Milk deterioration odor masking agent

A milk odor masking agent using specific compounds effectively masks spoilage odors in dairy products, improving their flavor and reducing unpleasant odors.

JP2026095489APending Publication Date: 2026-06-11T HASEGAWA CO LTD

Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
T HASEGAWA CO LTD
Filing Date
2026-03-25
Publication Date
2026-06-11

AI Technical Summary

Technical Problem

Conventional materials have not been sufficient to adequately address the deterioration odor of dairy products, necessitating the discovery of a useful material to improve the odor of spoiled milk.

Method used

A milk odor masking agent containing specific compounds such as isobutyl isobutyrate, isobutyl propionate, and others, which effectively mask the off-flavors and odors caused by milk spoilage, including 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide.

🎯Benefits of technology

The masking agent significantly reduces the perception of spoilage odors in dairy products, enhancing their flavor and palatability while maintaining a desirable taste profile.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

This product provides a masking agent for the odor of spoiled milk. [Solution] A milk odor masking agent is provided that contains one or more compounds selected from the following groups A or B: (Group A) Isobutyl isobutyrate, isobutyl propionate, butyl isobutyrate, butyl propionate, isopropyl isobutyrate, isopropyl 2-methylbutyrate, isopropyl propionate, propyl isobutyrate, propyl butyrate, propyl propionate, ethyl isobutyrate, hexyl formate, octanal, myrcene, diethyl sebacate, diethyl malate, ethyl tigrate, ethyl 3-hydroxyoctanoate; (Group B) 1-heptanol, 2-heptanol, ethyl hexanoate, allyl heptanoate, cyclohexyl butyrate, p-cymene, dimethyl succinate, diethyl tartrate, ethyl 3-hydroxybutyrate.
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Description

【Technical Field】 【0001】 The present invention relates to a milk deterioration odor masking agent. 【Background Art】 【0002】 Consumers' demands for the scent and taste (which may generally be referred to as flavor in this specification) of various consumer products such as food and drink products and cosmetics are increasing, and a plurality of technologies for improving unpleasant flavors have been proposed. 【0003】 For example, products containing milk may have a problem in that when exposed to light, compounds that exhibit an unpleasant odor are generated, and unpleasant odors such as a putrid odor and an odor like deteriorated oil (hereinafter, may be referred to as deterioration odor in this specification) may occur. 【0004】 Therefore, a plurality of technologies related to improving the deterioration odor of products containing milk have been proposed. In Patent Document 1, it is proposed to suppress the deterioration odor of dairy products with a deterioration odor generation inhibitor for milk or dairy products characterized by containing at least one selected from the group consisting of epicatechin, epigallocatechin, epigallocatechin gallate, chlorogenic acid, caffeic acid, ferulic acid, sinapic acid, rosmarinic acid, and gallic acid. In Patent Document 2, it is proposed to mask the deterioration odor of dairy products with a masking agent for dairy product deterioration odor containing at least one selected from the group consisting of sucralose, Lacanca extract, stevia extract, acesulfame potassium, aspartame, and thaumatin. 【Prior Art Documents】 【Patent Documents】 【0005】 【Patent Document 1】 Japanese Patent Application Laid-Open No. 2002-291406 【Patent Document 2】 Japanese Patent Application Laid-Open No. 2023-20971 【Summary of the Invention】 【Problems to be Solved by the Invention】 【0006】 However, conventionally used materials have not been sufficient to adequately address the deterioration odor of dairy products, and the discovery of a useful material that can improve the deterioration odor of dairy products has been a challenge. Therefore, the objective of the present invention is to provide a dairy deterioration odor masking agent containing a compound useful for improving the deterioration odor of dairy products. [Means for solving the problem] 【0007】 In light of the above problems, the inventors conducted diligent research and discovered that the specific components described below are useful in improving the odor of spoiled milk, leading to the present invention. 【0008】 Thus, a brief overview of some of the representative inventions disclosed in this application is as follows: [1] A milk odor masking agent containing one or more compounds selected from Group A or Group B below. (Group A) Isobutyl isobutyrate, isobutyl propionate, butyl isobutyrate, butyl propionate, isopropyl isobutyrate, isopropyl 2-methylbutyrate, isopropyl propionate, propyl isobutyrate, propyl butyrate, propyl propionate, ethyl isobutyrate, hexyl formate, octanal, myrcene, diethyl sebacate, diethyl malate, ethyl tigrate, ethyl 3-hydroxyoctanoate (Group B) 1-Heptanol, 2-Heptanol, Ethyl Hexanoate, Allyl Heptanoate, Cyclohexyl Butyrate, p-Cymene, Dimethyl Succinate, Diethyl Tartrate, Ethyl 3-Hydroxybutyrate [2] The milk spoilage odor masking agent according to [1], comprising one or more compounds selected from group A and one or more compounds selected from group B. [3] A flavoring composition containing the milk odor masking agent described in [1]. [4] A flavoring composition containing the milk odor masking agent described in [2]. [5] A method for improving the spoilage odor of a dairy product, comprising adding a milk spoilage odor masking agent described in [1] or [2], or a flavoring composition described in [3] or [4], to a dairy product. [6] A method for producing a dairy product, comprising adding a milk odor masking agent described in [1] or [2], or a flavoring composition described in [3] or [4], to a dairy product. [7] A composition that simulates the odor of spoiled milk, containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. [8] The milk spoilage odor imitation composition according to [7], further containing 1-octen-3-one. [9] A method for confirming the milk odor masking effect, comprising the steps of: (Step A) preparing a milk odor pseudo-composition containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide; (Step B) preparing a milk odor test composition by adding a milk odor masking candidate substance to the milk odor pseudo-composition; and (Step C) evaluating the milk odor of the milk odor test composition.

[10] The method for confirming the milk spoilage odor masking effect according to [9], wherein the milk spoilage odor pseudo-composition further contains 1-octen-3-one. [Effects of the Invention] 【0009】 This invention provides a milk spoilage odor masking agent that is effective in improving the spoilage odor of dairy products. [Modes for carrying out the invention] 【0010】 The present invention will be described in more detail below with specific examples. In this specification, "~" means a range including the lower and upper limits, concentration (ppt, ppb, ppm, etc.) and % represent mass concentration and mass %, respectively, unless otherwise specified, and concentration refers to the final concentration unless otherwise specified. In this specification, "greater than" means "above the lower limit". 【0011】 [Masking agent for milky odor deterioration] A milk-degradation odor masking agent according to one aspect of the present invention (hereinafter sometimes referred to as "the milk-degradation odor masking agent") is characterized by containing one or more compounds selected from group A or group B below (hereinafter sometimes referred to as "the compounds"). (Group A) Isobutyl isobutyrate, Isobutyl propionate, Butyl isobutyrate, Butyl propionate, Isopropyl isobutyrate, Isopropyl 2-methylbutyrate, Isopropyl propionate, Propyl isobutyrate, Propyl butyrate, Propyl propionate, Ethyl isobutyrate, Hexyl formate, Octanal, Myrcene, Diethyl sebacate, Diethyl malate, Ethyl tigrate tiglate, ethyl 3-hydroxyoctanoate (Group B) 1-Heptanol, 2-Heptanol, Ethyl hexanoate, Allyl heptanoate, Cyclohexyl butyrate, p-Cymene, Dimethyl succinate, Diethyl tartrate, Ethyl 3-hydroxybutyrate In this specification, "milk spoilage odor" refers to the off-flavor and off-odor (unpleasant odor) of dairy products caused by milk spoilage odor substances, and spoilage odor is typically the spoilage odor caused by photodegradation. Examples of milk spoilage odor include putrid odor, unpleasant odor like spoiled oil, unpleasant odor like potatoes, unpleasant odor like mushrooms, and unpleasant odor like green tea. 【0012】 In this specification, the term "milk off-odor substance" is not limited to any compound that contributes to the milk off-odor, but typically includes 1-octen-3-one, 3-methyl-2,4-nonandione, bovolide (3,4-Dimethyl-5-pentylidene-2(5H)-furanone), methional, trans-2-nonenal, dimethyl trisulfide, trans,trans-2,4-decadienal, or combinations of two or more of these, which are considered to contribute to the milk off-odor. For example, although the present invention is not limited to these, among the off-odors of spoiled milk, sulfides such as dimethyl trisulfide are thought to contribute to putrid odors, aldehydes such as trans-2-nonenal contribute to unpleasant odors like spoiled oil, methional contributes to unpleasant odors like potatoes, 1-octen-3-one contributes to unpleasant odors like mushrooms, and 3-methyl-2,4-nonanedione and bobolides contribute to unpleasant odors like green tea. 【0013】 The off-flavor of milk can be effectively masked by masking one or more of these off-flavor substances. In particular, the inventors have discovered for the first time that green tea-like 3-methyl-2,4-nonanedione and bobolide contribute to the off-flavor of milk, and that the off-flavor can be effectively masked by masking these substances. 【0014】 In this specification, masking of milk deterioration odor means making the milk deterioration odor less perceptible, including making the milk deterioration odor hardly perceptible or not perceptible at all. 【0015】 From the perspective of the masking effect of milk deterioration odor, the milk deterioration odor masking agent preferably contains one or more compounds selected from Group A and one or more compounds selected from Group B. In particular, among Group A, isobutyl isobutyrate and diethyl sebacate can be preferably used, and among Group B, 1-heptanol and diethyl tartrate can be preferably used. Therefore, the milk deterioration odor masking agent particularly preferably contains isobutyl isobutyrate and / or diethyl sebacate belonging to Group A, and 1-heptanol and / or diethyl tartrate belonging to Group B. 【0016】 Group A is particularly effective in masking the flavor of 1-octen-3-one, which is a milk deterioration odor substance. 【0017】 Group B is particularly effective in masking the flavors of 3-methyl-2,4-nonanedione and bourgeonal, which are milk deterioration odor substances. 【0018】 In this specification, dairy products refer to various consumer goods manufactured using milk as a raw material, or various consumer goods containing these, and representative examples of consumer goods include food and beverages. The flavor of such dairy products usually has a flavor derived from milk (hereinafter sometimes referred to as a milk-like flavor), but even if it does not have a milk-like flavor, or even if it has a milk-like flavor and one or more other flavors, it is not particularly limited as long as milk deterioration odor substances can occur. Specific examples of food and beverages include, but are not limited to, milk, powdered milk, butter, cheese, ice cream, yogurt, whey beverages, etc. Also, examples of those having a milk-like flavor and one or more other flavors include various fruit-flavored milk beverages that give a feeling of a milk-like flavor and various fruit flavors, yogurt-flavored whey beverages, coffee with milk (café milk), various tea beverages with milk (milk tea, matcha with milk, roasted green tea with milk, etc.), ice cream and yogurt, soups, stews, gratins, etc. using milk that give a feeling of a milk-like flavor and various flavors of livestock meat or seafood, and processed foods using milk, etc., but are not limited to these. 【0019】 In addition to the masking effect of the milk deterioration odor, the present milk deterioration odor masking agent may exhibit a flavor imparting effect derived from the present compound. In that case, by masking the milk deterioration odor and imparting a flavor, the flavor of various dairy products to which the present milk deterioration odor masking agent is added can be improved to be more excellent. 【0020】 The present milk deterioration odor masking agent may consist essentially of only the present compound, or may consist essentially of only the present compound and its solvent, and may contain any other components within the range where the effects of the present invention can be achieved. 【0021】 For the present compound, synthesized ones may be used, or extracts or dried products of natural substances such as animals and plants containing the present compound may be used. 【0022】 The form of the present milk deterioration odor masking agent is not particularly limited, and it may be a solution, an emulsion, a powder, or other solid substances. 【0023】 [Flavor-imparting composition] A flavor-imparting composition according to one aspect of the present invention (hereinafter sometimes referred to as the "flavor-imparting composition") is characterized by containing the milk-degradation odor masking agent. 【0024】 This flavoring composition can be used to impart flavor to various consumer goods by adding it to those goods. In particular, since this flavoring composition contains the milk spoilage odor masking agent, it can also be used to mask milk spoilage odors, making it useful as a flavoring composition for masking milk spoilage odors. 【0025】 In this specification, "flavor" means the sensations perceived by the senses of taste and / or smell. 【0026】 Representative examples of the flavor-imparting compositions in this case include various seasonings, oil and fat compositions, spices, and other flavor-imparting compositions that can impart taste, as well as fragrance compositions (flavors or fragrances). 【0027】 The flavor-imparting composition may consist substantially of the odor-masking agent in question, or it may contain other components. If it contains other components, any component usable in consumer goods may be used. In particular, if the flavor-imparting composition is a fragrance composition, any component usable in fragrance compositions may be used, and specific examples include γ-caprolactone, γ-heptalactone, γ-octaractone, γ-nonalactone, γ-decalactone, 7-decene-4-olide, 3-methyl-4-decene-4-olide, 3-methyl-5-decene-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradecalactone, δ-cap Lolactone, 2-hexen-5-olido, 2-hepten-5-olido, δ-octaractone, 2-octen-5-olido, 4-methyl-5-octanolide, δ-nonalactone, 2-nonene-5-olido, 4-methyl-5-nonanolide, δ-decalactone, 2-decen-5-olido, 4-methyl-5-decanolide, δ-undecalactone, 2-undecen-5-olido, 4-methyl-5-undecanolide, δ-dodecalactone, 2-dodecen-5-olido, 4- Lactones such as methyl-5-dodecanolide, δ-tridecalactone, 2-tridecene-5-olide, 4-methyl-5-tridecalactone, δ-tetradecalactone, 2-tetradecene-5-olide, 2-pentadecene-5-olide, 2-hexadecene-5-olide, 2-heptadecene-5-olide, 2-octadecene-5-olide, 2-nonadecene-5-olide, 2-eicosene-5-olide, ε-decalactone; propionic acid, butyric acid, valeric acid, isovaleric acid, Fatty acids such as caproic acid, trans-2-hexenoic acid, heptanoic acid, caprylic acid, nonanoic acid, 5-hydroxynonanoic acid, 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, myristic acid, pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid;Aldehydes such as acetaldehyde, propanal, butanal, 2-butenal, hexanal, 4-heptenal, 2,4-octadienal, nonanal, 2-nonenal, 2,4-nonadienal, 2,6-nonadienal, decanal, 2,4-decadienal, undecanal, 2,4-undecanal, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural, heliotropin diethyl acetal, etc.; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, butyl acetate Decyl, phenethyl acetate, ethyl lactate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl heptanoate, ethyl heptanoate, ethyl caprylate, isoamyl caprylate, heptyl caprylate, methyl nonanoate, ethyl nonanoate, methyl caprate, ethyl caprate, ethyl undecanoate, methyl laurate, ethyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, ethyl 5-hydroxyhexanoate, Esters such as ethyl 5-hydroxydecanoate, ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate, and ethyl 5-hydroxy-9-methyldecanoate; alcohols such as ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, and furfuryl alcohol; 2-heptanone, 2-octanone, and 3-octanone Ketones such as 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, 2,3-heptadione, acetylisovaleryl, p-methoxyacetophenone, benzophenone, and maltol; nitrogen-containing compounds such as phenylethyl anthranilate, trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, and methylpyrazine;Isobutyl mercaptan, 2,4-dithiapentane, dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, dimethyl sulfoxide, dimethyl sulfone, methanethiol, methylsulfonylmethane, methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, 2-methyl-3-frantiol, methional, ethyl thio, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, sulfrol, thiomethyl acetyl lactate, thiomethyl propionyl lactate, thiomethyl butyryl lactate Examples include known fragrance compounds such as sulfur-containing compounds including methyl esters, valeryl lactate thiomethyl ester, 2-methylbutyryl lactate thiomethyl ester, desilyl lactate thiomethyl ester, acetyl lactate thioethyl ester, propionyl lactate thioethyl ester, butyryl lactate thioethyl ester, valeryl lactate thioethyl ester, and isocaproyl lactate thiopropyl ester; lipase hydrolysates of milk fat; protease hydrolysates of milk protein; and fractions of milk or milk products derived from milk, concentrated milk, powdered milk, milk whey, butter, cheese, yogurt, or mixtures thereof. 【0028】 [Method for masking milk spoilage odor] A method for masking off-flavors of milk according to one aspect of the present invention (hereinafter referred to as "the milk off-flavor masking method") is characterized by including the addition of the milk off-flavor masking agent or the flavoring composition to a dairy product. 【0029】 As shown in the examples described below, this compound can mask the off-flavor of dairy products that exhibit an off-flavor of milk when added to them, and it can also mask the off-flavor of milk that develops due to deterioration of dairy products after the compound is added when added to dairy products that do not exhibit an off-flavor of milk when added to them. Therefore, in this method for masking off-flavor of milk, the dairy product to which this off-flavor masking agent or flavoring composition is added may be one that exhibits an off-flavor of milk or one that does not. 【0030】 The present invention is particularly useful as a method for masking one or more substances selected from the group consisting of 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, which are substances that cause milk spoilage, but the present invention is not limited thereto. 【0031】 From the viewpoint of masking the off-flavor of spoiled milk, the present method for masking off-flavor of spoiled milk preferably includes adding the present off-flavor masking agent or flavoring composition containing one or more compounds selected from group A and one or more compounds selected from group B to a dairy product, and particularly preferably includes adding the present off-flavor masking agent or flavoring composition containing isobutyl isobutyrate and / or diethyl sebacate belonging to group A and 1-heptanol and / or diethyl tartrate belonging to group B to a dairy product. 【0032】 In this milk off-odor masking method, the concentration of the compound in the dairy product can be adjusted to effectively obtain the milk off-odor masking effect. The inventors have confirmed that a masking effect of milk off-odor can be obtained by setting the concentration of all of the compounds in the range of approximately 1 ppt to 100 ppm. Preferably, the masking effect can be obtained by setting the concentration of each of the compounds as shown in Tables 1 and 2 below. Here, concentration range 1 means a concentration range in which a masking effect can be obtained without hardly perceiving the flavor derived from the compound, and concentration range 2 means a concentration range in which both a masking effect and the imparting of flavor derived from the compound can be obtained. In concentration range 2, the flavor of the product to which the compound is added can be improved not only by the masking effect of the compound but also by the flavor imparting effect derived from the compound, and typically, the palatability (or drinkability in the case of beverages) of the food or beverage to which the compound is added can be improved. 【0033】 Therefore, the milk spoilage odor masking method preferably includes adding the milk spoilage odor masking agent or the flavoring composition to a dairy product such that the final concentration of the compound is 1 ppt to 100 ppm (or the total concentration if multiple compounds are added). 【0034】 [Table 1] 【0035】 [Table 2] 【0036】 However, the concentration of the milk odor masking agent in question is not limited to the concentrations listed in Tables 1 and 2, and may be adjusted as appropriate depending on the degree of milk odor deterioration and the desired masking effect. 【0037】 Furthermore, when using multiple compounds in the milk spoilage odor masking method, the ratio of each compound is not particularly limited and can be arbitrarily determined according to the desired masking effect. 【0038】 [Milk deterioration odor pseudo composition] A composition simulating the odor of spoiled milk according to one aspect of the present invention (hereinafter sometimes referred to as the "present composition simulating the odor of spoiled milk") is characterized by containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. In this specification, the present composition simulating the odor of spoiled milk is a composition for reproducing the odor of spoiled milk (a composition for reproducing the odor of spoiled milk), and in particular in this application, it can be said to be a composition for confirming the effect of a candidate substance that can mask the odor of spoiled milk. 【0039】 In dairy products, 3-methyl-2,4-nonanedione and bobolide may be perceived as off-flavors if they are present at concentrations of 0.02 ppb or higher and 10 ppb or higher, respectively. The concentrations of 3-methyl-2,4-nonanedione and bobolide in the present dairy off-flavor pseudo-composition can be determined by referring to these concentrations. However, depending on the flavor and degree of deterioration of the dairy product, off-flavors may be perceived even at concentrations below these limits, and the present invention is not limited to these ranges. 【0040】 In their research on masking agents for milk spoilage odor, the inventors were the first to discover that 3-methyl-2,4-nonanedione and bobolide contribute to milk spoilage odor, and found that the spoilage odor of milk can be effectively masked by masking one or more of these agents. 【0041】 In one preferred embodiment of the present invention, the simulated milk odor composition contains either 3-methyl-2,4-nonanedione or bobolide as the milk odor substance. By containing only one compound, the effect on that compound can be accurately confirmed when used to search for milk odor masking compounds as described later, or when used to confirm the effect of known milk odor masking compounds. In another preferred embodiment of the present invention, the simulated milk odor composition may contain two milk odor substances: 3-methyl-2,4-nonanedione and bobolide. By containing two milk odor substances, it may be possible to confirm which of the two milk odor substances has a masking effect with fewer steps during the above-mentioned search and confirmation. 【0042】 In yet another preferred embodiment of the present invention, the milk spoilage odor-like composition may contain, in addition to one or two selected from 3-methyl-2,4-nonanedione and bobolide, 1-octen-3-one or other known milk spoilage odor-like substances. Examples of other known milk spoilage odor-like substances include, but are not limited to, methional, trans-2-nonenal, dimethyl trisulfide, and trans,trans-2,4-decadienal. By including three or more milk spoilage odor-like substances, it may be possible to determine which of these substances has a masking effect with less effort during the above-mentioned search and confirmation. In dairy products, 1-octen-3-one may be perceived as spoilage odor when present at a concentration of approximately 0.2 ppb or higher, and the concentration of 1-octen-3-one in the milk spoilage odor-like composition can be determined by referring to this concentration. However, depending on the flavor of the dairy product and the degree of spoilage of the dairy product, it may be perceived as spoilage odor even at concentrations below this, and the present invention is not limited to these ranges. 【0043】 Furthermore, in yet another preferred embodiment of the present invention, the milk-like odor-simulating composition may contain various components that contribute to milky flavor and various components found in dairy products. A preferred example is a dairy product containing one or two selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. 【0044】 [How to check the masking effect of milk spoilage odor] A method for confirming the milk deterioration odor masking effect according to one aspect of the present invention is characterized by a method comprising the following steps (hereinafter sometimes referred to as the "confirmation method"). (Step A) A step to prepare a composition that simulates the odor of spoiled milk, containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. (Step B) Step of preparing a milk odor test composition by adding a candidate substance for masking milk odor to the milk odor simulated composition. (Step C) Step to evaluate the milky odor of the milky odor test composition. The composition simulating the odor of spoiled milk is as described in the previous section. In the verification method, the composition simulating the odor of spoiled milk may further contain 1-octen-3-one as the substance causing the odor of spoiled milk. 【0045】 In this specification, the term "candidate milk odor masking substance" includes both known milk odor masking compounds and compounds whose milk odor masking effect is unknown but whose milk odor masking effect is to be confirmed. In this specification, the term "milk odor test composition" includes the candidate milk odor masking substance and 3-methyl-2,4-nonanedione and / or bobolide, and is used to confirm the masking effect of the candidate milk odor masking substance contained in the milk odor test composition on milk odor substances such as 3-methyl-2,4-nonanedione and / or bobolide. 【0046】 This verification method allows for the confirmation of the effectiveness of known milk odor masking compounds and the search for new milk odor masking compounds. [Examples] 【0047】 The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. 【0048】 [Example 1] Confirmation of milk spoilage odor substances 1 (1) Preparation of dairy products 0.21 kg of anhydrous citric acid and 0.07 kg of trisodium citrate were dissolved in water to prepare 10 kg of citric acid solution. Separately, 14 kg of fructose-glucose liquid sugar and 0.1 kg of soybean polysaccharide (Soyafive® S-DA-100) were added to 75 kg of water and stirred at 80°C for 10 minutes to dissolve and prepare a solution. The resulting solution was cooled to room temperature, and then 0.6 kg of skim milk powder was added and stirred until dissolved. The aforementioned citric acid solution was then added while stirring to prepare a mixture. This mixture was homogenized using a homogenizer at 15 MPa, heated to 95°C, and then hot-packed to prepare a dairy product. This dairy product is called Basic Milk Beverage 1. 【0049】 (2) Degradation treatment of basic milk beverages The basic milk beverage 1 obtained in (1) was placed in a transparent container with a lid, and the container was left undisturbed in an environment of 15,000 lux / h and 10°C for 188 hours (cumulative 2.82 million lux) to degrade the basic milk beverage and obtain a degraded basic milk beverage 1. 【0050】 (3) Estimation of substances causing off-flavors in milk Aroma was collected from both the deteriorated basic milk beverage 1 (2) and the freshly prepared basic milk beverage 1 that had not undergone deterioration treatment, using the SBSE (Stir Bar Sorptive Extraction) method with an adsorbent (Twister / Gerstel). After aroma collection, the adsorbent was subjected to GC-MS / Olfactometry to separate the aroma components using a thermal desorption apparatus (TDU / Gerstel). Among the aroma components separated by GC-MS / Olfactometry, a portion of the deteriorated basic milk beverage 1 was found to have an unpleasant odor when smelled. When the MS spectrum of that portion was compared, it was found to be 1-octen-3-one and 3-methyl-2,4-nonanedione, and these were presumed to be the substances responsible for the milk deterioration odor. 【0051】 (4) Confirmation of the contribution of off-flavors from spoiled milk (3) 1-octen-3-one and 3-methyl-2,4-nonanedione, which were identified as substances causing the milk spoilage odor, were added to the basic milk beverage 1 at the concentrations shown in Table 3 below to prepare simulated spoiled milk beverages 1-1 to 1-3 (one form of the simulated milk spoilage odor composition in this case). 【0052】 Then, ten well-trained panelists with over 10 years of experience conducted a sensory evaluation of the milk odor of each of the simulated spoiled milk beverages 1-1 to 1-3. In the sensory evaluation, the spoiled basic milk beverage 1 obtained in (2) was used as a control product, and the milk odor of each of the simulated spoiled milk beverages 1-1 to 1-3 was evaluated against the control product based on the following criteria. The evaluation was performed by tasting each beverage. 【0053】 (standard) Same as or almost the same as the degraded basic milk beverage 1: 4 points Similar to the degraded basic milk beverage 1: 3 points Slightly similar to degraded basic milk beverage 1: 2 points Similar to Degraded Basic Milk Beverage 1, but different: 1 point Completely different from the inferior basic milk beverage 1: 0 points 【0054】 [Table 3] 【0055】 From the above, it was confirmed that the off-odor of spoiled milk can be reproduced using 1-octen-3-one and 3-methyl-2,4-nonanedione, and that the off-odor of spoiled milk can be reproduced particularly well when both of these are used. 【0056】 [Example 2] Confirmation of milk spoilage odor substances 2 (1) Preparation of dairy products A commercially available yogurt drink was prepared as a dairy product and designated as Basic Dairy Beverage 2. 【0057】 (2) Degradation treatment of basic milk beverages The basic milk beverage 2 prepared in (1) was placed in a transparent container with a lid, and the container was left undisturbed in an environment of 2000 lux / h and 10°C for 336 hours (cumulative 672,000 lux) to degrade the basic milk beverage and obtain degraded basic milk beverage 2. 【0058】 (3) Estimation of substances causing off-flavors in milk For both the degraded basic milk beverage 2 and the untreated basic milk beverage 2 from (2), aroma collection was performed using the SBSE (Stir Bar Sorptive Extraction) method with an adsorbent (Twister / Gerstel). After aroma collection, the adsorbent was subjected to GC-MS / Olfactometry to separate the aroma components using a thermal desorption apparatus (TDU / Gerstel). Among the aroma components separated by GC-MS / Olfactometry, some components in the degraded basic milk beverage 2 were found to have an unpleasant odor when smelled. When the MS spectrum of these components was compared, they were identified as dimethyl trisulfide, methional, trans-2-nonenal, trans,trans-2,4-decadienal, 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, and these were presumed to be the substances responsible for the milk degradation odor. 【0059】 (4) Confirmation of the contribution of off-flavors from spoiled milk 1 (3) 3-methyl-2,4-nonanedione and bobolide, which were identified as substances causing the milk spoilage odor in (3), were added to the basic milk beverage 2 at the concentrations shown in Table 4 below to prepare simulated spoiled milk beverages 2-1 to 2-3 (one form of the simulated milk spoilage odor composition in this case). 【0060】 Then, ten well-trained panelists with over 10 years of experience conducted a sensory evaluation of the milk odor of each of the simulated spoiled milk beverages 2-1 to 2-3. In the sensory evaluation, the spoiled basic milk beverage 2 obtained in (2) was used as a control product, and the milk odor of each of the simulated spoiled milk beverages 2-1 to 2-3 was evaluated in comparison to the control product based on the following criteria. The evaluation was performed by tasting each beverage. 【0061】 (standard) Same as or almost the same as the degraded basic milk beverage 2: 4 points Similar to the degraded basic milk beverage 2: 3 points Slightly similar to Degraded Basic Milk Beverage 2: 2 points Similar to Degraded Basic Milk Beverage 2, but different: 1 point Completely different from the inferior basic milk beverage 2: 0 points 【0062】 [Table 4] 【0063】 From the above, it was confirmed that the off-odor of spoiled milk can be reproduced using 3-methyl-2,4-nonanedione and bobolide, and that the off-odor of spoiled milk is particularly well reproduced when both of these are used. In addition, 10 panelists commented that 3-methyl-2,4-nonanedione and bobolide are particularly good at reproducing the green tea-like odor of spoiled milk. 【0064】 (5) Confirmation of the contribution of milk spoilage odor 2 (3) A total of seven compounds, dimethyl trisulfide, methional, trans-2-nonenal, trans,trans-2,4-decadienal, 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, which were identified as substances causing the milk spoilage odor in (3), were added to the basic milk beverage 2 at the concentrations shown in Table 5 below to prepare a simulated spoiled milk beverage 2-4 (one form of the simulated milk spoilage odor composition in this case). 【0065】 Then, ten well-trained panelists with over 10 years of experience conducted a sensory evaluation of the off-odor of the simulated spoiled milk beverages. In the sensory evaluation, the spoiled milk odor of simulated spoiled milk beverages 2-4 was evaluated against the control product, using spoiled basic milk beverage 2 obtained in (2), based on the following criteria. The evaluation was performed by tasting each beverage. 【0066】 (standard) Same as or almost the same as the degraded basic milk beverage 2: 4 points Similar to the degraded basic milk beverage 2: 3 points Slightly similar to Degraded Basic Milk Beverage 2: 2 points Similar to Degraded Basic Milk Beverage 2, but different: 1 point Completely different from the inferior basic milk beverage 2: 0 points 【0067】 [Table 5] 【0068】 From the above, it was confirmed that the pseudo-degraded milk beverages 2-4 containing the compounds in Table 5 can effectively reproduce the odor of spoiled milk. 【0069】 [Example 3] Confirmation of the masking effect of milk spoilage odor 1 Water containing 0.5 ppb of 1-octen-3-one (1-octen-3-one aqueous solution) was prepared. To this 1-octen-3-one aqueous solution, 18 compounds from Group A (isobutyl isobutyrate, isobutyl propionate, butyl isobutyrate, butyl propionate, isopropyl isobutyrate, isopropyl 2-methylbutyrate, isopropyl propionate, propyl isobutyrate, propyl butyrate, propyl propionate, ethyl isobutyrate, hexyl formate, octanal, myrcene, diethyl sebacate, diethyl malate, ethyl tigrate, ethyl 3-hydroxyoctanoate) were added to the concentrations shown in Tables 6 and 7 (Examples 3-1 to 3-72). For each of the 72 resulting aqueous solutions, sensory evaluation was performed by 10 well-trained panelists with more than 10 years of experience to determine whether the odor of 1-octen-3-one was detected (masked). In the sensory evaluation, an aqueous solution of 1-octen-3-one without any compounds from Group A was used as a control. The odor of 1-octen-3-one was evaluated based on the following criteria, and the perceived flavor was commented on. The evaluation was performed by tasting the aqueous solution. Tables 6 and 7 show the average evaluation scores of the 10 panelists. 【0070】 (standard) I don't detect any 1-octene-3-on smell at all: 4 points I barely smell any 1-octen-3-on odor: 3 points Slightly detects the smell of 1-octen-3-on: 2 points I can clearly smell 1-octen-3-on: 1 point Strongly detectable odor of 1-octen-3-one (equivalent to the strength of an aqueous solution of 1-octen-3-one (concentration 0.5 ppb)): 0 points 【0071】 [Table 6] 【0072】 [Table 7] 【0073】 As shown in Tables 6 and 7, each compound in Group A was confirmed to be able to mask the odor of 1-octen-3-one. 【0074】 [Example 4] Confirmation of the masking effect of milk spoilage odor 2 Water containing 0.05 ppb of 3-methyl-2,4-nonanedione (3-methyl-2,4-nonanedione aqueous solution) was prepared. To this 3-methyl-2,4-nonanedione aqueous solution, nine compounds from Group B (1-heptanol, 2-heptanol, ethyl hexanoate, allyl heptanoate, cyclohexyl butyrate, p-cymene, dimethyl succinate, diethyl tartrate, and ethyl 3-hydroxybutyrate) were added to the concentrations shown in Tables 8 and 9 (Examples 4-1 to 4-36). For each of the 36 resulting aqueous solutions, a sensory evaluation was conducted by well-trained panelists with more than 10 years of experience to determine whether they could detect the odor of 3-methyl-2,4-nonanedione. In the sensory evaluation, a 3-methyl-2,4-nonanedione aqueous solution without the addition of Group B compounds was used as a control, and the odor of 3-methyl-2,4-nonanedione was evaluated compared to the control based on the following criteria. The evaluation was conducted by ingesting the aqueous solution. Tables 8 and 9 show the average evaluation scores of the 10 panelists. 【0075】 (standard) No smell of 3-methyl-2,4-nonanedione at all: 4 points I can barely detect the smell of 3-methyl-2,4-nonanedione: 3 points Slightly detectable odor of 3-methyl-2,4-nonanedione: 2 points I can clearly smell 3-methyl-2,4-nonanedione: 1 point Strong odor of 3-methyl-2,4-nonanedione (equivalent to the strength of an aqueous solution of 3-methyl-2,4-nonanedione (concentration 0.05 ppb)): 0 points 【0076】 [Table 8] 【0077】 [Table 9] 【0078】 As shown in Tables 8 and 9, each compound in Group B was confirmed to be able to mask the odor of 3-methyl-2,4-nonanedione. 【0079】 [Example 5] Confirmation of the masking effect of milk spoilage odor 3 Water containing 25 ppb of bobolide (bobolide aqueous solution) was prepared. To this bobolide aqueous solution, nine compounds from Group B (1-heptanol, 2-heptanol, ethyl hexanoate, allyl heptanoate, cyclohexyl butyrate, p-cymene, dimethyl succinate, diethyl tartrate, 3-hydroxybutyrate ethyl) were added to the concentrations shown in Tables 10 and 11 (Examples 5-1 to 5-36). The 36 resulting aqueous solutions were subjected to sensory evaluation by well-trained panelists with more than 10 years of experience to determine whether they detected the odor of bobolide. In the sensory evaluation, a bobolide aqueous solution without the addition of Group B compounds was used as a control, and the odor of bobolide was evaluated compared to the control based on the following criteria. The evaluation was performed by tasting the aqueous solution. Tables 10 and 11 show the evaluation scores of the 10 panelists. 【0080】 (standard) I don't smell any Boboride at all: 4 points I barely smell any Boboride: 3 points Slight smell of Boboride: 2 points I can definitely smell BoboRide: 1 point Strong smell of bobolide (equivalent to the smell of a bobolide aqueous solution (concentration 25 ppb)): 0 points 【0081】 [Table 10] 【0082】 [Table 11] 【0083】 As shown in Tables 10 and 11, each compound in Group B was confirmed to be able to mask the odor of bobolide. 【0084】 [Example 6] Confirmation of the effect of masking the odor of spoiled milk 4 (Simulated spoiled milk beverage 1) (1) Masking of 1-octen-3-on To the simulated degraded milk beverage 1-1 (containing 0.3 ppb of 1-octen-3-one) prepared in Example 1, compounds from Group A were added to prepare milk beverages at the concentrations shown in Tables 12 and 13 (Examples 6-1 to 6-72). For each of the 72 milk beverages obtained, sensory evaluation was conducted by 10 well-trained panelists with more than 10 years of experience to determine whether they could detect the odor of 1-octen-3-one. In the sensory evaluation, simulated degraded milk beverage 1-1 without the addition of Group A compounds was used as control product 6-1. The odor of 1-octen-3-one was evaluated based on the following criteria compared to control product 6-1, and comments were made on the perceived flavor. In the following criteria for this example, the target odor refers to the odor of 1-octen-3-one. The evaluation was performed by tasting the milk beverage. Tables 12 and 13 show the average evaluation scores and representative comments of the 10 panelists. 【0085】 (standard) No noticeable odor: 4 points Almost no noticeable odor: 3 points Slightly noticeable odor: 2 points The target odor is clearly noticeable: 1 point The target odor is strongly perceived (the strength of the target odor should be equivalent to that of control product 6-1): 0 points 【0086】 [Table 12] 【0087】 [Table 13] 【0088】 As shown in Tables 12 and 13, it was confirmed that each compound in Group A can mask the odor of 1-octen-3-one even in dairy products. (2) Masking of 3-methyl-2,4-nonanedione and bobolide To the simulated spoiled milk beverages 2-3 (containing 0.6 ppb of 3-methyl-2,4-nonanedione and 25 ppb of bobolide) prepared in Example 2, compounds from Group B were added to prepare milk beverages at the concentrations shown in Tables 14 and 15 (Examples 6-73 to 6-108). For each of the 36 milk beverages obtained, sensory evaluation was conducted by 10 well-trained panelists with more than 10 years of experience to determine whether they could detect the odors of 3-methyl-2,4-nonanedione and bobolide. In the sensory evaluation, simulated spoiled milk beverage 2-3 without the addition of Group B compounds was used as control product 6-2, and the odors of 3-methyl-2,4-nonanedione and bobolide were evaluated based on the following criteria compared to control product 6-2, and comments were made on the perceived flavors. In the following criteria for this example, the target odor refers to the odor of 3-methyl-2,4-nonanedione and the odor of bobolide. The evaluation was conducted by tasting the dairy beverage. Tables 14 and 15 show the average evaluation scores and representative comments from the 10 panelists. 【0089】 (standard) No noticeable odor: 4 points Almost no noticeable odor: 3 points Slightly noticeable odor: 2 points The target odor is clearly noticeable: 1 point The target odor is strongly perceived (the strength of the target odor should be equivalent to that of control product 6-2): 0 points 【0090】 [Table 14] 【0091】 [Table 15] 【0092】 As shown in Tables 14 and 15, it was confirmed that each compound in Group B can mask the odor of 3-methyl-2,4-nonanedione and bobolide in dairy products. 【0093】 [Example 7] Confirmation of the effect of masking the odor of spoiled milk 5 (2 simulated spoiled milk beverages) To the pseudo-degraded milk beverage 2-4 prepared in Example 2 (containing the compounds (milk degradation odor substances) shown in Table 5), compounds from Group A and Group B were added to achieve the concentrations shown in Table 16 below (in the table, 50 represents 50 ppb, and 500 represents 500 ppb) to prepare milk beverages (Examples 7-1 to 7-19). 【0094】 The off-odor of each of the obtained milk beverages was evaluated by 10 well-trained panelists with more than 10 years of experience. In the sensory evaluation, the simulated off-odor milk beverage 2-4 was used as control product 7, and each of the milk beverages from Examples 7-1 to 7-19 was compared to control product 7. The panelists were asked to score whether they could perceive the odor of each compound shown in Table 5 (in the criteria below for this example, the odor of each compound shown in Table 5 is referred to as the target odor) according to the following criteria, and to comment on the perceived flavor. Table 16 shows the average evaluation scores and representative comments of the 10 panelists. 【0095】 (standard) No noticeable odor: 4 points Almost no noticeable odor: 3 points Slightly noticeable odor: 2 points The target odor is clearly noticeable: 1 point The target odor is strongly perceived (assuming the same level of odor intensity as control product 7): 0 points 【0096】 [Table 16] 【0097】 As shown in Table 16, it was confirmed that a very high masking effect can be obtained by combining compounds from Group A and Group B. In this invention, the combination is not limited to the one in this example; compounds can be arbitrarily selected from Group A and Group B according to the desired odor-masking effect to determine the optimal combination. 【0098】 [Example 8] Confirmation of the masking effect of milk spoilage odor 6 (Simulated spoiled milk beverage 3) To the pseudo-degraded milk beverage 2-4 prepared in Example 2 (containing the compounds (milk degradation odor substances) shown in Table 5), one compound from Group A and one compound from Group B were added in combinations shown in Tables 17 to 25 below, each at a concentration of 10 ppb, to prepare a milk beverage (Examples 8-1 to 8-162). 【0099】 A sensory evaluation of the spoilage odor of each of the 162 milk beverages obtained was conducted by 10 well-trained panelists with more than 10 years of experience. In the sensory evaluation, simulated spoilage milk beverages 2-4 were used as control product 8, and the panelists were asked to comment on whether they could detect the odor of the compounds shown in Table 5 for each milk beverage from Examples 8-1 to 8-162 compared to control product 8. As a result, in each example, 9 to 10 out of 10 panelists responded that they could hardly detect any of the odors of the compounds shown in Table 5, and that the beverages had a pleasant, easy-to-drink milky flavor. 【0100】 [Table 17] 【0101】 [Table 18] 【0102】 [Table 19] 【0103】 [Table 20] 【0104】 [Table 21] 【0105】 [Table 22] 【0106】 [Table 23] 【0107】 [Table 24] 【0108】 [Table 25] 【0109】 As shown in Tables 17-25, it was confirmed that a high masking effect can be obtained by combining compounds from groups A and B. 【0110】 [Example 9] Confirmation of the masking effect of milk spoilage odor 7 (Degraded milk beverage 1) (1) Compounds of Group A To the deteriorated basic milk beverage 1 obtained in Example 1, 18 compounds from Group A (isobutyl isobutyrate, isobutyl propionate, butyl isobutyrate, butyl propionate, isopropyl isobutyrate, isopropyl 2-methylbutyrate, isopropyl propionate, propyl isobutyrate, propyl butyrate, propyl propionate, ethyl isobutyrate, hexyl formate, octanal, myrcene, diethyl sebacate, diethyl malate, ethyl tigrate, ethyl 3-hydroxyoctanoate) were added at the concentrations shown in Table 26 (Examples 9-1 to 9-18). For each of the 18 milk beverages obtained, sensory evaluation was conducted by 10 well-trained panelists with more than 10 years of experience to determine whether they perceived an off-flavor. In the sensory evaluation, deteriorated basic milk beverage 1 without the addition of Group A compounds was used as control product 9-1, and the off-flavor was evaluated based on the following criteria compared to control product 9-1, and the panelists were asked to comment on the perceived flavor. In the criteria for this embodiment, "perceiving an off-flavor" means perceiving the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, as well as other unpleasant odors. The evaluation was conducted by tasting the milk beverage. Table 26 shows the average evaluation scores of the 10 panelists. 【0111】 (standard) No unpleasant odor at all: 4 points Almost no unpleasant odor: 3 points Slightly noticeable off-flavor: 2 points A noticeable odor of spoilage: 1 point Strong odor of deterioration is detected (equivalent to the intensity of the odor of deterioration in control product 9-1): 0 points 【0112】 [Table 26] 【0113】 As shown in Table 26, the compounds in Group A were confirmed to have a high masking effect against the odor of deterioration. 【0114】 (2) Compounds of Group B To the deteriorated basic milk beverage 1 obtained in Example 1, nine compounds from Group B (1-heptanol, 2-heptanol, ethyl hexanoate, allyl heptanoate, cyclohexyl butyrate, p-cymene, dimethyl succinate, diethyl tartrate, and ethyl 3-hydroxybutyrate) were added at the concentrations shown in Table 27 (Examples 9-19 to 9-27). For each of the nine resulting milk beverages, sensory evaluation was conducted by 10 well-trained panelists with more than 10 years of experience to determine whether they perceived an off-flavor. In the sensory evaluation, deteriorated basic milk beverage 1 without the addition of Group B compounds was used as a control product 9-2, and the off-flavor was evaluated based on the following criteria compared to control product 9-2, with comments on the perceived flavor. In the following criteria for this example, "perceiving an off-flavor" means perceiving the odor of 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, and other unpleasant odors. The evaluation was performed by tasting the milk beverage. Table 27 shows the average evaluation scores of the 10 panelists. 【0115】 (standard) No unpleasant odor at all: 4 points Almost no unpleasant odor: 3 points Slightly noticeable off-flavor: 2 points A noticeable odor of spoilage: 1 point Strong odor of deterioration is detected (equivalent to the intensity of the odor of deterioration in control product 9-2): 0 points 【0116】 [Table 27] 【0117】 As shown in Table 27, the compounds in Group B were confirmed to have a high masking effect against the odor of deterioration. 【0118】 [Example 10] Confirmation of the masking effect of milk spoilage odor 8 (2 spoiled milk beverages) Four types of milk beverages were prepared (Examples 10-1 to 10-4) by adding compounds from Group A and Group B to each of the basic milk beverage 1 prepared in Example 1 and the basic milk beverage 2 (commercially available yogurt drink) prepared in Example 2, as shown in Table 28 below. 【0119】 The milk beverages obtained in Examples 10-1 and 10-2, as well as basic milk beverage 1, were subjected to light abuse under the same conditions as in Example 1 to obtain degraded masking milk beverages 10-1 and 10-2, and degraded basic milk beverage 1, respectively. Similarly, the milk beverages in Examples 10-3 and 10-4, as well as basic milk beverage 2, were subjected to light abuse under the same conditions as in Example 2 to obtain degraded masking milk beverages 10-3 and 10-4, and degraded basic milk beverage 2, respectively. 【0120】 The various degraded milk beverages obtained were subjected to sensory evaluation by 10 well-trained panelists with more than 10 years of experience. In the sensory evaluation, degraded basic milk beverage 1 was used as control product 10-1, and the panelists were asked to comment on whether they could detect a degraded odor in degraded masking milk beverages 10-1 to 10-2 compared to control product 10-1. Similarly, degraded basic milk beverage 2 was used as control product 10-2, and the panelists were asked to comment on whether they could detect a degraded odor (as defined above) in degraded masking milk beverages 10-3 to 10-4 compared to control product 10-2. In this example, "detecting a degraded odor" means detecting the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, as well as other unpleasant odors. Representative comments are shown in Table 28. 【0121】 [Table 28] 【0122】 From the above, it was confirmed that even when this compound is added to milk beverages before they deteriorate, the off-flavor is effectively masked. 【0123】 [Example 11] Confirmation of the masking effect of milk spoilage odor 9 (Degraded milk beverage 3) As shown in Table 29 below, yogurt flavor 1 without the compound in question (Comparative Example 11-1) and yogurt flavor 2 containing the compound in question (Example 11-1 (one embodiment of the milk spoilage odor masking agent or flavoring composition of the present invention)) were prepared. 【0124】 [Table 29] 【0125】 Then, 0.1% by mass of yogurt flavor 1 from Comparative Example 11-1 and yogurt flavor 2 from Example 11-1 were added to the basic milk beverage 1 prepared in Example 1 to obtain comparative milk beverage 11-2 and the milk beverage of Example 11-2. Then, comparative milk beverage 11-2 and the milk beverage of Example 11-2 were subjected to light abuse under the same conditions as in Example 1 to obtain degraded comparative milk beverage 11-2 and degraded masking milk beverage 11-2. 【0126】 Furthermore, 0.1% by mass of yogurt flavor 1 from Comparative Example 11-1 and yogurt flavor 2 from Example 11-1 were added to the basic milk beverage 2 prepared in Example 2 to obtain comparative milk beverage 11-3 and the milk beverage of Example 11-3. Then, comparative milk beverage 11-3 and the milk beverage of Example 11-3 were subjected to light abuse under the same conditions as in Example 2 to obtain degraded comparative milk beverage 11-3 and degraded masking milk beverage 11-3. 【0127】 Sensory evaluations were conducted on the various degraded milk beverages obtained by 10 well-trained panelists with more than 10 years of experience. In the sensory evaluation, degraded comparative milk beverage 11-2 was used as a control product, and the panelists were asked to comment on whether they could perceive a degraded odor in degraded masking milk beverage 11-2 compared to the control product. Similarly, degraded comparative milk beverage 11-3 was used as a control product, and the panelists were asked to comment on whether they could perceive a degraded odor in degraded masking milk beverage 11-3 compared to the control product. In this example, "perceiving a degraded odor" means perceiving the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and bobolide, as well as other unpleasant odors. Representative comments are shown in Table 30. 【0128】 [Table 30] 【0129】 As shown in Table 30, it was confirmed that the compound in question effectively masks the off-flavor when added to milk beverages before they deteriorate.

Claims

[Claim 1] A milky odor masking agent containing one or more compounds selected from group B below, The substance constituting the aforementioned milk spoilage odor is a milk spoilage odor masking agent comprising one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. (Group B) 1-Heptanol, 2-Heptanol, Ethyl Hexanoate, Allyl Heptanoate, Cyclohexyl Butyrate, p-Cymene, Dimethyl Succinate, Diethyl Tartrate, 3-Hydroxybutyrate [Claim 2] A flavor-imparting composition for masking milk-related odors, containing the milk-related odor masking agent described in claim 1. [Claim 3] A method for improving the spoilage odor of dairy products, comprising adding the milk spoilage odor masking agent described in claim 1, or the milk spoilage odor masking flavor-imparting composition described in claim 2, to a dairy product. [Claim 4] A composition that simulates the odor of spoiled milk, containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. [Claim 5] (Step A) A step of preparing a composition that simulates the odor of spoiled milk containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and bobolide. (Step B) A step of preparing a milk deterioration odor test composition by adding a candidate substance for masking milk deterioration odor to the milk deterioration odor pseudo composition, and (Step C) Step to evaluate the milk odor of the milk odor test composition. A method for confirming the masking effect of milk spoilage odor, including the following.