Mint flavor enhancer that gives a fresh leaf feel

Abstract

To provide a fresh leaf feeling enhancing agent for enhancing the fresh and green fresh leaf feeling of a mint perfume plant of the genus Mentha. [Solution] A mint fragrance composition containing 0.01 to 10,000 ppm of a mint fragrance enhancer that enhances the freshness of mint leaves, the mint fragrance comprising one or more active ingredients selected from specific organic sulfur compounds having a thiol (R-SH), sulfide (R-S-R'), or thioester (RS-CO-R') in its structure.

Description

[Technical field]

[0001] The present invention relates to a mint flavoring fresh leaf feel enhancer that imparts and enhances the fresh, green fresh leaf feel of a plant of the genus Mentha (also known as the genus Mint or Mentha) of the family Lamiaceae in the order Lamiales, a mint flavoring composition containing an effective amount of the fresh leaf feel enhancer, and a mint-flavored food or beverage or a mint-flavored oral composition containing them. [Background technology]

[0002] Mint flavors are generally produced by blending essential oils such as peppermint oil, spearmint oil, and peppermint oil derived from plants of the genus Mentha in the family Lamiaceae, with appropriate supplementation of synthetic flavors such as menthol, menthone, isomenthone, menthofuran, menthyl acetate, L-carvone, dihydrocarvone, pulegone, isopulegol, isoplegyl acetate, L-carveol, piperitone, piperitol, carvyl acetate, dihydrocarbyl acetate, and 1,8-cineole, which are components of these essential oils, in consideration of optimal preference, comfortable feel for the user, and functions and characteristics of each product, such as a flavoring composition for food or beverage or oral cavity. Regarding the production of flavors having mint notes, it has been proposed to use various hydrocarbons, alcohols, esters, aldehydes, ketones, acetals, phenols, lactones, sulfur compounds, nitrogen compounds, acids, and natural flavors in addition to the above-mentioned mint essential oil and synthetic flavors (Patent Document 1).

[0003] Recently, in pursuit of a more refreshing sensation, various menthol derivatives and skin-sensing cooling agents have been developed and are increasingly being used for a variety of functional purposes. Conventional products do not necessarily meet consumer demands, and so development of new variations of mint-based fragrances is underway.

[0004] As a method for improving the flavor of fragrances that are mainly composed of essential oils from plants of the genus Mentha, for example, a method has been proposed in which polygodial (a pungent component contained in plants such as Polygonaceae plants) is added to enhance the cooling sensation of mint-based fragrances (Patent Document 2). Also, a method is known in which the intensity of the refreshing sensation is enhanced by blending tea tree essential oil obtained from a plant of the Myrtaceae family (Patent Document 3).

[0005] On the other hand, in the current global trend of preferring natural flavors, there is a demand for a more natural flavor of essential oils from mint plants, and various techniques have been developed to enhance the natural feel. For example, a method has been proposed in which a luo han guo extract is added to a mint flavoring to enhance the mint flavor itself (Patent Document 4). However, there is still room for development in terms of a more natural mint flavor.

[0006] Regarding mint flavorings having a more natural feel, for example, a method of adding 1,3,5,8-undecatetraenes to mints has been proposed (Patent Document 5). Also proposed is a method of enhancing the mint flavor by adding one or more members selected from the group consisting of 6,8,10-undecatrien-3-one, 3-methyl-2,4-nonanedione, and 4-ethylguaiacol to a mint flavoring (Patent Document 6).

[0007] However, the above-mentioned technology is directed to improving the flavor of essential oil obtained by steam distillation of Mint plants, and has not yet resulted in the production of a natural mint fragrance that emphasizes the flavor of fresh Mint plants themselves. On the other hand, the affinity for herbs has led to the popularity of cocktails, chuhai and other alcoholic beverages, ice cream, and other beverages. The fresh leaves of the genus mint are increasingly being used in a variety of foods and beverages, including sweets such as creams, chocolates, and cakes, as well as in salads, tea, and coffee, and consumers are becoming more and more fond of the distinctive aroma and flavor of fresh mint leaves. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] JP 2004-018431 A [Patent Document 2] Japanese Patent Application Publication No. 07-145398 [Patent Document 3] Japanese Patent Application Publication No. 09-263786 [Patent Document 4] JP 2015-140381 A [Patent Document 5] JP 2007-246682 A [Patent Document 6] JP 2013-107976 A Summary of the Invention [Problem to be solved by the invention]

[0009] The problem that the present invention aims to solve is to provide a mint flavoring fresh leaf feel enhancer that imparts and enhances the fresh, green, fresh leaf feel of Mentha plants, a feeling that has not been fully taken into consideration in conventional methods for improving mint flavorings, a mint flavoring composition containing an effective amount of the fresh leaf feel enhancer, and mint-flavored food and beverages or mint-flavored oral compositions containing them. [Means for solving the problem]

[0010] In order to solve the above problems, the present inventors conducted extensive research and discovered that a specific organosulfur compound imparts and enhances the fresh, green, fresh leaf feel of Mint plants, thereby completing the present invention. That is, the present invention is as follows.

[0011] [1] The following formula (1): [ka] [During the ceremony: (I C x and C. y each represents a carbon atom; R 1is -H, -CH 3 or -CH 2 CH 3 represents; R 2 is -H, -CH 3 , -CH 2 CH 3 or -CH 2 CH 2 CH 3 Represents; R 3 is -H, -CH 3 or =O; R 4 -CH 2 -O-CH 3 , -CH 3 , -OH, -CH(OH)-CH 3 , =O, -CH 2 -OC(O)-CH 3 , -CH 2 -OC(O)-(CH 2 ) 2 CH 3 , -CH 2 -OC(O)-H, -H, -(CH 2 ) 3 CH 3 , -CH(CH 3 )-CH 3 , =C(CH 3 )-CH 3 , -C(O)-CH 3 , -CH 2 CH 3 , -CH 2 -OH, or -CH 2-OC(O)-(CH 2 ) 4 CH 3 represents; R 5 is -H, -CH 2 CH 3 , -CH 3 , -O-CH 3 or -O-CH 2 CH 3 represents; R 6 represents -H; Here, carbon atom C x Or C y A solid line extending from represents a single bond, a solid line with a dashed line represents a single bond or a double bond, and a dashed line alone represents a single bond or no bond. 3 and C. x If the bond between them is a double bond, R 2 does not exist, and R 4 and C. y If the bond between them is a double bond, R 6 does not exist; or, (II):C x and C. y each represents a carbon atom; R 1 -CHCHCH 3 represents; R 2 -CH 3 represents; R 3 -CH 3 represents; R 4 -CH 2 - stands for; R 5 -CH 2 CH 2 - stands for; Carbon atom C x and C y A solid line with a dashed line extending from represents a single bond, and a dashed line alone represents a single bond; R 4 and R 5 are R 12,8-epithio-p -Menthane is formed. A fresh leaf feel enhancing agent for a mint fragrance, comprising as an active ingredient one or more compounds selected from the group consisting of compounds represented by the following formula:

[0012] [2] The above mint fragrance fresh leaf feel enhancer, characterized in that the compound represented by formula 1 is the following compound: 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, 2-methylthioethanol, 2-mercapto-3-butanol, 3-methyl-2-butanethiol, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, S-methyl 2-methylbutanethioate, 3-methylthiopropyl acetate, 3-mercapto-3-methylbutan-1-ol, 3-mercaptohexyl hexanoate, 3-mercapto-2-butanone, methyl methylthioacetate, Ethyl methylthioacetate

[0013] [3] The above mint fragrance fresh leaf feel enhancer, characterized in that the compound represented by formula 1 is the following compound: 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 3-methyl-2-butanethiol, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-methylthiopropyl acetate, 3-mercapto-2-pentanone, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, S-methyl 2-methylbutanethioate, 2-methylthioethanol, 2-Mercapto-3-butanol

[0014] [4] The above mint fragrance fresh leaf feel enhancer, characterized in that the compound represented by formula 1 is the following compound: 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, 2-Methylthioethanol

[0015] [5] A mint flavoring composition comprising the above fresh leaf feeling enhancer and a mint flavoring, and containing the fresh leaf feeling enhancer in an amount of 0.01 to 10,000 ppm. [6] A mint-flavored food or drink, or a mint-flavored oral composition, comprising the above mint flavoring composition in an amount of 0.001 to 5.0% by mass. [7] A method for producing a mint flavoring composition, comprising adding the fresh leaf feeling enhancer to a mint flavoring in an amount of 0.01 to 10,000 ppm. [8] A method for enhancing the fresh mint leaf feel of a mint-flavored food or beverage or a mint-flavored oral composition, comprising adding 0.01 to 10,000 ppb of the fresh leaf feel enhancer to the mint-flavored food or beverage or mint-flavored oral composition. [9] A method for imparting a mint flavor having a fresh leaf feel to a food, beverage, or oral composition, comprising adding the above mint flavoring composition to the food, beverage, or oral composition in an amount of 0.001 to 5.0 mass %. Effect of the Invention

[0016] The fresh leaf feel enhancing agent for mint flavor of the present invention can impart and enhance the fresh, green fresh leaf feel of a Mint plant by adding an effective amount to a normal mint flavor. Furthermore, the mint flavoring composition containing the fresh leaf feeling enhancing agent of the present invention and a mint flavoring can impart a mint flavor with a fresh leaf feeling to foods and beverages. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] [1] Fresh leaf feel enhancer The specific sulfur-containing compound used as an active ingredient in the fresh-leaf feel enhancer of the present invention is an organic sulfur compound having a thiol (R-SH), a sulfide (RS-R') or a thioester (RS-CO-R') in its structure, and is a compound represented by the following formula (1). [ka] In the above formula (1), (I C x and C. y each represents a carbon atom; R 1 is -H, -CH 3 or -CH 2 CH 3 represents; R 2 is -H, -CH 3 , -CH 2 CH 3 or -CH 2 CH 2 CH 3 Represents; R 3 is -H, -CH 3 or =O; R 4 -CH 2 -O-CH 3 , -CH 3 , -OH, -CH(OH)-CH 3 , =O, -CH 2 -OC(O)-CH 3 , -CH 2 -OC(O)-(CH 2 ) 2 CH 3 , -CH 2 -OC(O)-H, -H, -(CH 2 ) 3 CH 3 , -CH(CH 3 )-CH 3 , =C(CH 3 )-CH 3 , -C(O)-CH 3 , -CH 2 CH 3 , -CH 2 -OH, or -CH 2 -OC(O)-(CH 2 ) 4 CH 3 represents; R 5 is -H, -CH 2 CH 3 , -CH 3 , -O-CH 3 or -O-CH 2 CH 3 represents; R 6 represents -H; Here, carbon atom C x Or C y A solid line extending from represents a single bond, a solid line with a dashed line represents a single bond or a double bond, and a dashed line alone represents a single bond or no bond. 3 and C. x If the bond between them is a double bond, R 2 does not exist, and R 4 and C. y If the bond between them is a double bond, R 6 does not exist.

[0018] Alternatively, in the above formula (1), (II):C x and C. y each represents a carbon atom; R 1 -CHCHCH 3 represents; R2 -CH 3 represents; R 3 -CH 3 represents; R 4 -CH 2 - stands for; R 5 -CH 2 CH 2 - stands for; Carbon atom C x and C y A solid line with a dashed line extending from represents a single bond, and a dashed line alone represents a single bond; R 4 and R 5 are R 1 With the carbon atoms bonded to the 1st and 2nd positions of the 2,8- It stands for pico-p-menthane. Here, 2,8-epithio-p-menthane is a sulfur-containing compound called 4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane or ZESTORIL, and has the following structure. [ka]

[0019] Specific examples of the sulfur-containing compound of the formula (1) include: 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, 2-methylthioethanol, 2-mercapto-3-butanol, 3-methyl-2-butanethiol, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, S-methyl 2-methylbutanethioate, 3-methylthiopropyl acetate, 3-mercapto-3-methylbutan-1-ol, 3-mercaptohexyl hexanoate, 3-mercapto-2-butanone, Methyl methylthioacetate, and An example is ethyl methylthioacetate.

[0020] Among the above compounds, 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 3-methyl-2-butanethiol, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-methylthiopropyl acetate, 3-mercapto-2-pentanone, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, S-methyl 2-methylbutanethioate, 2-methylthioethanol, 2-Mercapto-3-butanol is preferred.

[0021] Among them, particularly preferred compounds are 1-Methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methyl-2-butene-1-thiol, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, 2-Methylthioethanol The following can be mentioned.

[0022] Any of the above compounds can be prepared by known synthetic methods. In addition, since these are all commonly used as synthetic fragrances or reagents, commercially available products can be purchased as appropriate and used in the present invention. The fresh leaf feel referred to in the present invention is the green leaf feel peculiar to freshly picked mint leaves, and is a flavor that is accompanied by a sweet feel and a fresh feel. Here, various types of regular mint fragrances are commercially available, ranging from those that only have a slight feeling of fresh mint leaves to those that have no feeling at all, depending on the degree of processing and formulation during the manufacturing stage. However, by adding the fresh leaf feel enhancing agent of the present invention to a mint fragrance, a fresh leaf feel can be imparted to mint fragrances that have no fresh leaf feel at all, while the fresh leaf feel can be enhanced for mint fragrances that have a certain degree of fresh leaf feel. It was unexpected that compounds having an unpleasant odor such as organic sulfur compounds have the effect of enhancing the fresh leaf feeling of mint flavoring.

[0023] [2] Mint flavoring The mint flavor of the present invention is based on essential oils or extracts extracted from Mint plants by steam distillation, such as peppermint oil, spearmint oil, and peppermint oil, as described above, and can be produced alone or in combination of two or more of these natural flavors.

[0024] Furthermore, synthetic flavors that are components of these essential oils, such as menthol, menthone, isomenthone, menthofuran, menthyl acetate, L-carvone, dihydrocarvone, pulegone, isopulegol, isoplegyl acetate, L-carveol, piperitone, piperitol, carvyl acetate, dihydrocarvyl acetate, and 1,8-cineole, can be supplemented to produce the fragrance.

[0025] In addition to the above mint essential oil and synthetic flavoring, the composition can also be produced using synthetic flavorings such as various hydrocarbons, alcohols, esters, aldehydes, ketones, acetals, phenols, lactones, sulfur compounds, nitrogen compounds, and acids.

[0026] Examples of the synthetic flavors that can be used in the mint flavor of the present invention include, for example, ethyl acetoacetate, acetophenone, anisaldehyde, α-amylcinnamaldehyde, methyl anthranilate, ionone, isoeugenol, isoamyl isovalerate, ethyl isovalerate, allyl isothiocyanate, 3-butenyl isothiocyanate, 4-pentenyl isothiocyanate, benzyl isothiocyanate, 3-methylthiopropyl isothiocyanate, isothiocyanates,

[0027] isobutanol, indole and its derivatives, γ-undecalactone, esters, 2-ethyl-3,5-dimethylpyrazine and 2-ethyl-3,6-dimethylpyrazine, ethyl vanillin, ethers, eugenol, octanol, octanal, ethyl octanoate, isoamyl formate, geranyl formate, citronellyl formate, cinnamic acid, ethyl cinnamate, methyl cinnamate, ketones, geraniol, isoamyl acetate, ethyl acetate, geranyl acetate, cyclohexyl acetate,

[0028] Citronellyl acetate, cinnamyl acetate, terpinyl acetate, phenethyl acetate, butyl acetate, benzyl acetate, linalyl acetate, methyl salicylate, allyl cyclohexylpropionate, citral, citronellal, citronellol, 1,8-cineole, higher fatty acids, higher aliphatic alcohols, higher aliphatic aldehydes, higher aliphatic hydrocarbons, cinnamyl alcohol, cinnamaldehyde, thioethers, thiols, decanal, decanol, ethyl decanoate, terpineol, limonene, pinene, myrcene, tapinolene,

[0029] Terpene hydrocarbons, γ-nonalactone, vanillin, paramethylacetophenone, hydroxycitronellal, hydroxycitronellal dimethyl acetal, piperonal, isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, phenol ethers, phenols, furfural and its derivatives, propanol, isoamyl propionate, ethyl propionate,

[0030] Examples of synthetic or naturally derived fragrances include benzyl propionate, allyl hexanoate, ethyl hexanoate, ethyl heptanoate, l-perillaldehyde, benzyl alcohol, benzaldehyde, aromatic alcohols, aromatic aldehydes, d-borneol, maltol, methyl N-methylanthranilate, methyl β-naphthyl ketone, butyric acid, isoamyl butyrate, ethyl butyrate, cyclohexyl butyrate, butyl butyrate, lactones, and linalool.

[0031] [3] Mint flavor composition The mint flavor composition comprises the above mint flavor and a fresh leaf feel enhancing agent. The mint flavoring composition in the present invention is a material that imparts a mint flavor with a fresh leaf feel to food and beverages. It is similar to so-called mint-like food flavors in its usage method, addition amount, and addition effect, but is different in that the mint flavoring composition is intended to impart not only the mint scent but also the mint taste rich in the fresh leaf feel to food and beverages, and is called MINT in English. This corresponds to FLAVOR.

[0032] The above-mentioned organic sulfur compounds can impart and enhance the fresh, green, fresh leaf feel of a Mint plant, which is the effect of the present invention, when added to a general mint flavoring in a concentration range of usually 0.001 to 10,000 ppm, preferably 0.01 to 1,000 ppm, and more preferably 0.05 to 500 ppm. If the amount added is less than 0.001 ppm, the effect of the addition may not be sufficient, and if it exceeds 10,000 ppm, it may taste slightly artificial.

[0033] In the present invention, the fresh leaf feeling effect can be further increased by using a specific nitrogen-containing compound in addition to the above-mentioned organic sulfur compounds. Specific compounds that can be used in combination in the present invention include, for example, trimethylamine, diethylamine, triethylamine, propylamine, butylamine, pentylamine, isopentylamine, pyridine, 3-ethylpyridine, 2-acetylpyridine, 3-acetylpyridine, 2-isobutylpyridine, 3-isobutylpyridine, 2-n-pentylpyridine, pyrazine, 2-methylpyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, tetramethylpyrazine, 2- Examples include ethylpyrazine, 2-ethyl-3-methylpyrazine, 2-ethyl-5-methylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethylpyrazine, 2,3-diethyl-5-methylpyrazine, 2-acetylpyrrole, indole, and skatole, and preferably trimethylamine and / or isopentylamine are used.

[0034] When these nitrogen-containing compounds are added in an amount of usually 0.01 to 1000 parts by mass, preferably 0.05 to 500 parts by mass, and more preferably 0.1 to 100 parts by mass, per part by mass of the organosulfur compound represented by formula (1), the effect of the present invention, that is, the fresh leaf feel of a Mint plant, can be further imparted and enhanced. If the amount added is less than 0.01 parts by mass, the effect of the addition may be insufficient, whereas if it exceeds 1000 parts by mass, the flavor may be perceived as slightly artificial.

[0035] The mint flavoring composition of the present invention is preferably formulated in various forms for use. Examples of such formulations include water-soluble liquid formulations or oil-soluble liquid formulations by diluting with a solvent, and further emulsified formulations by emulsification. Examples of emulsifiers that can be used in emulsified formulations include processed starch, soybean saponin, Quillaja quilla extract, glycerin fatty acid esters, polyglycerin fatty acid esters, plant sterols, plant lecithin, sphingolipids, sucrose fatty acid esters, calcium stearoyl lactate, sorbitan fatty acid esters, soybean saponin, bile powder, animal sterols, propylene glycol fatty acid esters, fractionated lecithin, yucca foam extract, egg yolk lecithin, polysorbate 20, polysorbate 60, polysorbate 65, polysorbate 80, etc., and it is preferable to use them in combination with alcohol, polyhydric alcohol, sugar, etc. to form emulsified formulations.

[0036] Furthermore, the flavor composition of the present invention can be made into a powder formulation by powdering such as spray drying after emulsification. In this case, it is preferable to use various stabilizers and excipients in addition to the emulsifier. Examples of such stabilizers include gum arabic, dextrin, gelatin, cyclodextrin, methylcellulose, pectin, gelatin hydrolysate, carrageenan, gellan gum, furcellaran, alginic acid, enzymatically decomposed lecithin, casein, xanthan gum, pullulan, agar, and locust bean gum. Examples of excipients include sugars and sugar alcohols, and examples of sugars include monosaccharides such as glucose, fructose, and galactose, disaccharides such as sucrose and maltose, and starch partial hydrolysates obtained by liquefying starch, and examples of sugar alcohols include sorbitol, xylitol, and erythritol.

[0037] The flavor composition of the present invention may also be used by adding other food additives, such as sweeteners, colorants, preservatives, antioxidants, bittering agents, acidulants, strengthening agents, and manufacturing agents, during the preparation of the above-mentioned formulation.

[0038] [4] Targets for fresh leaf feel enhancers The fresh leaf feel enhancing agent of the present invention is not usually used alone, but is applied in the form of a mint flavoring composition combined with a mint flavoring to foods, beverages, or oral compositions to which a mint flavor is to be imparted. However, for foods, beverages, or oral compositions that already have a mint flavor, the fresh leaf feel enhancer can be used alone to enhance the fresh mint leaf feel. That is, by adding 0.01 to 10,000 ppb of a fresh leaf feel enhancing agent to a food or beverage or oral composition having a mint flavor, the fresh mint leaf feel can be imparted and enhanced to the food or beverage or oral composition having a mint flavor.

[0039] [5] Target of application of mint flavor composition The subject to which the mint flavoring composition containing the fresh leaf feel enhancing agent is added is not particularly limited as long as it is a food, beverage, or oral composition that imparts a mint flavor, and examples of such subject matter include beverages such as fruit juice drinks, fruit alcoholic beverages, liqueurs, carbonated drinks, soft drinks, energy supplements, and dairy drinks; frozen desserts such as ice cream, sorbets, and popsicles; desserts such as jellies and puddings; Western sweets such as cakes, chocolates, chewing gum, and candies; Japanese sweets such as yokan; jams; herbal teas, and oral products such as toothpaste and mouthwash.

[0040] The amount of the mint flavor composition of the present invention added to a food, drink, or oral composition is generally 0.0 0.01 to 5.0 mass%, preferably 0.01 to 2.0 mass%, more preferably 0.05 to 1.0 It can be used at a mass percent and can impart a mint flavor as well as the feel of fresh mint leaves. Regarding the timing of adding the mint flavor composition of the present invention in the manufacturing process of a food or beverage or oral composition, it can be added at any step or stage, similar to the case of ordinary flavors. EXAMPLES

[0041] The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples. The sulfur-containing compounds and nitrogen-containing compounds used in the examples and the compounds used in the comparative examples were all commercially available products.

[0042] [Test Example 1] A test was carried out to confirm the preferred range of the amount of the organosulfur compound used according to the present invention. The test method involved adding each of the above organic sulfur compounds to maltitol syrup (manufactured by Mitsubishi Corporation Foodtech Co., Ltd.), and having three experienced panelists determine the appropriate concentration to add to a mint flavoring intended for mint-flavored foods. The results are shown in Table 1.

[0043] [Table 1]

[0044] [Production Example 1] A mint flavor to which the fresh leaf feel enhancing agent was added was prepared according to the following recipe. [Table 2]

[0045] [Examples 1 to 13] The fresh leaf feel enhancer of the present invention was added to the mint flavor prepared in Manufacturing Example 1, with reference to the appropriate addition amount determined in Test Example 1, to prepare a mint flavoring composition for sugar candy, as shown in Table 3.

[0046] [Comparative Examples 1 and 2] To the mint flavor prepared in Production Example 1, 3-methyl-2,4-nonanedione and 4-ethylguaiacol proposed in Patent Document 6 as comparative examples were also added in the appropriate amounts proposed in Patent Document 6, to prepare mint flavor compositions of Comparative Examples 1 and 2, as shown in Table 3.

[0047] [Table 3]

[0048] [Test Example 2] (Evaluation in Sugar Candy) For Examples 1 to 13 and Comparative Examples 1 and 2, each mint flavoring composition was blended into a sugar candy as described below, and the fresh leaf feeling enhancing effect of each mint flavoring composition was evaluated. A mixture of sugar (Nissin Sugar Granulated Sugar), starch syrup (Nippon Starch Industry Co., Ltd.), and water was cooked to 150°C, then rapidly cooled to 120°C, and 1% by mass of the mint flavoring composition to be tested was added. The mixture was then molded in the usual manner to prepare sugar candies, which served as the evaluation base. The evaluation was carried out by 10 experienced panelists, who rated each item listed in Table 4 on a 7-point scale, with each control having 4 points, and calculated the average value. The mint flavor of Production Example 1 was used as a control, and the evaluation results are shown in Table 4.

[0049] Very weak: 1 point Weak: 2 points Slightly weak: 3 points Control: 4 points Slightly strong: 5 points Strong: 6 points Very strong: 7 points

[0050] [Table 4]

[0051] The results in Table 4 show that the sugar candies using the mint flavoring compositions of the present invention (Examples 1 to 13) have enhanced the characteristic green and fresh feel of fresh mint leaves.

[0052] [Examples 14 to 25] The fresh leaf feel enhancer of the present invention was added to the mint flavor prepared in Production Example 1 in the appropriate addition amount determined in Test Example 1, to prepare a mint flavor composition for sugarless gum as shown in Table 5.

[0053] [Table 5]

[0054] [Test Example 3] (Evaluation of sugarless gum) The mint flavor compositions of Examples 14 to 25 and Comparative Example 2 were blended into sugarless gum as described below, and the fresh leaf feel enhancing effect of each mint flavor composition was evaluated. 25 parts of chewing gum base (manufactured by Natural Base Co., Ltd.), 40 parts of xylitol (manufactured by Mitsubishi Corporation Food Tech Co., Ltd.), 19 parts of maltitol (manufactured by Mitsubishi Corporation Food Tech Co., Ltd.), and 16 parts of reduced palatinose (manufactured by Mitsui Sugar Co., Ltd.) were mixed and kneaded, and then 1% by mass of the mint flavoring compositions of Examples 14 to 25 and Comparative Example 2 was added, and the mixture was then molded by conventional methods to obtain an evaluation base. Next, the fresh leaf feeling enhancing effect of sugarless gums using the mint flavor compositions of Examples 14 to 25 and Comparative Example 2 was evaluated. The evaluation was performed by 10 experienced panelists using the same evaluation method as in Test Example 2, and the average values ​​were calculated. The sugarless gum using the mint flavor of Production Example 1 was used as a control, and the evaluation results are shown in Table 6.

[0055] [Table 6]

[0056] The results in Table 6 show that the sugarless gum using the mint flavor composition of the present invention has an enhanced characteristic green feel and characteristic fresh feel of fresh mint leaves. [Industrial Applicability]

[0057] According to the present invention, a mint flavoring composition can be obtained that imparts and enhances the feeling of fresh leaves, and by adding this flavoring composition, a mint-flavored food or beverage or a mint-flavored oral composition having a fresh mint feeling can be obtained. Therefore, the variety of mint flavors currently available on the market is increasing, and this will meet the needs of consumers with diversified tastes, leading to increased demand for foods, beverages, and oral compositions.

Claims

1. 1-methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, 2-methylthioethanol, 2-mercapto-3-butanol, 3-methyl-2-butanethiol, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, S-methyl 2-methylbutanethioate, 3-methylthiopropyl acetate, 3-mercapto-3-methylbutan-1-ol, 3-mercaptohexyl hexanoate, 3-mercapto-2-butanone, Methyl methylthioacetate or Ethyl methylthioacetate The fresh leaf feeling enhancing agent for mint flavoring contains one or two kinds selected from the group consisting of peppermint oil, spearmint oil and peppermint white oil as an active ingredient.

2. 1-methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 3-methyl-2-butanethiol, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-methylthiopropyl acetate, 3-mercapto-2-pentanone, ethyl thioacetate, S-methyl hexanethioate, isoamyl mercaptan, 2,8-epithio-p-menthane, 4-methylthio-4-methyl-2-pentanone, S-methyl 2-methylbutanethioate, 2-Methylthioethanol or 2-Mercapto-3-butanol The fresh leaf feeling enhancing agent for mint flavoring contains one or two kinds selected from the group consisting of peppermint oil, spearmint oil and peppermint white oil as an active ingredient.

3. 1-methoxy-3-methylbutane-3-thiol, 3-methylthiohexyl acetate, 4-mercapto-4-methyl-2-pentanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 2-methyl-1-butanethiol, 3-mercapto-3-methylbutyl acetate, 3-mercapto-3-methylbutyl formate, 3-mercapto-2-pentanone, 2,8-epithio-p-menthane, 4-Methylthio-4-methyl-2-pentanone or 2-Methylthioethanol The fresh leaf feeling enhancing agent for mint flavoring contains one or two kinds selected from the group consisting of peppermint oil, spearmint oil and peppermint white oil as an active ingredient.

4. A mint flavoring composition comprising the fresh leaf feeling enhancer according to any one of claims 1 to 3 and one or two mint flavorings selected from the group consisting of peppermint oil, spearmint oil, and peppermint white oil, and containing 0.01 to 10,000 ppm of the fresh leaf feeling enhancer.

5. A mint-flavored food or drink or a mint-flavored oral composition, comprising 0.001 to 5.0% by mass of the mint flavoring composition according to claim 4.

6. A method for producing a mint flavoring composition, comprising adding 0.01 to 10,000 ppm of the fresh leaf feeling enhancing agent according to any one of claims 1 to 3 to a mint flavoring containing one or two kinds selected from the group consisting of peppermint oil, spearmint oil, and peppermint white oil.

7. A method for enhancing the fresh mint leaf feel of a mint-flavored food or beverage or a mint-flavored oral composition, comprising adding 0.01 to 10,000 ppb of the fresh leaf feel enhancer according to any one of claims 1 to 3 to the mint-flavored food or beverage or mint-flavored oral composition, the mint-flavored food or beverage containing one or two selected from the group consisting of peppermint oil, spearmint oil, and peppermint white oil.

8. A method for imparting a mint flavor having a fresh leaf feel to a food, beverage, or oral composition, comprising adding 0.001 to 5.0 mass % of the mint flavoring composition according to claim 4 to the food, beverage, or oral composition.

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