Legume protein-derived bean odor masking agent

Abstract

To suppress odor derived from beans recognized when prepared processed foods, medicines or quasi drugs using bean-derived protein.SOLUTION: At least one type of compound selected from groups consisting of A to F is used as a bean odor masking agent derived from legume protein; (Group A) 1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, (Group B) 1,4-cineole, γ-heptalactone, menthyl lactate, ethyl lactate, γ-hexalactone, acetaldehyde diethyl acetal, and methyl salicylate, (Group C) ethyl acetoacetate, isobutyric maltol, and diethyl malonate, (Group D) methyl jasmonate, dihydrojasmonate methyl, heliotropin, ethyl pyruvate, butyryl butyric acid, stearic acid, and γ-butyrolactone, (Group E) ethyl lactate, 2-butanone, and nerol, (Group F) furfural, methyl salicylate, and 5(6)-decenoic acid.SELECTED DRAWING: None

Description

Technical Field

[0001] [Cross - reference to Related Applications] This application claims priority based on Japanese Patent Application No. 2018 - 105589, filed on May 31, 2018, the entire disclosure of which is incorporated herein by reference.

[0002] The present invention relates to a bean odor masking agent and a method for using the same. More specifically, the present invention relates to a bean - derived odor perceived when processing foods, pharmaceuticals or quasi - drugs using bean - derived proteins, and a bean odor masking agent preferably used to suppress an odor that requires masking (bean odor derived from bean proteins), and a method for masking bean odor using the bean odor masking agent.

Background Art

[0003] Conventionally, for foods, animal or plant proteins or their degradation products (including peptides) have been used to impart or improve nutrition, physiological functions or physical properties (such as foaming property, emulsifying property, binding property, etc.). Among them, proteins or their degradation products of beans such as soybeans are well - digestible, nutritionally excellent, low - calorie, and have excellent physiological effects such as reducing neutral fat and cholesterol, and thus are used in various health foods.

[0004] However, when preparing processed foods, pharmaceuticals or quasi - drugs using bean - derived proteins, they have a unique odor derived from beans.

[0005] Under these circumstances, it is often desired that processed foods using bean-derived protein have their characteristic odor reduced and exhibit a flavor similar to similar processed foods that do not use bean-derived protein. For this reason, various methods have been proposed to mask (reduce, improve, etc.) the bean odor (sometimes described as a peculiar odor, unpleasant odor, off-odor, etc.) caused by bean proteins. Specifically, all of these methods target the beany odor of soy protein, and methods for masking it include incorporating maltitol and arginine (Patent Document 1), spices (Patent Document 2), thaumatin (Patent Document 3), malt extract (Patent Document 4), reducing sugars and amino group-containing compounds (Patent Document 5), trehalose (Patent Document 6), whey protein (Patent Document 7), polyphenols extracted from tea (Patent Document 8), flavor oil extracted by heating edible oil with vegetables (Patent Document 9), ethyl decanoate (Patent Document 10), melanoidin and egg white hydrolysate (Patent Document 11), and the like. However, there is a strong desire to develop a new method that can mask the beany odor caused by legume proteins, not only for soybeans but for legumes in general. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2017-093349 [Patent Document 2] Japanese Patent Publication No. 2017-051161 [Patent Document 3] Japanese Patent Publication No. 2011-004699 [Patent Document 4] Japanese Patent Publication No. 2010-246449 [Patent Document 5] Japanese Patent Publication No. 2000-312562 [Patent Document 6] Japanese Patent Publication No. 10-066516 [Patent Document 7] Japanese Patent Publication No. 08-173050 [Patent Document 8] Japanese Patent Publication No. 08-103225 [Patent Document 9] Japanese Patent Publication No. 61-274661 [Patent Document 10] Japanese Patent Publication No. 2006-197857 [Patent Document 11] Japanese Patent Publication No. 03-155759 [Overview of the project] [Problems that the invention aims to solve]

[0007] The object of the present invention is to suppress the bean-derived odor perceived when processed foods, pharmaceuticals, or quasi-drugs are prepared using bean-derived proteins, which is a problem of the prior art. In this invention, the bean-derived odor perceived when processed foods, pharmaceuticals, or quasi-drugs are prepared using bean-derived proteins, and which is essentially an odor that needs to be masked, is collectively referred to as "bean odor." In this invention, bean odor is not limited to so-called unpleasant odors, but also includes odors that are essentially masked because they make it apparent that bean-derived proteins are included in food, etc. This bean odor is thought to mainly originate from the protein components in bean proteins (and / or their decomposition products due to heat processing, etc.) and / or the oil and fat components (and / or their decomposition products due to heat processing, etc.) that are usually contained in small amounts in bean protein powder, etc. Therefore, the object of the present invention is to provide a masking agent for the above-mentioned bean odor and its uses. Another object of the present invention is to provide a method for masking bean odor using the bean odor masking agent. [Means for solving the problem]

[0008] As a result of diligent research, the inventors have identified the main odor substances that constitute the bean odor perceived when processed foods and the like are prepared using bean-derived protein. Furthermore, the inventors have identified masking agent components that were not previously known to have a masking effect on these odor substances that constitute the bean odor.

[0009] The present invention was completed through further investigation based on the aforementioned findings and encompasses the following embodiments.

[0010] Item 1. A bean-derived bean odor masking agent containing at least one compound selected from the following groups A to F; (Group A) 1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, (Group B) 1,4-cineole, γ-heptalactone, menthyl lactate, ethyl lactate, γ-hexalactone, acetaldehyde diethyl acetal, and methyl salicylate. (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group D) Methyl jasmonate, methyl dihydrojasmonate, heliotropin, ethyl pyruvate, butyl butyryl lactate, stearic acid, and γ-butyrolactone, (Group E) Ethyl lactate, 2-butanone, and nerol, (Group F) Furfural, methyl cinnamate, and 5(6)-decenoic acid.

[0011] Item 2. The bean odor masking agent described in Item 1, wherein the above bean odor is caused by at least one compound selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

[0012] Item 3. A bean odor masking agent as described in Item 1 or 2, further containing one or more fragrance components.

[0013] Item 4. A fragrance composition, which is a bean odor masking agent as described in any one of items 1 to 3.

[0014] Item 5. A fragrance composition containing a bean odor masking agent and a fragrance component as described in any one of items 1 to 4.

[0015] Item 6. A method for masking beany odor, comprising the step of blending the beany odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5 into a composition containing legume protein.

[0016] Item 7. The method for masking beany odor according to Item 6, wherein the beany odor is caused by at least one compound selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

[0017] Item 8. A method for producing the above food, pharmaceutical product, or quasi-drug, comprising the step of blending the beany odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5 into a food, pharmaceutical product, quasi-drug, or raw material thereof containing legume protein.

[0018] Item 9. The production method according to Item 8, wherein the above food, pharmaceutical product, or quasi-drug contains at least one compound selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

[0019] Item 10. A food, pharmaceutical product, or quasi-drug containing legume protein, which is a food, pharmaceutical product, or quasi-drug in which the beany odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5 is blended.

Advantages of the Invention

[0020] According to the present invention, it is possible to provide a novel beany odor masking agent, a novel masking method using the novel masking agent, a method for producing a food, pharmaceutical product, or quasi-drug, and a food, pharmaceutical product, or quasi-drug obtained by the production method.

[0021] In this invention, "suppressing bean odor" or "masking bean odor" means that by adding the masking compound of the present invention to a composition having the bean odor, the bean odor is reduced or eliminated compared to before the addition of the masking compound. Furthermore, the present invention can also be applied to compositions that generate the bean odor over time or through a predetermined treatment (heating, light irradiation, etc.). In this case, adding the masking compound of the present invention to the composition means that the bean odor is suppressed (reduced) even after the predetermined treatment (heating, light irradiation, storage, etc.) compared to when the masking compound is not added. [Modes for carrying out the invention]

[0022] In this specification, the terms “contains” or “includes” are used to include the terms “consist of” and “consist of only.” Unless otherwise specified, the operations and processes described herein may be carried out at room temperature. In this specification, the term "room temperature" is to be understood in accordance with common technical knowledge and may mean, for example, a temperature within the range of 10°C to 35°C. Unless otherwise indicated, in this specification, “composition containing legume protein (food, pharmaceutical or quasi-drug, etc.)” includes compositions (food, pharmaceutical or quasi-drug, etc.) that contain legume protein and / or its hydrolysates, and further contain oils and / or their hydrolysates that are usually present in small amounts in legume protein powder, etc. Similarly, unless otherwise indicated, in this specification, “bean odor derived from legume protein” includes bean odor derived from legume protein components, their hydrolysates, oils and / or their hydrolysates that are present in small amounts in legume protein powder, etc.

[0023] The present invention will be described in detail below. (I) Bean odor masking agent The bean odor targeted by the bean odor masking agent of the present invention is, as described above, a bean-derived odor perceived when processed foods, pharmaceuticals, or quasi-drugs are prepared using bean-derived proteins, and masking essentially means masking the odor.

[0024] In the present invention, "legume protein" (sometimes referred to as "bean-derived protein" in this specification) means a food material whose main component is legume protein, and this includes the above-mentioned food material that contains small amounts of legume-derived oil and fat components, etc., in protein powder, etc. While not limited, bean-derived proteins can include, without limitation, proteins derived from soybeans, peas, chickpeas, flat beans (lentils), kidney beans, broad beans, etc., with proteins derived from soybeans, peas, chickpeas, etc., being preferred. The method of producing bean-derived protein and / or its hydrolysates is not particularly limited, as long as they are obtained by separating and purifying proteins and / or hydrolysates contained in beans. Furthermore, commercially available bean-derived proteins and / or their hydrolysates can also be used. Examples of soybean protein include defatted soybeans obtained by degreasing whole soybeans with organic solvents such as hexane and ethanol, soy milk obtained by water extraction of protein from defatted soybeans, isolated soybean protein obtained from soy milk by methods such as acid precipitation or alcohol precipitation, and concentrated soybean protein. Pea protein can be obtained, for example, by removing the outer skin of the pea seed, grinding it, extracting the protein with water, concentrating it, and drying it. Chickpea protein can be obtained by isolating and purifying it in the same way as soybean and pea protein. The above-mentioned bean-derived proteins, including commercially available products, are usually not 100% protein, but contain small amounts of oils and fats, which can affect the bean odor. Therefore, in the present invention, bean-derived protein may contain small amounts of oils and fats derived from the beans.

[0025] As described in the examples below, the inventors have identified the main odor substances in the bean odor caused by bean-derived proteins in relation to the present invention. Preferred specific examples of such main odor substances include hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

[0026] The bean odor masking agent of the present invention utilizes the masking effect (bean odor suppression effect) on the above-mentioned bean odor possessed by compounds belonging to the group consisting of groups A to F below, and is characterized by containing at least one compound selected from these compounds as an active ingredient: (Group A) 1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, (Group B) 1,4-cineole, γ-heptalactone, menthyl lactate, ethyl lactate, γ-hexalactone, acetaldehyde diethyl acetal, and methyl salicylate. (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group D) Methyl jasmonate, methyl dihydrojasmonate, heliotropin, ethyl pyruvate, butyl butyryl lactate, stearic acid, and γ-butyrolactone, (Group E) Ethyl lactate, 2-butanone, and nerol, (Group F) Furfural, methyl cinnamate, and 5(6)-decenoic acid.

[0027] These compounds (hereinafter collectively referred to as "masking compounds") are all commercially available and known compounds. In the present invention, "5(6)-decenoic acid" refers to a mixture of 5-decenoic acid and 6-decenoic acid. The mixing ratio of 5-decenoic acid and 6-decenoic acid is not particularly limited, but for example, a mixture of 1 part by mass of the former and 0.01 to 100 parts by mass, preferably 0.1 to 10 parts by mass of the latter, can be used. Furthermore, natural fragrances containing these compounds can be used as masking agents of the present invention, to the extent that they do not impair the effects of the present invention. Examples of such natural fragrances are not limited to these, but include: lime fragrance as a natural fragrance containing 1,4-cineole; apricot fragrance as a natural fragrance containing γ-hexalactone; vanilla fragrance as a natural fragrance containing heliotropin; and coffee fragrance as a natural fragrance containing furfural. All of these masking compounds can be suitably used as active ingredients in the bean odor masking agent of the present invention.

[0028] The bean odor masking agent of the present invention may contain only one of the above-mentioned masking compounds as an active ingredient, or it may contain two or more in any combination.

[0029] The compounds listed in Group A, namely 1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, are effective bean odor masking agents and, in particular, are effective masking agents for hexanal, one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group A, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by hexanal. These compounds listed in Group A can be used individually or in combination of two or more.

[0030] The compounds listed in Group B, 1,4-cineole, γ-heptalactone, menthyl lactate, ethyl lactate, γ-hexalactone, acetaldehyde diethyl acetal, and methyl salicylate, are compounds that function effectively as bean odor masking agents, and in particular, they function effectively as masking agents for (E,E)-2,4-decadienal, one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group B, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by (E,E)-2,4-decadienal. These compounds listed in Group B can be used individually or in combination of two or more.

[0031] The compounds listed in Group C, ethyl acetoethyl, maltol isobutyrate, and diethyl malonate, are compounds that function effectively as bean odor masking agents, and in particular, they function effectively as masking agents for guaiacol, one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group C, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by guaiacol. These compounds listed in Group C can be used individually or in combination of two or more.

[0032] The compounds listed in Group D, methyl jasmonate, methyl dihydrojasmonate, heliotropin, ethyl pyruvate, butyl butyryl lactate, stearic acid, and γ-butyrolactone, are compounds that function effectively as bean odor masking agents, and in particular, they function effectively as masking agents for trans-4,5-epoxy-(E)-2-decenal, which is one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group D, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by trans-4,5-epoxy-(E)-2-decenal. In a preferred embodiment of the present invention, at least one selected from the group consisting of methyl jasmonate, heliotropin, butyl butyryl lactate, and stearic acid may be used. These compounds listed in Group D can be used individually or in combination of two or more.

[0033] The compounds listed in Group E, ethyl lactate, 2-butanone, and nerol, are effective as bean odor masking agents, and in particular, they are effective as masking agents for 2-isobutyl-3-methoxypyrazine, one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group E, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by 2-isobutyl-3-methoxypyrazine. These compounds listed in Group E can be used individually or in combination of two or more.

[0034] The compounds listed in Group F, furfural, methyl cinnamate, and 5(6)-decenoic acid, are compounds that function effectively as bean odor masking agents, and in particular, they function effectively as masking agents for 2,5-dimethylpyrazine, one of the main odor substances of the aforementioned bean odor. Therefore, when using compounds belonging to Group F, the masking agents of the present invention can be used to mask the bean odor of processed foods, pharmaceuticals, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by 2,5-dimethylpyrazine. These compounds listed in Group F can be used individually or in combination of two or more.

[0035] The odor-masking agent of the present invention is characterized by containing one or more compounds selected from the group consisting of groups A to F (i.e., a group of compounds including all compounds belonging to group A, group B, group C, group D, group E, and group F). In the present invention, "two or more compounds selected from the group consisting of groups A to F" includes not only two or more compounds that include compounds belonging to different groups, but also two or more compounds that belong to the same group, unless otherwise explicitly stated. The masking effect can be obtained by using only one of the compounds, a better effect can be obtained by using two or more of the compounds, and an even better effect can be obtained by using three or more of the compounds.

[0036] In the present invention, from the viewpoint of the good masking effect, It is preferable to use a combination of at least one compound (a total of at least two compounds) selected from at least two groups from groups A to F. It is more preferable to use a combination of at least one compound (a total of at least three compounds) selected from at least three groups from groups A to F. It is even more preferable to use a combination of at least one compound (a total of at least four compounds) selected from at least four groups from groups A to F. It is even more preferable to use a combination of at least one compound (a total of at least five compounds) selected from at least five groups from groups A to F. It is particularly preferable to use a combination of at least one compound selected from each of the six groups A through F (a total of at least six compounds).

[0037] Of the masking agent compounds mentioned above, 1,4-cineole, γ-heptalactone, and menthyl lactate belong to two groups, A and B, respectively, while ethyl lactate belongs to two groups, B and E. In the present invention, a masking agent containing one of these two groups is included in the category of "a masking agent containing a combination of one or more compounds selected from two or more groups A to F (a total of two or more)" because it contains compounds belonging to the two groups to which the compound in question belongs. For example, by incorporating 1,4-cineole into a masking agent, the masking agent will contain compounds belonging to two groups, A and B. Therefore, a masking agent containing 1,4-cineole alone is included in the category of "a masking agent containing a combination of one or more compounds selected from two or more groups A to F (a total of two or more)." Furthermore, in the present invention, when using compounds belonging to multiple groups as masking agent compounds, these compounds may be used individually, or they may be used in combination with other masking agent compounds.

[0038] The masking agent of the present invention preferably includes a combination of multiple compounds (for example, two or more, preferably three or more, more preferably four or more, more preferably five or more, more preferably six) that belong to different groups. Here, "belonging to different groups" includes cases where the groups to which these compounds belong partially overlap but partially do not. Therefore, in the present invention, the combination of compounds that "belong to different groups" includes cases where there is some overlap but partially do not, such as the combination of 1,4-cineole (group A, group B) and ethyl lactate (group B, group E).

[0039] The masking agent of the present invention preferably contains one or more compounds selected from at least one group A to D among the above groups A to F. Furthermore, in embodiments where it is used for legumes such as soybeans and chickpeas, it is preferable to use one or more compounds selected from at least one group A to D. It is preferable to use a combination of at least one compound (a total of at least two compounds) selected from at least two groups A to D. It is more preferable to use a combination of at least one compound (a total of at least three compounds) selected from at least three groups from groups A to D. It is even more preferable to use a combination of at least one compound (at least four in total) selected from at least four groups from groups A to D. In embodiments used for legumes such as peas, at least one compound selected from groups A to F can be suitably used. Therefore, in embodiments used for legumes such as peas, the masking agent composition may contain at least one compound selected from at least one group from groups A to D, or it may contain at least one compound selected from at least one group from groups E to F.

[0040] In a preferred embodiment, the masking agent of the present invention comprises a masking agent compound having a masking effect on one or more of six odor substances (preferably two or more, more preferably three or more, more preferably four or more, more preferably five or more, and more preferably all six) of the following: hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine. In some preferred embodiments of the present invention, the masking agent of the present invention is one in which the bean odor is caused by at least one selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine, and which masks at least one (preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably six) bean odors selected from the group. In the present invention, among the above odor substances, it is preferable that the odor is caused by at least one selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, and trans-4,5-epoxy-(E)-2-decenal, and which masks at least one (preferably at least two, more preferably at least three, more preferably four) bean odors selected from the group. In embodiments where the product is used for legumes such as peas, any of the six odor substances mentioned above that mask the bean odor can be suitably used.

[0041] The amount of the masking compound used in the present invention (for example, the amount of the masking agent in the food, pharmaceutical, or quasi-drug of the present invention) should be an amount that provides a masking effect on the bean odor, and specifically, The concentration of each of these compounds in relation to the total amount of soy-derived protein-containing foods is It is preferable to use it in a range of 0.00001 ppb to 10000 ppb. It is more preferable to use it in a range of 0.0001 ppb to 1000 ppb, and It is even more preferable to use it in a range of 0.001 ppb to 100 ppb. From the viewpoint of providing a sufficient masking effect on the bean odor while suppressing the undesirable influence of the aroma and / or taste of the masking agent compound itself on the aroma and / or taste of the bean-derived protein-containing food, pharmaceutical, or quasi-drug, it is preferable to use the amount of the masking compound within the above range.

[0042] In the present invention, the total mass (or total concentration) of compounds from each of groups A to F is equal to the odor substance that is a suitable target for masking (i.e., a target that functions effectively as a masking agent) for each group (i.e., hexanal for the compounds described in group A, (E,E)-2,4-decadienal for the compounds described in group B, guaiacol for the compounds described in group C, and trans-4,5-epoxy- for the compounds described in group D). The ratio of (E)-2-decenal, 2-isobutyl-3-methoxypyrazine to the compounds listed in Group E, and 2,5-dimethylpyrazine to the compounds listed in Group F) to the mass (or concentration) is preferably, for example, in the range of 1:100000 to 100000:1, 1:10000 to 10000:1, 1:1000 to 10000:1, 1:1000 to 1000:1, 1:100 to 1000:1, or 1:10 to 10:1. In the present invention, when using compounds belonging to multiple groups as masking agent compounds, the above ratios are calculated assuming that compounds belonging to multiple groups are compounds of any of the groups to which they belong (for example, 1,4-cineole is a compound of both Group A and Group B).

[0043] The present invention makes it possible to mask the bean odor in a simple, safe, and unaffected manner at each stage of manufacturing, distribution, storage, and sales of bean-derived protein-containing foods, pharmaceuticals, or quasi-drugs, by using one or more compounds selected from the groups A to F, without affecting the aroma and / or taste of the final product.

[0044] The bean odor masking agent of the present invention may contain compounds other than the masking agent compound. The form of the bean odor masking agent of the present invention, and the type and amount of the other compounds, can be set as appropriate depending on the manner in which the bean odor masking agent of the present invention is used.

[0045] The bean odor masking agent of the present invention may consist solely of the masking agent compound, or it may contain a suitable diluent (thickener) or carrier in addition to the masking agent compound. In this case, the proportion of the masking agent compound in the bean odor masking agent can be appropriately set and adjusted from the range of 0.00000001 to 99% by mass (0.0001 to 990000 ppm) so that the bean odor masking agent exhibits an effect of suppressing the bean odor derived from bean proteins.

[0046] The diluent or carrier used in combination with the masking agent compound is not particularly limited as long as it does not impair the bean odor-suppressing effect of the masking agent compound on legume protein-derived bean odor. Examples include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, glucose, and sucrose; or liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin, glycerin fatty acid esters, and edible oils and fats. These diluents or carriers include additives used to prepare the bean odor masking agent of the present invention into a desired shape (dosage form), such as excipients, binders, disintegrants, emulsifiers, solvents, thickeners, lubricants, flavoring agents, and colorants. Among these, emulsifiers can be suitably used to disperse the masking agent compound in a liquid diluent to prepare an aqueous solution (dispersion, suspension) or an emulsion-type bean odor masking agent. Such emulsifiers are not limited, but examples include sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, lecithin, enzymatically hydrolyzed lecithin, quillaja extract, saponins, polysorbates, gum arabic, and ghati gum. By using such diluents or carriers, the bean odor masking agent of the present invention can be in liquid, suspension, emulsion, paste, powder, granule, and any other dosage form. The dosage form of the bean odor masking agent of the present invention can be appropriately determined according to the type and shape of the object to which the bean odor derived from bean proteins is to be suppressed.

[0047] Furthermore, the bean odor masking agent of the present invention may be prepared as a powder formulation by mixing an excipient such as dextrin with an aqueous solution in which the aforementioned masking agent compound is dissolved or dispersed, and then powdering it according to a standard method such as spray drying or freeze-drying, or it may be prepared as a granular formulation by further granulation.

[0048] The bean odor masking agent of the present invention can suppress the above-mentioned bean odor when added to foods (including beverages; the same applies herein), pharmaceuticals, or quasi-drugs (typically foods, pharmaceuticals, or quasi-drugs containing at least one of the aforementioned odor substances) that contain bean-derived proteins. For this reason, the bean odor masking agent of the present invention can be effectively used as an additive (food additive, pharmaceutical additive, quasi-drug additive) to foods, pharmaceuticals, or quasi-drugs containing the aforementioned bean-derived proteins. Such additives include additives that are added and blended into the raw materials for the manufacture of foods, pharmaceuticals, or quasi-drugs during the manufacturing process, and these additives include, for example, fragrance compositions.

[0049] The proportion of the bean odor masking agent of the present invention to a food, pharmaceutical, or quasi-drug (target composition) containing proteins can be appropriately selected and adjusted according to the type and amount of odor substances contained in the target composition, and the type and amount of masking compounds that the bean odor masking agent of the present invention uses as an active ingredient.

[0050] In a preferred embodiment, the bean odor masking agent of the present invention can exert the above-mentioned masking effect while suppressing the influence of the flavor of the masking compound itself by adjusting the amount of the masking compound contained as an active ingredient. Furthermore, since the masking compound used in the present invention has almost no effect on the aroma of other fragrance components, it can be used in combination with other fragrance components to prepare a fragrance composition that has the effect of masking the above-mentioned bean odor, and can be suitably used.

[0051] Furthermore, as shown in Experimental Examples 9-12 described later, the ratio of each masking compound contained in the bean odor masking agent of the present invention to 10,000 parts by mass of bean protein contained in the target composition (bean protein-containing composition) can also be set as follows. However, this is just an example and is not limited to this ratio. Compounds belonging to Group A: 0.000002 parts by mass or more, preferably 0.000002 to 0.002 parts by mass, more preferably 0.00002 to 0.0002 parts by mass, per 10,000 parts by mass of legume protein; Compounds belonging to Group B: 0.0000002 parts by mass or more, preferably 0.0000002 to 0.002 parts by mass, more preferably 0.000002 to 0.0002 parts by mass, per 10,000 parts by mass of legume protein; Compounds belonging to group C: 0.00000002 parts by mass or more, preferably 0.00000002 to 0.002 parts by mass, more preferably 0.0000002 to 0.0002 parts by mass, per 10,000 parts by mass of legume protein; Compounds belonging to group D: 0.0000002 parts by mass or more, preferably 0.0000002 to 0.002 parts by mass, more preferably 0.000002 to 0.0002 parts by mass, per 10,000 parts by mass of legume protein; Compounds belonging to group E: 0.000002 parts by mass or more, preferably 0.000002 to 0.002 parts by mass, more preferably 0.00002 to 0.0002 parts by mass, per 10,000 parts by mass of legume protein; Compounds belonging to group F: 0.00000002 parts by mass or more, preferably 0.00000002 to 0.02 parts by mass, more preferably 0.0000002 to 0.002 parts by mass, per 10,000 parts by mass of legume protein. The amount of protein contained in the legume protein-containing composition can be analyzed and quantified using the "nitrogen quantitative conversion method" described in column 3 of Appendix 9 of the Food Labeling Standards based on Article 4, Paragraph 1 of the Food Labeling Act (see Consumer Affairs Agency website / Food Labeling Act, etc. (Laws and Unified Information)). Details of the aforementioned nitrogen quantitative conversion method are shown in "1 Protein (1) Nitrogen Quantitative Conversion Method" of "Food Labeling Standards Appendix Analytical Methods for Nutritional Components, etc." (Consumer Affairs Agency Deputy Director-General's Notification No. 139, March 30, 2015).

[0052] (II) Fragrance composition The bean odor masking agent of the present invention is in the form of a fragrance formulation and can also be used as a fragrance composition. Therefore, the present invention also provides the use of the bean odor masking agent of the present invention as a fragrance composition, and a fragrance composition containing the bean odor masking agent. The fragrance composition contains one or more of the masking compounds described above, and depending on the form of the fragrance formulation, it may also contain the diluent or carrier described above, or it may contain one or more other fragrance components (fragrance compounds other than the masking compounds of the present invention). As described above, the fragrance composition of the present invention can be used to mask bean odor.

[0053] Such other fragrance components only need to not impair the effects of the present invention when used in combination with the masking compound described above, and preferably do not suppress the aroma of the other fragrance components when used in combination with the masking compound. Examples of such fragrance components include natural and synthetic fragrances listed in the "Patent Gazette of the Japan Patent Office: Collection of Well-Known and Conventional Technologies (Fragrances), Part II: Food Fragrances" (published January 14, 2000), edited by the Japan Patent Office. Specifically, these include citrus flavorings with the aroma of citrus fruits (orange, lemon, lime, grapefruit, yuzu, sudachi, etc.) (pp. 88-135), fruit flavorings with the aroma of fruits other than citrus fruits (apple, grape, strawberry, banana, peach, melon, apricot, plum, cherry, berries, etc.) (pp. 136-257), milk flavorings with the aroma of dairy products (milk flavor, butter flavor, cheese flavor, cream flavor, yogurt flavor, etc.) (pp. 258-347), vanilla flavorings with the aroma of vanilla beans (pp. 348-366), tea flavorings with the aroma of green tea, oolong tea, black tea, etc. (pp. 367-426), and cocoa and chocolate flavorings. Examples include core chocolate flavoring (pp. 427-446), coffee flavoring with a coffee aroma (pp. 447-475), mint flavoring with aromas such as peppermint and spearmint (pp. 476-495), spice flavoring with a spice aroma (pp. 496-580), nutty flavoring with the aroma of nuts such as almonds (pp. 581-608), liquor flavoring with the aroma of liquor (e.g., wine, whiskey, brandy, rum, gin, liqueur, etc.) (pp. 759-825), floral flavoring with a floral aroma (pp. 826-836), and vegetable flavoring with the aroma of vegetables (e.g., onion, garlic, leek, carrot, burdock, shiitake mushroom, matsutake mushroom, mitsuba, etc.) (pp. 837-907). Preferably, the flavorings include citrus flavorings, fruit flavorings, milk flavorings, cocoa / chocolate flavorings, coffee flavorings, and nut flavorings.

[0054] The fragrance composition of the present invention may contain one or more of the aforementioned masking compounds in a proportion of 0.0000001 to 99% by mass, to the extent that it achieves the effects of the present invention. If the fragrance composition of the present invention contains other fragrance components in addition to the above-mentioned masking compounds, the proportion of such other fragrance components may be 0.0000001 to 99% by mass, preferably 0.000001 to 50% by mass, although this is not limited to such proportions. In this case, it is preferable to adjust the proportion of the masking compounds so that the flavor of the masking compounds themselves does not affect the fragrance of other fragrance components that are added separately.

[0055] (III) Method for producing compositions (foods, pharmaceuticals, quasi-drugs, etc.) in which the bean odor is masked. By incorporating the aforementioned bean odor masking agent or fragrance composition of the present invention into the aforementioned bean protein-containing composition, a bean protein-containing composition in which the bean odor is suppressed can be produced.

[0056] The legume protein-containing compositions discussed here are compositions containing legume protein as described in (I) above, and are typically compositions that may have a beany odor due to at least one compound selected from the group consisting of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine. Examples include foods, pharmaceuticals, or quasi-drugs.

[0057] Specific examples of the aforementioned foods, pharmaceuticals, and quasi-drugs are not limited to these, but include, for example, processed meat products (hamburgers, sausages, patties, nuggets, etc.), processed seafood products (fish sausages, kamaboko, chikuwa, etc.), seasoning liquids or condiments for processing (pickling liquid, dressings, mayonnaise, etc.), processed dairy products (dairy beverages, yogurt, ice cream, etc.), processed egg products (thick omelets, pudding, etc.), nutritional supplements (powdered protein foods, etc.), and beverages (soy milk, milk substitutes, protein-containing jelly drinks, tonic drinks, etc.).

[0058] While not limited, the protein content of the legume protein-containing composition can be 0.1 to 100% by mass, preferably 0.5 to 90% by mass. The amount of odor substances contained in the legume protein-containing composition can be 0.0001 ppm or more, preferably 0.0005 to 10 ppm, and more preferably 0.001 to 1 ppm, as the total amount of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

[0059] The proportion of the bean odor masking agent or fragrance composition of the present invention to the bean protein-containing composition can be appropriately selected and adjusted depending on the type and amount of odor substances contained in the bean protein-containing composition, and the type and amount of masking compounds contained in the bean odor masking agent and fragrance composition of the present invention.

[0060] The timing and method of incorporating the bean odor masking agent or fragrance composition of the present invention into these legume protein-containing compositions are not particularly limited and can be carried out according to conventional methods at any stage in the manufacture of these products. For example, one method is to add the bean odor masking agent or fragrance composition of the present invention to the raw materials of a food, pharmaceutical, or quasi-drug and manufacture the food, pharmaceutical, or quasi-drug according to conventional methods.

[0061] The raw materials include legume proteins used in foods, pharmaceuticals, or quasi-drugs. Examples of such legume proteins include those described in (I) above, and this description may be incorporated herein. Furthermore, various other ingredients may be used as raw materials depending on the type of product, such as the food, pharmaceutical, or quasi-drug being used, and there are no particular restrictions.

[0062] According to the manufacturing method of the present invention, it is possible to prepare foods, pharmaceuticals, or quasi-drugs that contain legume protein while masking the beany odor.

[0063] (IV) Methods for masking the bean odor The present invention also provides a method for masking a bean odor, comprising the step of incorporating the aforementioned bean odor masking agent or fragrance composition into a composition containing bean protein.

[0064] The method may be carried out in accordance with the method described in the section "(III) Method for producing compositions (foods, pharmaceuticals, quasi-drugs, etc.) in which bean odor is masked," and that description may be incorporated herein by reference. [Examples]

[0065] The present invention will be described below using experimental examples and embodiments. However, the present invention is not limited to these experimental examples and embodiments. In the following examples, the numerical values ​​indicating quantity and concentration may be based on mass unless otherwise specified.

[0066] Experimental Example 1 (Identification of soy protein odor components) <Defatting chickpeas> 100g of chickpea flour (manufactured by RT Japan Co., Ltd.) was mixed with 1L of hexane and stirred for 15 minutes. After standing for 15 minutes, the mixture was filtered through filter paper. Another 1L of hexane was added to the filtration residue, stirred for 15 minutes, stood for 15 minutes, and filtered again to obtain the residue. This procedure was repeated three more times, meaning a total of 5L of hexane was used to defatt the chickpea flour. The residue was vacuum-dried under reduced pressure of 50mmHg at 30°C for 30 minutes to remove the hexane and obtain 92.3g of defatted chickpea flour.

[0067] <Preparation of a 5% soy protein solution> 100 g of commercially available pea protein powder was added to ion-exchanged water and stirred to obtain a 2000 g solution. After filling into 200 mL cans, it was sterilized by boiling (85 °C for 30 minutes) to prepare a 5% solution of pea protein powder. In addition, a 5% solution of soybean protein powder and a 5% solution of defatted quail bean powder were prepared in the same manner as above, except that soybean protein powder (manufactured by Fuji Oil Co., Ltd.) and the defatted quail bean powder described in <Defatting of quail beans> were used instead of pea protein powder.

[0068] <Identification of the main odor substances of bean odor> 100 mL of dichloromethane was added to 100 g of the prepared 5% solution of pea protein powder and stirred for 1 hour to extract the aroma components. After separating the dichloromethane layer, it was concentrated to obtain an extract. The extract was analyzed by GC / MS and GC / O, and as the main odor substances in the pea protein powder, six compounds, hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine, were identified.

[0069] Similarly, for soybean protein powder and defatted quail bean powder, four compounds, hexanal, (E,E)-2,4-decadienal, guaiacol, and trans-4,5-epoxy-(E)-2-decenal, were identified as the main odor substances in the bean odor.

[0070] <Measurement conditions of GC / MS> · GC / MS device: 5975B inert XL MSD (manufactured by Agilent Technologies) · Column: DB-WAX / length 60 m, inner diameter 0.25 mm (manufactured by Agilent Technologies) · Column temperature conditions: 50 °C (held for 2 minutes) ~ 220 °C, heating at 3 °C / min · Carrier gas: helium.

[0071] <Measurement conditions of GC / O> • GC / O system: 6890N (Agilent Technologies) / CharmAnalysis™ (Datu) • Column: DB-WAX / Length 15m, Inner diameter 0.32mm (manufactured by Agilent Technologies) Column temperature conditions: 40-220°C, heating rate: 6°C / min Carrier gas: Helium.

[0072] Experimental Example 2 (Verification of identified bean odor components) <Preparation of evaluation solution> (1) A 5% pea protein powder solution was diluted five times with deionized water to prepare a 1% pea protein powder solution. (2) An evaluation solution for verifying the bean odor component was prepared by adding the following six compounds to a 1% solution of pea protein powder. The amount of the six compounds added was such that the amount after addition was equivalent to the amount of the six compounds in a 5% solution of pea protein powder (i.e., the amount of the six compounds equivalent to a 4% solution was added): The bean-like odor components (6 compounds) of pea protein Hexanal: 80 ppb (E,E)-2,4-decadienal: 8 ppb Guaiacor: 0.1 ppb trans-4,5-epoxy-(E)-2-decenal: 0.5 ppb 2,5-Dimethylpyrazine: 5 ppb 2-Isobutyl-3-methoxypyrazine: 0.01 ppb.

[0073] The evaluation solution for verifying the beany odor components of soy protein was prepared using the same procedure, except that the following four compounds were added instead of the six compounds found in pea protein: Soy protein's beany odor components (4 compounds) Hexanal: 80 ppb (E,E)-2,4-decadienal: 8 ppb Guaiacor: 0.1 ppb trans-4,5-epoxy-(E)-2-decenal: 0.5 ppb.

[0074] <Addition of bean-like odor components> (1) Solution for verifying the bean odor of pea protein A solution was prepared by dissolving hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2,5-dimethylpyrazine, and 2-isobutyl-3-methoxypyrazine in 95% ethanol, and these were added to a 1% pea protein powder solution so that the concentrations of each component matched the amounts described above. (2) Soy protein bean odor verification solution A solution was prepared by dissolving hexanal, (E,E)-2,4-decadienal, guaiacol, and trans-4,5-epoxy-(E)-2-decenal in 95% ethanol, and this solution was added to a 1% soy protein powder solution so that the concentrations of each component matched the amounts described above.

[0075] <Evaluation Criteria> A 5% soy protein solution has a similar beany smell. A 1% soy protein solution has a similar beany smell. <Evaluation Results> The bean odor verification solution prepared above was subjected to sensory evaluation by four panelists well-trained in odor sensory evaluation, based on the evaluation criteria described above. The evaluation results are shown in Table 1 below.

[0076] [Table 1]

[0077] We confirmed that the bean odor in compositions containing bean proteins can be well reproduced by adding the above-mentioned main odor substances.

[0078] Experimental Example 3 (Masking effect of Group A compounds on hexanal) Hexanal was dissolved in 95% ethanol to a concentration of 0.01% by mass, and this solution was added to deionized water to a hexanal concentration of 20 ppb. To the hexanal-containing aqueous solution prepared in this way, each of the compounds from Group A (1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide) was dissolved in 95% ethanol and added to the solutions at the concentrations shown in Table 2. The masking effect on hexanal was confirmed by sensory evaluation. The sensory evaluation was conducted by four panelists (the panelists' skill levels were the same as above and will be the same hereafter) assigning scores to the following evaluation criteria: 4 points for ion-exchanged water containing 20 ppb of hexanal, and 0 points for ion-exchanged water, with the score being "4 points for strongly smelling hexanal odor" and 0 points for no hexanal odor at all. The average scores are shown in Table 2. <Evaluation Criteria> Strong hexanal odor: 4 points I can smell hexanal: 3 points Slight hexanal odor: 2 points I barely noticed any hexanal odor: 1 point No hexanal odor detected: 0 points

[0079] [Table 2]

[0080] Furthermore, the relationship between the concentration of group A compounds relative to hexanal and the masking effect was investigated. To the aqueous solution containing hexanal at a concentration of 20 ppb, 6-methyl-5-hepten-2-one was added to the concentrations shown in Table 3, and the relationship between the amount of 6-methyl-5-hepten-2-one and its masking effect on hexanal was evaluated using the same method as described above. The evaluation results are shown in Table 3.

[0081] [Table 3]

[0082] As shown in Table 3, the lowest evaluation score (average) at which the flavor of 6-methyl-5-hepten-2-one was not perceived (no hexanal odor was detected) was in the test with a 6-methyl-5-hepten-2-one concentration of 1 ppb. From the above results, it was found that the masking effect of the compounds in Group A tended to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approached 0.5 to 5.

[0083] Experimental Example 4 (Masking effect of Group B compounds on (E,E)-2,4-decadienal) In Experimental Example 3, the masking effect of Group B compounds on (E,E)-2,4-decadienal and the masking effect on the amount of ethyl lactate added were evaluated using the same method as in Experimental Example 3, except that Group A compounds were replaced with Group B compounds (1,4-cineole, γ-heptalactone, menthyl lactate, ethyl lactate, γ-hexalactone, acetaldehyde diethyl acetal, or methyl salicylate), hexanal was replaced with (E,E)-2,4-decadienal, and the concentration of (E,E)-2,4-decadienal in 95% ethanol was changed to 0.001% by mass, thereby changing the concentration of (E,E)-2,4-decadienal in the test solution to 2 ppb. <Evaluation Criteria> (E,E)-2,4-Decadienal odor is strongly present: 4 points (E,E)-2,4-Decadienal odor detected: 3 points Slight odor of (E,E)-2,4-decadienal: 2 points (E,E)-2,4-Decadienal: Almost no odor detected: 1 point (E,E)-2,4-Decadienal: No odor detected at all: 0 points *The evaluation of the ion-exchanged water containing 2 ppb of (E,E)-2,4-decadienal was given as "Strong (E,E)-2,4-decadienal odor: 4 points". The evaluation results are shown in Tables 4 and 5.

[0084] [Table 4]

[0085] [Table 5]

[0086] From the above results, it was found that the masking effect of the compounds in group B tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approaches 0.5 to 5.

[0087] Experimental Example 5 (Masking effect of C group compounds on guaiacol) In Experimental Example 3, the masking effect of Group C compounds on guaiacol and the masking effect on the amount of added diethyl malonate were evaluated using the same method as in Experimental Example 3, except that Group A compounds were replaced with Group C compounds (ethyl acetobutyrate, maltol isobutyrate, and diethyl malonate), hexanal was replaced with guaiacol, and the concentration of guaiacol in 95% ethanol was set to 0.001% by mass, thereby changing the concentration of guaiacol in the test solution to 1 ppb. <Evaluation Criteria> Strong guaiacol smell: 4 points Smells like guaiacol: 3 points Slight guaiacol smell: 2 points Almost no guaiacol smell: 1 point No guaiacol smell at all: 0 points *The evaluation of the deionized water containing 1 ppb of guaiacol was given as "Strong guaiacol odor: 4 points". The evaluation results are shown in Tables 6 and 7.

[0088] [Table 6]

[0089] [Table 7]

[0090] From the above results, it was found that the masking effect of the compounds in group C tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approaches 0.1.

[0091] Experimental Example 6 (Masking effect of Group D compounds on trans-4,5-epoxy-(E)-2-decenal) In Experimental Example 3, the masking effect of the Group D compound on trans-4,5-epoxy-(E)-2-decenal and the masking effect on the amount of heliotropin added were evaluated using the same method as in Experimental Example 3, except that the Group A compound was replaced with a Group D compound (methyl jasmonate, methyl dihydrojasmonate, heliotropin, ethyl pyruvate, butyl butyryl lactate, stearic acid, or γ-butyrolactone), hexanal was replaced with trans-4,5-epoxy-(E)-2-decenal, and the concentration of trans-4,5-epoxy-(E)-2-decenal in 95% ethanol was changed to 0.0001% by mass, thereby changing the concentration of trans-4,5-epoxy-(E)-2-decenal in the test solution to 0.6 ppb. <Evaluation Criteria> Strong odor of trans-4,5-epoxy-(E)-2-decenal: 4 points Odor of trans-4,5-epoxy-(E)-2-decenal: 3 points Slight odor of trans-4,5-epoxy-(E)-2-decenal: 2 points trans-4,5-epoxy-(E)-2-decenal: Almost no odor detected: 1 point No odor detected for trans-4,5-epoxy-(E)-2-decenal: 0 points *The evaluation of the deionized water containing 0.6 ppb of trans-4,5-epoxy-(E)-2-decenal was given as "Strong odor of trans-4,5-epoxy-(E)-2-decenal: 4 points". The evaluation results are shown in Tables 8 and 9.

[0092] [Table 8]

[0093] [Table 9]

[0094] From the above results, it was found that the masking effect of the compounds in group D tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approaches 5 / 3.

[0095] Experimental Example 7 (Masking effect of Group E compounds on 2-isobutyl-3-methoxypyrazine) In Experimental Example 3, the masking effect of Group E compounds on 2-isobutyl-3-methoxypyrazine and the masking effect on the amount of ethyl lactate added were evaluated using the same method as in Experimental Example 3, except that Group A compounds were replaced with Group E compounds (ethyl lactate, 2-butanone, or nerol), hexanal was replaced with 2-isobutyl-3-methoxypyrazine, and the concentration of 2-isobutyl-3-methoxypyrazine in 95% ethanol was set to 0.001% by mass, thereby changing the concentration of 2-isobutyl-3-methoxypyrazine in the test solution to 1 ppb. <Evaluation Criteria> Strong odor of 2-isobutyl-3-methoxypyrazine: 4 points Odor detected from 2-isobutyl-3-methoxypyrazine: 3 points Slight odor of 2-isobutyl-3-methoxypyrazine: 2 points 2-Isobutyl-3-methoxypyrazine: Almost no odor detected: 1 point No odor detected at all: 0 points *The evaluation of the ion-exchanged water containing 1 ppb of 2-isobutyl-3-methoxypyrazine was given as "Strongly detectable odor of 2-isobutyl-3-methoxypyrazine: 4 points". The evaluation results are shown in Tables 10 and 11.

[0096] [Table 10]

[0097] [Table 11]

[0098] From the above results, it was found that the masking effect of the compounds in group E tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approaches 10 to 100.

[0099] Experimental Example 8 (Masking effect of group F compounds on 2,5-dimethylpyrazine) In Experimental Example 3, the masking effect of the Group F compound on 2,5-dimethylpyrazine and the masking effect on the amount of furfural added were evaluated using the same method as in Experimental Example 3, except that the Group A compound was replaced with a Group F compound (furfural, methyl cinnamate, or 5(6)-decenoic acid), hexanal was replaced with 2,5-dimethylpyrazine, and the concentration of 2,5-dimethylpyrazine in 95% ethanol was set to 0.001% by mass, thereby changing the concentration of 2,5-dimethylpyrazine in the test solution to 4 ppb. <Evaluation Criteria> Strong odor of 2,5-dimethylpyrazine: 4 points I can detect a 2,5-dimethylpyrazine odor: 3 points Slightly detectable odor of 2,5-dimethylpyrazine: 2 points Almost no odor of 2,5-dimethylpyrazine: 1 point No 2,5-dimethylpyrazine odor detected: 0 points *The evaluation of the ion-exchanged water containing 4 ppb of 2,5-dimethylpyrazine odor was set as "Strongly detectable 2,5-dimethylpyrazine odor: 4 points". The evaluation results are shown in Tables 12 and 13.

[0100] [Table 12]

[0101] [Table 13]

[0102] From the above results, it was found that the masking effect of the compounds in group F tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odor substance approaches 2.5.

[0103] Experimental Example 9 (Masking effect of masking agent on 5% soy protein solution to mask soy odor 1) <Preparation of a 5% pea protein solution> In the same manner as in Experimental Example 1, <Preparation of 5% Soy Protein Solution>, 5% solutions of pea protein powder, soy protein powder, and defatted chickpea powder were prepared.

[0104] <Addition of masking agent components> To a 5% solution of the three types of bean proteins mentioned above, the masking agent components listed in Table 14, which had been pre-dissolved in 95% ethanol, were added in the amounts shown in the table.

[0105] <Evaluation Criteria> Soy protein solutions with concentrations of 1% to 4% were prepared by adding deionized water to 5% solutions of the three types of soy protein mentioned above, and the following evaluation points were set as the criteria for evaluating soy odor: 6 points. The bean-like smell is stronger than in the 5% solution. 5 points. The bean-like smell is about the same as a 5% solution. 4 points: The bean-like smell is about the same as in a 4% solution. 3. The bean-like smell is about the same as in a 3% solution. 2. The bean-like smell is about the same as in a 2% solution. 1. The bean-like smell is about the same as in a 1% solution. 0 points. The bean smell is weaker than in the 1% solution. <Evaluation Results> Based on the evaluation criteria described above, four panelists (individuals well-trained in sensory evaluation of odors) evaluated the bean odor of 5% solutions of various bean proteins prepared using the aforementioned <addition of masking agent components> method. The average evaluation scores are shown in Table 14 below. Furthermore, in all tests, no odor of the masking compound itself was detected.

[0106] [Table 14]

[0107] Experimental Example 10 (2) Masking effect of masking agent on 5% soy protein solution to reduce soy odor. A 5% aqueous solution of pea protein powder, prepared using the method described in Experimental Example 9, was to be mixed with the masking agents listed in Table 15 in the amounts shown in the table. The masking effect of the resulting 5% pea protein solution was evaluated for different concentrations of the masking agent, in the same manner as in Experimental Example 9. The results are shown in Table 15. In all tests, no odor was detected from the masking compounds themselves.

[0108] [Table 15]

[0109] From the results in Tables 14-15, 1,4-cineole (Group A, Group B), γ-heptalactone (Group A, Group B), 6-methyl-5-hepten-2-one (Group A), menthyl lactate (Group A, Group B), rose oxide (Group A), ethyl lactate (Group B, Group E), γ-hexalactone (Group B), acetaldehyde diethyl acetal (Group B), methyl salicylate (Group B), ethyl acetoethyl (Group C), maltol isobutyrate (Group C), diethyl malonate (Group C) It was found that methyl jasmonate (group D), methyl dihydrojasmonate (group D), heliotropin (group D), ethyl pyruvate (group D), butyl butyryl lactate (group D), stearic acid (group D), γ-butyrolactone (group D), 2-butanone (group E), nerol (group E), furfural (group F), methyl cinnamate (group F), and 5(6)-decenoic acid (group F) can effectively mask the bean odor in a 5% soy protein solution.

[0110] Experimental Example 11 (The effect of masking agents on masking the bean odor in hamburgers containing soy protein) <Preparation of hamburger patties containing soy protein> The ingredients shown in Table 16 below were mixed, molded (50g / piece), baked at 170°C for 1 minute on each side, and then steam-treated at 90°C for 10 minutes. The values ​​in the table represent parts by mass.

[0111] [Table 16]

[0112] <Preparation of hamburger patties containing pea protein> The ingredients shown in Table 17 below were mixed, molded (50g / piece), baked at 170°C for 1 minute on each side, and then steam-treated at 90°C for 10 minutes. The values ​​in the table represent parts by mass.

[0113] [Table 17]

[0114] <Evaluation Criteria> The control product (hamburger containing soy protein with no added masking agents) was evaluated as having a similar odor to the standard product (hamburger without soy protein) with a score of "4 points, strongly detectable soy odor," and the standard product (hamburger without soy protein) was evaluated as "0 points, no soy odor detected at all." The following evaluation points were then established as the criteria for evaluating soy odor: 4 points: Strong bean smell. 3 points: I can smell the bean odor. 2. I can detect a slight bean-like smell. 1. I hardly noticed any bean smell. 0 points. I couldn't detect any bean smell at all. <Evaluation Results> Based on the evaluation criteria described above, the masking agent-added hamburgers prepared in the aforementioned <Preparation of Soy Protein-Containing Hamburgers> and <Preparation of Pea Protein-Containing Hamburgers> were evaluated for bean odor by four panelists (individuals well trained in sensory evaluation of odors). The average evaluation scores are shown in Table 18 below. Furthermore, in all tests, the odor of the masking compound itself did not impair the flavor of the hamburger.

[0115] [Table 18]

[0116] Experimental Example 12 (The effect of masking agents on masking the bean odor in pea protein-containing pudding) <Preparation of pea protein-containing pudding> Of the formulations listed in Table 19 below, a powder mixture of sugar, pea protein, skim milk powder, gelling agent, and emulsifier was added to water and coconut oil while stirring with a stirrer, and the mixture was heated and stirred at 80°C for 10 minutes until dissolved.

[0117] After correcting the total volume with water, the mixture was stirred and homogenized, and then heated to 93°C. A masking agent solution was added, the mixture was filled into containers, and cooled to solidify to prepare the pudding. The values ​​in the table represent parts by mass.

[0118] [Table 19]

[0119] <Evaluation Criteria> The control product (pudding containing soy protein with no added masking agents) was evaluated as having an odor equivalent to the soy odor of the standard product (pudding without soy protein) as "4 points - strongly detectable soy odor," and the standard product (pudding without soy protein) was evaluated as "0 points - no soy odor detected at all." The following evaluation points were then established as the criteria for evaluating soy odor: 4 points: Strong bean smell. 3 points: I can smell the bean odor. 2. I can detect a slight bean-like smell. 1. I hardly noticed any bean smell. 0 points. I couldn't detect any bean smell at all. <Evaluation Results> Based on the evaluation criteria described above, the masking agent-added pudding prepared in the aforementioned <Preparation of Pea Protein-Containing Pudding> was evaluated for bean odor by four panelists (individuals well-trained in sensory evaluation of odors). The average evaluation scores are shown in Table 20 below. Furthermore, in all tests, the odor of the masking compound itself did not impair the flavor of the pudding.

[0120] [Table 20]

[0121] From the results in Tables 18 and 20 above, it was found that the masking compounds belonging to groups A to F above can effectively mask the bean odor. Furthermore, in experimental examples 3 to 12 above, the range of evaluation scores (difference between the maximum and minimum values) given by the panelists for the same sample was 0 or 1 for many samples, and within the range of 0 to 2 for all samples.

Claims

1. A bean-derived bean odor masking agent in a bean protein-containing composition, The bean odor masking agent contains at least one compound selected from the group consisting of group A and group B, and may further contain at least one compound selected from the group consisting of group C, group D, and group F. The substances constituting the beany odor derived from the aforementioned legume protein include hexanal and (E,E)-2,4-decadienal. A bean odor masking agent wherein the total amount of hexanal and (E,E)-2,4-decadienal in the aforementioned bean protein-containing composition is 0.0001 ppm or more; (Group A) 6-methyl-5-hepten-2-one, (Group B) γ-heptalactone, ethyl lactate, γ-hexalactone, (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group D) γ-butyrolactone, (Group F) Methyl cinnamate and 5(6)-10-hydroxy-2-decenoic acid (however, If a compound belonging to group A is contained, it shall contain 0.000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group B is contained, it shall contain 0.0000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group C is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group D is contained, it shall contain 0.0000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If the composition contains compounds belonging to group F, it shall contain at least 0.00000002 parts by mass per 10,000 parts by mass of legume protein in the legume protein-containing composition.

2. The bean odor masking agent according to claim 1, further containing one or more fragrance components.

3. A fragrance composition, a bean odor masking agent according to claim 1 or 2.

4. A fragrance composition for addition to a legume protein-containing composition, which contains a bean odor masking agent and a fragrance component, The legume protein-containing composition comprises hexanal and (E,E)-2,4-decadienal, The total amount of hexanal and (E,E)-2,4-decadienal contained in the legume protein-containing composition is 0.0001 ppm or more. The aforementioned bean odor masking agent, A fragrance composition that is a bean-derived bean odor masking agent in the bean protein-containing composition, comprising at least one compound selected from the group consisting of groups A to B, and may further contain at least one compound selected from the group consisting of groups C, D, and F; (Group A) 6-methyl-5-hepten-2-one, (Group B) Ethyl lactate, (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group D) γ-butyrolactone, (Group F) Methyl cinnamate and 5(6)-10-hydroxy-2-decenoic acid (however, If a compound belonging to group A is contained, it shall contain 0.000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group B is contained, it shall contain 0.0000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group C is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group D is contained, it shall contain 0.0000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. A fragrance composition that, when it contains a compound belonging to group F, contains 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition.

5. A method for masking a bean odor containing hexanal and (E,E)-2,4-decadienal, comprising the step of blending a bean odor masking agent according to any one of claims 1 to 3 or a fragrance composition according to claim 4 into a composition containing bean protein.

6. A method for producing the above-mentioned food, pharmaceutical, or quasi-drug containing hexanal and (E,E)-2,4-decadienal, comprising the step of incorporating a bean odor masking agent into the food, pharmaceutical, or quasi-drug containing bean protein or its raw material, The total amount of hexanal and (E,E)-2,4-decadienal contained in the food, pharmaceutical, or quasi-drug is 0.0001 ppm or more. The aforementioned bean odor masking agent, A method for masking the bean odor derived from bean protein in a bean protein-containing composition, comprising two compounds belonging to groups A and B below, and possibly further comprising at least one compound selected from the group consisting of groups C and F; (Group A) 6-methyl-5-hepten-2-one, (Group B) Ethyl lactate, (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group F) Methyl cinnamate and 5(6)-10-hydroxy-2-decenoic acid (however, If a compound belonging to group A is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group B is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group C is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If the composition contains compounds belonging to group F, it shall contain at least 0.00000002 parts by mass per 10,000 parts by mass of legume protein in the legume protein-containing composition.

7. Foods, pharmaceuticals, or quasi-drugs containing legume protein, A food, pharmaceutical, or quasi-drug containing hexanal and (E,E)-2,4-decadienal, which is formulated with a bean odor masking agent, The total amount of hexanal and (E,E)-2,4-decadienal contained in the food, pharmaceutical, or quasi-drug is 0.0001 ppm or more. The aforementioned bean odor masking agent is a bean protein-derived bean odor masking agent in a bean protein-containing composition, comprising two compounds belonging to groups A and B, and further comprising at least one compound selected from the group consisting of groups C and F, for use in food, pharmaceuticals, or quasi-drugs; (Group A) 6-methyl-5-hepten-2-one, (Group B) Ethyl lactate, (Group C) Acetate acetate, maltol isobutyrate, and diethyl malonate, (Group F) Methyl cinnamate and 5(6)-10-hydroxy-2-decenoic acid (however, If a compound belonging to group A is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group B is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If a compound belonging to group C is contained, it shall contain 0.00000002 parts by mass or more per 10,000 parts by mass of legume protein in the legume protein-containing composition. If the composition contains compounds belonging to group F, it shall contain at least 0.00000002 parts by mass per 10,000 parts by mass of legume protein in the legume protein-containing composition.

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