Flavor enhancer, flavor composition, consumer goods, and method for improving the flavor of consumer goods

Abstract

This invention provides a novel means for imparting, enhancing, or improving flavor. [Solution] The present invention relates to a flavor enhancer comprising a compound represented by the following formula (1-1) or (1-2). JPEG2026091398000020.jpg30130

Description

[Technical Field]

[0001] The present invention relates to a flavor enhancer, a flavor composition, a consumer product, and a method for improving the flavor of a consumer product. [Background technology]

[0002] The aroma and taste of food and beverages significantly influence consumer preferences, making them crucial elements that characterize those products. In recent years, with the diversification of consumer tastes, there has been a growing demand for food and beverages with a variety of aromas and flavors. Furthermore, aroma is an important element not only in food and beverages but also in the field of cosmetics, and with the increasing demand for high-end products, there is a growing need for products with natural-sounding aromas and flavors.

[0003] Against this backdrop, one technique used to enhance or impart desired aromas is to add fragrance components from food, beverages, and cosmetics as fragrance ingredients.

[0004] For example, Patent Document 1 proposes a milk-based fragrance composition containing lactones and at least one selected from the group consisting of fatty acids and hydrolyzed oils and fats, for the purpose of improving fragrance persistence and naturalness. Patent Document 1 also states that esters and the like may be added to the above-mentioned milk-based fragrance composition as fragrance / flavor imparters or enhancers / improvers. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2005-015685 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] With the increasing diversification of consumer preferences, there is a growing demand for novel fragrances used in consumer goods. There is a need for new fragrances that can impart, enhance, or improve the aroma and flavor of consumer products.

[0007] Therefore, the present invention has been made in view of the above circumstances, and aims to provide a novel means that can impart, enhance, or improve flavor. [Means for solving the problem]

[0008] The inventors of the present invention conducted extensive research to solve the above problems and discovered that optical isomers represented by the following formula (1-1) or formula (1-2) exhibit superior flavor imparting, enhancement, or improvement effects that differ from those of racemates, thus completing the present invention.

[0009] In other words, the above objective is achieved by the following means.

[0010] One aspect of the present invention is, [1] A flavor enhancer comprising a compound represented by the following formula (1-1):

[0011] [ka]

[0012] In the above equation (1-1), R 1 These are linear or branched alkyl groups having 1 to 4 carbon atoms.

[0013] Furthermore, other embodiments of the present invention include: [2] A flavor enhancer comprising a compound represented by the following formula (1-2):

[0014] [ka]

[0015] In the above equation (1-2), R 2is a linear or branched alkyl group having 1 to 4 carbon atoms.

[0016] Still another aspect of the present invention is [3] A fragrance composition (excluding those containing racemates) containing the fragrance imparting enhancer described in [1] above and / or the fragrance imparting enhancer described in [2] above.

[0017] Still another aspect of the present invention is [4] A consumer product containing the fragrance imparting enhancer described in [1] or [2] above or the fragrance composition described in [3] above.

[0018] [5] In the consumer product described in [4] above, based on the total mass of the consumer product, the total content concentration of the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2) is 0.01 mass ppt to 1 mass ppm (however, when the compound represented by the above formula (1-1) and the compound represented by the above formula (1-2) are in a enantiomeric relationship, those containing these compounds in a mass ratio of 50:50 are excluded) is preferable; [6] The consumer product described in [4] or [5] above is preferably a food or drink or a cosmetic.

[0019] Still another aspect of the present invention is [7] A method for improving the fragrance of a consumer product, which includes adding the fragrance imparting enhancer described in [1] or [2] above or the fragrance composition described in [3] above to the consumer product.

Effects of the Invention

[0020] According to the present invention, a novel means capable of imparting, enhancing or improving fragrance is provided.

Modes for Carrying Out the Invention

[0021] An embodiment of the present invention will be described in detail below. In this specification, "X~Y" indicating a range includes X and Y, meaning "X or more and Y or less," and "concentration (%, ppm, ppb, ppt)" represents "mass concentration" unless otherwise specified. Also, "A and / or B" means at least one of A and B, and refers to A, B, and combinations of A and B. Furthermore, unless otherwise specified, the operation and measurement of physical properties, etc., are performed under conditions of room temperature (20~25℃) / relative humidity 40~50%RH.

[0022] Furthermore, in this specification, "flavor" means one or more senses that can be altered by aroma, typically including smell and / or taste. In this specification, the term "flavoring imparted" includes adding a new flavor and / or enhancing a flavor, and also includes cases where the flavor is improved as a result of flavoring or enhancement. The "flavoring imparting and enhancing agents" described in detail below include agents that, upon addition, impart flavor to the target (mainly consumer goods), enhance the flavor of the target (mainly consumer goods), or provide both of these effects. Furthermore, in this specification, the flavor of food and beverages may be referred to as "aroma." Furthermore, in this specification, when "flavor" is used for things that are not normally consumed (e.g., cosmetics, air fresheners, etc.), it mainly refers to the "aroma" of that thing. Furthermore, in this specification, "addition" is almost synonymous with "compounding," and includes at least one of simply adding something to a substance by spraying, dropping, etc., and mixing it with a substance.

[0023] [Flavor enhancer] According to one aspect of the present invention, a flavor enhancer comprising a compound represented by the following formula (1-1) is provided:

[0024] [ka]

[0025] In the above equation (1-1), R 1This is a linear or branched alkyl group having 1 to 4 carbon atoms. In this specification, the above flavor enhancer is also simply referred to as "flavor enhancer according to the present invention" or "flavor enhancer (3S form)".

[0026] Furthermore, according to another aspect of the present invention, a flavor enhancer comprising a compound represented by the following formula (1-2) is provided:

[0027] [ka]

[0028] In the above equation (1-2), R 2 This is a linear or branched alkyl group having 1 to 4 carbon atoms. In this specification, the above flavor enhancer is also simply referred to as "flavor enhancer according to the present invention" or "flavor enhancer (3R form)".

[0029] To our surprise, the inventors have discovered that the optical isomers represented by formula (1-1) or formula (1-2) exhibit superior flavor imparting, enhancement, or improvement effects that differ from those of the racemic mixture. Specifically, while the aroma of the racemic mixture of the fatty acid ester is a mellow, fruity note, the aroma of the compound represented by formula (1-1) is a bright, vibrant, fresh, fruity note, and the aroma of the compound represented by formula (1-2) is a ripe fruit or aged liquor-like fruity note. Furthermore, the inventors have also discovered that, compared to the racemic mixture, each of the optical isomers can impart, enhance, or improve the flavor of consumer goods to which they are added, even in small amounts.

[0030] The following describes the flavor enhancer (3S form) and the flavor enhancer (3R form) according to the present invention.

[0031] Flavor enhancer (3S form) The flavor enhancer (3S form) according to the present invention consists substantially of only the fatty acid ester represented by the above formula (1-1). Here, it is stated that it "consists substantially of only X" because the flavor enhancer (3S form) may contain impurities that are inevitably introduced during the synthesis process, etc., as long as they do not affect the flavor. In a more preferred embodiment, the flavor enhancer (3S form) according to the present invention consists solely of the fatty acid ester represented by the above formula (1-1).

[0032] In the above equation (1-1), R 1 R is a linear or branched alkyl group having 1 to 4 carbon atoms. Examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl groups. Among these, R 1 The group is preferably a methyl group or an ethyl group, and more preferably an ethyl group. That is, the flavor enhancer (3S form) is preferably methyl 3-methylpentanoate (3S) or ethyl 3-methylpentanoate (3S), and more preferably ethyl 3-methylpentanoate (3S).

[0033] The above-mentioned flavor enhancer (3S form) can be produced by esterifying the corresponding fatty acid ((S)-3-methylvaleric acid) by a known method. The method of obtaining (S)-3-methylvaleric acid is not particularly limited; it can be obtained by any method, such as purchasing commercially available reagents or synthesizing it by a known method. Alternatively, the above-mentioned flavor enhancer (3S form) can also be produced by esterifying racemic 3-methylvaleric acid by a known method to obtain a fatty acid ester, and then separating the 3S form from the fatty acid ester using separation means such as column chromatography.

[0034] The target products (consumer goods) and concentration of the above-mentioned flavor enhancer (3S form) will be explained in detail in the [Consumer Goods] section below.

[0035] Flavor enhancer (3R variant) The flavor enhancing agent (3R form) according to the present invention consists essentially of only the fatty acid ester represented by the above formula (1-2). That is, the flavor enhancing agent (3R form) may contain impurities inevitably mixed in the process such as synthesis as long as it does not affect flavor imparting. In a more preferred embodiment, the flavor enhancing agent (3R form) according to the present invention consists of only the fatty acid ester represented by the above formula (1-2).

[0036] In the above formula (1-2), R 2 is a linear or branched alkyl group having 1 to 4 carbon atoms. Specific examples of such an alkyl group include the same specific examples as the alkyl group as R 1 . Among them, R 2 is preferably a methyl group or an ethyl group, and more preferably an ethyl group. That is, the flavor enhancing agent (3R form) is preferably methyl 3-methylpentanoate (3R) or ethyl 3-methylpentanoate (3R), and more preferably ethyl 3-methylpentanoate (3R).

[0037] The above flavor enhancing agent (3R form) can be produced by esterifying the corresponding fatty acid ((R)-3-methylvaleric acid) by a known method. The method for obtaining (R)-3-methylvaleric acid is not particularly limited, and it can be obtained by any method such as purchasing a commercially available reagent or synthesizing it by a known method. Further, the above flavor enhancing agent (3R form) can also be produced by esterifying racemic 3-methylvaleric acid by a known method to obtain a fatty acid ester, and then separating the 3R form from the above fatty acid ester using a separation means such as column chromatography.

[0038] The addition target (consumer goods) and addition concentration of the above flavor enhancing agent (3R form) will be described in detail in the following section [Consumer Goods].

[0039] [Flavor composition] According to another aspect of the present invention, a fragrance composition (excluding one containing a racemic mixture) is provided, comprising the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form). By adding this fragrance composition to various consumer goods, excellent flavor can be imparted, enhanced, or improved in those consumer goods. In this specification, the above-mentioned fragrance composition is also simply referred to as "the fragrance composition according to the present invention" or "fragrance composition."

[0040] The above-mentioned flavor enhancer (fatty acid ester) contained in the fragrance composition may be a single type, or two or more types may be mixed, as long as the fatty acid ester does not form a racemic mixture. In this specification, "racemic mixture" refers to an equimolar (50:50) mixture of the compound represented by formula (1-1) and the compound represented by formula (1-2) that are enantiomers of each other, i.e., a racemic mixture. Therefore, an example of a racemic mixture is an equimolar mixture of ethyl 3-methylpentanoate (3S) and ethyl 3-methylpentanoate (3R). On the other hand, an equimolar mixture of methyl 3-methylpentanoate (3S) and ethyl 3-methylpentanoate (3R) is not included in a racemic mixture because these compounds are not enantiomers of each other.

[0041] As described above, a fragrance composition according to one embodiment of the present invention may contain the compound represented by formula (1-1) (flavor enhancer (3S isomer)) and the compound represented by formula (1-2) (flavor enhancer (3R isomer)). In this case, the mixing ratio of the compound represented by formula (1-1) (flavor enhancer (3S isomer)) and the compound represented by formula (1-2) (flavor enhancer (3R isomer)) is not particularly limited, but for example, the mass ratio (3S isomer:3R isomer) of the flavor enhancer (3S isomer) and the flavor enhancer (3R isomer) may be less than 100:greater than 0 to greater than 0:less than 100, 15:85 to 85:15, or 30:70 to 70:30 (except when the 3R isomer and the 3S isomer are enantiomers, in which case 50:50 is excluded). Furthermore, the molar ratio (3S:3R) of the flavor enhancer (3S isomer) to the flavor enhancer (3R isomer) may be less than 100:greater than 0 to greater than 0:less than 100, 15:85 to 85:15, or 30:70 to 70:30 (except when the 3R and 3S isomers are enantiomers, in which case 50:50 is excluded). The above mass ratio and molar ratio can be appropriately adjusted depending on the aroma and flavor of the product to which the flavoring composition is added (consumer goods) and the purpose for which the flavoring composition is added. The above mass ratio and molar ratio can be confirmed by methods such as gas chromatography.

[0042] Furthermore, in the above embodiments, the fragrance composition preferably contains methyl 3-methylpentanoate (3S) and / or ethyl 3-methylpentanoate (3S), and methyl 3-methylpentanoate (3R) and / or ethyl 3-methylpentanoate (3R), and more preferably contains ethyl 3-methylpentanoate (3S) and ethyl 3-methylpentanoate (3R) (except when the fragrance composition contains a racemic mixture thereof).

[0043] In another embodiment, the fragrance composition contains the compound represented by formula (1-1) (flavor enhancer (3S isomer)) (preferably, the mass ratio (3S isomer:3R isomer) is 100:0. Also, preferably, the molar ratio (3S isomer:3R isomer) is 100:0). Furthermore, in yet another embodiment, the fragrance composition contains the compound represented by formula (1-2) (flavor enhancer (3R isomer)) (preferably, the mass ratio (3S isomer:3R isomer) is 0:100. Also, preferably, the molar ratio (3S isomer:3R isomer) is 0:100). From the viewpoint of easily obtaining the desired effect with a smaller amount of addition, it is preferable that the fragrance composition according to one embodiment of the present invention contains the compound represented by formula (1-1) (flavor enhancer (3S isomer)). From a similar viewpoint, the fragrance composition according to one embodiment of the present invention is more preferably composed of methyl 3-methylpentanoate (3S) or ethyl 3-methylpentanoate (3S), and is particularly preferably composed of ethyl 3-methylpentanoate (3S).

[0044] A fragrance composition according to one embodiment of the present invention contains the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form) as active ingredients. Here, "containing the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form) as active ingredients" means containing them in an amount sufficient to exhibit the desired aroma. Therefore, the fragrance composition may contain only the above-mentioned flavor enhancer (3S form), only the above-mentioned flavor enhancer (3R form), or only the above-mentioned flavor enhancer (3S form) and the above-mentioned flavor enhancer (3R form) (excluding racemic mixtures), but may contain other components (optional components) as long as they do not impair the desired flavor (aroma).

[0045] In the fragrance composition according to the present invention, in addition to the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form) (i.e., active ingredient), specific examples of other components (optional components) that may be further included include various types of fragrance compounds, fragrance compositions, pigments, vitamins, functional substances, fish extracts, livestock extracts, animal and plant extracts, animal and vegetable oils and fats, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, emulsifiers, specific gravity adjusters, antioxidants, and the like. For example, natural essential oils, natural fragrances, and synthetic fragrance compounds can be cited as described in "Japan Patent Office Gazette, Collection of Well-Known and Conventional Technologies (Fragrances), Part II: Food Fragrances, published January 14, 2000," "Survey on the Actual Use of Food Fragrance Compounds in Japan" (FY2000 Ministry of Health and Welfare Research Report, Japan Fragrance Manufacturers Association, published March 2001), and "Synthetic Fragrances: Chemistry and Product Knowledge" (Revised and Enlarged Edition published December 20, 2016, edited by the Synthetic Fragrance Editorial Committee, Chemical Daily Co., Ltd.).

[0046] More specific examples of fragrance compounds include hydrocarbon compounds such as monoterpenes like α-pinene, β-pinene, myrcene, camphene, and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene; and 1,3,5-undecatriene.

[0047] Examples of alcohol compounds include saturated or unsaturated alcohols such as butanol, pentanol, 3-octanol, hexanol, (E)-2-hexen-1-ol (trans-2-hexenol), (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol; terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenolate, farnesol, nerolidol, cedrol, and terpineol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0048] Examples of aldehyde compounds include saturated or unsaturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, (E)-2-hexenal, and 2,4-octadienal; terpene aldehydes such as citronellal, hydroxycitronellal, citral, myrthenal, and perillaldehyde; and aromatic aldehydes such as benzaldehyde, cinnamaldehyde, amylcinnamaldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolylaldehyde.

[0049] Examples of ketone compounds include saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, and acetoin; diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethylmaltol, cyclotene, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone; terpene ketones such as carvone, menthone, and nootkatone; ketones derived from terpene decomposition products such as α-ionone, β-ionone, and β-damascenone; and aromatic ketones such as raspberry ketone.

[0050] Examples of furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, mentfuran, theaspiran, estragole, eugenol, and 1,8-cineole.

[0051] Examples of ester compounds include aliphatic esters such as ethyl acetate, isoamyl acetate, ethyl propionate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, ethyl caproate, isoamyl isovalerate, ethyl octanoate, and ethyl nonanoate; terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, and terpenyl acetate; and aromatic esters such as benzyl acetate, benzyl butyrate, methyl salicylate, benzyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

[0052] Examples of lactone compounds include saturated and unsaturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, δ-dodecalactone, 7-decene-4-olide, and 2-decene-5-olide.

[0053] Examples of acidic compounds include saturated or unsaturated fatty acids such as acetic acid, butyric acid, octanoic acid, isovaleric acid, caproic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0054] Examples of nitrogen-containing compounds include pyridine, alkyl-substituted pyrazines, methyl anthranilate, and trimethylpyrazine.

[0055] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, and furfuryl mercaptan.

[0056] Examples of natural essential oils include sweet orange, bitter orange, petitgrain, lemon, grapefruit, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, labdanum, elderflower, and clary sage.

[0057] Examples of various plant and animal extracts include extracts of herbs or spices, various tea extracts such as coffee, green tea, black tea, or oolong tea, and milk or dairy products and various enzyme hydrolysates such as lipases and / or proteases thereof.

[0058] In one embodiment, the preferred fragrance compound (optional component) preferably includes one or more selected from the group consisting of alcohol compounds, aldehyde compounds, ketone compounds, ester compounds, lactone compounds, acid compounds, nitrogen-containing compounds, and natural essential oils.

[0059] In other embodiments, the preferred fragrance compounds (optional components) preferably include one or more selected from the group consisting of hexanol, (E)-2-hexen-1-ol (trans-2-hexenol), linalool, octanal, decanal, diacetyl, maltol, ethylmaltol, nootkatone, β-ionone, ethyl acetate, ethyl propionate, ethyl butyrate, ethyl hexanoate, ethyl octanoate, benzyl acetate, methyl cinnamate, γ-decalactone, butyric acid, isovaleric acid, methyl anthranilate, and natural essential oils (preferably grapefruit essential oil).

[0060] In other embodiments, preferred fragrance compounds (optional components) preferably include one or more selected from the group consisting of isobutyraldehyde, isovaleraldehyde, 2-methylbutyraldehyde, guaiacol, 4-ethylguaiacol, 4-vinylguaiacol, 2,6-dimethoxyphenol, phenol, p-cresol, m-cresol, o-cresol, skatole, indole, phenylacetaldehyde, ethyl phenylacetate, 2-phenylethyl acetate, sotolon, homosotonol, homofuraneol, furaneol acetate, ethylcyclopentenolone, 2-methoxy-3-isobutylpyrazine, 2-methoxy-3-isopropylpyrazine, phenylacetic acid, 3-phenylpropionic acid, 3-mercapto-3-methylbutyl formate, and 3-mercapto-3-methylbutyl acetate.

[0061] Other particularly preferred fragrance compounds or extracts include: Republished 2018-110587, JP 2020-65448, Republished 2016-72114, Republished 2016-72111, JP 2015-149950, JP 2013-252112, JP 2009-278957, JP 2008-25 Examples include fragrance compounds or extracts described in Japanese Patent Publication No. 9472, Japanese Patent Publication No. 2006-191925, Japanese Patent Publication No. 2007-61046, Japanese Patent Publication No. 2004-81053, Japanese Patent Publication No. Hei 2-104242, Japanese Patent Publication No. Sho 62-269642, Japanese Patent Publication No. Sho 59-109133, Japanese Patent Publication No. Sho 58-111641, and Japanese Patent Publication No. Sho 52-110873.

[0062] In addition to the above, the fragrance composition according to the present invention may contain, as necessary, components commonly used in fragrance compositions. For example, it may contain fragrance fixatives such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Harcolin, medium-chain triglyceride, and medium-chain diglyceride.

[0063] Furthermore, the other components (optional components) mentioned above may be used individually or in combination of two or more.

[0064] The fragrance composition according to the present invention can take the form of a solution obtained by dissolving the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form) in a water-soluble or oil-soluble solvent, an emulsified formulation, a powder formulation, or other solid formulation (such as solid fat). In other words, the fragrance composition according to the present invention may be a water-soluble fragrance composition, an oil-soluble fragrance composition, an emulsified fragrance composition, a powder fragrance composition, or a solid fragrance composition.

[0065] Examples of the above-mentioned water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, and dipropylene glycol. These may be used individually or in combination of two or more (in the form of a mixed solvent). Of these, if the fragrance composition is to be added to food or beverages, it is preferable to use one or more selected from the group consisting of ethanol, glycerin, and propylene glycol, with ethanol and / or propylene glycol being particularly preferred.

[0066] Examples of the oil-soluble solvents mentioned above include vegetable oils and fats, animal oils and fats, refined oils and fats (for example, processed oils such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and trippropionine), various essential oils, and triethyl citrate. These may be used individually or in combination of two or more (in the form of a mixed solvent).

[0067] Furthermore, to obtain an emulsified formulation, the above-mentioned flavor enhancer (3S form) and / or the above-mentioned flavor enhancer (3R form) and other components (optional components) as needed can be emulsified together with a water-soluble solvent and an emulsifier. The emulsification method is not particularly limited, and an emulsified liquid with excellent stability can be obtained by using various types of emulsifiers that have been conventionally used in food and beverages (for example, fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters, lecithin, modified starch, sorbitan fatty acid esters, quillaja extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein quillaja saponin, or sodium caseinate) and emulsifying them using known mixing methods (homomicker, colloid mill, rotary disc homogenizer, high-pressure homogenizer, etc.). The amount of these emulsifiers used is not strictly limited and can be varied over a wide range depending on the type of emulsifier used. However, generally, an amount of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass, is appropriate for 1 part by mass of the total of the above-mentioned flavor enhancer (3S form) and the above-mentioned flavor enhancer (3R form). In addition, to stabilize the emulsified state, in addition to water, one or more polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup may be added to the emulsified liquid.

[0068] Furthermore, the emulsified liquid obtained as described above can be dried to form a powder formulation if desired. During the powdering process, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup may be added as needed. The amounts used can be appropriately selected according to the desired characteristics of the powder formulation.

[0069] The method for producing the fragrance composition according to the present invention is not particularly limited, and it can be produced by mixing the compound represented by formula (1-1) and / or the compound represented by formula (1-2) with other components (optional components) that are added as needed. In this case, the method of adding each component and the method of mixing are not particularly limited, and known methods can be used. Furthermore, the order in which each component is added is not particularly limited.

[0070] In the fragrance composition according to the present invention, the concentrations of the above-mentioned flavor enhancer (3S form) and the above-mentioned flavor enhancer (3R form) can be arbitrarily determined according to the target of the fragrance composition, and are not particularly limited. In this specification, the above-mentioned flavor enhancer (3S form) (compound represented by formula (1-1) above) and the above-mentioned flavor enhancer (3R form) (compound represented by formula (1-2) above) are collectively referred to as "active ingredients".

[0071] In one embodiment, the concentration of the active ingredient in the fragrance composition (the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2)) is, for example, in the range of 0.1 ppb to 1% relative to the total mass of the fragrance composition. Furthermore, the concentration of the active ingredient in the fragrance composition can be, but is not limited to, the range of 1 ppb to 0.1% (1000 ppm), 10 ppb to 100 ppm, 100 ppb to 100 ppm, 10 ppb to 10 ppm, or 100 ppb to 10 ppm.

[0072] Regarding the concentration of the active ingredient in the fragrance composition, as another example, when the fragrance composition contains substantially only the active ingredient, or only the active ingredient and its solvent or dispersion medium, the concentration is preferably 10 ppb to 100% of the total mass of the fragrance composition, and may be 10 ppm to 99%.

[0073] As another example, regarding the concentration of the active ingredient in a fragrance composition, if the fragrance composition contains other components in addition to the active ingredient and its solvent or dispersion medium, the concentration can be arbitrarily determined according to the target of the addition and the flavor characteristics of the fragrance composition, but it is preferably 1 ppb to 0.1% of the total mass of the fragrance composition, and may be 10 ppb to 100 ppm, 100 ppb to 100 ppm, 10 ppb to 10 ppm, or 100 ppb to 10 ppm. More specifically, the lower limit can be any of 1 ppb, 10 ppb, 100 ppb, 10 ppm, 100 ppm, 1000 ppm, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, or 85%, and the upper limit can be any of 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10%, 5%, 1%, 0.1% (1000 ppm), or 100 ppm, and the range can be any combination of these lower and upper limits, but is not limited to these.

[0074] Furthermore, if the fragrance composition contains two or more compounds represented by formula (1-1) and / or formula (1-2), it is preferable that their total amount be within the above range.

[0075] The target products (consumer goods) to which the above fragrance composition can be added will be explained in detail in the following section on [Consumer Goods], but examples include food and beverages and cosmetics. Therefore, specific examples of the fragrance composition according to the present invention include fragrance compositions for food and beverages (also called flavor compositions) and fragrance compositions for cosmetics (also called fragrance compositions).

[0076] [Consumer goods] According to another aspect of the present invention, consumer goods (excluding those containing a racemic mixture) containing the above-mentioned flavor enhancer or fragrance composition are provided. By adding the above-mentioned flavor enhancer or fragrance composition to various consumer goods, excellent flavor can be imparted, enhanced, or improved in those consumer goods. In this specification, the above-mentioned consumer goods are also simply referred to as "consumer goods according to the present invention" or "consumer goods."

[0077] Examples of articles (consumer goods) to which the above-mentioned flavor enhancer or fragrance composition can be added include, as mentioned above, food and beverages, cosmetics, pharmaceuticals, health and hygiene products, etc., but are not particularly limited. Among these, food and beverages or cosmetics are preferred as the target for the above-mentioned flavor enhancer or fragrance composition. That is, in a preferred embodiment, the consumer goods according to the present invention are food and beverages or cosmetics.

[0078] 《Food and beverages》 One embodiment of the present invention is a food or beverage comprising the above-mentioned flavor enhancer or flavor composition. The food or beverage may contain the compound represented by formula (1-1) and / or the compound represented by formula (1-2) individually, or as a mixture (excluding those containing a racemic mixture).

[0079] The flavor enhancer and flavor composition according to the present invention can enhance the aroma and flavor of food and beverages having various aromas. As described above, the flavor enhancer and flavor composition have fruity notes reminiscent of ripe fruit or aged spirits, as well as bright, vibrant, fresh fruity notes. Therefore, the flavor enhancer or flavor composition can enhance aromas and flavors such as citrus and fruitiness, particularly in food and beverages with fruity aromas, such as food and beverages containing fruit (which may be fruit juice or pulp). Furthermore, in beverages such as tea and coffee containing the flavor enhancer or flavor composition, aromas and flavors such as aftertaste and richness can be enhanced, and in alcoholic beverages and alcoholic-flavored beverages containing these, aromas and flavors such as bitterness and savoryness can be enhanced. Thus, food and beverages containing the flavor enhancer or flavor composition according to the present invention may be given fruit-like aromas and flavors, as well as have their existing aromas enhanced.

[0080] Examples of consumer goods include, but are not limited to, food and beverages. Preferably, examples include food and beverages containing fruit (which may be fruit juice or pulp), teas such as black tea, beverages such as coffee, alcoholic beverages and alcoholic beverages, desserts, confectionery, dairy products, bread, rice dishes, pickles, seafood, prepared foods, meat, soups, curry, stew, seasonings, sauces, and various other food and beverages, but are not limited to these.

[0081] More specific examples of food and beverages include fruit juices and soft drinks containing fruit juice, fruit pulp drinks and fruit drinks containing fruit pieces, such as apples, strawberries, grapes, citrus fruits (grapefruit, oranges, lemons, etc.), passion fruit, mangoes, lychees, guavas, pomegranates, acerola, watermelons, melons, Japanese pears, Western pears, peaches, persimmons, prunes, kiwis, pineapples, bananas, figs, plums, quince, loquats, blueberries, raspberries, and cherries; vegetables such as tomatoes, bell peppers, celery, melons, bitter melons, carrots, potatoes, asparagus, bracken, and fiddlehead ferns, and these Vegetable-based beverages and vegetable soups containing vegetables; beverages such as coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, carbonated drinks (including ciders with various citrus flavors), and lactic acid bacteria beverages; beverages containing herbal medicines and herbs; functional beverages such as cola drinks, fruit juices, dairy drinks, sports drinks, honey drinks, vitamin supplements, mineral supplements, nutritional drinks, nourishing drinks, and lactic acid bacteria beverages; non-alcoholic beverages such as alcohol-flavored beverages (including beer, plum wine, and chuhai); wine, sake, whiskey, and brewing. Alcoholic beverages including rum, shochu, awamori, sake, beer, chuhai, cocktail drinks, sparkling wine, fruit wine, medicinal wine, beer, so-called "third beer" and other brewed alcoholic beverages (sparkling) or liqueurs (sparkling), or alcoholic beverages containing these; various plant-based milks such as almond milk, oat milk, soy milk, rice milk, and coconut milk; desserts such as ice cream, lacto ice cream, frozen desserts, pudding, jelly, mousse, and daily desserts (especially those with vanilla flavor) and mixes for making them; rice crackers, arare, and other sweets. Sweets such as koshian, mochi, manju, uiro, anko, yokan, mizuyokan, kintama, jelly, castella, candy, biscuits, crackers, potato chips, cookies, pies, pudding, buttercream, custard cream, cream puffs, waffles, sponge cake, donuts, chocolate, chewing gum, caramel, candy, peanut paste or other pastes; bread, udon, ramen, Chinese noodles, sushi, gomoku-meshi, fried rice, pilaf, gyoza wrappers, shumai wrappers, okonomiyaki, takoyaki, and other breads, noodles, rice dishes, and other grains;Pickles such as fermented rice bran pickles, pickled plums, fukujinzuke, bettara pickles, senmaizuke, rakkyo, miso pickles, takuan pickles, and pickling mixes; fish such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flounder, sand eel, sweetfish; squid such as Japanese flying squid, spear squid, cuttlefish, firefly squid; octopus such as common octopus, baby octopus; shrimp such as kuruma prawns, spot prawns, spiny lobsters, black tiger prawns; king crab, snow crab, swimming crab Seafood such as crabs (including hairy crabs), clams, cockles, scallops, oysters, and mussels; processed seafood products such as canned goods, boiled fish, tsukudani (simmered seafood), surimi (fish paste), processed seafood products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, and tempura; meats such as chicken, pork, beef, lamb, and horse meat; curry, stew, beef stew, Hayashi rice sauce, meat sauce, mapo tofu, hamburgers, dumplings, kamameshi mix, and soups (corn soup). Processed foods and beverages using meat, such as tomato soup, consommé soup, meatballs, braised pork, and canned meat; table salt, seasoned salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, furikake, ochazuke mix, margarine, mayonnaise, dressing, vinegar, sanbaizu, powdered sushi vinegar, Chinese seasoning mix, tempura dipping sauce, noodle dipping sauce (kombu dashi or katsuobushi dashi, etc.), sauces (medium-thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew mix, Examples include soup bases, dashi stock (such as kelp or bonito stock), compound seasonings, new mirin, mixed flours such as fried chicken batter and takoyaki batter, and other seasonings; animal or plant-based dashi-flavored foods and beverages to which these seasonings are added; dairy products such as cheese, yogurt, and butter; various fermented products made from various microorganisms such as brewer's yeast, baker's yeast, and lactic acid bacteria; simmered dishes such as vegetable stews, Chikuzen-ni, Oden, and hot pots; ingredients and side dishes for takeout bento boxes; and so on.

[0082] Such food and beverages containing the flavor enhancer or flavor composition according to the present invention can be manufactured using methods known to those skilled in the art.

[0083] In one embodiment, the concentration of the active ingredients in food and beverages (the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2)) varies depending on the purpose of their addition and the type of food and beverage, but for example, it can be in the range of 0.01 ppt to 1 ppm relative to the total mass of the food and beverage. That is, in a preferred embodiment, the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2) is 0.01 ppt to 1 ppm relative to the total mass of the consumer good (food and beverage) (however, if the compound represented by formula (1-1) and the compound represented by formula (1-2) are enantiomers, it is preferable to exclude those containing these compounds in a 50:50 mass ratio). By setting the above concentration to 0.01 ppt or higher, it is possible to provide food and beverages with enhanced desired aroma and flavor, or food and beverages with more pronounced conventional aroma characteristics. On the other hand, by setting the above-mentioned concentration to 1 ppm or less, it is possible to suppress the imparting and emphasis of excessive aroma and flavor characteristics (suppression of the imparting and emphasis of aroma and flavor characteristics as off-odors). Furthermore, the concentration of the active ingredient in food and beverages can be within any of the following ranges: 0.1 ppt to 1 ppm, 1 ppt to 100 ppb, 5 ppt to 50 ppb, or 10 ppt to 10 ppb, but is not limited to these ranges.

[0084] Furthermore, the concentration of active ingredients in food and beverages may be set with a lower limit of 0.01 ppt, 0.1 ppt, 1 ppt, 5 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, or 100 ppb, and an upper limit of 1 ppm, 100 ppb, 50 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, or 0.1 ppt, and may be within any combination of these lower and upper limits, but is not limited to these.

[0085] Furthermore, if the food or beverage contains two or more compounds represented by formula (1-1) and / or formula (1-2), it is preferable that their total amount be within the above range.

[0086] The method of adding the above-mentioned flavor enhancer or flavor composition to food and beverages is not particularly limited, and the flavor enhancer or flavor composition may be added all at once or separately, in stages or continuously. Furthermore, the mixing method is not particularly limited, and known methods can be used.

[0087] 《Cosmetics》 One embodiment of the present invention is a cosmetic product comprising the above-mentioned flavor enhancer or the above-mentioned fragrance composition. The cosmetic product may contain the compound represented by formula (1-1) and / or the compound represented by formula (1-2) individually, or as a mixture (excluding those containing a racemic mixture).

[0088] According to the above-mentioned flavor enhancer or fragrance composition, the fragrance of cosmetics having various fragrance notes can be enhanced, and in particular, the existing fragrances of cosmetics having fruity fragrance notes can be emphasized.

[0089] Cosmetics as an example of consumer goods are not particularly limited, but preferably include, but are not limited to, various types of cosmetics such as perfumes, health and hygiene detergents, hair care products, cosmetics, skin care products, facial cleansers, sunscreens, fragrance products, deodorizers (fragrance deodorizers), and room fragrances.

[0090] More specific examples of cosmetics include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoo, conditioner, and hair styling products (hair cream, pomade, etc.); cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, facial emulsion, facial cream, facial gel, serum, and face masks; deodorant products such as antiperspirant spray, deodorant wipes, deodorant cream, and deodorant stick; inorganic salt-based, cooling, and charcoal-based products. Examples include bath additives such as acid-based, skincare-based, enzyme-based, and herbal-based bath additives; sun tanning cosmetics such as suntan products and sunscreen products; health and hygiene detergents such as facial soaps and facial creams, body soaps and body washes, laundry soaps, laundry detergents, disinfectant detergents, deodorizing detergents, fabric softeners, dish soaps, and cleaning detergents; health and hygiene materials such as toothpaste, tissues, and toilet paper; and fragrance products such as air fresheners and room fragrances for rooms and cars.

[0091] Such cosmetic products containing a flavor enhancer or fragrance composition according to the present invention can be manufactured using methods known to those skilled in the art.

[0092] Cosmetics may contain other additives so as not to impair the desired fragrance, that the above-mentioned flavor enhancer or fragrance composition is dispersed uniformly and at an appropriate concentration.

[0093] Other additives are not particularly limited and known additives can be used, as well as other components (optional components) listed in the section on [Fragrance Composition] above. These other additives may be used individually or in combination of two or more.

[0094] In one embodiment, the concentration of the active ingredients in the cosmetic product (the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2)) varies depending on the purpose for which they are added and the type of cosmetic product, but for example, it can be in the range of 0.01 ppt to 1 ppm relative to the total mass of the cosmetic product. That is, in a preferred embodiment, the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2) is 0.01 ppt to 1 ppm relative to the total mass of the consumer good (cosmetic product) (however, if the compound represented by formula (1-1) and the compound represented by formula (1-2) are enantiomers, it is preferable to exclude cases where these compounds are contained in a mass ratio of 50:50). By setting the above concentration, the desired fragrance and flavor in the cosmetic product can be easily enhanced, the characteristics of the conventional fragrance can be more easily emphasized, and the addition and emphasis of excessive fragrance and flavor characteristics can be suppressed. Furthermore, the concentration of the active ingredient in cosmetics may be within the range of 0.1 ppt to 1 ppm, 1 ppt to 100 ppb, 5 ppt to 50 ppb, or 10 ppt to 10 ppb, but is not limited to these ranges.

[0095] Furthermore, the concentration of the active ingredient in cosmetics may be within any combination of the following ranges, but is not limited to these limits: a lower limit of 0.01 ppt, 0.1 ppt, 1 ppt, 5 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, or 100 ppb, and an upper limit of 1 ppm, 100 ppb, 50 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, or 0.1 ppt.

[0096] Furthermore, if the cosmetic product contains two or more compounds represented by formula (1-1) and / or formula (1-2), it is preferable that their total amount be within the above range.

[0097] The method of adding the above-mentioned flavor enhancer or fragrance composition to the cosmetic product is not particularly limited, and the flavor enhancer or fragrance composition may be added all at once or separately, in stages or continuously. Furthermore, the mixing method is not particularly limited, and known methods can be used.

[0098] [Methods for improving the flavor of consumer goods] Another aspect of the present invention provides a method for improving the flavor of consumer goods (excluding cases where the consumer goods contain a racemic mixture), which includes adding the above-mentioned flavor enhancer or fragrance composition to the consumer goods. The optical isomers represented by formula (1-1) or formula (1-2) have superior aromas different from those of the racemic mixture. Therefore, by adding the flavor enhancer or fragrance composition according to the present invention to various consumer goods, it is possible to impart superior flavor to the consumer goods or to enhance or improve the aroma and flavor that the consumer goods conventionally possess. In other words, the flavor enhancer or fragrance composition according to the present invention can be used to improve the flavor of consumer goods and can improve the flavor of the consumer goods to which it is added. In this specification, the above-mentioned flavor improvement method is also simply referred to as "flavor improvement method according to the present invention" or "flavor improvement method".

[0099] The consumer goods to which the above additives are applied are not particularly limited, but examples include food and beverages, cosmetics, pharmaceuticals, or health and hygiene products, and are preferably food and beverages or cosmetics. Specific examples of these consumer goods are as described in the [Consumer Goods] section above.

[0100] In the flavor enhancement method according to the present invention, the amount of flavor enhancer or flavor composition added to the consumer goods (amount added) is only the amount in which the flavor of the consumer goods is improved by the active ingredient, and can be arbitrarily set according to the type and form of the consumer goods. In this case, an example of the concentration of the active ingredient in the consumer goods (total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2) above) is as described in the [Consumer Goods] section above.

[0101] In the flavor enhancement method according to the present invention, the method of adding the flavor enhancer or fragrance composition to the consumer goods is not particularly limited, and the flavor enhancer or fragrance composition may be added all at once or separately, in stages or continuously. Furthermore, the mixing method is not particularly limited, and known methods can be used. In addition, there are no particular limitations on the timing of adding the flavor enhancer or fragrance composition to the consumer goods.

[0102] In a preferred embodiment of the flavor enhancement method according to the present invention, the consumer good is food or beverage, and a flavor enhancer or flavor composition is added such that the concentration of the active ingredient (total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2)) is in the range of 0.01 ppt to 1 ppm relative to the total mass of the food or beverage.

[0103] Furthermore, in the flavor improvement method according to the present invention, in another preferred embodiment, the consumer product is a cosmetic product, and a flavor enhancer or fragrance composition is added such that the concentration of the active ingredient (total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2)) is in the range of 0.01 ppt to 1 ppm relative to the total mass of the cosmetic product.

[0104] According to each of the preferred embodiments described above, the effect of improving the flavor of food, beverages, or cosmetics is more easily obtained.

[0105] The concentration of the above-mentioned active ingredient (concentration in food, beverages, or cosmetics) may be within the range of 0.1 ppt to 1 ppm, 1 ppt to 100 ppb, 5 ppt to 50 ppb, or 10 ppt to 10 ppb, but is not limited to these ranges. [Examples]

[0106] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. Unless otherwise specified, each operation was performed under conditions of room temperature (25°C) / relative humidity of 40-50%RH. Hereafter, unless otherwise specified, "ppt", "ppb", "ppm", and "%" mean "mass ppt", "mass ppb", "mass ppm", and "mass %", respectively.

[0107] [Synthesis Example 1] Synthesis of ethyl 3-methylpentanoate (racemic mixture) Esterification was carried out using commercially available 3-methylpentanoic acid and ethanol in the presence of an acid catalyst (p-toluenesulfonic acid) to obtain ethyl 3-methylpentanoate (racemic mixture).

[0108] [Synthesis Example 2] Synthesis of ethyl (3S)-3-methylpentanoate Esterification was carried out using commercially available (3S)-3-methylpentanoic acid and ethanol in the presence of an acid catalyst (p-toluenesulfonic acid) to obtain ethyl (3S)-3-methylpentanoate.

[0109] [Synthesis Example 3] Synthesis of ethyl (3R)-3-methylpentanoate Esterification was carried out using commercially available (3R)-3-methylpentanoic acid and ethanol in the presence of an acid catalyst (p-toluenesulfonic acid) to obtain ethyl (3R)-3-methylpentanoate.

[0110] [Manufacturing Example 1] Adjustment of Optical Isomer Ratio Using the (3S)-3-methylpentanoate ethyl and (3R)-3-methylpentanoate ethyl (hereinafter also referred to as "the compound") obtained in each of the above synthesis examples, these compounds were blended (mixed) so that the content (mass percentage) of the (3S) isomer was 16.7%, 33.3%, 66.7%, and 83.3%, respectively, to prepare the mixtures.

[0111] [Example 1] Aroma evaluation of the compound For each compound obtained in the above synthesis examples, a 1% by mass ethanol solution was prepared, and the aroma of each compound was evaluated. The results are shown in Table 1.

[0112] [Table 1]

[0113] [Example 2-1] Preparation of grapefruit flavor composition A basic grapefruit fragrance composition was prepared according to the formulation shown in Table 2 below.

[0114] [Table 2]

[0115] Using the ethyl (3S)-3-methylpentanoate obtained in Synthesis Example 2, the ethyl (3R)-3-methylpentanoate obtained in Synthesis Example 3, and each mixture prepared in Production Example 1, ethanol solutions were prepared with an active ingredient concentration (i.e., the total concentration of ethyl (3S)-3-methylpentanoate and ethyl (3R)-3-methylpentanoate) of 1% by mass.

[0116] The above solution was added to the grapefruit basic fragrance composition so that the concentration of the active ingredient in the grapefruit basic fragrance composition was as shown in Table 5 below, thereby preparing the fragrance compositions of the present invention, products 2-1 to 2-18. Then, the obtained fragrance compositions of the present invention, products 2-1 to 2-18, were subjected to sensory evaluation by 10 well-trained panelists (with more than 10 years of experience). In the sensory evaluation, the aroma of the present invention products 2-1 to 2-18 was commented on in comparison to the grapefruit basic fragrance composition without the compound in question, which was used as control product 2-1.

[0117] [Example 2-2] Preparation of grape flavor composition A basic grape (red grape) fragrance composition was prepared according to the formulation shown in Table 3 below.

[0118] [Table 3]

[0119] In Example 2-1 described above, the fragrance compositions of Products 2-19 to 2-36 of the present invention were prepared in the same manner as in Example 2-1, except that the grapefruit basic fragrance composition was changed to a grape basic fragrance composition (Table 5). Then, the obtained fragrance compositions of Products 2-19 to 2-36 of the present invention were subjected to sensory evaluation by 10 well-trained panelists (with 10 years or more of experience). For the sensory evaluation, a grape basic fragrance composition without the compound in question was used as a control product 2-2, and the panelists were asked to comment on the aroma of Products 2-19 to 2-36 of the present invention compared to control product 2-2.

[0120] [Examples 2-3] Preparation of Strawberry Flavor Composition A basic strawberry fragrance composition was prepared according to the formulation shown in Table 4 below.

[0121] [Table 4]

[0122] In the above Example 2-1, the fragrance compositions of Products 2-37 to 2-54 of the present invention were prepared in the same manner as in Example 2-1, except that the grapefruit basic fragrance composition was changed to a strawberry basic fragrance composition (Table 5). Then, the obtained fragrance compositions of Products 2-37 to 2-54 of the present invention were subjected to sensory evaluation by 10 well-trained panelists (with 10 years or more of experience). For the sensory evaluation, a strawberry basic fragrance composition without the compound in question was used as a control product 2-3, and the panelists were asked to comment on the aroma of Products 2-37 to 2-54 of the present invention compared to control product 2-3.

[0123] [Table 5-1]

[0124] [Table 5-2]

[0125] [Example 3-1] Preparation of grapefruit juice Using the ethyl (3S)-3-methylpentanoate obtained in Synthesis Example 2, the ethyl (3R)-3-methylpentanoate obtained in Synthesis Example 3, and each mixture prepared in Production Example 1, ethanol solutions were prepared with an active ingredient concentration (i.e., the total concentration of ethyl (3S)-3-methylpentanoate and ethyl (3R)-3-methylpentanoate) of 1% by mass.

[0126] The above solution was added to commercially available grapefruit juice so that the concentration of the active ingredient corresponded to the concentrations of products 3-1 to 3-24 in Table 6 below, thereby preparing grapefruit juices of products 3-1 to 3-24.

[0127] Then, the grapefruit juices of the obtained products 3-1 to 3-24 of the present invention were subjected to sensory evaluation by 10 well-trained panelists (with more than 10 years of experience). The sensory evaluation was conducted by having the panelists comment on the aroma and flavor of products 3-1 to 3-24 compared to grapefruit juice without the compound in question (control product 3-1), and by averaging the scores given by the panelists to the fruitiness compared to control product 3-1 according to the evaluation criteria below. Here, fruitiness is defined as the sensation of actually eating a grapefruit.

[0128] <Evaluation Criteria for Fruitiness> Significantly increased compared to control product 3-1: 5 points Significantly increased compared to control product 3-1: 4 points Compared to control product 3-1, there was a certain degree of increase: 3 points Slightly increased compared to control product 3-1: 2 points Equivalent to control product 3-1: 1 point.

[0129] [Example 3-2] Preparation of passion fruit juice In the above Example 3-1, passion fruit juices for products 3-25 to 3-48 of the present invention were prepared in the same manner as in Example 3-1, except that grapefruit juice was replaced with passion fruit juice (commercially available) (Table 6).

[0130] Then, the passion fruit juices of the present invention products 3-25 to 3-48 were subjected to sensory evaluation by 10 well-trained panelists (with 10 or more years of experience). The sensory evaluation was conducted by having the panelists comment on the aroma and flavor of the present invention products 3-25 to 3-48 compared to a control product 3-2, and by averaging the scores given by the panelists for the fruitiness compared to the control product 3-2, according to the evaluation criteria below. Here, fruitiness is defined as the sensation of actually eating a passion fruit.

[0131] <Evaluation Criteria for Fruitiness> Significantly increased compared to control product 3-2: 5 points Significantly increased compared to control product 3-2: 4 points Compared to control product 3-2, there was a certain degree of increase: 3 points Slightly increased compared to control product 3-2: 2 points Equivalent to control product 3-2: 1 point.

[0132] [Table 6-1]

[0133] [Table 6-2]

[0134] [Example 4-1] Coffee preparation Using each compound obtained in Synthesis Examples 1 to 3 and each mixture prepared in Production Example 1, ethanol solutions were prepared with an active ingredient concentration (i.e., the total concentration of (3S)-3-methylpentanoate ethyl and (3R)-3-methylpentanoate ethyl) of 1% by mass.

[0135] The above solution was added to commercially available unsweetened black coffee so that the concentration of the active ingredient corresponded to the concentrations of products 4-1 to 4-24 and comparative products 4-1 to 4-4 in Table 7 below, thereby preparing coffee products 4-1 to 4-24 and comparative products 4-1 to 4-4.

[0136] Then, the resulting coffee products 4-1 to 4-24 and comparative products 4-1 to 4-4 were subjected to sensory evaluation by 10 well-trained panelists (with 10 or more years of experience). The sensory evaluation was conducted by having the panelists comment on the aroma and flavor of coffee products 4-1 to 4-24 and comparative products 4-1 to 4-4 compared to control product 4-1, and by averaging the scores given by the panelists to the sense of luxury compared to control product 4-1 according to the evaluation criteria below. Here, "sense of luxury" means that the coffee has a rich and elegant aroma and flavor, like freshly brewed coffee from a specialty coffee shop.

[0137] <Evaluation Criteria for a Sense of Luxury> Significantly increased compared to control product 4-1: 5 points Significantly increased compared to control product 4-1: 4 points Compared to control product 4-1, there was a certain degree of increase: 3 points Slightly increased compared to control product 4-1: 2 points Equivalent to control product 4-1: 1 point.

[0138] [Example 4-2] Preparation of Black Tea Except for replacing black coffee with bottled unsweetened black tea (commercial product) as in Example 4-1 above, the black teas of the present invention products 4-25 to 4-48 and comparative product 4-5 were prepared in the same manner as in Example 4-1 above (Table 7).

[0139] Then, the resulting teas of the present invention (products 4-25 to 4-48) and comparative product 4-5 were subjected to sensory evaluation by 10 well-trained panelists (with 10 or more years of experience). The sensory evaluation involved comparing the flavor of the present invention (products 4-25 to 4-48) and comparative product 4-5 with a control product (4-2) that did not contain the compound in question. The panelists commented on the aroma and flavor of the teas compared to control product 4-2, and then averaged the scores they gave to each product based on the following evaluation criteria. Here, "premium quality" refers to the rich and elegant flavor of tea with a fruity aroma, reminiscent of tea served in a coffee shop.

[0140] <Evaluation Criteria for a Sense of Luxury> Significantly increased compared to control product 4-2: 5 points Significantly increased compared to control product 4-2: 4 points Compared to control product 4-2, there was a certain degree of increase: 3 points Slightly increased compared to control product 4-2: 2 points Equivalent to control product 4-2: 1 point.

[0141] In Examples 4-1 and 4-2 described above, when the concentration of the active ingredient in the present invention was 0.01 ppt, the evaluation (score) for premium quality was similar to that of a comparative product at the same concentration. However, when the concentration of the active ingredient was 10 ppt or higher, the results surpassed those of the comparative product at the same concentration. Furthermore, compared to a comparative product with a similar evaluation (score), the results showed that the present invention required a lower concentration of the active ingredient. This demonstrates that the flavor enhancer (flavor composition) according to the present invention is superior to racemic mixtures in its effect of imparting, enhancing, or improving aroma and flavor even with small amounts of addition.

[0142] [Table 7-1]

[0143] [Table 7-2]

[0144] [Table 7-3]

[0145] [Example 5] Effect of adding to beer-flavored beverages Using the ethyl (3S)-3-methylpentanoate obtained in Synthesis Example 2, the ethyl (3R)-3-methylpentanoate obtained in Synthesis Example 3, and each mixture prepared in Production Example 1, propylene glycol solutions were prepared with an active ingredient concentration (i.e., the total concentration of ethyl (3S)-3-methylpentanoate and ethyl (3R)-3-methylpentanoate) of 1% by mass.

[0146] The above solution was added to commercially available beer-flavored beverages so that the concentration of the active ingredient corresponded to the concentrations of products 5-1 to 5-24 in Table 8 below, thereby preparing the beer-flavored beverages of products 5-1 to 5-24.

[0147] Then, the beer-flavored beverages of the present invention, products 5-1 to 5-24, were subjected to sensory evaluation by 10 well-trained panelists (with 10 years or more of experience). The sensory evaluation was conducted by having the panelists comment on the aroma and flavor of products 5-1 to 5-24 compared to a beer-flavored beverage without the compound in question, which was used as the control product 5-1, and by averaging the scores given by the panelists for the sense of fullness compared to the control product 5-1 according to the evaluation criteria below. Here, "fullness" was defined as a feeling that the aroma and flavor were stronger and that the beverage had more body.

[0148] <Evaluation criteria regarding the feeling of satisfaction from drinking> Significantly increased compared to control product 5-1: 5 points Significantly increased compared to control product 5-1: 4 points Compared to control product 5-1, there was a certain degree of increase: 3 points Slightly increased compared to control sample 5-1: 2 points Equivalent to control product 5-1: 1 point.

[0149] [Table 8]

[0150] [Example 6] Effect of adding to cosmetics Using the ethyl (3S)-3-methylpentanoate obtained in Synthesis Example 2, the ethyl (3R)-3-methylpentanoate obtained in Synthesis Example 3, and each mixture prepared in Production Example 1, ethanol solutions were prepared with an active ingredient concentration (i.e., the total concentration of ethyl (3S)-3-methylpentanoate and ethyl (3R)-3-methylpentanoate) of 1% by mass.

[0151] The above solution was added to a commercially available liquid laundry detergent labeled as having a muscat scent, so that the concentration of the active ingredient reached 1 ppb, to prepare the laundry detergents of the present invention, products 6-1 to 6-6.

[0152] Then, the obtained products 6-1 to 6-6 of the present invention were subjected to sensory evaluation by 10 well-trained panelists (with more than 10 years of experience). In the sensory evaluation, the panelists commented on the differences in aroma when comparing products 6-1 to 6-6 with the corresponding control product 6, using the above-mentioned commercially available liquid laundry detergent without the compound in question as control product 6.

[0153] Table 9 shows the results of the sensory evaluation of products 6-1 to 6-6 of the present invention.

[0154] [Table 9]

[0155] [Example 7] Effect of adding to yogurt Using the ethyl (3S)-3-methylpentanoate obtained in Synthesis Example 2 and the ethyl (3R)-3-methylpentanoate obtained in Synthesis Example 3, ethanol solutions with a concentration of 1% by mass of either ethyl (3S)-3-methylpentanoate or ethyl (3R)-3-methylpentanoate were prepared, respectively.

[0156] The above solutions were added to commercially available plain yogurt, respectively, so that the concentration of (3S)-3-methylpentanoate ethyl or (3R)-3-methylpentanoate ethyl was 1 ppb, to prepare plain yogurts of the present invention products 7-1 ((3S) form) and 7-2 ((3R) form).

[0157] Then, sensory evaluations of the obtained products 7-1 and 7-2 of the present invention were conducted by 10 well-trained panelists (with more than 10 years of experience). In the sensory evaluation, the panelists were asked to comment on the differences in aroma when comparing products 7-1 and 7-2 to the corresponding control product 7, using the commercially available plain yogurt without the compound in question as control product 7. As a result, all panelists agreed that the milk fat content was enhanced compared to control product 7, that product 7-1 had a fruity fermented taste, and that product 7-2 had a rich and full-bodied taste.

[0158] [Example 8] Effect of adding to vanilla ice cream Vanilla ice cream of the present invention products 8-1 ((3S)) and 8-2 ((3R)) was prepared in the same manner as in Example 7, except that plain yogurt was replaced with commercially available vanilla ice cream. During preparation, commercially available vanilla ice cream was thawed at room temperature, a solution of the compound was added, and after addition, it was cooled again in a freezer and evaluated.

[0159] Then, sensory evaluations of the obtained products 8-1 and 8-2 of the present invention were conducted by 10 well-trained panelists (with more than 10 years of experience). In the sensory evaluation, the panelists were asked to comment on the differences in aroma when comparing products 8-1 and 8-2 to the corresponding control product 8, using the commercially available vanilla ice cream without the compound in question as control product 8. As a result, all panelists agreed that the milk fat content was enhanced compared to control product 8, product 8-1 had a fruity fermented flavor, and product 8-2 had a rich and full-bodied flavor.

Claims

1. Flavor enhancers comprising compounds represented by the following formula (1-1): 【Chemistry 1】 In the above formula (1-1), R １ These are linear or branched alkyl groups having 1 to 4 carbon atoms.

2. Flavor enhancers comprising compounds represented by the following formulas (1-2): 【Chemistry 2】 In the above formula (1-2), R ２ These are linear or branched alkyl groups having 1 to 4 carbon atoms.

3. A flavor composition comprising the flavor enhancer described in claim 1 and / or the flavor enhancer described in claim 2 (excluding those containing a racemic mixture).

4. A consumer product comprising the flavor enhancer described in claim 1 or 2.

5. The consumer good according to claim 4, wherein the total concentration of the compound represented by formula (1-1) and the compound represented by formula (1-2) is 0.01 ppt to 1 ppm by mass, based on the total mass of the consumer good (however, if the compound represented by formula (1-1) and the compound represented by formula (1-2) are enantiomers, the consumer good is not included in a 50:50 mass ratio).

6. The consumer goods according to claim 4, wherein the consumer goods are food or beverages or cosmetics.

7. A method for improving the flavor of a consumer product, comprising adding the flavor enhancer described in claim 1 or 2 to the consumer product.

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