Milk degradation odor masking agent

Abstract

To provide a milk degradation odor masking agent.SOLUTION: There is provided a milk degradation odor masking agent which contains one or two or more compounds selected from a following group A or group B. (Group A) is constituted by 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 tiglate, ethyl 3-hydroxyoctanoate and (Group B) is constituted by 1-heptanol, 2-heptanol, ethyl hexanoate, allyl heptanoate, cyclohexyl butyrate, p-cymene, dimethyl succinate, diethyl tartrate, ethyl 3-hydroxybutyrate.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a milk deterioration odor masking agent. [Background technology]

[0002] Consumer demands for the scent and taste (sometimes collectively referred to as flavor in this specification) of various consumer goods such as foods, beverages, and cosmetics are becoming more sophisticated, and several technologies have been proposed to improve unpleasant flavors.

[0003] For example, when milk-containing products are exposed to light, compounds that have unpleasant odors are produced, which can cause unpleasant odors such as putrid odors or odors like deteriorated oil (hereinafter referred to as deteriorated odors in this specification).

[0004] Accordingly, several technologies have been proposed for improving the deterioration odor of milk-containing products. Patent Document 1 proposes suppressing the deterioration odor of dairy products using an inhibitor for the production of deterioration odor of 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. Patent Document 2 proposes masking the deterioration odor of dairy products using a masking agent for the deterioration odor of dairy products, containing at least one selected from the group consisting of sucralose, Monk Fruit extract, stevia extract, acesulfame potassium, aspartame, and thaumatin. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2002-291406 A [Patent Document 2] JP 2023-20971 A Summary of the Invention [Problem to be solved by the invention]

[0006] However, conventionally used materials have not been able to sufficiently improve the deterioration odor of dairy products, and it has been an issue to discover a useful material that can improve the deterioration odor of dairy products. Therefore, the issue of the present invention is to provide a milk deterioration odor masking agent containing a compound that is useful for improving the deterioration odor of dairy products. [Means for solving the problem]

[0007] The present inventors have conducted intensive research in view of the above problems and have found that the specific components described below are useful for improving the odor of deteriorated milk, thereby completing the present invention.

[0008] Thus, a brief summary of representative inventions among those disclosed in this application is as follows. [1] A milk deterioration odor masking agent containing one or more compounds selected from the following Group A or Group 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 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 [2] The milk deterioration odor masking agent according to [1], which contains one or more compounds selected from the group A and one or more compounds selected from the group B. [3] A flavoring composition containing the milk deterioration odor masking agent described in [1]. [4] A flavoring composition containing the milk deterioration odor masking agent described in [2]. [5] A method for improving the deterioration odor of a dairy product, comprising adding a milk deterioration odor masking agent described in [1] or [2], or a flavor-imparting composition described in [3] or [4] to a dairy product. [6] A method for producing a dairy product, comprising adding a milk deterioration odor masking agent described in [1] or [2], or a flavoring composition described in [3] or [4] to a dairy product. [7] A composition simulating a stagnant milk odor, comprising one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride. [8] The composition for simulating a milk stagnant odor described in [7], further comprising 1-octen-3-one. [9] A method for confirming the effect of masking a milk deterioration odor, comprising: (Step A) preparing a milk deterioration odor simulating composition containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride; (Step B) adding a candidate substance for masking a milk deterioration odor to the milk deterioration odor simulating composition to prepare a milk deterioration odor test composition; and (Step C) evaluating the milk deterioration odor of the milk deterioration odor test composition.

[10] The method for confirming the effect of masking milk deterioration odor described in [9], wherein the milk deterioration odor simulating composition further contains 1-octen-3-one. Effect of the Invention

[0009] The present invention makes it possible to provide a milk deterioration odor masking agent that is effective in improving the deterioration odor of dairy products. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present invention will be described in more detail below with reference to specific examples. In this specification, "to" means a range including a lower limit and an upper limit, and concentrations (ppt, ppb, ppm, etc.) and % mean mass concentration and mass %, respectively, unless otherwise specified, and concentrations are final concentrations unless otherwise specified. In this specification, "over" means "exceeding" which does not include the lower limit.

[0011] [Masking agent for milk odor] The milk deterioration odor masking agent according to one embodiment of the present invention (hereinafter, sometimes referred to as the present milk deterioration odor masking agent) is characterized by containing one or more compounds (hereinafter, sometimes referred to as the present compound) selected from the following Group A or Group 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 tiglate 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, the term "deteriorated milk odor" refers to the unpleasant taste and odor (unpleasant odor) of dairy products caused by substances that cause deterioration of milk odors, and the deterioration odor is typically a deterioration odor caused by photodegradation. Examples of the deterioration odor of milk include putrid odor, unpleasant odors like deteriorated oil, unpleasant odors like potatoes, unpleasant odors like mushrooms, and unpleasant odors that give an unpleasant feeling like green tea.

[0012] In this specification, the term "stale milk odor substances" refers to compounds that contribute to the smell of stale milk, but is not limited to these. Representative examples are 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 a combination of two or more of these compounds that are thought to contribute to the smell of stale milk. For example, although the present invention is not limited to these, it is believed that, among the odors of deteriorated milk, the putrid odor is contributed by sulfides such as dimethyl trisulfide, the unpleasant odor like deteriorated oil is contributed by aldehydes such as trans-2-nonenal, the unpleasant odor like potato is contributed by methional, the unpleasant odor like mushroom is contributed by 1-octen-3-one, and the unpleasant odor like green tea is contributed by 3-methyl-2,4-nonanedione and boboride.

[0013] The odor of deteriorated milk can be effectively masked by masking one or more of the flavors of such substances that cause deteriorated milk odor. In particular, the present inventors have discovered for the first time that green tea-like 3-methyl-2,4-nonanedione and boboride contribute to the odor of deteriorated milk, and have discovered that the odor of deteriorated milk can be effectively masked by masking them.

[0014] In this specification, masking the deteriorated milk odor means making the deteriorated milk odor less noticeable, and also includes making the deteriorated milk odor almost unnoticeable or not noticeable at all.

[0015] From the viewpoint of the masking effect of the deteriorated milk odor, the present masking agent for the deteriorated milk odor preferably contains one or more compounds selected from Group A and one or more compounds selected from Group B. In particular, isobutyl isobutyrate and diethyl sebacate are preferably used among the compounds in Group A, and 1-heptanol and diethyl tartrate are preferably used among the compounds in Group B. Therefore, the present masking agent for the deteriorated milk odor 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, a substance that produces a milky odor.

[0017] Group B is particularly effective in masking the flavors of 3-methyl-2,4-nonanedione and boboride, which are substances that cause milk deterioration.

[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 the dairy product is usually derived from milk (hereinafter, sometimes referred to as milk-like flavor), but there is no particular limitation as long as it can produce milk deterioration odor substances, even if it does not have a milk-like flavor or has a milk-like flavor and one or more other flavors. Specific examples of food and beverages include, but are not limited to, milk, powdered milk, butter, cheese, ice cream, yogurt, whey drinks, etc. In addition, examples of those having a milk-like flavor and one or more other flavors include various fruit-flavored milk drinks that give a milk-like flavor and various fruit flavors, yogurt-flavored whey drinks, coffee with milk (milk coffee), various tea drinks with milk (milk black tea, milk matcha, milk roasted green tea, etc.), ice cream and yogurt, and processed foods using milk such as soups, stews, gratins, etc. that give a milk-like flavor and various meat or seafood flavors, but are not limited to these.

[0019] The milk deterioration odor masking agent of the present invention may exert a flavor imparting effect derived from the compound of the present invention in addition to the effect of masking the milk deterioration odor. In this case, the milk deterioration odor is masked and a flavor is imparted, so that the flavor of various dairy products to which the milk deterioration odor masking agent of the present invention is added can be improved to be more excellent.

[0020] The milk deterioration odor masking agent of the present invention may consist essentially of the compound of the present invention alone, or may consist essentially of the compound of the present invention and a solvent for the compound, or may contain any other component within the range in which the effects of the present invention can be achieved.

[0021] The present compound may be a synthesized product, or an extract or dried product of natural products 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, emulsion, powder, or other solid matter.

[0023] [Flavoring composition] A flavoring composition according to one embodiment of the present invention (hereinafter, sometimes referred to as the present flavoring composition) is characterized by containing the present milk deterioration odor masking agent.

[0024] The present flavoring composition can be added to various consumer goods to impart flavor to the consumer goods to which it is added. In particular, since the present flavoring composition contains the present milk deterioration odor masking agent, it can also be used to mask the milk deterioration odor, and is useful as a flavoring composition for masking milk deterioration odor.

[0025] As used herein, flavor refers to sensations sensed by taste and / or smell.

[0026] Representative examples of the flavor-imparting composition of the present invention include flavor-imparting compositions such as various seasonings, oil and fat compositions, and spices capable of imparting flavor, as well as flavor compositions (flavors or fragrances).

[0027] The present flavoring composition may consist essentially of the present deterioration odor masking agent, or may contain other components. When other components are contained, any component usable in consumer goods may be used. In particular, when the present flavoring composition is a fragrance composition, any component usable in fragrance compositions may be used, and specific examples thereof include γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, 7-decen-4-olide, 3-methyl-4-decen-4-olide, 3-methyl-5-decen-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradecalactone, δ ...γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-decalactone, γ-dec lactone, 2-hexen-5-olide, 2-hepten-5-olide, δ-octalactone, 2-octen-5-olide, 4-methyl-5-octanolide, δ-nonalactone, 2-nonen-5-olide, 4-methyl-5-nonanolide, δ-decalactone, 2-decen-5-olide, 4-methyl-5-decanolide, δ-undecalactone, 2-undecen-5-olide, 4-methyl-5-undecanolide, δ-dodecalactone, 2-dodecen-5-olide, 4- Lactones such as methyl-5-dodecanolide, δ-tridecalactone, 2-tridecen-5-olide, 4-methyl-5-tridecanolide, δ-tetradecalactone, 2-tetradecen-5-olide, 2-pentadecen-5-olide, 2-hexadecen-5-olide, 2-heptadecen-5-olide, 2-octadecen-5-olide, 2-nonadecen-5-olide, 2-eicosene-5-olide, and 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-undecadienal, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural, and heliotropin diethyl acetal; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, dodecanal, 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, acetyl isovaleryl, 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-furanthiol, methional, ethyl thioacetate, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, sulfurol, acetyl lactate thiomethyl ester, propionyl lactate thiomethyl ester, butyryl lactate thiomethyl ester Examples of such compounds include known flavoring compounds such as sulfur-containing compounds such as thiomethyl lactate, thiomethyl lactate of valeryl lactate, thiomethyl lactate of 2-methylbutyryl lactate, thiomethyl lactate of decyl lactate, thioethyl lactate of acetyl lactate, thioethyl lactate of propionyl lactate, thioethyl lactate of butyryl lactate, thioethyl lactate of valeryl lactate, and thiopropyl lactate of isocaproyl lactate; lipase decomposition products of milk fat; protease decomposition products of milk proteins; fractions of milk or milk products from milk, concentrated milk, milk powder, milk whey, butter, cheese, yogurt, or mixtures thereof;

[0028] [How to mask the smell of milky stench] A method for masking a milk deterioration odor according to one embodiment of the present invention (hereinafter referred to as the present method for masking a milk deterioration odor) is characterized by including adding the present milk deterioration odor masking agent or the present flavor imparting composition to a dairy product.

[0029] As shown in the examples described later, the compound of the present invention can be added to a dairy product that gives off a deteriorated milk odor to mask the deteriorated milk odor, and can also be added to a dairy product that does not give off a deteriorated milk odor to mask the deteriorated milk odor caused by the deterioration of the dairy product after the addition of the compound of the present invention to mask the deteriorated milk odor. Therefore, in the method for masking a deteriorated milk odor of the present invention, the dairy product to which the masking agent for the deteriorated milk odor of the present invention or the flavor-imparting composition for the present invention is added may be one that gives off a deteriorated milk odor or one that does not give off a deteriorated milk odor.

[0030] The present method for masking milk deterioration odors is particularly useful as a method for masking one or more substances selected from the group consisting of milk deterioration odor substances 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, but the present invention is not limited thereto.

[0031] From the viewpoint of the masking effect of milk deterioration odor, the present method for masking milk deterioration odor preferably includes adding the present masking agent for milk deterioration odor or the present flavor-imparting 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 masking agent for milk deterioration odor or the present flavor-imparting 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 the present invention, the concentration of the compound in the dairy product can be adjusted to effectively obtain the effect of masking the deteriorated milk odor in the present invention. The present inventors have confirmed that the masking effect of the deteriorated milk odor can be obtained by setting the concentration of all the present compounds within the range of approximately 1 ppt to 100 ppm. Preferably, the masking effect can be obtained by setting the concentration of each of the present compounds as shown in Tables 1 and 2 below. Here, the concentration range 1 means a concentration range in which the masking effect can be obtained without feeling the flavor derived from the present compound, and the concentration range 2 means a concentration range in which the masking effect and the flavor derived from the present compound can be obtained. In the concentration range 2, the flavor of the object to which the compound is added can be improved not only by the masking effect of the present compound but also by the flavor-imparting effect derived from the present compound, and typically, the ease of eating (ease of drinking in the case of a beverage) of the food or drink to which the compound is added can be improved.

[0033] Therefore, the present method for masking the deteriorated milk odor preferably includes adding the present masking agent or the present flavoring composition to a dairy product so that the final concentration of the present compound is 1 ppt to 100 ppm (the total concentration if multiple present compounds are added).

[0034] [Table 1]

[0035] [Table 2]

[0036] However, the concentration of the present milk deterioration odor masking agent in the target to which it is added is not limited to the concentrations shown in Tables 1 and 2, and may be appropriately adjusted depending on the level of milk deterioration odor and the desired masking effect.

[0037] Furthermore, when a plurality of the present compounds are used in the present method for masking the milk deterioration odor, the amount ratio of each of the present compounds is not particularly limited and can be arbitrarily determined depending on the desired masking effect.

[0038] [Milk deterioration odor pseudo composition] The composition simulating the deteriorated milk odor according to one embodiment of the present invention (hereinafter, sometimes referred to as the present deteriorated milk odor simulating composition) is characterized by containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride. In this specification, the present deteriorated milk odor simulating composition is a composition for reproducing the deteriorated milk odor (a composition for reproducing the deteriorated milk odor), and in particular, in this application, it can be said to be a composition for confirming the effect of a candidate substance capable of masking the deteriorated milk odor.

[0039] In dairy products, 3-methyl-2,4-nonanedione and boboride may be perceived as a stagnant odor when present at concentrations of 0.02 ppb or more and 10 ppb or more, respectively, and the concentrations of 3-methyl-2,4-nonanedione and boboride in the present stagnant dairy odor simulating composition can be determined by referring to these concentrations. However, depending on the flavor of the dairy product and the degree of stagnant dairy product, the stagnant odor may be perceived even if the concentration is lower than these concentrations, and the present invention is not limited to these ranges.

[0040] In investigating masking agents for milk deterioration odor, the inventors discovered for the first time that 3-methyl-2,4-nonanedione and boboride contribute to the deterioration of milk odor, and discovered that the deterioration of milk odor can be effectively masked by masking one or more of these.

[0041] In a preferred embodiment of the present invention, the present imitation milk odor composition contains one of 3-methyl-2,4-nonanedione and boboride as the imitation milk odor substance. By containing only one compound, when used to search for a imitation milk odor masking compound described below or when used to confirm the effect of a known imitation milk odor masking compound, the effect on the compound can be confirmed accurately. In another preferred embodiment of the present invention, the present imitation milk odor composition may contain two substances, 3-methyl-2,4-nonanedione and boboride, as the imitation milk odor substances. By containing two substances of imitation milk odor, it may be possible to confirm which of the two substances of imitation milk odor has a masking effect with a small number of steps during the above-mentioned search or confirmation.

[0042] In yet another preferred embodiment of the present invention, the present composition for simulating a deteriorated milk odor may contain 1-octen-3-one or other known substances for simulating a deteriorated milk odor in addition to one or two selected from 3-methyl-2,4-nonanedione and boboride. Examples of other known substances for simulating a deteriorated milk odor include, but are not limited to, methional, trans-2-nonenal, dimethyl trisulfide, and trans, trans-2,4-decadienal. By including three or more substances for simulating a deteriorated milk odor, it may be possible to confirm with a small number of steps which of these substances for simulating a deteriorated milk odor has a masking effect during the above-mentioned search and confirmation. When 1-octen-3-one is contained in a dairy product at a concentration of approximately 0.2 ppb or more, it may be perceived as a deteriorated odor, and the concentration of 1-octen-3-one in the present composition for simulating a deteriorated milk odor can be determined with reference to this concentration. However, depending on the flavor of the dairy product or the degree of deterioration of the dairy product, it may be perceived as a deteriorated odor even if it is below this concentration, and the present invention is not limited to these ranges.

[0043] In yet another preferred embodiment of the present invention, the composition simulating a stale milk odor may contain various components that contribute to a milk-like flavor or various components contained in dairy products. A preferred example is a dairy product containing one or two components selected from the group consisting of 3-methyl-2,4-nonanedione and boboride.

[0044] [How to check the effectiveness of masking milk odor] A method for confirming the effect of masking milk deterioration odor according to one embodiment of the present invention is characterized by including the following steps (hereinafter, sometimes referred to as the present confirmation method). (Step A) A step of preparing a composition simulating a stagnant milk odor containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride. (Step B) A step of adding a candidate substance for masking milk odor to the milk odor simulant composition to prepare a milk odor test composition. (Step C) A step of evaluating the milk deterioration odor of the milk deterioration odor test composition The imitation composition of the stagnant milk odor is as described above. In the present confirmation method, the imitation composition of the stagnant milk odor may further contain 1-octen-3-one as a substance that causes the stagnant milk odor.

[0045] In this specification, the term "milk deterioration odor masking candidate substance" refers to both a known milk deterioration odor masking compound and a compound whose milk deterioration odor masking effect is not known, and whose milk deterioration odor masking effect is to be confirmed. In this specification, the term "milk deterioration odor test composition" refers to a milk deterioration odor masking candidate substance, as well as 3-methyl-2,4-nonanedione and / or boboride, and is used to confirm the masking effect of the milk deterioration odor masking candidate substance contained in the milk deterioration odor test composition on milk deterioration odor substances such as 3-methyl-2,4-nonanedione and / or boboride.

[0046] This confirmation method makes it possible to confirm the effectiveness of known milk deterioration odor masking compounds and to search for new milk deterioration odor masking compounds. EXAMPLES

[0047] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to these.

[0048] [Example 1] Confirmation of substances with deteriorated milk odor 1 (1) Preparation of dairy products 0.21 kg of citric acid (anhydrous) 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 polysaccharides (SOYAFIBE (registered trademark) S-DA-100) were added to 75 kg of water and dissolved by stirring at 80°C for 10 minutes to prepare a solution. The resulting solution was cooled to room temperature, and then 0.6 kg of skim milk powder was added and dissolved by stirring. The above-mentioned citric acid solution was added thereto while stirring to prepare a mixed solution. This mixed solution was homogenized at 15 MPa using a homogenizer, heated to 95°C, and filled with a hot pack to prepare a dairy product. This dairy product is called basic milk drink 1.

[0049] (2) Deterioration treatment of basic dairy beverages The basic milk beverage 1 obtained in (1) was placed in a transparent container with a lid, and the container was left in an environment of 15,000 lux / h and 10°C for 188 hours of light abuse (accumulated 2.82 million lux) to deteriorate the basic milk beverage, thereby obtaining deteriorated basic milk beverage 1.

[0050] (3) Estimation of substances causing milk stale odor (2) Aroma collection was performed for the deteriorated basic milk drink 1 and the unaged basic milk drink 1 immediately after preparation using an adsorbent (Twister / Gerstel) by the Stir Bar Sorptive Extraction (SBSE) method. After aroma collection, the adsorbent was used in a thermal desorption device (TDU / Gerstel) to separate the aroma components, which were then subjected to GC-MS / Olfactometry. Among the aroma components separated using GC-MS / Olfactometry, there were some parts in the deteriorated basic milk drink 1 that had an unpleasant odor when smelled. When the MS spectrum of these parts was compared, they were found to be 1-octen-3-one and 3-methyl-2,4-nonanedione, and these were presumed to be the substances with the deteriorated milk odor.

[0051] (4) Confirmation of the contribution of milk stale odor 1-Octen-3-one and 3-methyl-2,4-nonanedione, which were assumed to be the substances with a stagnant milk odor in (3), were added to the basic milk beverage 1 at the concentrations shown in Table 3 below to prepare pseudo-stagnant milk beverages 1-1 to 1-3 (one embodiment of the present stagnant milk odor pseudo-composition).

[0052] Then, ten well-trained panelists with over 10 years of experience conducted a sensory evaluation of the milky deterioration odor of each of the simulated deteriorated milk beverages 1-1 to 1-3. In the sensory evaluation, the deteriorated basic milk beverage 1 obtained in (2) was used as a control, and the milky deterioration odor of each of the simulated deteriorated milk beverages 1-1 to 1-3 was compared to the control product and evaluated based on the following criteria. The evaluation was performed by holding each beverage in the mouth.

[0053] (standard) Same or almost the same as degraded basic milk drink 1: 4 points Similar to Deteriorated Basic Milk Drink 1: 3 points Slightly similar to Deteriorated Basic Milk Drink 1: 2 points Slightly similar to, but different from, Deteriorated Basic Milk Drink 1: 1 point Completely different from deteriorated basic milk drink 1: 0 points

[0054] [Table 3]

[0055] From the above, it was confirmed that the odor of aged milk can be reproduced using 1-octen-3-one and 3-methyl-2,4-nonanedione, and that the odor of aged milk can be reproduced particularly well when these two types are used together.

[0056] [Example 2] Confirmation of substances with deteriorated milk odor 2 (1) Preparation of dairy products A commercially available yogurt drink was prepared as a dairy product and designated as basic dairy drink 2.

[0057] (2) Deterioration treatment of basic dairy beverages The basic milk drink 2 prepared in (1) was placed in a transparent container with a lid, and the container was left in an environment of 2000 lux / h and 10°C for 336 hours of light abuse (accumulated 672,000 lux) to deteriorate the basic milk drink, thereby obtaining deteriorated basic milk drink 2.

[0058] (3) Estimation of substances causing milk stale odor (2) Aroma collection was performed for both the deteriorated basic milk drink 2 and the unaged basic milk drink 2 by the Stir Bar Sorptive Extraction (SBSE) method using an adsorbent (Twister / Gerstel). After aroma collection, the adsorbent was used in a thermal desorption device (TDU / Gerstel) to separate the aroma components, which were then subjected to GC-MS / Olfactometry. Among the aroma components separated using GC-MS / Olfactometry, there were some parts in the deteriorated basic milk drink 2 that had an unpleasant odor when smelled. When the MS spectrum of these parts was compared, it was found that they were dimethyl trisulfide, methional, trans-2-nonenal, trans, trans-2,4-decadienal, 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, and these were presumed to be the substances that caused the deterioration of milk odor.

[0059] (4) Confirmation of the contribution of milk deterioration odor 1 (3) 3-methyl-2,4-nonanedione and boboride, which were assumed to be the substances with a stagnant milk odor in the above, were added to the basic milk beverage 2 at the concentrations shown in Table 4 below to prepare pseudo-stagnant milk beverages 2-1 to 2-3 (one embodiment of the present stagnant milk odor pseudo-composition).

[0060] Then, ten well-trained panelists with 10 years or more of experience conducted a sensory evaluation of the milky deterioration odor of each of the simulated deteriorated milk beverages 2-1 to 2-3. In the sensory evaluation, the deteriorated basic milk beverage 2 obtained in (2) was used as a control, and the milky deterioration odor of each of the simulated deteriorated milk beverages 2-1 to 2-3 was compared to the control product and evaluated based on the following criteria. The evaluation was performed by holding each beverage in the mouth.

[0061] (standard) Same or almost the same as degraded basic milk drink 2: 4 points Similar to Deteriorated Basic Milk Drink 2: 3 points Slightly similar to Deteriorated Basic Milk Drink 2: 2 points Slightly similar to, but different from, Deteriorated Basic Milk Drink 2: 1 point Completely different from deteriorated basic milk drink 2: 0 points

[0062] [Table 4]

[0063] From the above, it was confirmed that 3-methyl-2,4-nonanedione and boboride can reproduce the odor of deteriorated milk, and that the odor of deteriorated milk can be reproduced particularly well when these two types are used together. In addition, ten panelists commented that 3-methyl-2,4-nonanedione and boboride can reproduce the odor of deteriorated milk, particularly the green tea-like odor, very well.

[0064] (5) Confirmation of the contribution of milk stale odor 2 A total of seven compounds, namely dimethyl trisulfide, methional, trans-2-nonenal, trans, trans-2,4-decadienal, 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, which were estimated to be the substances causing stagnant milk odor in (3), were added to the basic milk beverage 2 at the concentrations shown in Table 5 below to prepare artificial stagnant milk beverage 2-4 (one embodiment of the present stagnant milk odor artificial composition).

[0065] Then, ten well-trained panelists with 10 years or more of experience conducted a sensory evaluation of the deteriorated odor of the simulated deteriorated milk beverages. In the sensory evaluation, the deteriorated basic milk beverage 2 obtained in (2) was used as a control, and the deteriorated milk odor of the simulated deteriorated milk beverages 2-4 was compared to the control product and evaluated based on the following criteria. The evaluation was performed by holding each beverage in the mouth.

[0066] (standard) Same or almost the same as degraded basic milk drink 2: 4 points Similar to Deteriorated Basic Milk Drink 2: 3 points Slightly similar to Deteriorated Basic Milk Drink 2: 2 points Slightly similar to, but different from, Deteriorated Basic Milk Drink 2: 1 point Completely different from deteriorated basic milk drink 2: 0 points

[0067] [Table 5]

[0068] From the above, it was confirmed that the pseudo-staled milk drink 2-4 containing the compounds in Table 5 was able to effectively reproduce the staled milk odor.

[0069] [Example 3] Confirmation of the effect of masking milk odor 1 Water containing 0.5 ppb of 1-octen-3-one (1-octen-3-one aqueous solution) was prepared. 18 kinds of compounds of 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 tiglate, ethyl 3-hydroxyoctanoate) were added to this 1-octen-3-one aqueous solution to the concentrations shown in Tables 6 and 7 (Examples 3-1 to 3-72). For each of the 72 kinds of aqueous solutions obtained, a sensory evaluation was performed by 10 well-trained panelists with more than 10 years of experience on whether the odor of 1-octen-3-one was felt (whether it was masked). In the sensory evaluation, the odor of 1-octen-3-one was compared to a control solution containing no Group A compounds, and the panelists were asked to comment on the perceived flavor and aroma based on the following criteria. The evaluation was performed by holding the solution in the mouth. Tables 6 and 7 show the average evaluation scores of the 10 panelists.

[0070] (standard) No smell of 1-octen-3-one: 4 points Almost no smell of 1-octen-3-one: 3 points Slight odor of 1-octen-3-one: 2 points The odor of 1-octen-3-one is clearly detectable: 1 point Strong odor of 1-octen-3-one (same strength as 1-octen-3-one aqueous solution (concentration 0.5 ppb)): 0 points

[0071] [Table 6]

[0072] [Table 7]

[0073] As shown in Tables 6 and 7, it was confirmed that each compound in Group A was capable of masking the odor of 1-octen-3-one.

[0074] [Example 4] Confirmation of the effect of masking milk odor 2 Water containing 0.05 ppb of 3-methyl-2,4-nonanedione (3-methyl-2,4-nonanedione aqueous solution) was prepared. Nine compounds of 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 this 3-methyl-2,4-nonanedione aqueous solution to the concentrations shown in Tables 8 and 9 (Examples 4-1 to 4-36). For each of the 36 aqueous solutions obtained, a well-trained panelist with 10 years or more of experience conducted a sensory evaluation to determine whether the odor of 3-methyl-2,4-nonanedione was felt. In the sensory evaluation, a 3-methyl-2,4-nonanedione aqueous solution to which no compound of group B was added was used as a control, and the odor of 3-methyl-2,4-nonanedione compared to the control was evaluated based on the following criteria. The evaluation was performed by holding the aqueous solution in the mouth. Tables 8 and 9 show the average evaluation scores of the 10 panelists.

[0075] (standard) No smell of 3-methyl-2,4-nonanedione: 4 points Almost no smell of 3-methyl-2,4-nonanedione: 3 points Slight odor of 3-methyl-2,4-nonanedione: 2 points The odor of 3-methyl-2,4-nonanedione is clearly detectable: 1 point The odor of 3-methyl-2,4-nonanedione is strongly felt (same strength as that of 3-methyl-2,4-nonanedione aqueous solution (concentration 0.05 ppb)): 0 points

[0076] [Table 8]

[0077] [Table 9]

[0078] As shown in Tables 8 and 9, it was confirmed that each compound in Group B was capable of masking the odor of 3-methyl-2,4-nonanedione.

[0079] [Example 5] Confirmation of the effect of masking milk odor 3 Water containing 25 ppb of boboride (aqueous boboride solution) was prepared. Nine compounds of 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 this aqueous boboride solution to the concentrations shown in Tables 10 and 11 (Examples 5-1 to 5-36). For the 36 aqueous solutions obtained, a well-trained panelist with 10 years or more of experience conducted a sensory evaluation to determine whether the odor of boboride was felt. In the sensory evaluation, an aqueous boboride solution without the addition of a compound of group B was used as a control product, and the odor of boboride was compared with that of the control product and evaluated based on the following criteria. The evaluation was performed by holding the aqueous solution in the mouth. Tables 10 and 11 show the evaluation scores of the 10 panelists.

[0080] (standard) No smell of BoboRide at all: 4 points Almost no smell of BoboRide: 3 points Slight smell of Boboride: 2 points The smell of Bobolide is clearly detectable: 1 point Strong smell of boboride (same strength as boboride solution (concentration 25 ppb)): 0 points

[0081] [Table 10]

[0082] [Table 11]

[0083] As shown in Tables 10 and 11, it was confirmed that each compound in Group B was capable of masking the odor of boboride.

[0084] [Example 6] Confirmation of the effect of masking the stagnant milk odor 4 (pseudo-stagnant milk beverage 1) (1) Masking of 1-octen-3-one The pseudo-deteriorated milk beverage 1-1 (containing 0.3 ppb of 1-octen-3-one) prepared in Example 1 was added with the compounds of Group A to the concentrations shown in Tables 12 and 13 to prepare milk beverages (Examples 6-1 to 6-72). For each of the 72 types of milk beverages obtained, a sensory evaluation was performed by 10 well-trained panelists with 10 years or more of experience to determine whether the odor of 1-octen-3-one was felt. In the sensory evaluation, the pseudo-deteriorated milk beverage 1-1 to which no compounds of Group A were added was used as the control product 6-1, and the odor of 1-octen-3-one was evaluated in comparison with the control product 6-1 based on the following criteria, and the panelists were asked to comment on the flavor and aroma felt. In the following criteria of this example, the target odor means the odor of 1-octen-3-one. The evaluation was performed by holding the milk beverage in the mouth. Tables 12 and 13 show the average evaluation scores and representative comments of the 10 panelists.

[0085] (standard) No odor detected: 4 points The target odor is barely detectable: 3 points Slightly detectable target odor: 2 points The target odor can be clearly sensed: 1 point The target odor is strongly felt (the intensity of the target odor is 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 in dairy products. (2) Masking of 3-methyl-2,4-nonanedione and boboride The pseudo-deteriorated milk beverage 2-3 (containing 0.6 ppb of 3-methyl-2,4-nonanedione and 25 ppb of boboride) prepared in Example 2 was added with the compounds of group B to the concentrations shown in Tables 14 and 15 to prepare milk beverages (Examples 6-73 to 6-108). For each of the 36 types of milk beverages obtained, a sensory evaluation was conducted by 10 well-trained panelists with more than 10 years of experience to determine whether the odors of 3-methyl-2,4-nonanedione and boboride were felt. In the sensory evaluation, the pseudo-deteriorated milk beverage 2-3 to which no compounds of group B were added was used as control product 6-2, and the odors of 3-methyl-2,4-nonanedione and boboride were compared with control product 6-2 and evaluated based on the following criteria, and the participants were asked to comment on the flavors and flavors felt. In the following criteria of this example, the target odor means the odor of 3-methyl-2,4-nonanedione and the odor of boboride. The evaluation was performed by holding the milk drink in the mouth. Tables 14 and 15 show the average evaluation scores and representative comments of the 10 panelists.

[0089] (standard) No odor detected: 4 points The target odor is barely detectable: 3 points Slightly detectable target odor: 2 points The target odor can be clearly sensed: 1 point The target odor is strongly felt (the intensity of the target odor is the same as 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 was able to mask the odor of 3-methyl-2,4-nonanedione and boboride in dairy products.

[0093] [Example 7] Confirmation of the effect of masking the stagnant milk odor 5 (pseudo-stagnant milk drink 2) To the simulated stagnant milk beverage 2-4 (containing the compounds (stagnant milk odor substances) shown in Table 5) prepared in Example 2, compounds in Group A and compounds in Group B were added to 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 deteriorated odor of each of the obtained milk beverages was subjected to a sensory evaluation by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, the pseudo-deteriorated milk beverage 2-4 was used as control product 7, and the milk beverages of Examples 7-1 to 7-19 were compared with control product 7. The panelists were asked to score whether they could detect the odor of each compound shown in Table 5 (in the following criteria of 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 flavor they could detect. Table 16 shows the average evaluation scores and representative comments of the 10 panelists.

[0095] (standard) No odor detected: 4 points The target odor is barely detectable: 3 points Slightly detectable target odor: 2 points The target odor can be clearly sensed: 1 point The target odor is strongly felt (the intensity of the target odor is equivalent to that of 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 the compounds of Group A and Group B. Note that, in the present invention, the combination is not limited to that of this example, and the optimal combination can be considered by selecting any compound from Group A and Group B according to the desired deterioration odor masking effect.

[0098] [Example 8] Confirmation of the effect of masking the stagnant milk odor 6 (pseudo-stagnant milk beverage 3) The simulated stagnant milk beverage 2-4 (containing the compounds (stagnant milk odor substances) shown in Table 5) prepared in Example 2 was added with one compound from Group A and one compound from Group B in the combinations shown in Tables 17 to 25 below at a concentration of 10 ppb each to prepare milk beverages (Examples 8-1 to 8-162).

[0099] The deteriorated odor of each of the obtained 162 types of milk beverages was subjected to a sensory evaluation by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, the pseudo-deteriorated milk beverage 2-4 was used as control product 8, and the panelists were asked to comment on whether they could smell the odor of the compounds shown in Table 5 for each of the milk beverages of Examples 8-1 to 8-162 compared to control product 8. As a result, in each example, 9 to 10 out of 10 panelists answered that they could hardly smell any of the compounds shown in Table 5, and that the beverages were easy to drink and had a pleasant milk-like 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 to 25, it was confirmed that a high masking effect was obtained by combining the compounds of groups A and B.

[0110] [Example 9] Confirmation of the effect of masking the deteriorated milk odor 7 (deteriorated milk drink 1) (1) Compounds of group A To the deteriorated basic milk drink 1 obtained in Example 1, 18 types of compounds of 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 tiglate, ethyl 3-hydroxyoctanoate) were added to the concentrations shown in Table 26 (Examples 9-1 to 9-18). For each of the obtained 18 types of milk drinks, a sensory evaluation was performed by 10 well-trained panelists with more than 10 years of experience to determine whether they had a deteriorated odor. In the sensory evaluation, the deteriorated basic milk drink 1 to which no compounds of Group A were added was used as control product 9-1, and the deteriorated odor compared to control product 9-1 was evaluated based on the following criteria, and the participants were asked to comment on the flavor they felt. In the following criteria of this example, "smelling a deteriorated odor" means smelling the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, and other unpleasant odors. The evaluation was performed by holding the milk drink in the mouth. Table 26 shows the average evaluation scores of 10 panelists.

[0111] (standard) No smell of deterioration: 4 points Almost no smell of deterioration: 3 points Slight odor of deterioration: 2 points The smell of deterioration is clearly noticeable: 1 point Strong odor of deterioration (same intensity as control product 9-1): 0 points

[0112] [Table 26]

[0113] As shown in Table 26, it was confirmed that the compounds in Group A have a high masking effect against deterioration odors.

[0114] (2) Compounds of group B Nine compounds of 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 deteriorated basic milk beverage 1 obtained in Example 1 to the concentrations shown in Table 27 (Examples 9-19 to 9-27). For each of the nine milk beverages obtained, a sensory evaluation was performed by 10 well-trained panelists with more than 10 years of experience to determine whether the deteriorated odor was felt. In the sensory evaluation, the deteriorated basic milk beverage 1 to which no compounds of group B were added was used as control product 9-2, and the deteriorated odor was compared with control product 9-2 based on the following criteria, and the panelists were asked to comment on the flavor felt. In the following criteria of this example, "the deteriorated odor is felt" means that the odor of 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, and other unpleasant odors are felt. The evaluation was performed by putting the milk beverage in the mouth. Table 27 shows the average evaluation scores of the 10 panelists.

[0115] (standard) No smell of deterioration: 4 points Almost no smell of deterioration: 3 points Slight odor of deterioration: 2 points The smell of deterioration is clearly noticeable: 1 point Strong odor of deterioration (same intensity as control product 9-2): 0 points

[0116] [Table 27]

[0117] As shown in Table 27, it was confirmed that the compounds in Group B have a high masking effect against deterioration odors.

[0118] [Example 10] Confirmation of the effect of masking the deteriorated milk odor 8 (deteriorated milk drink 2) Four types of milk beverages were prepared (Examples 10-1 to 10-4) by adding compounds of Group A and compounds of Group B as shown in Table 28 below to basic milk beverage 1 prepared in Example 1 and basic milk beverage 2 (commercially available yogurt drink) prepared in Example 2.

[0119] The obtained milk drinks of Examples 10-1 and 10-2, and the basic milk drink 1 were subjected to light abuse under the same conditions as in Example 1 to obtain deteriorated masked milk drinks 10-1 and 10-2, and deteriorated basic milk drink 1, respectively. In addition, the milk drinks of Examples 10-3 and 10-4, and the basic milk drink 2 were subjected to light abuse under the same conditions as in Example 2 to obtain deteriorated masked milk drinks 10-3 and 10-4, and deteriorated basic milk drink 2, respectively.

[0120] The obtained various deteriorated milk beverages were subjected to a sensory evaluation by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, the deteriorated base milk beverage 1 was used as the control product 10-1, and the panelists were asked to comment on whether the deteriorated masked milk beverages 10-1 to 10-2 had a deteriorated odor compared to the control product 10-1. In addition, the deteriorated base milk beverage 2 was used as the control product 10-2, and the panelists were asked to comment on whether the deteriorated masked milk beverages 10-3 to 10-4 had a deteriorated odor (the deterioration odor is defined as above) compared to the control product 10-2. In this example, "the deteriorated odor is felt" means that the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, and other unpleasant odors are felt. Representative comments are shown in Table 28.

[0121] [Table 28]

[0122] From the above, it was confirmed that the deterioration odor was effectively masked even when the compound of the present invention was added to a milk beverage before the deterioration.

[0123] [Example 11] Confirmation of the effect of masking the deteriorated milk odor 9 (deteriorated milk drink 3) As shown in Table 29 below, yogurt flavor 1 not containing the compound of the present invention (Comparative Example 11-1) and yogurt flavor 2 containing the compound of the present invention (Example 11-1 (one embodiment of the milk deterioration odor masking agent or flavor-imparting composition of the present invention)) were prepared.

[0124] [Table 29]

[0125] Then, 0.1% by mass of each of the yogurt flavor 1 of Comparative Example 11-1 and the yogurt flavor 2 of Example 11-1 was added to the basic milk drink 1 prepared in Example 1 to obtain a comparative milk drink 11-2 and a milk drink of Example 11-2. Then, the comparative milk drink 11-2 and the milk drink of Example 11-2 were subjected to light abuse under the same conditions as in Example 1 to obtain a deteriorated comparative milk drink 11-2 and a deteriorated masking milk drink 11-2.

[0126] In addition, 0.1% by mass of each of the yogurt flavor 1 of Comparative Example 11-1 and the yogurt flavor 2 of Example 11-1 was added to the basic milk drink 2 prepared in Example 2 to obtain the comparative milk drink 11-3 and the milk drink of Example 11-3. The comparative milk drink 11-3 and the milk drink of Example 11-3 were then subjected to light abuse under the same conditions as in Example 2 to obtain the deteriorated comparative milk drink 11-3 and the deteriorated masked milk drink 11-3.

[0127] The obtained deteriorated milk beverages were subjected to a sensory evaluation by 10 well-trained panelists with 10 years or more of experience. In the sensory evaluation, the deteriorated comparative milk beverage 11-2 was used as a control, and the panelists were asked to comment on whether the deteriorated masked milk beverage 11-2 had a deteriorated odor compared to the control. In addition, the deteriorated comparative milk beverage 11-3 was used as a control, and the panelists were asked to comment on whether the deteriorated masked milk beverage 11-3 had a deteriorated odor compared to the control. In this example, "perceiving a deteriorated odor" means perceiving the odors of 1-octen-3-one, 3-methyl-2,4-nonanedione, and boboride, 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 odor of deterioration was effectively masked even when the compound of the present invention was added to a milk beverage before the deterioration.

Claims

1. A milk deterioration odor masking agent comprising one or more compounds selected from the following group A or group 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 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

2. The milk deterioration odor masking agent according to claim 1, comprising one or more compounds selected from the group A and one or more compounds selected from the group B.

3. A flavoring composition comprising the milky odor masking agent according to claim 1.

4. A flavoring composition comprising the milky odor masking agent according to claim 2.

5. A method for improving the stagnant odor of dairy products, comprising adding the milk stagnant odor masking agent according to claim 1 or 2, or the flavor imparting composition according to claim 3 or 4 to a dairy product.

6. A method for producing a dairy product, comprising adding the milk stagnant odor masking agent according to claim 1 or 2, or the flavor imparting composition according to claim 3 or 4 to a dairy product.

7. A composition simulating a stagnant milk odor, comprising one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride.

8. The composition according to claim 7, further comprising 1-octen-3-one.

9. (Step A) preparing a milk stagnant odor simulating composition containing one or two compounds selected from the group consisting of 3-methyl-2,4-nonanedione and boboride; (Step B) adding a candidate substance for masking milk deterioration odor to the milk deterioration odor simulating composition to prepare a milk deterioration odor test composition; and (Step C) A step of evaluating the milk deterioration odor of the milk deterioration odor test composition A method for confirming the effect of masking milk deterioration odor, including:

10. The method for confirming the effect of masking milky odor according to claim 9, wherein the milky odor simulating composition further contains 1-octen-3-one.

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