JP7627116B2 - Bean-flavor masking agent derived from legume protein - Google Patents

Description

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.

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 odor masking agent that is suitably used to suppress the bean odor (bean odor derived from bean proteins) that is perceived when a processed food, medicine, or quasi-drug is prepared using bean-derived protein and that requires masking, and a method for masking the bean odor using the bean odor masking agent.

Conventionally, animal and vegetable proteins or their hydrolysates (including peptides) have been used in foods to impart or improve nutrition, physiological functions, or physical properties (foaming, emulsifying, binding, etc.). In particular, proteins and their hydrolysates from beans such as soybeans are easily digested and absorbed, are nutritionally excellent, are low in calories, and have excellent physiological effects such as lowering neutral fats and cholesterol, and therefore are used in various health foods.

However, when processed foods, medicines or quasi-drugs are prepared using bean-derived proteins, they have a characteristic odor derived from beans.

Under such circumstances, it is often desired that processed foods using bean-derived proteins have a reduced peculiar odor and exhibit a flavor similar to that of similar processed foods that do not use bean-derived proteins. For this reason, various methods have been proposed for masking (sometimes referred to as reducing, improving, etc.) the bean odor (sometimes referred to as a peculiar odor, unpleasant odor, offensive odor, etc.) caused by bean proteins. Specifically, all of these are aimed at the beany smell of soybean protein, and methods of masking this have been proposed, including blending maltitol and arginine (Patent Document 1), blending spices (Patent Document 2), blending thaumatin (Patent Document 3), blending malt extract (Patent Document 4), blending reducing sugars and amino group-containing compounds (Patent Document 5), blending trehalose (Patent Document 6), blending whey protein (Patent Document 7), blending polyphenols extracted from teas (Patent Document 8), blending flavor oils extracted by adding vegetables to edible oils and heating (Patent Document 9), blending ethyl decanoate (Patent Document 10), and blending melanoidin and egg white hydrolysates (Patent Document 11).
However, there is a strong demand for the development of a new method that can mask the beany odor caused by bean proteins, which is effective not only for soybeans but also for all legumes.

Patent Publication 2017-093349 Patent Publication 2017-051161 JP2011-004699 Patent Publication 2010-246449 JP2000-312562A JP 10-066516 A JP 08-173050 JP 08-103225 A JP 61-274661 Patent Publication 2006-197857 JP 03-155759

The object of the present invention is to suppress the bean-derived odor that is perceived when a processed food, medicine, or quasi-drug is prepared using a bean-derived protein, which is a problem of the conventional art. In the present invention, the bean-derived odor that is perceived when a processed food, medicine, or quasi-drug is prepared using a bean-derived protein and is masked is collectively referred to as bean odor. In the present invention, the bean odor is not limited to a so-called unpleasant odor, but also includes a masked odor that makes the user feel that a bean-derived protein is blended in a food, etc. The bean odor is considered to be mainly derived from the protein components in the bean protein (and/or their decomposition products by heat processing, etc.) and/or the oil and fat components (and/or their decomposition products by 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 bean odor and its use. The object of the present invention is also to provide a method for masking the bean odor using the bean odor masking agent.

As a result of extensive research, the inventors have identified the main odor substances that constitute the bean odor that are perceived when processed foods and the like are prepared using bean-derived proteins. The inventors have also identified a masking agent component that was not known to have a masking effect on the odor substances that constitute the bean odor.

The present invention was completed based on this knowledge and through further research, and includes the following embodiments.

Item 1. A bean odor masking agent derived from bean protein, comprising at least one compound selected from the group consisting of 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) ethyl acetoacetate, 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.

Item 2. A bean odor masking agent according to item 1, wherein the bean odor is an odor 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.

Item 3. A bean odor masking agent according to item 1 or 2, further comprising one or more fragrance ingredients.

Item 4. A bean odor masking agent according to any one of items 1 to 3, which is a fragrance composition.

Item 5. A fragrance composition containing the bean odor masking agent according to any one of items 1 to 4 and a fragrance component.

Item 6. A method for masking a bean odor, comprising the step of blending the bean odor masking agent described in any one of items 1 to 4 or the flavor composition described in item 5 into a composition containing bean protein.

Item 7. A method for masking a bean odor as described in Item 6, wherein the bean odor is an odor 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.

Item 8. A method for producing a food, drug, or quasi-drug, comprising the step of blending the bean odor masking agent described in any one of items 1 to 4 or the flavor composition described in item 5 with a food, drug, or quasi-drug or a raw material thereof that contains a bean protein.

Item 9. The manufacturing method according to item 8, wherein the food, drug 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.

Item 10. A food, medicine, or quasi-drug containing a bean protein,
Item 5. A food, medicine, or quasi-drug containing the bean odor masking agent according to any one of items 1 to 4 or the flavor composition according to item 5.

According to the present invention, it is possible to provide a novel masking agent for bean odor, a novel masking method using the novel masking agent, a method for producing a food, a medicine or a quasi-drug, and a food, a medicine or a quasi-drug obtained by the method.

In the present invention, "suppressing beany odor" or "masking beany odor" means that by adding the masking compound of the present invention to a composition having the above-mentioned beany odor, the beany odor is reduced or eliminated compared to before the masking compound is added. The present invention can also be applied to compositions that generate the beany odor over time or by a specified treatment (heating, light exposure, etc.), and in this case, adding the masking compound of the present invention to the composition means that the beany odor is suppressed (reduced) even after the specified treatment (heating, light exposure, storage, etc.) compared to when the masking compound is not added.

As used herein, the phrase "comprise" or "containing" is intended to encompass the phrase "consisting of" and the phrase "consisting only of".
The operations and steps described herein may be carried out at room temperature unless otherwise specified.
In this specification, the term "room temperature" is understood in accordance with common technical knowledge and can mean, for example, a temperature within the range of 10°C to 35°C.
Unless otherwise specified, in this specification, "compositions containing pulse protein (foods, medicines, quasi-drugs, etc.)" include compositions (foods, medicines, quasi-drugs, etc.) that contain pulse protein and/or hydrolyzates thereof and further contain fats and oils and/or hydrolyzates thereof that are usually contained in small amounts in pulse protein powders, etc. Similarly, unless otherwise specified, in this specification, "beany smell derived from pulse protein" includes bean protein components, hydrolyzates thereof, fats and oils components contained in small amounts in pulse protein powders, etc., and/or beany smell derived from hydrolyzates thereof.

The present invention will be described in detail below.
(I) bean-flavor masking agent
The bean odor that is the target of the bean odor masking agent of the present invention is, as described above, a bean-derived odor that is perceived when processed foods, medicines, or quasi-drugs are prepared using bean-derived proteins, and essentially refers to the odor that is being masked.

In the present invention, "legume protein" (sometimes referred to as legume-derived protein in the present specification) means a food material mainly composed of legume protein components, and includes the above-mentioned food material containing legume-derived oil and fat components contained in small amounts in protein powders, etc. Legume-derived proteins include, but are not limited to, proteins derived from soybeans, peas, chickpeas, lentils, kidney beans, fava beans, etc., and are preferably derived from soybeans, peas, chickpeas, etc. The legume-derived protein and/or its hydrolyzate may be produced by any method, as long as the protein and/or its hydrolyzate contained in the legumes is separated and purified. Commercially available legume-derived protein and/or its hydrolyzate may also be used. Examples of soybean protein include defatted soybeans obtained by defatting whole soybeans with organic solvents such as hexane and ethanol, soy milk obtained by extracting proteins from the defatted soybeans with water, and further isolated soybean protein and concentrated soybean protein obtained by acid precipitation or alcohol precipitation from soy milk. The pea protein may be, for example, a protein obtained by removing the outer skin of bean seeds, grinding the seeds, extracting the protein with water, concentrating and drying the protein. The chickpea protein may be, for example, a protein obtained by separating and purifying the chickpea protein in the same manner as soybeans and peas. The above-mentioned bean-derived proteins, including commercially available ones, are usually not 100% protein components, but contain a small amount of fats and oils, which may affect the bean odor. Therefore, in the present invention, the bean-derived protein may contain a small amount of fats and oils derived from the beans.

As described in the Examples below, the present inventors have identified major odorants in the bean odor caused by bean-derived proteins in the present invention. Preferred examples of such major odorants include hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

The bean odor masking agent of the present invention utilizes the bean odor masking effect (bean odor suppressing effect) of the compounds belonging to the following groups A to F, and is characterized in that it contains 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) ethyl acetoacetate, 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.

These compounds (hereinafter collectively referred to as "masking compounds") are all known and commercially available compounds. In the present invention, "5(6)-decenoic acid" refers to a mixture of 5-decenoic acid and 6-decenoic acid. The blending ratio of 5-decenoic acid and 6-decenoic acid is not particularly limited, but for example, 0.01 to 100 parts by mass, preferably 0.1 to 10 parts by mass, of the latter can be used per 1 part by mass of the former. In addition, natural flavors containing the compounds can be used as the masking agent of the present invention, as long as they do not impair the effects of the present invention. Examples of such natural flavors include, but are not limited to, lime flavor as a natural flavor containing 1,4-cineole; apricot flavor as a natural flavor containing γ-hexalactone; vanilla flavor as a natural flavor containing heliotropin; and coffee flavor as a natural flavor containing furfural. Any of these masking compounds can be suitably used as an active ingredient of the beany odor masking agent of the present invention.

The beany odor masking agent of the present invention may contain only one of the above masking compounds as an active ingredient, or may contain any combination of two or more of them.

The compounds in Group A, 1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, are compounds that function effectively as bean odor masking agents, and in particular, function effectively as a masking agent for hexanal, which is one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group A is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by hexanal. These compounds in Group A can be used alone or in combination of two or more.

The compounds 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, function effectively as a masking agent for (E,E)-2,4-decadienal, which is one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group B is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by (E,E)-2,4-decadienal. These compounds in Group B can be used alone or in combination of two or more.

The compounds in Group C, ethyl acetoacetate, maltol isobutyrate, and diethyl malonate, are compounds that function effectively as bean odor masking agents, and in particular, function effectively as masking agents for guaiacol, one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group C is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, or quasi-drugs containing bean-derived proteins by suppressing the odor caused by guaiacol. These compounds in Group C can be used alone or in combination of two or more.

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, function effectively as a masking agent for trans-4,5-epoxy-(E)-2-decenal, which is one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group D is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, 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 can be used. These compounds listed in Group D can be used alone or in combination of two or more.

The compounds in Group E, ethyl lactate, 2-butanone, and nerol, are compounds that function effectively as bean odor masking agents, and in particular, function effectively as a masking agent for 2-isobutyl-3-methoxypyrazine, one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group E is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, or quasi-drugs that contain bean-derived proteins by suppressing the odor caused by 2-isobutyl-3-methoxypyrazine. These compounds in Group E can be used alone or in combination of two or more.

The compounds in Group F, furfural, methyl cinnamate, and 5(6)-decenoic acid, are compounds that function effectively as bean odor masking agents, and in particular, function effectively as a masking agent for 2,5-dimethylpyrazine, one of the main odor substances of the bean odor described above. Therefore, when a compound belonging to Group F is used, the masking agent of the present invention can be used to mask the bean odor of processed foods, medicines, or quasi-drugs that contain bean-derived proteins by suppressing the odor caused by 2,5-dimethylpyrazine. These compounds in Group F can be used alone or in combination of two or more.

The deterioration odor masking agent of the present invention is characterized in that it contains one or more compounds selected from the group consisting of Groups A to F (i.e., a compound group including all of the 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 including compounds belonging to different groups, but also two or more compounds that only belong to the same group, unless otherwise specified.
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.

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

Among the above masking agent compounds, 1,4-cineole, γ-heptalactone, and menthyl lactate belong to two groups, group A and group B, respectively, and ethyl lactate belongs to two groups, group B and group E. In the present invention, a masking agent containing one of the compounds belonging to these two groups is a compound containing compounds belonging to the two groups to which the compound belongs, and is therefore included in the category of "masking agents containing a combination of at least one compound selected from at least two groups among groups A to F (two or more in total)." For example, by adding 1,4-cineole to a masking agent, the masking agent contains compounds belonging to two groups, group A and group B, and therefore a masking agent containing 1,4-cineole alone is included in the category of "masking agents containing a combination of at least one compound selected from at least two groups among groups A to F (two or more in total)." In the present invention, when a compound belonging to a plurality of groups is used as a masking agent compound, the compound may be used alone or in combination with other masking agent compounds other than the compound.

The masking agent of the present invention preferably contains, as a masking agent compound, a combination of multiple compounds (e.g., 2 or more, preferably 3 or more, more preferably 4 or more, more preferably 5 or more, more preferably 6) whose groups do not match each other (belong to different groups). Here, "the groups do not match each other (belong to different groups)" includes cases where the groups to which multiple compounds belong partially overlap but do not match in part. Thus, in the present invention, combinations of compounds "which do not match each other (belong to different groups)" include cases where the groups partially overlap but do not match in part, such as the combination of 1,4-cineole (groups A and B) and ethyl lactate (groups B and E).

The masking agent of the present invention preferably contains one or more compounds selected from at least one of groups A to D among the above groups A to F. In addition, in an embodiment in which the masking agent is used for beans such as soybeans and chickpeas, it is preferable to use one or more compounds selected from at least one of groups A to D,
It is preferable to use a combination of one or more compounds selected from two or more groups among Groups A to D (two or more compounds in total),
It is more preferable to use a combination of one or more compounds selected from three or more groups among Groups A to D (a total of three or more compounds),
It is even more preferable to use a combination of one or more compounds selected from at least four groups among groups A to D (four or more in total). In an embodiment in which the masking agent composition is used on legumes such as peas, at least one compound selected from the group consisting of groups A to F can be suitably used. Thus, in an embodiment in which the masking agent composition is used on legumes such as peas, the masking agent composition may contain one or more compounds selected from at least one group among groups A to D, and may contain one or more compounds selected from at least one group among groups E to F.

In a preferred embodiment, the masking agent of the present invention comprises a masking agent compound having a masking effect against one or more (preferably two or more, more preferably three or more, more preferably four or more, more preferably five or more, more preferably all six) of six odor substances: 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 includes an odor 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 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 odor selected from the group. In the present invention, among the above odor substances, an odor 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 masks at least one (preferably at least two, more preferably at least three, more preferably four) bean odor selected from the group is preferred. In an embodiment in which the composition is used for beans such as peas, any of the six odor substances described above that can mask the beany odor can be suitably used.

The amount of the masking compound used in the present invention (for example, the content of the masking agent of the present invention in a food, drug, or quasi-drug) may be an amount that exerts a masking effect on the bean odor. Specifically, the concentration of each of the compounds in the whole food or the like containing bean-derived protein is
It is preferable to use it so that the concentration is within the range of 0.00001 ppb to 10,000 ppb.
It is more preferable to use it so that the concentration is within the range of 0.0001 ppb to 1000 ppb, and even more preferable to use it so that the concentration is within the range of 0.001 ppb to 100 ppb.
It is preferable to set the amount of the masking compound used within the above range in order to sufficiently provide a bean odor masking effect while preventing the aroma and/or taste of the masking agent compound itself from undesirably affecting the aroma and/or taste of the bean-derived protein-containing food, medicine or quasi-drug.

In the present invention, the total mass (or total concentration) of the compounds in each group of groups A to F is determined based on the amount of odorant that is a suitable target for masking (i.e., a target that effectively functions as a masking agent) of the respective group (i.e., hexanal for the compounds in group A, (E,E)-2,4-decadienal for the compounds in group B, guaiacol for the compounds in group C, trans-4,5-epoxy- (E)-2-decenal, 2-isobutyl-3-methoxypyrazine for the compounds described in Group E, 2,5-dimethylpyrazine for the compounds described in Group F) with respect to the mass (or concentration), for example, a ratio in the range of 1:100000 to 100000:1, a ratio in the range of 1:10000 to 10000:1, a ratio in the range of 1:1000 to 1000:1, a ratio in the range of 1:100 to 100:1, or a ratio in the range of 1:10 to 10:1 is preferable. In the present invention, when a compound belonging to multiple groups is used as the masking agent compound, in calculating the above ratio, the compound belonging to multiple groups is calculated as being a compound of any group to which the compound belongs (for example, 1,4-cineole is both a compound of Group A and a compound of Group B).

By using one or more compounds selected from the group consisting of groups A to F, the present invention can mask the bean odor easily, safely, and without affecting the aroma and/or taste of the final product at each stage of the production, distribution, storage, and sale of bean-derived protein-containing foods, medicines, or quasi-drugs.

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 appropriately set depending on the usage mode of the bean odor masking agent of the present invention.

The bean odor masking agent of the present invention may consist of the masking agent compound alone, or may contain a suitable diluent (thickener) or carrier in addition to the masking agent compound. In this case, the ratio of the masking agent compound in the bean odor masking agent can be appropriately set and adjusted within the range of 0.00000001 to 99% by mass (0.0001 to 990000 ppm) so that the bean odor masking agent exerts the effect of suppressing the bean odor derived from legume proteins.

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 derived from bean protein of the masking agent compound. Examples include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, glucose, sucrose, etc.; or liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin, glycerin fatty acid esters, 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 (formulation), such as excipients, binders, disintegrants, emulsifiers, dissolving agents, thickeners, lubricants, flavoring agents, colorants, etc. Among them, emulsifiers can be suitably used to prepare an aqueous solution (dispersion, suspension) or emulsion-like bean odor masking agent by dispersing the masking agent compound in a liquid diluent. Examples of such emulsifiers include, but are not limited to, sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, lecithin, enzymatically decomposed lecithin, Quillaja extract, saponin, polysorbate, gum arabic, and gum ghatti. By using such diluents or carriers, the beany odor masking agent of the present invention can be made into any dosage form, such as liquid, suspension, emulsion, paste, powder, granule, and others. The dosage form of the beany odor masking agent of the present invention can be appropriately set depending on the type and shape of the object to be suppressed from the beany odor derived from bean protein.

The beany odor masking agent of the present invention may also be prepared as a powder formulation by mixing an excipient such as dextrin with an aqueous solution in which the above-mentioned masking agent compound is dissolved or dispersed, and powdering the mixture according to a standard method such as spray drying or freeze drying, or may be further granulated to prepare a granular formulation.

The bean odor masking agent of the present invention can be added to foods (including beverages; the same applies in this specification), medicines, or quasi-drugs (typically foods, medicines, or quasi-drugs containing at least one of the odor substances described above) containing bean-derived proteins to suppress the bean odor. Therefore, the bean odor masking agent of the present invention can be effectively used as an additive (food additive, medicine additive, quasi-drug additive) for foods, medicines, or quasi-drugs containing the bean-derived proteins described above. The additives include additives that are added to and mixed with the raw materials for foods, medicines, or quasi-drugs during the manufacturing stage of these foods, medicines, or quasi-drugs, and these additives include, for example, fragrance compositions.

The blending ratio of the bean odor masking agent of the present invention to a food, medicine, or quasi-drug containing protein (target composition) can be appropriately selected and adjusted depending on the type and amount of odorous substances contained in the target composition, and the type and amount of the masking compound that is the active ingredient of the bean odor masking agent of the present invention.

In a preferred embodiment, the beany 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 blending amount of the masking compound contained as an active ingredient. In addition, since the masking compound used in the present invention has almost no effect on the fragrance tone 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 beany odor, and can be used suitably.

As shown in Experimental Examples 9 to 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 containing bean protein (bean protein-containing composition) can also be set as follows: However, this is only an example and the present invention 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, and more preferably 0.0000002 to 0.002 parts by mass, per 10,000 parts by mass of bean protein.
The amount of protein contained in the legume protein-containing composition can be analyzed and quantified by 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 (laws and regulations and centralized information)). Details of the nitrogen quantitative conversion method are shown in "1. Protein (1) Nitrogen quantitative conversion method" in "Food Labeling Standards, Appendix: Analysis methods for nutritional components, etc." (Consumer Affairs Agency Deputy Director General's Notice No. 139, March 30, 2015).

(II) Fragrance composition The bean odor masking agent of the present invention has the form of a fragrance preparation 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 may further contain the diluent or carrier described above depending on the form of the fragrance preparation, or may contain one or more other fragrance components (fragrance compounds other than the masking compound of the present invention). As described above, the fragrance composition of the present invention can be used to mask bean odor.

Such other flavoring ingredients should not impair the effects of the present invention when used in combination with the masking compound described above, and it is preferable that the odor of the other flavoring ingredients is not suppressed when used in combination with the masking compound. Examples of such flavoring ingredients include the natural flavors and synthetic flavors described in the Japan Patent Office's "Patent Office Gazette: Well-Known and Commonly Used Technology Collection (Flavors) Part II Food Flavors" (published January 14, 2000). Specifically, the following categories are listed: citrus-based flavors having the aroma of citrus fruits (orange, lemon, lime, grapefruit, yuzu, sudachi, etc.) (pp. 88-135); fruit-based flavors having the aroma of fruits other than citrus fruits (apple, grape, strawberry, banana, peach, melon, apricot, plum, cherry, berries, etc.) (pp. 136-257); milk-based flavors having the aroma of dairy products (milk flavor, butter flavor, cheese flavor, cream flavor, yogurt flavor, etc.) (pp. 258-347); vanilla-based flavors having the aroma of vanilla beans (pp. 348-366); tea-based flavors having the aroma of green tea, oolong tea, black tea, etc. (pp. 367-426); Examples of flavors include core chocolate flavors (pages 427-446), coffee flavors having a coffee aroma (pages 447-475), mint flavors having the aroma of peppermint, spearmint, etc. (pages 476-495), spice flavors having the aroma of spices (pages 496-580), nut flavors having the aroma of nuts such as almonds (pages 581-608), liquor flavors having the aroma of liquor (e.g., wine, whiskey, brandy, rum, gin, liqueur, etc.) (pages 759-825), flower flavors having a floral aroma (pages 826-836), and vegetable flavors having the aroma of vegetables (e.g., onion, garlic, green onion, carrot, burdock, shiitake mushroom, matsutake mushroom, mitsuba, etc.) (pages 837-907). Preferred examples of the flavors include citrus flavors, fruit flavors, milk flavors, cocoa/chocolate flavors, coffee flavors, and nut flavors.

The fragrance composition of the present invention may contain one or more of the above-mentioned masking compounds in a ratio of 0.0000001 to 99% by mass, as long as the effect of the present invention is achieved. When the fragrance composition of the present invention contains other fragrance components in addition to the above-mentioned masking compounds, the blending ratio of the other fragrance components can be, but is not limited to, 0.0000001 to 99% by mass, preferably 0.000001 to 50% by mass. In this case, it is preferable to adjust the blending ratio of the masking compound so that the flavor of the masking compound itself blended in the fragrance composition does not affect the fragrance tone of the other fragrance components blended separately.

(III) Method for producing a composition (food, medicine, quasi-drug, etc.) in which the bean odor is masked By blending the bean odor masking agent or fragrance composition of the present invention described above with a composition containing the bean protein described above, a bean protein-containing composition in which the bean odor is suppressed can be produced.

The pulse protein-containing composition of interest here is a composition containing the pulse protein described in (I) above, and is typically a composition that may have a bean 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, and specific examples of such compositions include foods, medicines, and quasi-drugs.

Specific examples of the foods, medicines, and quasi-drugs include, but are not limited to, processed meat products (hamburgers, sausages, patties, nuggets, etc.), processed seafood products (fish sausages, kamaboko, chikuwa, etc.), seasonings or condiments for processing (pickle liquid, dressings, mayonnaise, etc.), processed dairy products (dairy drinks, yogurt, ice cream, etc.), processed egg products (thick omelets, puddings, etc.), nutritional supplements (powdered protein foods, etc.), beverages (soy milk, milk substitutes, protein-containing jelly drinks, tonic drinks, etc.), etc.

Although 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 odorous substances contained in the legume protein-containing composition can be, for example, 0.0001 ppm or more, preferably 0.0005 to 10 ppm, more preferably 0.001 to 1 ppm, in total, of hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine.

The blending ratio 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 odorous 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.

The timing and method of blending the bean odor masking agent or flavor composition of the present invention with these legume protein-containing compositions are not particularly limited, and can be carried out according to a conventional method at any stage of manufacturing these products. For example, there can be mentioned a method of adding the bean odor masking agent or flavor composition of the present invention to the raw materials of a food, medicine, or quasi-drug, and manufacturing the food, medicine, or quasi-drug according to a conventional method.

The raw materials include legume proteins to be incorporated into foods, medicines, or quasi-drugs. Examples of the legume proteins include those described in (I) above, and the description here is incorporated by reference. In addition, various ingredients can be used as raw materials depending on the type of product, such as a food, medicine, or quasi-drug, and are not particularly limited.

According to the manufacturing method of the present invention, it is possible to prepare foods, medicines or quasi-drugs that contain bean protein but have a masked bean odor.

(IV) Method for masking bean odor The present invention also provides a method for masking bean odor, which comprises the step of blending the above-mentioned bean odor masking agent or flavor composition into a composition containing bean protein.

This method can be carried out in accordance with the method described in the section entitled "(III) Method for producing compositions (foods, medicines, quasi-drugs, etc.) with masked bean odor," and said description is incorporated herein by reference.

The present invention will be described below with reference to Experimental Examples and Examples, but the present invention is not limited to these Experimental Examples and Examples.
In the following examples, amounts and concentrations may be based on mass unless otherwise specified.

Experimental Example 1
(Identification of bean protein odor components)
<Defatting chickpeas>
1 L of hexane was added to 100 g of chickpea flour (manufactured by RT Japan Co., Ltd.) and stirred for 15 minutes. After standing for 15 minutes, the mixture was filtered using filter paper. An additional 1 L of hexane was added to the filtration residue, which was stirred for 15 minutes, stood for 15 minutes, and filtered again to obtain a residue. This operation was carried out three more times, that is, a total of 5 L of hexane was used to defatt the chickpea flour. The residue was vacuum-dried at 30° C. for 30 minutes under a reduced pressure of 50 mmHg to remove the hexane, and 92.3 g of defatted chickpea flour was obtained.

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

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

Similarly, for soy protein powder and defatted chickpea powder, four compounds were identified as the main odorants in the bean odor: hexanal, (E,E)-2,4-decadienal, guaiacol, and trans-4,5-epoxy-(E)-2-decenal.

<GC/MS measurement conditions>
GC/MS device: 5975B inert XL MSD (Agilent Technologies)
Column: DB-WAX/length 60 m, inner diameter 0.25 mm (Agilent Technologies)
Column temperature conditions: 50°C (held for 2 minutes) to 220°C, increasing temperature by 3°C/minute. Carrier gas: helium.

<GC/O measurement conditions>
GC/O device: 6890N (Agilent Technologies)/CharmAnalysis™ (Datu)
Column: DB-WAX/length 15 m, inner diameter 0.32 mm (manufactured by Agilent Technologies)
Column temperature conditions: 40 to 220°C, increasing temperature at 6°C/min. Carrier gas: helium.

Experimental Example 2
(Verification of identified bean-smell components)
<Preparation of evaluation solutions>
(1) A 5% pea protein powder solution was diluted 5 times with ion-exchanged water to prepare a 1% pea protein powder solution.
(2) The following six compounds were added to a 1% solution of pea protein powder to prepare an evaluation solution for verifying bean odor components. The amounts of the six compounds added were such that the amounts of the six compounds after addition were equivalent to the amounts of the six compounds in a 5% solution of pea protein powder (i.e., the amounts of the six compounds added were equivalent to the amounts of the 4% solution):
Bean-flavor components of pea protein (6 compounds)
Hexanal: 80 ppb
(E,E)-2,4-decadienal: 8 ppb
Guaiacol: 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.

The evaluation solution for verifying the beany odor components of soy protein was prepared in the same manner, except that the following four compounds were added instead of the six compounds of pea protein:
Bean-flavor components of soy protein (4 types of compounds)
Hexanal: 80 ppb
(E,E)-2,4-decadienal: 8 ppb
Guaiacol: 0.1 ppb
trans-4,5-epoxy-(E)-2-decenal: 0.5 ppb.

<Addition of bean-smelling components>
(1) Pea protein bean odor verification solution Hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2,5-dimethylpyrazine, and 2-isobutyl-3-methoxypyrazine were dissolved in 95% ethanol to prepare solutions, and these solutions were added to a 1% pea protein powder solution so that the concentrations of each component became the amounts described above.
(2) Soy protein bean odor verification solution Hexanal, (E,E)-2,4-decadienal, guaiacol, and trans-4,5-epoxy-(E)-2-decenal were dissolved in 95% ethanol to prepare a solution, and the solution was added to a 1% soy protein powder solution so that the concentration of each component became the amount described above.

<Evaluation criteria>
Close to the bean smell of a 5% soy protein solution Close to the bean smell of a 1% soy protein solution <Evaluation results>
The bean odor test solutions prepared above were subjected to a sensory evaluation based on the above evaluation criteria by four panelists well trained in the sensory evaluation of odors. The evaluation results are shown in Table 1 below.

It was confirmed that by adding the above-mentioned main odor substances, the bean odor in a composition containing bean protein was successfully reproduced.

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 ion-exchanged water to a hexanal concentration of 20 ppb. To the hexanal-containing aqueous solution thus prepared, a solution in which each of the compounds of group A (1,4-cineole, γ-heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide) was dissolved in 95% ethanol was added to each of the compounds to the concentrations shown in Table 2, and the masking effect against hexanal was confirmed by sensory evaluation.
The sensory evaluation was performed by setting the following evaluation criteria, with the ion-exchanged water containing 20 ppb of hexanal being rated as "strong hexanal odor: 4 points" and the ion-exchanged water being rated as "no hexanal odor: 0 points", and having four panelists (the proficiency of the panelists is the same as above/same below) give evaluation points. The average evaluation points are shown in Table 2.
<Evaluation criteria>
Strong hexanal odor: 4 points Hexanal odor: 3 points Hexanal odor is slightly felt: 2 points Hexanal odor is barely felt: 1 point Hexanal odor is not felt at all: 0 points

In addition, the relationship between the concentration of Group A compounds and their masking effect against hexanal was examined.
To the aqueous solution having a hexanal concentration of 20 ppb, 6-methyl-5-hepten-2-one was added to give a concentration shown in Table 3, and the relationship between the amount of 6-methyl-5-hepten-2-one and the masking effect against hexanal was evaluated in the same manner as above. The evaluation results are shown in Table 3.

As shown in Table 3, the test with 1 ppb of 6-methyl-5-hepten-2-one concentration gave the lowest evaluation score (average) at the limit where the flavor of 6-methyl-5-hepten-2-one was not perceived (no hexanal odor was perceived).The above results show that the masking effect of the compounds in Group A tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 0.5-5.

Experimental Example 4
(Masking effect of group B compounds on (E,E)-2,4-decadienal)
In Experimental Example 3, the masking effect of the group B compound against (E,E)-2,4-decadienal and the masking effect relative to the amount of ethyl lactate added were evaluated in the same manner as in Experimental Example 3, except that the group A compound was replaced with a group B compound (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, so that the concentration of (E,E)-2,4-decadienal in the test solution was changed to 2 ppb.
<Evaluation criteria>
Strong (E,E)-2,4-decadienal odor: 4 points (E,E)-2,4-decadienal odor: 3 points Slight (E,E)-2,4-decadienal odor: 2 points Hardly any (E,E)-2,4-decadienal odor: 1 point No (E,E)-2,4-decadienal odor at all: 0 points *The evaluation of ion-exchanged water containing 2 ppb of (E,E)-2,4-decadienal was made as "Strong (E,E)-2,4-decadienal odor: 4 points."
The evaluation results are shown in Tables 4 and 5.

The above results show that the masking effect of compounds in Group B tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 0.5 to 5.

Experimental Example 5
(Masking effect of group C compounds on guaiacol)
In Experimental Example 3, the masking effect of the Group C compounds on guaiacol and the masking effect relative to the amount of diethyl malonate added were evaluated in the same manner as in Experimental Example 3, except that the Group A compounds were replaced with Group C compounds (ethyl acetoacetate, maltol isobutyrate, and diethyl malonate), hexanal was replaced with guaiacol, and the concentration of guaiacol in 95% ethanol was changed to 0.001 mass% so that the concentration of guaiacol in the test solution was changed to 1 ppb.
<Evaluation criteria>
Strong guaiacol odor: 4 points Slight guaiacol odor: 3 points Slight guaiacol odor: 2 points Almost no guaiacol odor: 1 point No guaiacol odor at all: 0 point *The evaluation of the ion-exchanged water containing 1 ppb of guaiacol was made as "strong guaiacol odor: 4 points."
The evaluation results are shown in Tables 6 and 7.

The above results show that the masking effect of compounds in Group C tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 0.1.

Experimental Example 6
(Masking effect of D group compounds on trans-4,5-epoxy-(E)-2-decenal)
In Experimental Example 3, 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, so that the concentration of trans-4,5-epoxy-(E)-2-decenal in the test solution was changed to 0.6 ppb. In the same manner as in Experimental Example 3, the masking effect of the group D compound against trans-4,5-epoxy-(E)-2-decenal and the masking effect against the amount of heliotropin added were evaluated.
<Evaluation criteria>
Strongly smells of trans-4,5-epoxy-(E)-2-decenal: 4 points; Slightly smells of trans-4,5-epoxy-(E)-2-decenal: 3 points; Slightly smells of trans-4,5-epoxy-(E)-2-decenal: 2 points; Almost no smell of trans-4,5-epoxy-(E)-2-decenal: 1 point; No smell of trans-4,5-epoxy-(E)-2-decenal at all: 0 points *The evaluation of ion-exchanged water containing 0.6 ppb of trans-4,5-epoxy-(E)-2-decenal was made as "Strongly smells of trans-4,5-epoxy-(E)-2-decenal: 4 points."
The evaluation results are shown in Tables 8 and 9.

The above results show that the masking effect of compounds in Group D tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 5/3.

Experimental Example 7
(Masking effect of E group compounds on 2-isobutyl-3-methoxypyrazine)
In Experimental Example 3, the masking effect of the Group E compound against 2-isobutyl-3-methoxypyrazine and the masking effect relative to the amount of ethyl lactate added were evaluated in the same manner as in Experimental Example 3, except that the Group A compound was replaced with a Group E compound (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 changed to 0.001 mass% so that the concentration of 2-isobutyl-3-methoxypyrazine in the test solution was changed to 1 ppb.
<Evaluation criteria>
Strong 2-isobutyl-3-methoxypyrazine odor: 4 points Slight 2-isobutyl-3-methoxypyrazine odor: 3 points Slight 2-isobutyl-3-methoxypyrazine odor: 2 points Almost no 2-isobutyl-3-methoxypyrazine odor: 1 point No 2-isobutyl-3-methoxypyrazine odor: 0 point *The evaluation of ion-exchanged water containing 1 ppb of 2-isobutyl-3-methoxypyrazine was made as "Strong 2-isobutyl-3-methoxypyrazine odor: 4 points."
The evaluation results are shown in Tables 10 and 11.

The above results show that the masking effect of compounds in Group E tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 10-100.

Experimental Example 8
(Masking effect of F group compounds on 2,5-dimethylpyrazine)
In Experimental Example 3, the masking effect of the F group compound against 2,5-dimethylpyrazine and the masking effect relative to the amount of furfural added were evaluated in the same manner as in Experimental Example 3, except that the A group compound was replaced with the F group 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 changed to 0.001% by mass, making the concentration of 2,5-dimethylpyrazine in the test solution 4 ppb.
<Evaluation criteria>
Strong 2,5-dimethylpyrazine odor: 4 points Slight 2,5-dimethylpyrazine odor: 3 points Slight 2,5-dimethylpyrazine odor: 2 points Hardly any 2,5-dimethylpyrazine odor: 1 point No 2,5-dimethylpyrazine odor at all: 0 point *The ion-exchanged water containing 4 ppb of 2,5-dimethylpyrazine odor was rated as "Strong 2,5-dimethylpyrazine odor: 4 points."
The evaluation results are shown in Tables 12 and 13.

The above results show that the masking effect of compounds in group F tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 2.5.

Experimental Example 9
(Effect of masking agent on bean odor of 5% bean protein solution 1)
<Preparation of 5% bean protein solution>
In the same manner as in Experimental Example 1 <Preparation of 5% soy protein solution> described above, 5% solutions of pea protein powder, soy protein powder, and chickpea defatted powder were prepared.

<Addition of masking agent component>
To the 5% solutions of the above three types of soy protein, the masking agent components shown in Table 14 below, which had been dissolved in 95% ethanol in advance, were added in the amounts shown in the table.

<Evaluation criteria>
Ion-exchanged water was added to 5% solutions of the above three types of bean protein to prepare bean protein solutions with bean protein concentrations of 1% to 4%. The following evaluation points were set as the evaluation criteria for bean odor:
6 points: The beany smell is stronger than the 5% solution. 5 points: The beany smell is about the same as the 5% solution. 4 points: The beany smell is about the same as the 4% solution. 3 points: The beany smell is about the same as the 3% solution. 2 points: The beany smell is about the same as the 2% solution. 1 point: The beany smell is about the same as the 1% solution. 0 points: The beany smell is weaker than the 1% solution. <Evaluation Results>
According to the above evaluation criteria, the bean odor of the 5% solutions of various bean proteins prepared in the above-mentioned <Addition of masking agent components> was evaluated by four panelists (those well trained in sensory evaluation of odors). The evaluation scores (average) are shown in Table 14 below. In addition, in all tests, the odor of the masking compound itself was not detected.

Experimental Example 10
(Effect of masking agent on bean odor of 5% bean protein solution 2)
To a 5% aqueous solution of pea protein powder prepared by the method described in Experimental Example 9, the masking agent shown in Table 15 below was added in the amount shown in the table. The masking effect of the resulting 5% pea protein solution at different concentrations of the masking agent was evaluated in the same manner as in Experimental Example 9. The results are shown in Table 15. In addition, in all tests, the odor of the masking compound itself was not detected.

From the results in Tables 14 and 15, 1,4-cineole (groups A and B), γ-heptalactone (groups A and B), 6-methyl-5-hepten-2-one (group A), menthyl lactate (groups A and B), rose oxide (group A), ethyl lactate (groups B and E), γ-hexalactone (group B), acetaldehyde diethyl acetal (group B), methyl salicylate (group B), ethyl acetoacetate (group C), maltol isobutyrate (group C), diethyl malonate (group C). ), 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) were found to be able to effectively mask the beany odor in a 5% bean protein solution.

Experimental Example 11
(Bean odor masking effect of masking agent in soy protein-containing hamburger)
<Preparation of soy protein-containing hamburger>
The raw materials shown in the recipe in Table 16 below were mixed and molded (50 g/piece), then baked at 170° C. for 1 minute on each side and steam treated at 90° C. for 10 minutes. The values in the table indicate parts by weight.

Preparation of hamburger steak containing pea protein
The raw materials shown in the recipe in Table 17 below were mixed and molded (50 g/piece), then baked at 170° C. for 1 minute on each side and steam treated at 90° C. for 10 minutes. The values in the table indicate parts by weight.

<Evaluation criteria>
The bean odor of the control product (hamburger steak containing soy protein with no masking agent added) was evaluated as "4 points, strong bean odor" and the standard product (hamburger steak containing no soy protein) was evaluated as "0 points, no bean odor at all." The following evaluation points were set as the evaluation criteria for bean odor:
4 points: Strong bean smell 3 points: Slight bean smell
2 points: A slight bean smell
1 point: Almost no bean smell
0 points: No bean smell at all <Evaluation results>
According to the above evaluation criteria, the bean odor of the masking agent-added hamburgers prepared in the above-mentioned <Preparation of soy protein-containing hamburgers> and <Preparation of pea protein-containing hamburgers> was evaluated by four panelists (those well trained in sensory evaluation of odor). The evaluation scores (average) are shown in Table 18 below. In addition, in all tests, the odor of the masking compound itself did not impair the flavor of the hamburger.

Experimental Example 12
(Effect of masking agents on bean flavor in pudding containing pea protein)
Preparation of pudding containing pea protein
According to the formulation shown 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 to 80°C for 10 minutes with stirring to dissolve.

After adjusting the total amount with water, the mixture was stirred and homogenized, and heated to 93°C. The masking agent solution was added, the mixture was filled into a container, and the mixture was cooled and solidified to prepare the pudding. The values in the table indicate parts by weight.

<Evaluation criteria>
The bean odor of the control product (a pudding containing soy protein with no masking agent added) was evaluated as "4 points, a strong bean odor" and the standard product (a pudding containing no soy protein) was evaluated as "0 points, no bean odor at all." The following evaluation points were set as the evaluation criteria for the bean odor:
4 points: Strong bean smell
3 points: Bean smell
2 points: A slight bean smell
1 point: Almost no bean smell
0 points: No bean smell at all <Evaluation results>
According to the above evaluation criteria, the beany odor of the masking agent-added pudding prepared in the above-mentioned <Preparation of pea protein-containing pudding> was evaluated by four panelists (those well trained in sensory evaluation of odor). The evaluation scores (average) are shown in Table 20 below. In addition, in all tests, the odor of the masking compound itself did not impair the flavor of the pudding.

The results in Tables 18 and 20 above show that the masking compounds belonging to groups A to F above can effectively mask beany odor. In addition, in the above Experimental Examples 3 to 12, the range of evaluation scores (difference between maximum and minimum values) given by the panelists for the same sample was 0 or 1 for many samples, and was within the range of 0 to 2 for all samples.

Claims (7)

A bean odor masking agent derived from bean protein in a bean protein-containing composition, comprising at least one compound selected from the group consisting of the following groups A to F:
The total amount of substances constituting a bean odor derived from bean protein in the bean protein-containing composition is 0.0001 ppm or more;
a masking agent, wherein the substances constituting the bean odor derived from the bean protein include hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine;
(Group A) 6-methyl-5-hepten-2-one and rose oxide,
(Group B) γ-heptalactone, ethyl lactate, γ-hexalactone,
(Group C) ethyl acetoacetate, maltol isobutyrate, and diethyl malonate,
(Group D) γ-butyrolactone,
(Group F) Methyl cinnamate and 5(6)-decenoic acid (wherein
When the compound belonging to group A is contained, the compound is contained in an amount of 0.000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group B is contained, the compound is contained in an amount of 0.0000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group C is contained, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group D is contained, the compound is contained in an amount of 0.0000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group F is contained, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition. The bean odor masking agent according to claim 1, further comprising one or more fragrance ingredients. The bean odor masking agent according to claim 1 or 2 , which is a fragrance composition. A flavor composition for adding to a bean protein-containing composition, comprising a bean odor masking agent and a flavoring component, wherein the bean protein-containing composition comprises hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine, and 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 contained in the bean protein-containing composition is 0.0001 ppm or more, and the bean odor masking agent is
A bean odor masking agent derived from bean protein in the bean protein-containing composition, which contains at least one compound selected from the group consisting of the following groups A to F:
(Group A) 6-methyl-5-hepten-2-one and rose oxide,
(Group B) Ethyl lactate,
(Group C) ethyl acetoacetate, maltol isobutyrate, and diethyl malonate,
(Group D) γ-butyrolactone,
(Group F) Methyl cinnamate and 5(6)-decenoic acid (wherein
When the compound belonging to group A is contained, the compound is contained in an amount of 0.000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group B is contained, the compound is contained in an amount of 0.0000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group C is contained, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group D is contained, the compound is contained in an amount of 0.0000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the flavor composition contains a compound belonging to group F, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the bean protein in the bean protein-containing composition. A method for masking bean odors caused by hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine, 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. A method for producing a food, drug or quasi-drug containing hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine and 2,5-dimethylpyrazine, comprising the step of blending a bean odor masking agent with a food, drug or quasi-drug containing bean protein or a raw material thereof, wherein 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 contained in the food, drug or quasi-drug is 0.0001 ppm or more, and the bean odor masking agent is
A bean odor masking agent derived from bean protein in a bean protein-containing composition, comprising at least one compound selected from the group consisting of the following groups A, C, and F;
(Group A) Rose oxide,
(Group C) ethyl acetoacetate, maltol isobutyrate, and diethyl malonate,
(Group F) Methyl cinnamate and 5(6)-decenoic acid (wherein
When the compound belonging to group A is contained, the compound is contained in an amount of 0.000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group C is contained, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the bean protein-containing composition contains a compound belonging to group F, the bean protein-containing composition contains 0.00000002 parts by mass or more per 10,000 parts by mass of bean protein in the bean protein-containing composition. A food, medicine or quasi-drug containing legume protein,
A bean odor masking agent derived from bean protein in a bean protein-containing composition, comprising a food, drug or quasi-drug containing hexanal, (E,E)-2,4-decadienal, guaiacol, trans-4,5-epoxy-(E)-2-decenal, 2-isobutyl-3-methoxypyrazine and 2,5-dimethylpyrazine and containing a bean odor masking agent, wherein 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 contained in the food, drug or quasi-drug is 0.0001 ppm or more, and the bean odor masking agent contains at least one compound selected from the group consisting of the following groups A, C and F;
(Group A) Rose oxide,
(Group C) ethyl acetoacetate, maltol isobutyrate, and diethyl malonate,
(Group F) Methyl cinnamate and 5(6)-decenoic acid (wherein
When the compound belonging to group A is contained, the compound is contained in an amount of 0.000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the compound belonging to group C is contained, the compound is contained in an amount of 0.00000002 parts by mass or more per 10,000 parts by mass of the pulse protein in the pulse protein-containing composition;
When the bean protein-containing composition contains a compound belonging to group F, the bean protein-containing composition contains 0.00000002 parts by mass or more of the compound belonging to group F per 10,000 parts by mass of the bean protein in the bean protein-containing composition.