JP7305702B2 - Milky flavor imparting composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a composition capable of imparting a milky flavor, and more particularly to a composition that imparts a milky flavor containing 3-hydroxyhexanoic acid.

Currently, several compounds have been proposed for use in imparting milky flavor. For example, in Patent Document 1, one or two selected from the group consisting of methyl 2-methyl-3-furyl disulfide, bis(2-methyl-3-furyl) disulfide, methylfurfuryl disulfide and difurfuryl disulfide It is described that the fragrance composition containing the above disulfide compound can impart and enhance the natural feeling, freshness, and plump milky feeling of milk, dairy products, food and drink containing milk or dairy products, or dairy product substitutes. , Patent Document 2 describes that by including 12-methyltridecanal in dairy products such as butter, cheese, and milk at a concentration of 1 ppt to 100 ppm, the feeling of milk fat, the body, and the richness can be enhanced. Patent Document 3 discloses milk, dairy products, milk or dairy products containing a milk flavor-imparting or milk flavor-improving agent containing (E)-6-nonenal as an active ingredient at a concentration of 0.05 ppt to 2 ppb. It is described that the rich richness and milk fat feeling peculiar to milk can be imparted or improved by including a product or a dairy product substitute.

The components of milk are roughly divided into water, milk fat, and non-fat milk solids (including proteins, carbohydrates, vitamins, and minerals), and both milk fat and non-fat milk solids are important for milky flavor. is thought to play an important role. However, conventional compounds such as those described above are not sufficiently effective in imparting a rich and rich flavor, such as the flavor of skim milk containing a large amount of non-fat milk solids, which is an important factor in milk-like flavor. However, even if conventional milk-like flavor-imparting materials are used, the overall milk-like flavor may be insufficiently rich, and there has been a demand for a more excellent material for imparting a milk-like flavor.

JP-A-2008-92890 JP 2010-158210 A JP 2017-18025 A

An object of the present invention is to provide a flavor-imparting composition capable of imparting a milk-like flavor to various consumer goods such as food and drink, cosmetics, and hygiene products when added to the consumer goods.

The present inventors have made intensive studies to solve the above problems, and found that 3-hydroxyhexanoic acid is effective in imparting a milky flavor.

Thus, the present invention provides the following.
[1] A milky flavor imparting composition containing 3-hydroxyhexanoic acid.
[2] to [1], wherein the ratio ((R):(S)) of the optical isomers ((R) form and (S) form) of 3-hydroxyhexanoic acid is 20:80 to 100:0; A milky flavoring composition as described.
[3] The composition for imparting a milky flavor according to [1] or [2], wherein the milky flavor is the richness of milk.
[4] A method for imparting a milky flavor to a flavor imparting composition, comprising adding the milky flavor imparting composition according to any one of [1] to [3] to another flavor imparting composition.
[5] A method for imparting a milky flavor to consumer goods, comprising adding the milky flavor imparting composition according to any one of [1] to [3] to the consumer goods.
[6] A method for producing a consumable product imparted with a milky flavor, comprising adding the composition for imparting a milky flavor according to any one of [1] to [3] to the consumable product.

INDUSTRIAL APPLICABILITY The present invention has made it possible to provide a composition effective in imparting a milky flavor.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail with specific examples. In the present specification, "to" means a range including lower and upper limits, and concentrations (ppt, ppb, ppm, etc.) and % represent mass concentration and mass%, respectively, unless otherwise specified.
(Milk-like flavor imparting composition)
A milky flavor-imparting composition according to one embodiment of the present invention (hereinafter sometimes referred to as a milky flavor-imparting composition of the present invention) contains 3-hydroxyhexanoic acid represented by the following formula (1) as an active ingredient. It is characterized by containing it, and by adding it to various consumer goods such as food and drink, cosmetics, and hygiene products, it is possible to impart a milky flavor to the consumer goods.

3-hydroxyhexanoic acid was analyzed several decades ago in mango and papaya (Z. Lebensm. Unters. Forsch. 180 (1985), 394-397) and in pig fat (Agric. Biol. Chem. 33 (1969), 1411-1418), as one of the various components identified in the analysis of strawberries (J. Agric. Food Chem. 23 (1975), 482-484); Among the various hydroxy acids with 6 to 10, 12, 14 and 16 carbon atoms identified from the supernatant and/or the milk fat fraction, it has been reported as one of those identified from the supernatant (J. Dairy Sci. (J. Dairy Sci. ( 1977), 60 (5), 718-20), and others are known to be used as materials for polymers (for example, JP 2019-19071 and WO 2014/133088). It is a compound that has never been reported to be effective for It was completely unexpected that the addition of an appropriate amount of this compound to various consumer goods could exhibit an excellent milk-like flavor-imparting effect.

In 3-hydroxyhexanoic acid, the optical isomer may be only the (R) form, only the (S) form, or a mixture thereof, preferably only the (R) form or (R) form and (S) more preferably a mixture of (R)-isomer and (S)-isomer. In the present specification, when simply referred to as "3-hydroxyhexanoic acid", unless otherwise specified, the (R) form only, the (S) form only, and a mixture thereof at any ratio are collectively referred to. do.

Both the (R) and (S) forms of 3-hydroxyhexanoic acid themselves have a spicy, slightly fruity cumin-like aroma, but the (S) form is slightly more cumin-like than the (R) form, The ratio of the (R) form and the (S) form can be adjusted according to the desired perfuming effect.

In the mixture of the (R) form and the (S) form of 3-hydroxyhexanoic acid, the ratio of the (R) form and the (S) form ((R):(S)) is arbitrary, and (R):( S) is 10:90 (in other words, (R)-isomer is 10%, (S)-isomer is 90%), 20:80 ((R)-isomer is 20%, (S)-isomer is 80%), 40:60 ( (R) form 40%, (S) form 60%), 50:50 ((R) form 50%, (S) form 50%, i.e. racemate), 60:40 ((R) form 60%, (S ) body 40%), 70: 30 ((R) 70%, (S) body 30%), 80: 20 ((R) 80%, (S) body 20%), 90: 10 ((R) body 90%, (S) form 10%) can be exemplified. From the viewpoint of milky flavor quality, (R):(S) = 20:80 to 100: 0 (in other words, the (R) form in the mixture is 20% or more and 100% or less), more preferably (R): (S) = 40: 60 to 100: 0 (in other words, the (R) form is in the range of 40% or more and 100% or less), and specific examples of preferred ratios include (R): (S) = 40: 60, 50: 50 (also referred to as racemate), 60: 40, 70: 30, 80:20, 90:10, or 100:0.

The method of obtaining the (R)-form, (S)-form of 3-hydroxyhexanoic acid, and the mixture thereof is not particularly limited. You may get Synthesis of (R)- and/or (S)-form is described in Patent Publication No. 3704731, J. Am. Org. Chem. , 52, 2201-2206 (1987), Enzyme Microb. Technol. , 13(8), 655-660 (1991), J. Am. Org. Chem. , 59(23), 6882-4 (1994); Helvetica Chimica Acta, 69(7), 1699-703 (1986); Am. Chem. Soc. , 103(8), 2127-2129 (1981), International Publication No. 2008/113190, Patent No. 3579352, etc., but is not limited to these documents, and can be synthesized by any method. can.

As used herein, the term "milk-like flavor" refers to a flavor reminiscent of various animal milks such as cow's milk and goat's milk (hereinafter sometimes simply referred to as milk), or various dairy products produced using the same. Examples of dairy products include adjusted milk, processed milk, skim milk, skimmed concentrated milk, milk drinks, fermented milk (yogurt, etc.), butter, cheese, cream, ice cream, condensed milk, powdered milk, whey powder, and buttermilk powder. preferably skim milk or skim concentrated milk, but not limited thereto. In one embodiment of the present invention, the milky flavor preferably includes one or more of raw milk feeling, milk fat feeling, milk richness, milk volume and milk umami, and more preferably at least milk richness. . In the present specification, the raw milk feeling means the feeling of unprocessed natural milk; the richness of milk is the mellow and lingering taste unique to milk felt when eating milk or dairy products. It is a rich feeling, preferably a rich feeling derived from non-fat milk solids (for example, a rich flavor like skim milk or skim concentrated milk containing a large amount of non-fat milk solids). The voluminous feeling of milk means the feeling that the milk-like flavor is strong overall and the aftertaste of the flavor continues richly; It means a strong umami sensation that can be felt not only in raw milk but also in fermented milk. By adding a milk-like flavor imparting composition containing 3-hydroxyhexanoic acid to consumer goods, the consumer goods are imparted with a milk-like flavor, preferably raw milk feeling, milk fat feeling, milk richness and milk volume. A milky flavor containing one or more of the umami sensation of milk can be imparted, whereby the overall milky flavor of the consumer goods can be made into a milky flavor that is more natural, satisfying and has a rich aftertaste. . For non-edible consumer goods (fragrance compositions, cosmetics, etc., which perceive aroma rather than taste), a milk-like aroma can be effectively imparted, particularly preferably a milk-like aroma containing the volume of milk. Thus, the entire milk-like aroma of the consumer goods can be made into a more natural, satisfying milk-like aroma with a rich aftertaste. Examples of consumer goods include food and drink, cosmetics, medical hygiene products, and other flavor-imparting compositions. is not limited to

As used herein, flavor means one or more senses that may be altered by smell, typically including smell and/or taste. As used herein, the term "flavoring" includes adding or enhancing said flavor. Also, the flavor may be improved as a result of "flavoring". Furthermore, as a result of imparting flavor, sensations other than olfactory and/or gustatory sensations, such as cold sensation, warm sensation, texture (such as throat, hardness, viscosity, etc., also referred to as texture), carbonic acid sensation, hotness, etc. It may enhance, suppress, or improve a feeling, etc. Moreover, in this specification, the flavor of food and drink may be called flavor. As used herein, addition includes at least one of simply adding to an object by spraying, dripping, etc., and mixing with an object.

The milk-like flavor-imparting composition of the present invention may be one that can impart a milk-like flavor to consumer goods when added to the consumer goods. It may be one that gives a flavor different from the milk-like flavor.

Examples of the milky flavor-imparting composition of the present invention include compositions capable of imparting flavor to various consumer goods such as food and drink, cosmetics, hygiene products, and other flavor-imparting compositions (typical examples include perfume compositions). ); various extracts that can impart flavor to various consumer goods; other food additives that can impart flavor to various foods and drinks; additives that can impart flavor to various cosmetics and medical hygiene products; not.

The composition for imparting a milky flavor of the present invention contains, in addition to 3-hydroxyhexanoic acid, other active ingredients for imparting a milky flavor, other active ingredients for imparting a flavor, and a solvent, as long as the effects of the present invention are not impaired. and antioxidants, but may consist essentially of 3-hydroxyhexanoic acid. When the milky flavor-imparting composition of the present invention also contains components other than 3-hydroxyhexanoic acid, 3-hydroxyhexanoic acid ((R) form, (S) form, or The concentration of the mixture of these arbitrary proportions) can be arbitrarily determined according to the aroma characteristics of the milky flavor-imparting composition and the object of addition. In this specification, the concentration is the final concentration unless otherwise specified.

When the milky flavor-imparting composition of the present invention does not substantially contain components other than 3-hydroxyhexanoic acid and its solvent (specific examples will be described later), 3- The concentration of hydroxyhexanoic acid can be exemplified within the range of 0.1% to 99.9%. Preferred examples are 1% to 99.9%, 10% to 99.9%, 20% to 99.9%, 50% to 99.9%, 70% to 99.9%, 80% to 99.9% , 90%-99.9%, 95%-99.9%, and 99%-99.9%.

An example of such a concentration is 3-hydroxyhexane in the milky flavoring composition of the present invention, particularly when the milky flavoring composition of the present invention contains a flavoring active ingredient other than 3-hydroxyhexanoic acid. The acid concentration ranges from 0.1 ppt to 0.1%, preferably from 10 ppt to 0.1%, and more preferably from 0.1 ppb to 100 ppm. More specifically, the lower limit is any one of 0.1 ppt, 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, 1 ppm, 10 ppm, and 100 ppm, and the upper limit is 0.1%, 100 ppm, 10 ppm, 1 ppm, and 100 ppb. , 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, and any combination of these lower and upper limits, but are not limited thereto. In particular, when the composition for imparting a milky flavor of the present invention has a milky flavor, these concentrations are preferred. When the concentration of 3-hydroxyhexanoic acid in the milky flavor-imparting composition of the present invention is 0.1 ppt or more, the addition effect of the compound is felt, and when it is 0.1% or less, the fragrance derived from the compound is prominent. Although a milky flavor can be imparted to the milky flavor-imparting composition without excess, depending on the formulation and flavor characteristics of the milky flavor-imparting composition, a concentration below the lower limit or a concentration above the upper limit may be adopted. good.

In addition to 3-hydroxyhexanoic acid, examples of other optional compounds or components that may be contained in the milky flavor-imparting composition of the present invention include various types of flavor compounds or flavor compositions, oil-soluble dyes, Vitamins, functional substances, fish extracts, meat extracts, plant extracts, yeast extracts, animal and plant proteins, animal and plant protein decomposition products, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, etc. can be exemplified. For example, "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavors, Issued on January 14, 2000", "Survey on the Usage of Food Flavoring Compounds in Japan" (2000 Welfare Science Research Report, Japan Perfumery Industry Association, published March 2001) and "Synthetic Perfume Chemistry and Product Knowledge" (published December 20, 2016, enlarged new edition, edited by the Synthetic Perfume Editorial Committee, The Chemical Daily) natural essential oils, natural fragrances, fragrance compounds, etc.

Specific examples of fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, myrcene, camphene and limonene, sesquiterpenes such as valencene, cedrene, caryophyllene and longifolene, and 1,3,5-un. decatriene and the like.

Alcohol compounds include saturated or unsaturated alcohols such as butanol, pentanol, 3-octanol, hexanol, (Z)-3-hexen-1-ol, prenol, 2,6-nonadienol, linalool, geraniol, citronellol, tetrahydro terpene alcohols such as myrcenol, farnesol, nerolidol, cedrol and terpineol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol and cinnamyl alcohol.

Aldehyde compounds include saturated or unsaturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, (E)-2-hexenal, and 2,4-octadienal, citronellal, hydroxycitronellal, citral, myrtenal, perillaldehyde, and the like. aromatic aldehydes such as terpenealdehyde, benzaldehyde, cinnamaldehyde, amylcinnamaldehyde, vanillin, ethylvanillin, heliotropine, and p-tolylaldehyde.

Ketone compounds include saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, 2,5- diketones and hydroxyketones such as dimethyl-4-hydroxy-3(2H)-furanone, terpene ketones such as carvone, menthone, nootkatone, ketones derived from terpene degradation products such as α-ionone, β-ionone, β-damascenone, Aromatic ketones such as raspberry ketones are included.

Furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, 1,8-cineole, and the like.

Ester compounds include ethyl acetate, isoamyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate. , ethyl caproate, isoamyl isovalerate, ethyl nonanoate, etc. Terpene alcohol esters, such as linalyl acetate, geranyl acetate, lavandulil acetate, terpenyl acetate, benzyl acetate, benzyl butyrate, methyl salicylate, benzyl salicylate, cinnamon aromatic esters such as methyl acid, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate;

The lactone compounds include saturated or unsaturated lactones such as γ-decen-decenate, γ-dodecalactone, δ-decen-decenate, δ-dodecalactone, 7-decen-4-olide, 2-decene-5-olide.

Acid 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, linolenic acid.

Nitrogen-containing compounds include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, trimethylpyrazine, and the like.

Sulfur-containing compounds include methanethiol, dimethylsulfide, dimethyldisulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2 -methyl-1-butanethiol, and furfuryl mercaptan.

Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang ylang. , anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, labdanum.

Various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or processed milk products, and various enzymatic decomposition products thereof such as lipase and/or protease.

Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, grapefruit, lime, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, Jasmine, ylang-ylang, anise, cloves, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, labdanum, etc.

Various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or processed milk products, and various enzymatic decomposition products thereof such as lipase and/or protease.

Examples of compounds that can be preferably used in combination to impart a milky flavor include γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decenalactone, 7-decene-4-olide, 3- methyl-4-decen-4-olide, 3-methyl-5-decen-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradelactone, δ-caprolactone, 2 -hexene-5-olide, 2-heptene-5-olide, δ-octalactone, 2-octene-5-olide, 4-methyl-5-octanolide, δ-nonalactone, 2-nonene-5-olide, 4- methyl-5-nonanolide, delta-decalactone, 2-decen-5-olide, 4-methyl-5-decanolide, delta-undecenolide, 2-undecene-5-olide, 4-methyl-5-undecanolide, delta- dodecen-5-olide, 4-methyl-5-dodecanolide, δ-tridecalactone, 2-tridecen-5-olide, 4-methyl-5-tridecanolide, δ-tetradelactone, 2-tetradecene -5-olide, 2-pentadecene-5-olide, 2-hexadecene-5-olide, 2-heptadecene-5-olide, 2-octadecene-5-olide, 2-nonadecen-5-olide, 2-eicosene-5 - Lactones such as Olide, ε-Decalactone, Sotolone; Capric acid, 2-decenoic acid, 4-decenoic acid, 5-decenoic acid, 6-decenoic acid, 9-decenoic acid, 5-hydroxydecenoic acid, 5-hydroxyundecanoic acid, lauric acid, 5-hydroxydodecanoic acid, myristin Acids such as pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, phenylacetic acid, 3-phenylpropionic acid; acetaldehyde, propanal, butanal, 2-butenal, Hexanal, octanal, 4-heptenal, 2,4-octadienal, nonanal, 2-nonenal, 2,4-nonadienal, 2,6-nonadienal, decanal, 2,4-decadienal, undecanal, 2,4-un Aldehydes such as decadienal, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, dodecyl acetate, phenethyl acetate, ethyl lactate, ethyl butyrate, 2-methylbutyric acid Ethyl, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl heptanoate, ethyl heptanoate, ethyl caprylate, isoamyl caprylate, heptyl caprylate, methyl nonanoate, ethyl nonanoate, capric acid Methyl, ethyl caprate, ethyl undecanoate, methyl laurate, ethyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, diethyl sebacate, ethyl 5-hydroxyhexanoate, ethyl 5-hydroxydecanoate , ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate, ethyl 5-hydroxy-9-methyldecanoate; ethanol, propanol, Alcohols such as butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, furfuryl alcohol; 2-heptanone, 2-octanone, 3-octanone, 1-octen-3-one, 2-nonanone, 3-nonanone, 8-nonen-2-one, 2-undecanone, 2-tridecanone, acetoin, 5-hydroxy-4-octanone, diacetyl, 2,3-pentadione, 2,3-hexadione, 2, Ketones such as 3-heptadione, acetylisovaleryl, p-methoxyacetophenone, benzophenone, furaneol, and maltol; Nitrogen-containing compounds such as phenylethylanthranilate, trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, and methylpyrazine ; methyl mercaptan, isobutyl mercaptan, 2,4-dithiapentane, dimethylsulfide, dimethyldisulfide, 2,4-dithiapentane, dimethyltrisulfide, dimethylsulfoxide, dimethylsulfone, methanethiol, methylsulfonylmethane, methylisothiocyanate, ethyliso Thiocyanate, allyl isothiocyanate, 2-methyl-3-butanethiol, methional, ethyl thioacetate, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, sulfurol, acetyl lactic acid thiomethyl ester, propionyl lactic acid Thiomethyl ester, Butyryl lactic acid thiomethyl ester, Valeryl lactic acid thiomethyl ester, 2-Methylbutyryl lactic acid thiomethyl ester, Decylyl lactic acid thiomethyl ester, Acetyl lactic acid thioethyl ester, Propionyl lactic acid thioethyl ester, Butyryl lactic acid thioethyl ester, Valeryl lactic acid sulfur-containing compounds such as thioethyl ester and isocaproyl lactic acid thiopropyl ester; , 3-phenylpropionic acid, butyric acid, capric acid, and δ-decalactone are preferably used in combination.

In addition to flavoring compounds, lipase digests of milk fat; protease digests of milk proteins; fractions of milk or dairy products from milk, concentrated milk, milk powder, milk whey, butter, cheese, yoghurt or mixtures thereof. ; and the like.

The milky flavor imparting composition of the present invention can be prepared by adding 3-hydroxyhexanoic acid to a suitable solvent or dispersion medium by a known method. Examples of the form of the milky flavor-imparting composition of the present invention include solutions in which 3-hydroxyhexanoic acid and other components are dissolved in a water-soluble or oil-soluble solvent, emulsified formulations, powder formulations, and other solid formulations (solid fats, pastes, etc.). ) and the like are preferable.

Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, and propylene glycol. Among these, ethanol or glycerin is particularly preferable from the viewpoint of use in foods and drinks. Oil-soluble solvents include vegetable oils, animal oils, refined oils (for example, processed oils such as medium-chain fatty acid triglycerides and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethyl citrate. etc. can be exemplified.

Also, in order to prepare an emulsified preparation, 3-hydroxyhexanoic acid can be emulsified with a water-soluble solvent and an emulsifier. The method for emulsifying 3-hydroxyhexanoic acid is not particularly limited, and various types of emulsifiers conventionally used in food and drink, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, shochu. Sugar fatty acid ester, polyglycerol fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quillaya extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein quillayasaponin, casein A highly stable emulsified liquid can be obtained by using an emulsifier such as sodium and performing emulsification using a homomixer, a colloid mill, a rotating disc type homogenizer, a high pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited, and can vary over a wide range depending on the type of emulsifier used. to about 100 parts by weight, preferably about 0.1 to about 50 parts by weight. In order to stabilize the emulsification, such a water-soluble solvent liquid contains, in addition to water, polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup. One type or a mixture of two or more types can be added.

Moreover, the emulsion thus obtained can be made into a powder formulation by drying if desired. At the time of powderization, if necessary, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as appropriate. The amount of these agents to be used can be appropriately selected according to the desired properties of the powder formulation.

The milky flavoring composition of the present invention may, if desired, further contain ingredients commonly used in the flavoring compositions described above, such as perfumes. For example, solvents such as water and ethanol, and perfume retention such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hacoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride, etc. agent.
(Method for imparting milky flavor to various consumer goods)
The milky flavor imparting composition of the present invention can be added to any of various consumer goods and used to impart a milky flavor to the consumer goods to which it is added. By imparting a milky flavor to various consumer goods, a milky flavored consumer product is produced. Therefore, in the present invention, the method for imparting a milk-like flavor to various consumer goods can also be said to be a method for producing consumer goods imparted with a milk-like flavor. The various consumer goods to which the milky flavor-imparting composition of the present invention is added may be materials used in the manufacture of certain consumer goods or in-process products during the manufacture of certain consumer goods. It may be one that can be used as it is. Examples include, but are not limited to, food and drink, cosmetics, hygiene products, and other flavoring compositions. For example, flavor-imparted consumer goods can be produced by adding the milk-like flavor-imparting composition of the present invention to various consumer goods such as food and drink, cosmetics, and hygiene products. Further, by adding the milk-like flavor-imparting composition of the present invention to another flavor-imparting composition to further impart flavor, a new flavor-imparting composition imparted with a milk-like flavor may be produced. This new flavoring composition can also be used in the manufacture of various consumer goods as the milky flavoring composition of the present invention. For example, a milky flavor-imparting composition containing 3-hydroxyhexanoic acid itself can be added to various consumer goods such as food and drink, cosmetics, and medical hygiene products, or to various consumer goods such as other flavor-imparting compositions. Alternatively, one or more water-soluble flavors, emulsified flavors, arbitrary flavor compounds, natural essential oils (for example, the above-mentioned "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Flavor), Part II Food Flavor") , “Survey on the actual use of food flavoring compounds in Japan”, and “Flavoring compounds described in “Synthetic flavoring chemistry and product knowledge”), and may be added to various consumer goods.

Preferable examples of consumer goods to which the milk-like flavor composition of the present invention can be added include foods and drinks, cosmetic products, and hygiene products having milk-like flavor. Milky flavor is as described above.

In addition, the consumer goods to which the milky-flavor imparting composition of the present invention is added may further have any other flavor in addition to the milky flavor. Specific examples of flavors other than milky flavors include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat; strawberry, blueberry, Various fruit flavors such as raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat grape, and kyoho (except for the citrus mentioned above); vanilla flavor; green tea, black tea , oolong tea, various tea flavors such as herbal tea; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; Various spices or herbal flavors such as ginger, perilla, ginger, star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, laurel, garlic, wasabi; various nut flavors such as almonds, cashews, walnuts; wine, brandy, Various alcoholic beverage flavors such as whiskey, rum, gin, liqueur, sake, shochu, and beer; Vegetable flavors such as onion, celery, carrot, tomato, and cucumber; Animal meat flavors such as chicken, duck, pork, beef, mutton, and horse meat. red fish such as tuna; white fish such as mackerel, sea bream, salmon and horse mackerel; freshwater fish such as sweetfish, trout and carp; Various seafood and seaweed flavors such as various seaweeds such as kelp; various grain flavors such as rice, barley, wheat, and malt; livestock oils and fats such as beef tallow, chicken oil, and lard, and various fish oils, etc. Various oil and fat flavors;

More specifically, milk drinks and confectionery creams having various fruit flavors including citrus; milk-flavored frozen desserts having vanilla flavor (vanilla ice cream, etc.); coffee-flavored milk coffee beverages; cocoa-flavored cocoa beverages Milk tea with various tea flavors such as black tea and matcha; Mint milk drinks with various mint flavors; Milk drinks with spice flavors such as cinnamon and ginger; Milk drinks with nut flavors; and seaweed-flavored cream or paste; and the like, but not limited to these, and may be any flavor that can be combined with the milk-like flavor.

Examples of food and drink are preferably food and drink that can have a flavor containing a milky flavor. , yogurt, butter, daily spreads, margarine, shortening, nut milk (almond milk, etc.), soy milk and other dairy products or dairy product substitutes; Foods and drinks that can make you feel the flavor including milky flavor include frozen desserts, jelly, sponge cake, hard candy, tablet candy, biscuits, crackers, potato chips, cookies, pies, puddings, butter cream, custard cream, cream puffs, Confectionery such as waffles, sponge cakes, donuts, chocolate, chewing gum, caramel, candy, pastes such as peanut paste; Processed foods and beverages such as stew ingredients and soup ingredients; Various yeasts (brewer's yeast, baker's yeast, etc.) ), fermented products by various microorganisms such as lactic acid bacteria; Coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, carbonated drinks (such as cider with various flavors such as citrus), etc.; Cola drinks, fruit juice drinks , sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nutrition drinks, lactic acid drinks, etc.; Alcoholic beverages; wine, shochu, awamori, refined sake, beer, chuhai, cocktail drinks, low-malt beer, fruit wine, spiced wine, so-called "third beer" and other brewed alcoholic beverages (sparkling) or liqueurs (sparkling) ), etc., or alcoholic beverages containing these; fruit juice drinks such as apples, grapes, citrus fruits (grapefruit, orange, lemon, etc.), soft drinks containing fruit juice, fruit pulp drinks and fruit drinks containing fruit; .

In addition, rice crackers, rice crackers, koshi, mochi, steamed buns, uiro, red bean paste, yokan, water yokan, kingyoku, bread, udon, ramen, Chinese noodles, sushi, gomoku rice, fried rice, pilaf, gyoza skin, shumai Bread, noodles, and rice such as sardine skin, okonomiyaki, and takoyaki; fish such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flatfish, sand eel, and sweetfish; squid, octopus such as common octopus and octopus, prawns such as tiger prawns, botan prawns, spiny lobsters and black tigers, crabs such as king crabs, snow crabs, blue crabs and horse crabs, clams, clams, scallops, oysters, mussels and other shellfish Seafood such as ; Canned food, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, and other processed seafood foods; chicken, pork, beef , mutton, horse meat and other livestock meat; curry, stew, beef stew, hayashi rice sauce, meat sauce, hamburger, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, simmered cubes, canned meat, etc. Seasonings such as margarine, mayonnaise, dressings, sauces (chuno sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, etc., animal or plant seasonings added with these seasonings Stock-flavored foods and drinks; Boiled vegetables, Chikuzen-ni, oden, hot pot dishes, etc.; Ingredients and side dishes for take-out lunch boxes; vegetables, vegetable drinks containing these vegetables, vegetable-containing foods and drinks such as vegetable soups; drinks containing herbal medicines and herbs;

Cosmetics or medical hygiene products to which the milky flavor-imparting composition of the present invention can be added are not particularly limited. hair care products such as pomade); cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic milky lotion, cosmetic cream, cosmetic gel, serum, pack; antiperspirant spray, deodorant sheet, Deodorant products such as deodorant creams and deodorant sticks; bath additives such as inorganic salts, cooling, carbon dioxide, skin care, enzymes, and herbal medicines; suntan products and sunscreen products; Facial cleansers such as facial cleansing creams, body soaps, body soaps, laundry soaps, laundry detergents, disinfectant detergents, deodorant detergents, softeners, kitchen detergents, cleaning detergents, and other health and hygiene detergents; toothpastes, health and hygiene materials such as tissue paper and toilet paper; aromatic deodorants for rooms and cars, and aromatic products such as room fragrances; and the like. The usable flavor tone is not particularly limited, and may be any flavor tone that can be improved by 3-hydroxyhexanoic acid or a flavor imparting composition containing it. , caramel, etc., can be suitably used for fragrances including fragrances reminiscent of milk-based sweets.

In the present invention, the production of 3-hydroxyhexanoic acid in various consumer goods such as foods and drinks, cosmetics, medical hygiene products, and other flavor-imparting compositions to which the milky flavor-imparting composition of the present invention is added. The concentration can be arbitrarily determined according to the flavor of the consumer product, the degree of desired effect, and the like.

As an example of the concentration of 3-hydroxyhexanoic acid in consumer goods, when the milky flavor imparting composition of the present invention is added to another flavor imparting composition, the above section of "milk flavor imparting composition" can be employed.

As an example of the concentration of 3-hydroxyhexanoic acid in consumer goods, when adding the milky flavor-imparting composition of the present invention to food and drink, the concentration of 3-hydroxyhexanoic acid is Concentrations include concentrations in the range of 1 ppt to 10 ppm, more preferably concentrations in the range of 1 ppb to 1 ppm. More specifically, the lower limit is any one of 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, and 1 ppm, and the upper limit is any of 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, and 10 ppt. and upper limits in any combination. Examples of preferred concentration ranges other than the concentration ranges described above include concentrations of 3-hydroxyhexanoic acid of 10ppt to 10ppb, 10ppt to 100ppb, 100ppt to 10ppb, 100ppt to 100ppb, 1ppb to 10ppb, 1ppb to 10ppb, It can be selected from 1 ppb to 100 ppb and 100 ppt to 1 ppm depending on the flavor characteristics of food and drink, but is not limited to these. Although it depends on the type and flavor of the food and drink, when the concentration of 3-hydroxyhexanoic acid in the food and drink is 1 ppt or more, the effect of imparting a milky flavor is felt, and when it is 10 ppm or less, the aroma of 3-hydroxyhexanoic acid itself is felt. However, depending on the flavor of the food and drink to which it is added, it may be added at a concentration below the lower limit or above the upper limit.

As an example of the concentration of 3-hydroxyhexanoic acid in consumer goods, when adding the milky flavor imparting composition of the present invention to cosmetics, the concentration of 3-hydroxyhexanoic acid is Concentrations may range from 1 ppt to 1%. More specifically, the lower limit is 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, or 0.1%, and the upper limit is 1%, 0.1%, 100 ppm, 10 ppm, Any of 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, and 10 ppt include, but are not limited to, any combination of these lower and upper limits. Examples of preferred concentrations include the concentration of 3-hydroxyhexanoic acid with respect to the total mass of cosmetics, from each range of 100ppb to 100ppm, 1ppm to 100ppm, 1ppm to 0.1%, and 10ppm to 0.1%, Although it can be selected according to the fragrance characteristics of cosmetics, it is not limited to these. Although it depends on the type and fragrance of the cosmetic product, when the concentration of 3-hydroxyhexanoic acid in the cosmetic product is 1 ppt or more, the effect of imparting a milky fragrance may be felt, and when it is 1% or less, the 3-hydroxy Although the aroma of hexanoic acid itself can be imparted to the cosmetic product to which it is added, a milky aroma can be imparted to the cosmetic product to which the hexanoic acid is added. good too.

A milky flavor can be imparted by adding an effective amount of the milky flavor-imparting composition of the present invention to consumer goods such as food and drink, cosmetics, and hygiene products. It is possible to improve the milky flavor of the consumer goods to which the is added and improve the palatability. The milky flavor-imparting composition of the present invention can enhance, for example, the top flavor of the milky flavor, and the richness and/or flavor lingering of the middle and last flavors. In particular, the richness and aftertaste of the middle and last flavors can be enhanced.

Furthermore, the milky flavor-imparting composition of the present invention has bitterness, astringency, harshness (collectively referred to as astringent taste), and protein odor that are felt peculiar to protein-rich foods and drinks as a result of imparting a milky flavor. It can also be used to mask offensive odors such as That is, the flavor-imparting composition of the present invention can be added to a protein-rich food or drink that may have a problem of having a pronounced astringent taste or protein odor and being perceived as an off-taste or off-flavour. It can be used to mask protruding offensive odors and unpleasant tastes by imparting a thickness of . Specific examples of such food and drink include various high-nutrition foods such as protein beverages, concentrated liquid diets, and high-nutrient beverages that may contain milk or dairy products, meat substitutes using vegetable protein (also referred to as vegetable meat, etc.). etc., but not limited to these. In order to obtain the masking effect, the concentration of 3-hydroxyhexanoic acid in food and drink can be adjusted. For example, in the aforementioned concentration range of 1 ppt to 1 ppm, by adding a slightly higher concentration to a protein-rich food or drink, it is possible to sufficiently impart milk-like richness and obtain a sufficient masking effect. Examples of the concentration range in which the masking effect is likely to be obtained include a lower limit of 0.01 ppb, 0.1 ppb, 1 ppb, 10 ppb, 20 ppb, 50 ppb, 100 ppb, 200 ppb, and 500 ppb, and an upper limit of 1 ppm, 500 ppb, 200 ppb, and 100 ppb. , 50 ppb, 20 ppb, 10 ppb, 1 ppb, or 0.1 ppb, and the concentration range may be any combination thereof. However, it may be determined according to the desired degree of masking effect and the flavor characteristics of the food or drink to which it is added.

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples.

[Example 1] Example of addition to flavor-imparting composition (Example 1-1) Effect of addition to milk-like flavor-imparting composition According to the general formulation shown in Table 1 below, a basic milk-like flavor exhibiting a milk-like scent is obtained. A formulated perfume composition was prepared.

On the other hand, a 10% ethanol solution of 3-hydroxyhexanoic acid ((R):(S)=50:50) was prepared as the milky flavor-imparting composition of the present invention (Inventive Product 1-1). Furthermore, as a comparative product, a 10% ethanol solution of cuminaldehyde, which is the main aroma component of cumin, which is the aroma that can be felt from 3-hydroxyhexanoic acid, was prepared as a flavor imparting composition of comparative product 1-1, and the aroma of milk was obtained. A 10% ethanol solution of hexanoic acid, which is one of the components, was prepared as a flavor imparting composition of Comparative Product 1-2.

Then, various amounts of 3-hydroxyhexanoic acid ((R):(S) = 50:50) were added to the basic milk-like blended perfume composition as shown in Table 2 below to obtain the composition of the present invention. were prepared as one aspect of the milk-like flavor-imparting composition (Invention Products 1-2 to 1-7). In addition, comparative product 1-1 was added to the basic milk-like blended perfume composition so that the cuminaldehyde concentration shown in Table 2 below was obtained to prepare a comparative product 1-3 perfume composition, and comparative product 1-2. was added to the basic milk-like blended perfume composition so that the concentration of hexanoic acid shown in Table 2 below was obtained to prepare a perfume composition of Comparative Products 1-4.

Then, a sensory evaluation was performed for each of the fragrance compositions of the present invention product and the comparative product. In the sensory evaluation, 10 well-trained panelists with 10 years or more of experience were asked to evaluate the natural feeling of the fragrance of the fragrance compositions of the present invention and the comparative product when the basic milk-like blended fragrance composition was used as a control product. They were asked to score based on the criteria, and to freely comment on their sense of flavor compared to the control product. Panelists' average scores and representative comments are shown in Table 2.
(Reference) Natural feeling compared to the control product (Natural feeling means a natural scent reminiscent of milk itself)
4 points: A very strong improvement effect was felt 3 points: A strong improvement effect was felt 2 points: An improvement effect was felt 1 point: A slight improvement effect was felt 0 points: No improvement effect was felt rice field

As shown in Table 2, the milk-like flavor-imparting composition of the present invention (Inventive Product 1-1), which is a 10% ethanol solution of 3-hydroxyhexanoic acid, was added to the basic milk-like blended flavor composition (control product). The resulting milky flavor-imparting compositions containing 3-hydroxyhexanoic acid (Products 1-2 to 1-7 of the present invention) have an enhanced overall volume of the milky flavor compared to the control product. It was confirmed that by adding the milk-like flavor-imparting composition of the invention to another flavor-imparting composition, a milk-like flavor can be imparted to the other flavor-imparting composition. The effects of 3-hydroxyhexanoic acid include cuminaldehyde, which has an aroma similar to that of 3-hydroxyhexanoic acid, and effects that cannot be obtained from hexanoic acid present in milk like 3-hydroxyhexanoic acid, especially in milk. It was excellent in the voluminousness and richness of the fragrance, and the naturalness of the milky fragrance as a whole.

(Example 1-2) Examination of optical isomer ratio Next, at 100 ppm, which was evaluated as one of the concentrations in the milk-like flavor-imparting composition particularly excellent in the milk-like flavor-imparting effect in Example 1-1, 3- The optical isomer ratio (R):(S) of hydroxyhexanoic acid was varied as shown in Table 3 below and added to the basic milk-like blended flavor composition (control product) to provide the milk-like flavor of the present invention. As one aspect of the composition, milky flavor compositions (Products 1-8 to 1-13 of the present invention) were obtained, and the effect of imparting flavor at each isomer ratio was confirmed by sensory evaluation. In the sensory evaluation, in the same manner as in Example 1-1, 10 well-trained panelists with 10 years or more of experience were asked to evaluate the natural feeling of the fragrance of the milk-like fragrance composition of the present invention compared to the control product as follows. They were asked to score according to the criteria and to freely comment on the sensations they felt regarding the scent. Panelists' average scores and representative comments are shown in Table 3.
(Reference) Natural feeling compared to the control product (Natural feeling means a natural scent reminiscent of milk itself)
4 points: A very strong improvement effect was felt 3 points: A strong improvement effect was felt 2 points: An improvement effect was felt 1 point: A slight improvement effect was felt 0 points: No improvement effect was felt rice field

As shown in Table 3, any optical isomer ratio (R): (S) has a milky flavor-imparting effect, but the higher the ratio of the (R) isomer, the more excellent the natural feeling. It was confirmed that the natural feeling was clearly superior to the control product when the content was 20% or more, and that the (R) form was particularly superior when the content was 40% or more.

[Example 2] Example of addition to dairy products (1)
(Example 2-1) Effect of Addition to Concentrated Skim Milk Commercially available concentrated skim milk was prepared and diluted 3-fold with water. On the other hand, a 99% ethanol solution of 3-hydroxyhexanoic acid ((R):(S) = 50:50) was prepared as a milky flavor-imparting composition of the present invention (Invention Product 2-1). . Then, the milk of the product 2-1 of the present invention was added to the commercially available diluted skimmed milk concentrate so that the concentration of 3-hydroxyhexanoic acid ((R):(S) = 50:50) was as shown in Table 4 below. The flavor imparting composition was added to prepare dairy products of the present invention (Products 2-2 to 2-8 of the present invention). In addition, a 99% ethanol solution of hexanoic acid was prepared and used as a comparative flavoring composition (comparative product 2-1). The dairy products of the present invention and comparative products were sensory evaluated by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, 10 panelists were asked to score according to the following criteria, and to select a commercially available diluted concentrated skimmed milk product as a control product, and freely select the flavor that was felt stronger than the control product. Panelists' average scores and representative comments are shown in Table 3.
(Reference) Regarding the effects of imparting richness compared to the control product, enhancing the aftertaste of milky flavor, and improving palatability (palatableness means the feeling that it is delicious and makes you want to eat it again next time)
4 points: A very strong effect was felt 3 points: A strong effect was felt 2 points: An effect was felt 1 point: A little effect was felt 0 points: No effect was felt

As shown in Table 4, by adding a milky flavor-imparting composition containing 3-hydroxyhexanoic acid (Product 2-1 of the present invention) to a dairy product (diluted skimmed concentrated milk product), the milky flavor was added to the dairy product. It was confirmed that the flavor can be imparted, and that the richness of the milk of the flavor, the aftertaste of the milky flavor, and the palatability can be improved. It was confirmed that the milk-like flavor-imparting effect was obtained at least within the concentration range of 1ppt to 10ppm in food and drink, and that the effect was particularly high at 1ppb to 100ppb.

(Example 2-2) Examination of optical isomer ratio Next, at 10 ppb, which is one of the concentrations in dairy products evaluated to have a particularly high milk-like flavor-imparting effect in Example 2-1, 3-hydroxyhexane The optical isomer ratio of the acid (R): (S) is varied as shown in Table 5 below and added to the diluted concentrated skim milk product to obtain the dairy product of the present invention (products of the present invention 2-9 to 2- 14) was obtained, and the effect of imparting a milky flavor at each isomer ratio was confirmed by sensory evaluation. In the sensory evaluation, 10 well-trained panelists with 10 years or more of experience evaluated the flavor of the dairy product of the present invention using a 3-fold diluted product of commercially available skimmed concentrated milk as a control product, and scored according to the following criteria. , were allowed to freely comment on the sensations felt about the flavor. Panelists' average scores and representative comments are shown in Table 5.
(Reference) Regarding each effect of imparting richness of milk compared to the control product, enhancing the aftertaste of milk-like flavor, and improving palatability (Palatability means feeling delicious and making you want to eat again next time )
4 points: A very strong effect was felt 3 points: A strong effect was felt 2 points: An effect was felt 1 point: A little effect was felt 0 points: No effect was felt

As shown in Table 5, any optical isomer ratio (R): (S) has the effect of imparting a milky flavor, but the higher the ratio of the (R) isomer, the more rich the milk is imparted, and the more the milky flavor is. It was confirmed that the aftertaste enhancement and improvement of palatability are excellent, and the natural feeling is clearly superior to the control product when the (R) form is 20% or more, and is particularly superior when the (R) form is 40% or more.

[Example 3] Example of addition to dairy products (2)
(Example 3-1) Effect of addition to cheese-flavored food and drink A commercially available cheese sauce was prepared. On the other hand, a 95% ethanol solution of 3-hydroxyhexanoic acid ((R):(S)=50:50) was prepared as the milky flavor imparting composition of the present invention (Inventive Product 3-1). The obtained present invention 3-1 was added dropwise to a commercially available cheese sauce, and the 3-hydroxyhexanoic acid ((R): (S) = 50:50) concentration was adjusted to the concentration shown in Table 6 below. The cheese sauce of the present invention was prepared by adding to the sauce and stirring well. Then, the cheese sauce of the present invention was sensory evaluated by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, subjects were scored according to the following criteria, and subjects were asked to freely select the flavor that they felt was strong compared to a commercially available cheese sauce as a control. Panelists' average scores and representative comments are shown in Table 6.
(Reference) Regarding the effects of imparting richness to milk, enhancing the aftertaste of milk-like flavor, and improving palatability compared to the control product do)
4 points: A very strong effect was felt 3 points: A strong effect was felt 2 points: An effect was felt 1 point: A little effect was felt 0 points: No effect was felt

As shown in Table 6, by adding a milky flavor-imparting composition containing 3-hydroxyhexanoic acid (Product 3-1 of the present invention) to a dairy product (cheese sauce), a milky flavor is imparted to the dairy product. confirmed that it can be done. In particular, it was confirmed that the effect of imparting a milky flavor is high at 1 ppb to 100 ppb.

(Example 3-2) Examination of optical isomer ratio Various optical isomer ratios (R):(S) were added to the commercially available cheese sauce as shown in Table 7 below, and the effect of imparting a milky flavor at each ratio was confirmed by sensory evaluation. In the sensory evaluation, a commercially available cheese sauce was used as a control product, and scores were given according to the following criteria. made a comment. Panelists' average scores and representative comments are shown in Table 7.
(Reference) Regarding each effect of imparting richness of milk compared to the control product, enhancing the aftertaste of milk-like flavor, and improving palatability (Palatability means feeling delicious and making you want to eat again next time )
4 points: A very strong effect was felt 3 points: A strong effect was felt 2 points: An effect was felt 1 point: A little effect was felt 0 points: No effect was felt

As shown in Table 7, it was confirmed that the higher the ratio of the (R) form, the better the richness, aftertaste, and palatability, and that the (R) form was particularly excellent at 40% or more.

[Example 4] Example of addition to dairy products (3)
Commercially available butter was prepared and left at room temperature for 10 minutes to soften. On the other hand, a 92% MCT (medium chain fatty acid triglyceride) solution of 3-hydroxyhexanoic acid ((R):(S) = 50:50) was prepared and used as the milky flavor-imparting composition of the present invention ( Item 4-1). The product 4-1 of the present invention was added dropwise to the softened commercially available butter, and the 3-hydroxyhexanoic acid ((R):(S) = 50:50) was added to the commercially available butter so that the concentration was as shown in Table 8 below. By adding and kneading well, the butter of the present invention was prepared (Products 4-2 to 4-6 of the present invention). The butter of the present invention was subjected to sensory evaluation by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, the subjects were asked to freely select the flavor that they felt was stronger than the control product. Representative comments are shown in Table 8.

As shown in Table 8, adding a milk-like flavor-imparting composition containing 3-hydroxyhexanoic acid (Product 4-1 of the present invention) to a dairy product (butter) can impart a milk-like flavor to the dairy product. was confirmed.

[Example 5] Example of addition to dairy products (4)
A commercially available whey protein drink was prepared, and the milky flavor composition of the present invention prepared in Example 1 (Inventive Product 1-7) was added thereto with 3-hydroxyhexanoic acid ((R): (S) = 50 :50) at a concentration of 100 ppb to obtain the dairy product of the present invention (whey protein drink, product 5-1 of the present invention).

Then, using a commercially available product as a control product, the flavor of the whey protein drink of the present invention was sensory evaluated by five well-trained panelists with 10 years or more of experience, and they were asked to comment on the perceived flavor. As a result, 4 out of 5 panelists answered that the product of the present invention felt that the bitterness, astringency, and harshness were suppressed compared to the commercially available whey protein drink, and that it was easier to drink and had better palatability. bottom.

[Example 6] Example of addition to food and drink having milk-like flavor Commercially available milk coffee and milk-containing lactic acid bacteria beverages were prepared. Then, the milky flavor composition of the present invention prepared in Example 1 (Invention Product 1-6) was added to commercially available milk coffee and lactic acid bacteria beverages, and 3-hydroxyhexanoic acid ((R): (S) = 50 :50) to a concentration of 100 ppb to obtain the milk coffee of the present invention (product 6-1 of the present invention) and the lactic acid bacteria beverage of the present invention (product 6-2 of the present invention). Using the commercially available product as a control product, the flavor of the product of the present invention was sensory evaluated by five well-trained panelists with 10 years or more of experience, and they were asked to comment on the perceived flavor. As a result, all five panelists felt that the milk coffee of the present invention (product 6-1 of the present invention) had a feeling that more milk was used than the control product, and the milk had a rich flavor. While the richness was enhanced, the feeling of oil and fat was moderate and a good milky flavor was felt, and the aftertaste of the milky flavor became richer even after eating. Product 6-2) of the present invention gave a feeling that more milk was used than the control product, and the richness due to the richness of milk was enhanced, giving a satisfying feeling. They answered that the aftertaste remained richer and that the drinking experience increased.

[Summary of Examples]
As shown by specific examples in Examples 1 to 6, the milky flavor-imparting composition of the present invention containing 3-hydroxyhexanoic acid contains richness and voluminousness, which could not be sufficiently imparted until now. Since it is possible to impart flavor, it is possible to effectively impart milk-like richness, aftertaste, richness, etc., compared to conventional products, and to improve the palatability and natural feeling of the overall milk-like flavor. very useful for

Claims (6)

A milky flavoring composition comprising 3-hydroxyhexanoic acid. The milky flavor according to claim 1, wherein the ratio (R):(S) of the optical isomers ((R) form and (S) form) of 3-hydroxyhexanoic acid is 20:80 to 100:0. Application composition. 3. The composition for imparting a milky flavor according to claim 1 or 2, wherein the milky flavor is the richness of milk. A method for imparting a milky flavor to a flavoring composition, comprising adding the milky flavoring composition according to any one of claims 1 to 3 to another flavoring composition. A method of imparting a milky flavor to a consumer product comprising adding a milky flavoring composition according to any one of claims 1 to 3 to the consumer product. A method for producing a milky-flavored consumable product comprising adding a milky-flavored composition according to any one of claims 1 to 3 to the consumable product.