acetophenone and the like are preferred, but not limited to these substances.

In the present invention, the organic solvent extraction component of seaweed means an aroma component extracted by solvent from wet seaweed. Among the detected components, α-yonone and β-yonone are particularly preferable. , Carvone, menthol, menthol,
Amyl alcohol, isoamyl alcohol, benzyl alcohol, 2-phenylethanol, any aliphatic carboxylic acids having 2 to 18 carbon atoms, any aromatic carboxylic acids having 7 to 10 carbon atoms, and the like are preferable, but are not limited to these substances. Not something.

An arbitrary aliphatic carboxylic acid having 2 to 18 carbon atoms means a monocarboxylic acid having 2 to 18 carbon atoms having a linear, branched or alicyclic saturated or unsaturated aliphatic hydrocarbon group. Acids, specifically, acetic acid, propionic acid, n
-Butanoic acid, n-pentanoic acid, n-hexanoic acid, n-heptanoic acid, n-octanoic acid, n-nonanoic acid, n-decanoic acid, n-dodecanoic acid, n-tetradecanoic acid (myristic acid), n- Hexadecanoic acid (palmitic acid), n-octadecanoic acid (stearic acid), oleic acid, linoleic acid, linoleic acid, palmitoleic acid, 2-methylpropionic acid, 2-methylbutanoic acid butanoic acid, 2-methylpentanoic acid, 2-methyl Hexanoic acid, 2-methylheptanoic acid, 2-methyloctanoic acid, 2-methylnonanoic acid, 2-
Methyldecanoic acid, 2-methyldodecanoic acid, 2-methyltetradecanoic acid, 2-methylhexadecanoic acid, 2-ethylhexonic acid, 3-methylbutanoic acid, 3-methylpentanoic acid, 3-methylhexanoic acid, 3-methylhexylcarboxylic acid, Examples include cyclohexylacetic acid, but are not limited to these compounds.

The arbitrary aromatic carboxylic acids having 7 to 10 carbon atoms are carboxylic acids having 7 to 10 carbon atoms having a benzene ring, and specific examples thereof include benzoic acid and phenylacetic acid. However, the present invention is not limited to this compound.

The fragrance composition of the present invention comprising the above-mentioned components such as 3-octanone and at least one member selected from the group consisting of an air-dispersed odorous substance component of the seaweed and an organic solvent-extracted component of the seaweed is useful in various cosmetics It can be used by adding to the ingredients. The total amount of components selected from the air-dispersed aroma substance component and the organic solvent extractable component of seaweed in the fragrance composition of the present invention varies depending on the purpose or the type of the fragrance composition, and generally the fragrance composition Approx.
It can be used in a wide range from about 1 to about 99.9% by weight.

Thus, according to the present invention, it is possible to provide a novel fragrance composition, particularly a novel marine-like fragrance composition, which imparts aroma and flavor characteristics using the above-mentioned component such as 3-octanone as an active ingredient. Characterized by containing the composition, such as cosmetics and other external preparations for skin, such as perfume, eau de toilette, and aromatic cosmetics such as colons,
Hair cosmetics such as shampoos, rinses, treatments, hair tonics, hair creams, pomades,
Cream, emulsion (milk), lotion, face wash,
The present invention can provide basic cosmetics such as packs, make-up cosmetics such as white powder, foundation and lipstick, and cosmetics such as body shampoos, soaps, bath additives, aromatics, aromatic deodorants, and deodorants.

[0039]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. The measuring instruments and measuring conditions used in the reference examples are shown below.

(1) Gas chromatograph; equipment: HP-5890A (manufactured by Hewlett-Packard) Column: HP-20M (0.25 mm × 25 m) (manufactured by Hewlett-Packard) Carrier gas: helium Measurement temperature: 55 ° C. to 215 ° C. Detector: Flame ion detector (2) GC / MS analyzer Equipment: TRIO-1000 (manufactured by VG) Column: BC WAX (0.25 mm × 60 m) Carrier gas: Helium Measurement temperature: 70 ° C to 220 ° C (4 ° C / min heating)

Reference Example 1 (Collecting and Analyzing Aroma Substances Emitted from the Seaweed in the Atmosphere) Various wet seaweeds that had been launched on the rocks in the shallow waters of Tenjinjima Seaside Nature Education Center in Yokosuka City, Kanagawa Prefecture, were collected to collect odors. Into a Tedlar pack (Tokyo Deodorant Co.) for 4 hours at a flow rate of 100 ml / min. Of clean air, and a collection tube containing 400 mg of Tenax (Allteck Co.) for odorous substances emitted from the wet seaweed into the atmosphere. Collected on.
The odorous substances were eluted with diethyl ether and analyzed using a gas chromatograph and a GC / MS analyzer.
Shown in

Reference Example 2 (Collection and Analysis of Aroma Substances Emitted from Atmosphere of Seaweed) Six hours after collection of the seaweed used in Reference Example 1, it was placed in a Tedlar bag for collecting aroma, and clean air was supplied at a flow rate of 100.
The odorous substances emitted from the wet seaweed into the atmosphere were collected in a collection tube containing 400 mg of Tenax through 14 hours at 0 ml / min. Table 1 shows the results obtained by eluting the odorous substances with diethyl ether and analyzing them using a gas chromatograph and a GC / MS analyzer.

Reference Example 3 (Collection and Analysis of Components Extracted from Organic Solvents of Seaweed) 500 mg of the same seaweed as used in Reference Example 1 was extracted with 500 ml of diethyl ether, dehydrated, filtered, and the solvent was distilled off. Table 1 shows the results obtained by analyzing the diethyl ether extract of the aroma component extracted from fresh seaweed using a gas chromatograph and a GC / MS analyzer.

Reference Example 4 (Collection and Analysis of Components Extracted from Organic Solvents of Seaweed) 500 mg of the same seaweed as used in Reference Example 1 was added to pentane 5
The pentane extract of the aroma component extracted from the fresh seaweed obtained by extracting with 00 ml, dehydrating and filtering and then distilling off the solvent was analyzed using a gas chromatograph and a GC / MS analyzer, and the results are shown in Table 1. .

[0045]

[Table 1]

Examples 1 to 4 and Comparative Example 1 The fragrance compositions of Examples 1 to 4 and Comparative Example 1 were prepared by mixing and stirring the components according to the formulation in Table 2 below, and sensory evaluation was conducted by 10 panelists. Was done. Table 3 shows the results.

[0047]

[Table 2]

[0048]

[Table 3]

Example 5 (Fragrance for shampoo) A fragrance for shampoo having the following composition was produced by a conventional method.

[0050]

[Table 4]

Example 6 (Flavor for Bath Agent) A fragrance for bath agent having the following composition was produced by a conventional method.

[0052]

[Table 5]

Example 7 (Fragrance for soap) A flavor for soap having the following composition was produced by a conventional method.

[0054]

[Table 6]

Example 8 (Fragrance for fragrance) A fragrance for fragrance having the following composition was produced by a conventional method.

[0056]

[Table 7]

Example 9 (Bath agent) A bath agent was prepared by a conventional method according to the following formulation.

[0058]

[Table 8]

Example 10 (Shampoo) A shampoo was prepared by a conventional method according to the following formulation.

[0060]

[Table 9]

The bath preparation of Example 9 and the shampoo of Example 10 both had excellent sea-like scents.

[0062]

According to the present invention, it is possible to provide a fragrance composition that is inexpensive, easily available, practically valuable, and reminiscent of the sea that characteristically images the natural environment.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61K 7/46 311 A61K 7/46 311 315 315Z 331 331 355 355A 355E 355E 7/50 7/50 (72) Invention Person Mountain ▲ Saki ▼ Tetsuro 1-4-11 Nishi-Hachiman, Hiratsuka-shi, Kanagawa Prefecture Takasago International Co., Ltd. (72) Inventor Hisao Iwai 1-4-11, Nishi-Hachiman, Hiratsuka-shi, Kanagawa Takasago International Corporation Inside the Research Institute, Inc. (72) Masao Kubota, 5-28-3 Kotobukicho, Odawara-shi, Kanagawa Prefecture Kanebo Co., Ltd. Cosmetics Research Institute (72) Ryoichi Komagaki 5-3-28, Kotobukicho, Odawara-shi, Kanagawa Prefecture Kanebo Co., Ltd. Cosmetics Research Laboratory F-term (reference) 4C083 AA111 AA122 AB101 AB102 AC032 AC102 AC171 AC172 AC211 AC212 AC55 2 AC642 AC712 AC782 AC792 AC841 AC842 AD132 AD152 AD162 AD532 BB41 CC25 CC38 DD27 EE06 FF01 4H059 BA15 BA22 BA23 BA85 BB02 BB14 BB15 BB19 BB22 BB44 BB45 BC44 CA11 DA09

Claims (3)

[Claims] 1. A method comprising the steps of: (1) 3-octanone, 5-propyl-5-hydroxy-3,4-dimethyl-2 (5H) -furanone,
Methanes containing two or more bromine atoms and the following general formula (1) (Wherein, R ¹ represents a hydrogen atom or a methyl group; R ² , R ³ ,
R ⁴ each independently represents a hydrogen atom or a bromine atom, and at least one is a bromine atom. A fragrance composition comprising at least one member selected from the group consisting of compounds represented by the formula (1). 2. The fragrance composition according to claim 1, further comprising at least one component selected from the group consisting of an air-dispersed aroma substance of seaweed and an organic solvent extracted from seaweed. 3. A cosmetic comprising the fragrance composition according to claim 1 or 2.