JP2020050837A - Flavor improver - Google Patents

Abstract

To provide a novel flavor improver.SOLUTION: Provided is a flavor improver, comprising, as an active ingredient, one kind or two or more kinds selected from the group consisting of 3-methyl-2-furan acetic acid, 4-methyl-2-furan acetic acid, and 5-methyl-2-furan acetic acid. Also provided are: a perfume composition comprising the flavor improver in an amount of 0.01 ppb to 200 ppm as a total concentration of one kind or two or more kinds selected from the group consisting of 3-methyl-2-furan acetic acid, 4-methyl-2-furan acetic acid, and 5-methyl-2-furan acetic acid; foods and beverages having the same added in a concentration of 0.01ppb to 200ppb; and cosmetics having the same added in a concentration of 0.01ppb to 20 ppm.SELECTED DRAWING: None

Description

  The present invention relates to a flavor improving agent, and more specifically, one or two selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid. The present invention relates to a flavor improving agent containing at least one species as an active ingredient, and a flavor composition containing the same as an active ingredient.

  In recent years, consumers' demands for foods and drinks and cosmetics have become more sophisticated and diversified. In particular, attention has been paid to scents, and the characteristics of scents are important factors for the appeal of products. For example, there is an increasing demand for a flavor compound that can improve the flavor, for example, impart or enhance the persistence, natural feeling, volume feeling, ripening feeling, and the like to the flavor and taste by blending.

  Heretofore, various fragrance compounds capable of improving fragrance and flavor have been proposed.

  For example, furans to which the compound as the active ingredient of the flavor improving agent of the present invention belongs are known in many compounds exhibiting aroma, and methylfurfurals whose molecular weight and structure are close to those of the active ingredient of the present invention are beer flavor imparting agents. (Patent Document 1), fermented milk-like flavor composition (Patent Document 2), cocoa-like flavor composition (Patent Document 3), fruit-like flavor composition (Patent Document 4), spice flavor (Patent Document 5), and many others. Has been proposed for the incorporation of scents into compositions. Further, it has been proposed that a compound containing an acetic acid moiety contained in a compound as an active ingredient of the flavor improving agent of the present invention in a molecule is also incorporated into a flavor composition. As an example, phenylacetic acid is a beer flavoring agent ( A number of fragrance compositions have been proposed, such as Patent Document 1), a cocoa-like flavor composition (Patent Document 3), and a fruit-like flavor composition (Patent Document 4).

  However, development of a new flavor compound having a high flavor improving effect, which imparts a better flavor to consumer products and enables differentiation from the flavor of existing products, has been awaited.

  On the other hand, 3-methyl-2-furanacetic acid, which is an active ingredient of the present invention, is known as a synthetic material of a pharmaceutical compound (Patent Documents 6 and 7), and 4-methyl-2-furanacetic acid is 3-methyl-furanacetic acid. Similar to 2-furanacetic acid, it is known as a synthetic material for pharmaceutical compounds (Patent Documents 6 and 7) and a synthesis method (Non-Patent Document 1). 5-Methyl-2-furanacetic acid is a yeast autolysate. (Non-Patent Document 2), but it was not known at all that their odor characteristics and their use for improving flavor were also known.

JP-A-2005-027309 JP 2006-124490 A JP 2006-121958 A JP 2005-015686 A JP 2005-011382 A WO 99/16763 JP-A-04-235970

Synlett, 1993, (1), p. 40 Nahrung, 1979, 23 (7), p. 673-80

  An object of the present invention is to provide a novel flavor improving agent.

  The present inventors diligently searched for unknown useful fragrance compounds, and were selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid. One or more types have been found to be useful for improving various flavors.

Thus, the present invention provides the following.
[1] It is selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid represented by the following formulas (1) to (3), respectively. A flavor improving agent containing one or more kinds as an active ingredient.

[2] The flavor improving agent according to [1], which is one selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid, or A fragrance composition containing 0.01 ppb to 200 ppm as two or more concentrations.
[3] The flavor improving agent according to [1] or the flavor composition according to [2], using 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furan. A food or drink which is added at a concentration of 0.01 ppb to 200 ppb as a single concentration or a total concentration of two or more selected from the group consisting of acetic acid.
[4] The flavor improving agent according to [1] or the flavor composition according to [2], using 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furan. A cosmetic product which is added at a concentration of 0.01 ppb to 20 ppm as a single concentration or a total concentration of two or more selected from the group consisting of acetic acid.
[5] The flavor improving agent according to [1] or the flavor composition according to [2], using 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furan. A method for improving flavor of a food or drink, comprising adding at a concentration of 0.01 ppb to 200 ppb as a single concentration or a total concentration of two or more selected from the group consisting of acetic acid.
[6] The flavor improving agent according to [1] or the flavor composition according to [2], using 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furan. A method for improving the flavor of a cosmetic product, which comprises adding at a concentration of 0.01 ppb to 20 ppm as one concentration or a total concentration of two or more selected from the group consisting of furan acetic acid.

  According to the present invention, a novel flavor improving agent can be provided.

  Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited thereto. In this specification, “to” means a range including a lower limit and an upper limit, and the concentration represents a mass concentration unless otherwise specified.

(Flavor improver of the present invention)
Effective at least one or more selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid of the formula (1) of the present invention. The flavor improver contained as a component will be described in detail.

(3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid)
3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid, which are the active ingredients of the flavor improver of the present invention, have the following formulas (1), (2) and It is a compound represented by (3). Hereinafter, in this specification, they may be referred to as a 3-methyl form, a 4-methyl form and a 5-methyl form, respectively.

  3-Methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid themselves exhibit odors such as honey-like, flower-like, sweat-like, etc. By doing so, the flavor can be improved. For example, 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid are themselves as the flavor improver of the present invention or the active ingredient of the flavor improver of the present invention. In addition, it can be used in various articles as one kind or a mixture of two or more kinds to improve its flavor. The compounding object is not particularly limited, and examples thereof include consumer goods such as foods and drinks, cosmetics, and medical hygiene products. Furthermore, the 3-methyl form, the 4-methyl form and the 5-methyl form can be blended in various flavor compositions as one kind or a mixture of two or more kinds to improve the fragrance. As used herein, the term “flavor” refers to a sensation felt by a human when smelling an article and / or eating and drinking the article, and includes, for example, a sense sensed by smell, taste, or both. It shall be used in. In foods and drinks, it is sometimes called flavor.

(A method for obtaining 3-methyl-2-furanacetic acid of the formula (1))
The method for obtaining 3-methyl-2-furanacetic acid (3-methyl form) is not particularly limited, and for example, can be synthesized according to the following reaction route.

  That is, starting from 3-furanmethanol of the formula (4) as a starting material, Johnson-Claisen rearrangement is caused by the action of orthoacetate to obtain an ester compound of the formula (5), and then the ester compound of the formula (1) is obtained by ester hydrolysis. Can be obtained. The reaction conditions for Johnson-Claisen rearrangement and hydrolysis may be arbitrarily adjusted as long as the target compound is obtained. Hereinafter, specific examples will be described.

Johnson-Claisen rearrangement is usually performed under acidic conditions. As the acid, any known acid may be used. Examples thereof include phenol, propionic acid, pivalic acid, and an acidic cation exchange resin (eg, Diaion ^TM WK40L (Mitsubishi Chemical)), and a preferred example is phenol. But not limited thereto. The amount of the acid used may be arbitrarily adjusted according to the reaction time, the amount of the catalyst remaining in the reaction product, the amount of by-products, the yield, and the like. For example, the amount is usually per 1 mol of 3-furanmethanol of the formula (4). It can be in the range of 0.005 to 0.5 equivalent, preferably 0.01 to 0.1 equivalent. The amount of the orthoester used in this reaction is usually in the range of 1.0 to 5.0 equivalents, preferably 2.0 to 3.0 equivalents per 1 mol of 3-furanmethanol of the formula (4). be able to. Regarding the temperature conditions, this transfer reaction is usually performed under heating, and the specific temperature range depends on the nature of the solvent, but is usually in the range of 70 ° C to 180 ° C, preferably 90 ° C to 160 ° C. Is within. The reaction is usually completed within several hours. The reaction time may be determined while monitoring the progress of the reaction by gas chromatography, thin-layer chromatography, or the like. The ester compound of the formula (5) obtained by the Johnson-Claisen rearrangement may be purified, if necessary, by using a means such as column chromatography and vacuum distillation.

  The hydrolysis reaction is not particularly limited, and may be hydrolysis using an acid catalyst or hydrolysis using an alkali catalyst (saponification). The latter reaction, which is an irreversible reaction and does not require a large amount of water, is preferable. In the case of performing hydrolysis using an alkali catalyst, a carboxylate is first obtained.However, a solution containing the carboxylate can be converted to a carboxylic acid by adding an acid, for example, concentrated hydrochloric acid to lower the pH. it can. The reaction solvent is not particularly limited as long as it is inert to the ester compound of the formula (5) or the 3-methyl compound of the formula (1) and the reagent, which are the reaction substrates, and is soluble in these. In the case of hydrolysis using an acid catalyst, water can be used. In the case of hydrolysis using an alkali catalyst, generally, ethanol or hydrated ethanol which can also dissolve the carboxylate as a reaction product can be used. The used amount may be usually 2 to 50 times, preferably 10 to 30 times the weight of the ester compound of the formula (5). Although the amount of the reaction catalyst is also arbitrary, it can be used usually within a range of 1.0 to 5.0 equivalents, preferably 1.5 to 3.0 equivalents per 1 mol of the ester compound of the formula (5). . The temperature of the hydrolysis reaction is arbitrary as long as the hydrolysis reaction proceeds, but is generally performed while heating to increase the reaction rate to some extent. The reaction is usually completed within several hours. The reaction time may be determined while monitoring the progress of the reaction by gas chromatography, thin-layer chromatography, or the like. The 3-methyl form of the formula (1) obtained by this hydrolysis may be purified by means such as column chromatography and vacuum distillation as required.

(A method for obtaining 4-methyl-2-furanacetic acid of the formula (2))
The method for obtaining 4-methyl-2-furanacetic acid (4-methyl form) is not particularly limited, and examples thereof include Carling and Paul, Synlett, (1), p. 40 (1993).

(Method for obtaining 5-methyl-2-furanacetic acid of formula (3))
The method for obtaining 5-methyl-2-furanacetic acid (5-methyl form) is not particularly limited, and for example, can be synthesized according to the following reaction route.

  That is, using an aldehyde compound of the formula (6) as a starting material, an enol ether compound of the formula (7) is obtained by a known Wittig reaction, which is hydrolyzed under acidic conditions to obtain an aldehyde compound of the formula (8). And converting the aldehyde compound of the formula (8) into a carboxylic acid by oxidation to obtain a 5-methyl compound of the formula (3). Each reaction condition may be arbitrarily adjusted as long as the target compound is obtained. Hereinafter, specific examples will be described.

  The conditions and reagents for the Wittig reaction may be those usually employed. Although phosphorus ylide is not particularly limited, for example, (methoxymethyl) triphenylphosphonium chloride can be suitably used. The aldehyde compound of the formula (6) can be used in an amount of usually 0.6 to 1.2 mol, preferably 0.8 to 1.0 mol, per 1 mol of phosphorus ylide. Examples of the solvent include an inert organic solvent. Specific examples include ethers (eg, diethyl ether, diisopropyl ether, methyl-t-butyl ether, 1,4-dioxane, tetrahydrofuran, etc.), halogenated hydrocarbons (eg, Examples thereof include dichloromethane, chloroform, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, etc.) and polar solvents (eg, dimethylformamide, dimethylsulfoxide, acetonitrile, etc.), and particularly, toluene, tetrahydrofuran, dimethylsulfoxide, dimethyl Formamide or a mixed solvent thereof is preferred.

  The acid used at the time of hydrolysis of the enol ether compound of the formula (7) is not particularly limited, and examples thereof include hydrochloric acid, sulfuric acid and nitric acid. Hydrochloric acid is preferable, and is usually used per mole of the enol ether compound of the formula (7). It can be used in the range of 0.6 to 1.2 equivalents, preferably 0.8 to 1.0 equivalents. The reaction temperature is usually in the range of -78C to 60C, preferably -10C to 25C. The reaction is usually completed within a few hours. The reaction time may be determined while monitoring the progress of the reaction by gas chromatography, thin-layer chromatography, or the like.

  The oxidation method is not particularly limited, either, and the aldehyde may be converted to a carboxylic acid by various oxidizing agents (for example, various peroxides such as potassium permanganate, hydrogen peroxide, and organic peroxide) or by pinic oxidation. . Pinic oxidation, in which the oxidation reaction can proceed under mild conditions with selectivity, is preferably employed.As the conditions for the pinic oxidation, usually, sodium chlorite is used to remove by-product sodium hypochlorite. Performed in the presence of 2-methyl-2-butene. Alcohols or mixed solvents of alcohols and water are suitably used as the solvent, and examples of the alcohols include tetrahydrofuran and butanol. The reaction temperature is 15 to 60C, more preferably about 20 to 50C. The reaction is usually completed within a few hours. Similarly to the 3-methyl form of the formula (1), the reaction time may be determined while monitoring the progress of each reaction by gas chromatography, thin-layer chromatography, or the like. The obtained 5-methyl form of the formula (3) may be purified by means of column chromatography, distillation under reduced pressure or the like, if necessary.

(Fragrance composition of the present invention)
The fragrance compound of the present invention is selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid represented by formulas (1) to (3). It contains a predetermined amount of one or more compounds, and can be blended into various articles. Examples of the articles include, as described above, consumer goods such as food and drink, cosmetics, and medical hygiene. The form of the fragrance composition of the present invention is not particularly limited, and examples thereof include a water-soluble fragrance composition, an oil-soluble fragrance composition, an emulsified fragrance composition, and a powdered fragrance composition.

  The fragrance composition of the present invention can be used for the purpose of improving the flavor of the article by blending it into various articles. In addition, for example, when the fragrance composition of the present invention exhibits a citrus-like aroma, the flavor may be improved and a citrus-like scent may be imparted by adding the fragrance composition to food or drink.

  The concentrations of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid in the fragrance composition of the present invention are arbitrarily determined according to the composition of the fragrance composition. it can.

  As an example of the concentration, the concentration of any one of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid with respect to the total mass of the fragrance composition, or The total concentration of these two or three types is 0.01 ppb to 200 ppm, preferably 0.1 ppm to 100 ppm. More specifically, the lower limit is any one of 0.01 ppb, 0.1 ppb, 1 ppb, 10 ppb, 100 ppb, 1 ppm, 10 ppm, and 100 ppm, and the upper limit is 200 ppm, 100 ppm, 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, As 0.1 ppb, the lower limit and the upper limit can be in any range, but not limited thereto. In addition, depending on the formulation and flavor of the fragrance composition, if the above concentration in the fragrance composition is less than 0.01 ppm, the compounding effect may be felt to be low, and if it exceeds 200 ppm, the compound-derived effect may be felt. It may be felt that the scent is strong and gives an undesirable change to the scent characteristics of the fragrance composition to be compounded.

  In addition, the fragrance compound of the present invention further comprises, in addition to 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and / or 5-methyl-2-furanacetic acid, any other compound or component. May be included.

  Examples of such compounds or components include fragrance compounds or fragrance compositions of various types, oil-soluble pigments, vitamins, functional substances, fish meat extracts, animal meat extracts, plant extracts, yeast extracts, animal and plant proteins. , Plant and animal protein degradation products, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents and the like. For example, "Patent Office Gazette, Collection of Well-known and Conventional Techniques (Flavours) Part II Food Flavors, Published January 14, 2000", "Survey on the Use of Food Flavor Compounds in Japan" (2000 Report, Japan Fragrance Association, published in March 2001) and "Synthetic Fragrance Chemistry and Product Knowledge" (published new edition on December 20, 2016, edited by the Fragrance Editing Committee, Chemical Daily) Natural essential oils, natural fragrances, and synthetic fragrances.

  As other examples of the synthetic fragrance compound, examples of the hydrocarbon compound include monoterpenes such as α-pinene, β-pinene, myrcene, camphene, and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene; -Undecatriene and the like.

  Examples of the alcohol compound include linear or branched saturated alkanols such as butanol, pentanol, 3-octanol and hexanol, and linear or branched unsaturated compounds such as (Z) -3-hexen-1-ol, prenol and 2,6-nonadienol. Examples include saturated alcohols, terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, and cedrol, and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

  Examples of the aldehyde compound include linear or branched saturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and hydroxycitronellal; linear unsaturated aldehydes such as (E) -2-hexenal and 2,4-octadienal; and citronellal. And terpene aldehydes such as citral, miltenal, and perilaldehyde, and aromatic aldehydes such as benzaldehyde, cinnamylaldehyde, vanillin, ethylvanillin, heliotropin, and p-tolylaldehyde.

  Examples of the ketone compound include linear / saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cycloten, Linear or cyclic diketones such as 2,5-dimethyl-4-hydroxy-3 (2H) -furanone and terpene ketones such as hydroxyketone, carvone, mentone, nootkatone, terpenes such as α-ionone, β-ionone, β-damacenone An aromatic ketone such as a ketone derived from a decomposition product and a raspberry ketone may be used.

  Examples of the furan or ether compound include furfuryl alcohol, furfural, rose oxide, linalool oxide, mentfuran, theaspirane, estragole, eugenol, and 1,8-cineole.

  Examples of the ester compound include ethyl acetate, isoamyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, and ethyl heptanoate. , Aliphatic esters such as ethyl caproate, isoamyl isovalerate and ethyl nonanoate, terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terdinyl acetate, benzyl acetate, methyl salicylate, methyl cinnamate, propion And aromatic esters such as cinnamyl acid, ethyl benzoate, cinnamyl isovalerate and ethyl 3-methyl-2-phenylglycidate.

  Examples of the lactone compound include saturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, and δ-dodecalactone, and unsaturated lactones such as 7-decene-4-olide and 2-decene-5-olide. .

  Examples of the acid compound include saturated and unsaturated fatty acids such as acetic acid, butyric acid, octanoic acid, isovaleric acid, caproic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

  Examples of the nitrogen-containing compound include indole, skatole, pyridine, alkyl-substituted pyrazine (such as trimethylpyrazine), and methyl anthranilate.

  Examples of the sulfur-containing compound include methanethiol, dimethylsulfide, dimethyldisulfide, allylisothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, -Methyl-1-butanethiol and furfurylmercaptan.

  Natural essential oils include sweet orange, bitter orange, petitgren, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang ylang , Anise, clove, ginger, nutmeg, cardamom, cedar, hinoki, vetiver, patchouli, labdanum and the like.

  Examples of various animal and plant extracts include extracts of vanilla, herbs or spices, extracts of coffee, green tea, black tea, or oolong tea, and various enzymatic degradation products such as lipase and / or protease, milk or dairy products, and the like. Various enzymatic degradation products such as lipase and / or protease are included.

  The fragrance composition of the present invention comprises 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and / or 5-methyl-2-furanacetic acid itself, or one or more of these as an active ingredient. The flavor improver of the present invention, which is contained in the present invention, can be prepared by blending it with an appropriate solvent or dispersion medium by a known method.

  As the form of the fragrance composition of the present invention, 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and / or 5-methyl-2-furanacetic acid and other components can be used in a water-soluble or oil-soluble solvent. , An emulsion formulation, a powder formulation, and other solid formulations (such as solid fat) are preferred.

  Examples of the water-soluble solvent include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol and the like. Among them, ethanol or glycerin is particularly preferred from the viewpoint of use in foods and drinks. Examples of the oil-soluble solvent include vegetable fats and oils, animal fats and oils, refined fats and oils (for example, processed fats and oils such as medium-chain fatty acid triglyceride, and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethyl citrate And the like.

  In addition, in order to prepare an emulsified preparation, 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and / or 5-methyl-2-furanacetic acid itself, or one or more of these compounds are used. It can be obtained by emulsifying the flavor improver of the present invention contained as an active ingredient together with a water-soluble solvent and an emulsifier. The emulsification method is not particularly limited, and various types of emulsifiers conventionally used in foods and drinks, for example, fatty acid monoglyceride, fatty acid diglyceride, fatty acid triglyceride, propylene glycol fatty acid ester, sucrose fatty acid ester, poly Glycerin fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quilt extract, arabic gum, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, caseinky ryasaponin, sodium caseinate, etc. Emulsification using a homomixer, a colloid mill, a rotating disk homogenizer, a high-pressure homogenizer, or the like can provide an emulsion having excellent stability. The use amount of these emulsifiers is not strictly limited, and can be varied over a wide range depending on the kind of the emulsifier to be used, but usually, 3-methyl-2-furanacetic acid, 4-methyl-2-furan. A suitable amount is about 0.01 to about 100 parts by weight, preferably about 0.1 to about 50 parts by weight, based on 1 part by weight of furan acetic acid and / or 5-methyl-2-furan acetic acid. In addition, in order to stabilize the emulsification, such a water-soluble solvent liquid, in addition to water, for example, glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, polyhydric alcohols such as reduced starch syrup One or more mixtures can be blended.

  The emulsion thus obtained can be dried to give a powder formulation if desired. Upon powdering, if necessary, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, reduced starch syrup, and the like can be appropriately blended. These amounts can be appropriately selected according to the characteristics desired for the powder preparation.

  The fragrance composition of the present invention may further contain, if necessary, components commonly used in the fragrance composition. For example, water, solvents such as ethanol, and fragrance retention such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercoline, medium-chain fatty acid triglyceride, and medium-chain fatty acid diglyceride Agents can be included.

(Use for various goods)
The flavor improving agent and the flavor composition of the present invention can be used by being blended with various articles or the flavor compositions used therein.

  The flavor improving agent or the flavor composition of the present invention may be incorporated into the flavor composition or the food or drink alone, or may contain one or more water-soluble flavors, emulsified flavor compositions, arbitrary flavor compounds, and natural flavors. Essential oils (e.g., described in the above-mentioned "Patent Office Gazette, Collection of Well-known and Conventional Techniques (Flavours) Part II Food Flavors", "Survey on Usage of Food Flavor Compounds in Japan" and "Synthetic Flavor Chemistry and Product Knowledge" Perfume compound).

  Foods and beverages in which the flavor improver or the flavor composition of the present invention can be blended are not particularly limited, and examples thereof include lemon, orange, grapefruit, lime, mandarin, tangerine, kabos, sudachi, hassaku, iyokan, yuzu, shikuwasa, kumquat. Various citrus flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat, Kyoho, etc. Various fruit flavors; milk, yogurt , Butter, milk flavor; vanilla flavor; various tea flavors such as green tea, black tea, oolong tea and herbal tea; coffee flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; cinnamon, chamomile, cardamom, and capa Way, cumin, clove, pepper, coriander, sansho, perilla, ginger, star anise, thyme, pepper, nutmeg, basil, marjoram, rosemary, laurel, wasabi and other spices or herbs; almonds, cashew nuts, walnuts, etc. Beverage flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; and vegetable flavors such as carrots, tomatoes, and cucumber. .

  Examples of more specific foods and drinks include rice crackers, hail, okoshi, rice cakes, buns, seaweed, bean jam, sheep, mizujitsukan, kinjoku, jelly, castella, candy, biscuits, crackers, potato chips, cookies, Pastes such as pie, pudding, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy, peanut paste, etc .; bread, udon, ramen, Chinese noodles, sushi, Gomoku, fried rice, pilaf, gyoza skin, shomai skin, bread such as okonomiyaki, takoyaki, noodles, rice; rice bran pickled, plum dried, fukugami pickled, betta pickled, senmai pickled, rakkyo, miso pickled, takuan pickled and their pickles Pickles such as pickles, pickles, mackerel, sardines Fish such as saury, salmon, tuna, skipjack, whale, flatfish, squid, ayu, squid such as squid, squid, crested squid, firefly squid, octopus such as octopus, lobster, prawn, button prawn, lobster, black tiger Crabs such as shrimp, king crab, snow crab, blue crab, crab, clams, clams, scallops, oysters, shellfish such as mussels, etc .; canned foods, boiled fish, tsukudani, surimi, fishery products (chikuwa, kamaboko) , Fried, tempura, etc .; processed foods and drinks of fish and shellfish; livestock meat such as chicken, pork, beef, lamb, horse meat; curry, stew, beef stew, hayashi rice sauce, meat sauce, Mabo tofu, hamburger, gyoza, pot rice, soups (corn soup, tomato soup, conso Processed foods and beverages using meat such as meat soup, meat dumplings, boiled meat, canned meat, etc .; table salt, seasoned salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hashoshi, sprinkle, ochazuke, Margarine, mayonnaise, dressing, vinegar, three tablespoons vinegar, powdered sushi vinegar, Chinese ingredients, tempura, mentsuyu (such as kelp or bonito), sauces (such as medium-concentrated sauce, tomato sauce), ketchup, grilled meat sauce, curry roux, stew Seasonings such as soup stock, soup stock, dashi stock (such as kelp soup or bonito stock), complex seasonings, new mirin, mixed powders such as fried and takoyaki flour, and these seasonings are added. Dairy products such as cheese, yogurt, and butter; boiled vegetables such as boiled vegetables, chikuzen boiled, oden, hot pots; take-out lunch box tools and prepared foods; Fruit juices such as apples, grapes, and citrus fruits (grapefruit, orange, lemon, etc.), juice drinks and soft drinks with fruit juices, fruit juice drinks and fruit drinks with grains; tomatoes, peppers, celery, cucumber, bitter melon, carrots, Vegetables such as potatoes, asparagus, bracken, spring, and vegetable-containing beverages such as vegetable-based beverages and vegetable soups; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, wine, beer, non-alcoholic Favorite beverages such as beer; beverages containing crude drugs and herbs; cola drinks, fruit drinks, milk drinks, beer taste drinks, sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nutritional drinks, lactic acid bacteria drinks, Alcohol flavored with various alcoholic beverages (beer flavor, plum wine flavor, Chuhai flavor, etc.) Non-alcoholic favorite beverages such as strike beverages; alcoholic beverages such as chuhai, cocktail drinks, low-malt beer, fruit liquor, condiments, and other brews (sparkling) or liqueurs (sparkling) such as so-called "third beer" And the like.

  Cosmetics which can be blended with the flavor improver or the fragrance composition of the present invention are not particularly limited. Examples thereof include perfume such as eau de cologne, eau de toilette, eau de parfum and parfum; shampoo, rinse and hair styling (hair cream, pomade etc.) Cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic lotion, cosmetic cream, cosmetic gel, serum, pack, etc .; antiperspirant spray, deodorant sheet, deodorant cream, Deodorant products such as deodorant sticks; bath salts such as inorganic salts, refreshing, carbon dioxide, skin care, enzymes and crude drugs; tanning cosmetics such as suntan products and sunscreen products; face soaps and facial cleansers Face wash, body soap and body soap, wash Health and hygiene detergents such as soap, laundry detergent, disinfectant detergent, deodorant detergent, softener, kitchen detergent and cleaning detergent; health and hygiene materials such as toothpaste, tissue paper, toilet paper; Aromatic deodorants in cars and the like, and aromatic products such as room fragrances; The fragrance which can be used is not particularly limited, and may be any favorable fragrance capable of improving the flavor by the flavor improving agent or the fragrance composition of the present invention, for example, vanilla, citrus, floral, fruity, It can be suitably used for green tone, spice tone and the like.

  In the present invention, the concentration of any one compound of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid in various articles such as foods and drinks and cosmetics, Alternatively, the total concentration of two or more of these can be arbitrarily determined according to the flavor of the article, the degree of desired effect, and the like.

  As an example of the concentration, in the case of food and drink, any of the compounds of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid is used based on the total mass of the food and drink. The concentration of one kind or the total concentration of two or more kinds thereof is in the range of 0.01 ppb to 200 ppb. More specifically, the lower limit is any of 0.01 ppb, 0.1 ppb, 1 ppb, 10 ppb, and 100 ppb, and the upper limit is 200 ppb, 100 ppb, 10 ppb, 1 ppb, or 0.1 ppb. Within, but not limited to, any combination of values. As an example of a preferable concentration, the concentration can be selected from the above concentrations of 0.1 ppb to 100 ppb, 1 ppb to 100 ppb, and 0.1 ppb to 10 ppb, based on the total mass of the food or drink, depending on the flavor characteristics of the food or drink. It is not limited to these. In addition, depending on the type and flavor of the food and drink, if the concentration in the food and drink is less than 0.01 ppb, it may be felt that the flavor improving effect is low. It may be felt that the aroma is prominent and undesirably alters the flavor of the food or drink to be compounded.

  In the case of cosmetics, the concentration of any one compound of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid with respect to the total mass of the cosmetic, Alternatively, the total concentration of two or more of these may be in the range of 0.01 ppb to 20 ppm. More specifically, the lower limit is any one of 0.01 ppb, 0.1 ppb, 1 ppb, 10 ppb, 100 ppb, 1 ppm, and 10 ppm, and the upper limit is any one of 20 ppm, 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, and 0.1 ppb. Examples include, but are not limited to, the range of any combination of the lower limit and the upper limit. As an example of a preferable concentration, the concentration can be selected from the respective ranges of 10 ppb to 10 ppm, 100 ppb to 10 ppm, and 1 ppm to 10 ppm based on the total mass of the cosmetic according to the odor characteristics of the cosmetic. It is not limited to. In addition, although it depends on the type and flavor of the cosmetics, if the concentration in the cosmetics is less than 0.01 ppb, the effect of improving the flavor may be felt to be low. It may be perceived as giving an undesired alteration to the aroma of cosmetics.

  Flavor to be blended by blending any one of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid compounds, or a mixture of two or more of these compounds Although the whole is good, it is possible to improve the volume, body, satisfaction, sustainability, etc., particularly from middle to last. For example, by adding a small amount of the compound of the present invention to articles such as foods and drinks and cosmetics, body feeling with natural feeling reminiscent of animal and plant materials used in foods and drinks and cosmetics, gorgeousness, aging The feeling, richness, taste, and the like are enhanced, and the effect of maintaining it in a good balance is exerted.

[Example 1] Synthesis of 3-methyl-2-furanacetic acid In a 500 mL eggplant flask, 3-furanmethanol (the following formula (4), 9.8 g, 100 mmol), triethyl orthoacetate (MeC (OEt) ₃ , 162) 0.3 g, 1.00 mol, 10 equiv) and phenol (1.88 g, 20 mmol, 0.2 equiv) were added, and the mixture was refluxed for 64 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 50: 1 to 20: 1) to obtain an ester compound represented by the following formula (5) as a pale yellow oily substance. (1.64 g, 9.75 mmol, 10% yield).

  Next, an ester compound of the formula (5) (1.00 g, 5.95 mmol), methanol (10 mL) and tap water (1 mL) were charged into a 30 mL eggplant flask, and lithium hydroxide monohydrate (1.25 g, 29.8 mmol, 5 equivalents) and stirred at room temperature for 1 hour. Ether (10 mL) was added to the reaction solution, and the aqueous phase was extracted. 2N HCl (10 mL) was added to the aqueous phase, and extracted with ether (10 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to Kugelrohr distillation (0.1 kPa, 〜145 ° C.) to obtain the desired 3-methyl-2-furanacetic acid (compound of the formula (1)) as a white solid (516.1 mg, 3.68 mmol). , Yield 62%, purity 99.1%).

  Physical properties of the obtained compound were as follows.

¹ H NMR (CDCl ₃ , 400 MHz) δ 1.98 (s, 3H), 3.63 (s, 2H), 6.12 (d, J = 1.2 Hz, 1H), 7.26 (d, J = 1.2 Hz, 1H).
¹³ C NMR (CDCl ₃ , 100 MHz) δ 9.76, 31.83, 113.05, 117.42, 141.31, 142.42, 175.55.
MS (EI, 70 eV) (m / z): 140 (41), 96 (8), 95 (100), 67 (8), 65 (7), 41 (9)
In this way, a 3-methyl form (Product 1 of the present invention) usable as the flavor improving agent of the present invention was obtained. The scent was somewhat honeyy, with a heavy, slightly sweet scent.

[Example 2] Synthesis of 4-methyl-2-furanacetic acid 4-Methyl-2-furanacetic acid represented by the following formula (2) was prepared according to the method of Carling and Paul, Synlett, (1), p. 40 (1993) to obtain a 4-methyl form (Product 2 of the present invention) which can be used as a flavor improving agent of the present invention. The scent was like Honey.

To four-necked flask 2L of Example 3 5-Methyl-2-furan acetic acid, the (methoxymethyl) triphenyl phosphonium chloride _{(ClPh 3 PCH 2 OMe, 102.2g} , 298mmol, 1.5 eq) The mixture was heated under reduced pressure and stirred for 1 hour. Dry tetrahydrofuran (THF, 300 mL) was added, and a solution of potassium tert-butoxide (t-BuOK, 31.26 g, 279 mmol, 1.4 equivalents) in dry THF (300 mL) was added dropwise over 40 minutes under a nitrogen atmosphere and ice-water cooling. did. After stirring at the same temperature for 30 minutes, a dry THF solution (100 mL) of 5-methylfurfural (21.88 g, 199 mmol) of the following formula (6) was added dropwise over 30 minutes, and the mixture was stirred at the same temperature for 1 hour. Water (1 L) was added to the reaction solution, and extracted with heptane (300 mL). The organic phase was washed with water (1 L) and saturated saline (500 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to distillation under reduced pressure to obtain the enol ether compound of the formula (7) (19.78 g, 143 mmol, yield 72%, purity 91.7%) as a pale yellow oily substance.

Next, an enol ether compound of the formula (7) (1.80 g, 13.0 mmol), THF (52 mL) and 2N HCl (6.5 mL) were charged into a 30-mL eggplant flask, and the mixture was stirred for 1 hour while heating under reflux. Separately, NaClO ₂ (3.52 g, 39.0 mmol, 3 eq.), Na ₂ HPO ₄ (5.54 g, 39.0 mmol, 3 eq.), NaH ₂ PO ₄ .2H ₂ O (12 .17 g, 78 mmol, 6 equiv), 2-methyl-2-butene (2.07 mL, 19.5 mmol, 1.5 equiv), tert-butanol (20 mL) and tap water (78 mL) were charged and cooled to room temperature. The reaction solution was added dropwise. The reaction solution was stirred at the same temperature for 30 minutes, and the reaction solution was extracted with ether (60 mL × 2). The organic phases were combined and back-extracted with saturated aqueous sodium hydrogen carbonate (200 mL), and the resulting aqueous phase was adjusted to pH = 1 with 2N HCl. The aqueous phase was extracted again with ether (50 mL x 4), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to Kugelrohr distillation to obtain the desired 5-methyl-2-furanacetic acid (compound of the formula (3)) as a pale yellow solid (567.4 mg, 4.05 mmol, yield 31%, purity 97). .3%).

  Physical properties of the obtained compound were as follows.

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ 2.27 (s, 3H), 3.68 (s, 2H), 5.92 (br s, 1H), 6.12 (br s, 1H), 9. 04 (br s, 1H).
¹³ C NMR (CDCl ₃ , 100 MHz) δ 13.48, 33.84, 106.41, 109.16, 144.90, 151.96, 175.96.
MS (EI, 70 eV) (m / z): 140 (38), 96 (7), 95 (100), 43 (8)
In this way, a 5-methyl form (Product 3 of the present invention) usable as the flavor improving agent of the present invention was obtained. The aroma was sweaty.

[Example 4] Effect of incorporation into vanilla-like perfume composition A general vanilla-like basic blended perfume composition having the following formulation was prepared.

  A perfume composition of the present invention is prepared by blending a 3-methyl form, a 4-methyl form or a 5-methyl form with the vanilla-like basic blended perfume composition so that the concentration thereof is as shown in Table 2 below. I got In addition, 2-hydroxyacetylfuran, which is reported to be identified from vanilla as a compound having a similar structure and exhibiting a scent, is prepared, and a vanilla-like basic blended fragrance composition is prepared so as to have a concentration shown in Table 2 below. To obtain a comparative fragrance composition.

  And about the fragrance | flavor composition of this invention, the sensory evaluation of the fragrance by the odor paper was performed by 15 skilled perfumers. In the sensory evaluation, a score on the volume feeling and a comment on the odor were made to be answered as compared with the vanilla-like basic blended fragrance composition according to the above general formula. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average scores and comments of the expert perfumers at each concentration were as follows.

  As shown in Table 2, it was confirmed that the 3-methyl form, the 4-methyl form, and the 5-methyl form all exhibited the same effect, enhanced sweetness and the like, and provided an excellent sense of volume.

Example 5 Effect of Incorporation into Vanilla-Flavored Milk Beverage A commercially available vanilla-flavored milk beverage was prepared. In contrast, among the vanilla-flavored flavor compositions of the present invention prepared in Example 4, 3-methyl form, The 4-methyl form and the 5-methyl form having a concentration of 10 ppm in the fragrance composition (Products 16 to 18 of the present invention) were converted into a commercially available vanilla flavor having a 3-methyl form, 4-methyl form or 5-methyl form. The vanilla-flavored milk drink of the present invention was prepared by mixing the milk drink with the total mass of the milk drink so as to have the concentration shown in Table 3 below (the present invention product). In addition, as a comparative example, the vanilla-flavored composition of Comparative Product 1 prepared in Example 4 was used, and the concentration of 2-hydroxyacetylfuran based on the total mass of a commercially available vanilla-flavored milk beverage was as shown in Table 3 below. A vanilla-flavored milk drink was added as described above (comparative product).

  Using a commercially available vanilla-flavored milk drink as a control, sensory evaluation was performed by 15 skilled perfumers on the flavors of the product of the present invention and the comparative product as compared to the control. In the sensory evaluation, a score was given for the body feeling and the taste, and a comment was given regarding the flavor. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response at each concentration was as follows.

  As shown in Table 3, all of the products of the present invention exhibited the same excellent flavor improving effect by the addition of the 3-methyl, 4-methyl or 5-methyl form. The taste was enhanced, and the sweetness, ripening, richness, flavor cohesion, balance, and the like were improved, and the effect was different from 2-hydroxyacetylfuran having a similar structure, and more excellent. .

[Example 6] Effect of incorporation into various fruit flavored foods and drinks Commercially available strawberry jam and marmalade were prepared, and these jams were used as flavor enhancers of the present invention as 3-methyl, 4-methyl or 5-methyl derivatives. The methyl form was blended so that the concentration was as shown in the following Tables 4 and 5 with respect to the total mass of each commercially available jam to obtain jams and marmalades of the present invention. In addition, phenylacetic acid was prepared as a compound having the same functional group and exhibiting a fragrance, and was blended with commercially available strawberry jam and marmalade so as to have the concentrations shown in Tables 4 and 5 below. Obtained.
Using the above commercially available strawberry jam or marmalade as a control, these jams were subjected to a sensory evaluation by 15 skilled perfumers for the flavor of the product of the present invention and the comparative product as compared with the control. In the sensory evaluation, a score was given for the body feeling and the taste, and a comment was given regarding the flavor. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response at each concentration was as follows.

  As shown in Tables 4 and 5, each of the products of the present invention exerts the same effect by blending the 3-methyl form, 4-methyl form or 5-methyl form, specifically, the body feeling and taste. The feeling was enhanced, and the sweetness, ripening, richness, juiciness, flavor unity, balance, etc. were improved, and the effect was different and superior to phenylacetic acid having a similar structure.

[Example 7] Effect of incorporation into beer-taste beverage A commercially available non-alcoholic beer was prepared, and on the other hand, as a flavor improving agent of the present invention, a 3-methyl form, a 4-methyl form or a 5-methyl form was prepared. The non-alcoholic beer of the present invention was obtained by blending such that the concentration was as shown in Table 6 below based on the total mass of commercially available non-alcoholic beer. With respect to these non-alcoholic beers of the present invention, the above commercially available non-alcoholic beer was used as a control product, and a sensory evaluation was conducted by 15 skilled perfumers on the flavor of the product of the present invention as compared with the control product. In the sensory evaluation, scores on body feeling and taste and comments on flavor were made to be answered. The score is based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response at each concentration was as follows.

  As shown in Table 6, all of the products of the present invention exhibited the same effects by the addition of the 3-methyl, 4-methyl or 5-methyl form. The taste, the unity of the flavor, the balance and the like were improved, and the product had an excellent flavor.

[Example 8] Effect of incorporation into spice-flavored food and drink A commercially available onion dressing was prepared, and on the other hand, as a flavor improving agent of the present invention, a 3-methyl form, a 4-methyl form or a 5-methyl form was prepared. The dressing of the present invention was obtained by blending such that the concentration was as shown in Table 7 below with respect to the total mass of the commercially available dressing. Using the commercially available dressing as a control, the sensory evaluation of the flavor of the product of the present invention as compared with the control was performed by 15 skilled perfumers. In the sensory evaluation, a score was given for the body feeling and the taste, and a comment was given regarding the flavor. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response at each concentration was as follows.

  As shown in Table 7, all of the products of the present invention are improved in sweetness, body feeling, taste, unity of flavor, balance, and the like by blending the 3-methyl form, 4-methyl form or 5-methyl form. It had an excellent flavor.

[Example 9] Effect of blending vanilla-like scent with shampoo Commercially available shampoo with vanilla-like fragrance was prepared, and as a flavor improver of the present invention, 3-methyl, 4-methyl or 5-methyl was used. The body was blended so as to have the concentration shown in Table 8 below based on the total mass of the commercially available shampoo. In addition, 2-hydroxyacetylfuran used as a compound of Comparative Example in Example 4 was blended with the unscented shampoo so as to have a value shown in Table 8 below to obtain a shampoo of a comparative product. Then, the hair was washed by a skilled perfumer and the sensory evaluation was performed on the scent during hair washing. In the sensory evaluation, a score regarding the volume of the fragrance and a comment regarding the fragrance were made to be answered for the present invention as compared with the comparative product. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response was as follows:

  As shown in Table 8, all of the products of the present invention have an excellent fragrance with improved sweetness, voluminous feel, balance, fragrance persistence, etc., and the effect is similar to 2-hydroxy having a similar structure. Unlike acetylfuran, it was better.

[Example 10] Effect of blending strawberry-flavored body soap with body soap A commercially available strawberry-flavored body soap was prepared, and as a flavor improver of the present invention, 3-methyl, 4-methyl or 5 The -methyl form was blended with the total amount of the body soap so as to have the concentration shown in Table 9 below to obtain a body soap of the present invention. In addition, phenylacetic acid used as a compound of Comparative Example in Example 6 was mixed with a commercially available shampoo so as to have a concentration shown in Table 9 below to obtain a comparative shampoo. Then, the hair was washed by a skilled perfumer and the sensory evaluation was performed on the scent during hair washing. In the sensory evaluation, a score regarding the volume of the fragrance and a comment regarding the fragrance were made to be answered for the present invention as compared with the comparative product. The scores are based on the following criteria: greatly enhanced = 4 points, clearly enhanced = 3 points, slightly enhanced = 2 points, no change = 1 point, uncomfortable = 0 points Was selected. The average response was as follows:

  As shown in Table 9, all of the products of the present invention were improved in sweetness, voluminous feel, balance, sustainability of fragrance, etc. by blending of 3-methyl form, 4-methyl form or 5-methyl form, and were excellent in fragrance. The effect was different from and superior to phenylacetic acid having a similar structure.

[Example 11] The effect of using two or more selected from 3-methyl, 4-methyl and 5-methyl in combination of two or more was confirmed.

  Specifically, as shown in Table 10 below, two or three selected from 3-methyl, 4-methyl and 5-methyl forms were added to the vanilla-based basic blended flavor composition described in Example 4. Seeds were blended.

  Then, the fragrances of the obtained four kinds of fragrance compositions were smelled by 15 skilled perfumers and commented on the fragrance. As a result, the rich sweetness and voluminousness of vanilla were enhanced in any of the present invention products. It is an evaluation that a feeling of ripening is imparted, the balance is good, and the fragrance is maintained, and the same as in Example 4, when 100 ppm of the 3-methyl form, the 4-methyl form or the 5-methyl form was compounded alone. It was an evaluation.

  From this, it was confirmed that the same flavor improving effect can be felt even when the 3-methyl form, 4-methyl form and 5-methyl form are used alone or in combination of two or more kinds.

Claims (6)

Selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid and 5-methyl-2-furanacetic acid represented by the following formulas (1), (2) and (3), respectively. A flavor improver comprising one or more of the following as active ingredients.

  The flavor-improving agent according to claim 1, wherein the flavor-improving agent is selected from the group consisting of 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid. A fragrance composition containing 0.01 ppb to 200 ppm as a total concentration of at least one species.   The flavor improver according to claim 1 or the flavor composition according to claim 2 comprises 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid. A food or drink which is added at a concentration of 0.01 ppb to 200 ppb as a single concentration or a total concentration of two or more selected from the group.   The flavor improver according to claim 1 or the flavor composition according to claim 2 comprises 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid. A cosmetic product which is added at a concentration of 0.01 ppb to 20 ppm as a single concentration or a total concentration of two or more selected from the group.   The flavor improver according to claim 1 or the flavor composition according to claim 2 comprises 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid. A method for improving flavor of a food or drink, comprising adding at a concentration of 0.01 ppb to 200 ppb as one concentration or a total concentration of two or more selected from the group.   The flavor improving agent according to claim 1 or the flavor composition according to claim 2, from 3-methyl-2-furanacetic acid, 4-methyl-2-furanacetic acid, and 5-methyl-2-furanacetic acid. A method for improving the flavor of a cosmetic product, comprising adding at a concentration of 0.01 ppb to 20 ppm as one concentration or a total concentration of two or more selected from the group consisting of: