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WO2019230903A1 - Agent pour masquer une odeur de fève provenant d'une protéine de fève - Google Patents

Agent pour masquer une odeur de fève provenant d'une protéine de fève Download PDF

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Publication number
WO2019230903A1
WO2019230903A1 PCT/JP2019/021584 JP2019021584W WO2019230903A1 WO 2019230903 A1 WO2019230903 A1 WO 2019230903A1 JP 2019021584 W JP2019021584 W JP 2019021584W WO 2019230903 A1 WO2019230903 A1 WO 2019230903A1
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WO
WIPO (PCT)
Prior art keywords
bean
group
odor
protein
masking agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/021584
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English (en)
Japanese (ja)
Inventor
一成 越前谷
都子 大畑
朋奈 桐村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
San Ei Gen FFI Inc
Original Assignee
San Ei Gen FFI Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by San Ei Gen FFI Inc filed Critical San Ei Gen FFI Inc
Priority to JP2020522597A priority Critical patent/JP7627116B2/ja
Publication of WO2019230903A1 publication Critical patent/WO2019230903A1/fr
Anticipated expiration legal-status Critical
Priority to JP2025006468A priority patent/JP2025039874A/ja
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00—Working-up of proteins for foodstuffs
    • A23J3/14—Vegetable proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof

Definitions

  • 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 a processed food, a pharmaceutical product or a quasi-drug is prepared using a bean-derived protein, and an odor that requires masking (a bean odor derived from a bean protein). It is related with the bean smell masking agent used suitably in order to suppress), and the bean smell masking method using the bean smell masking agent.
  • animal or vegetable proteins or their degradation products have been used to provide or improve nutrition, physiological functions or physical properties (foaming properties, emulsifying properties, binding properties, etc.) for foods.
  • beans and other proteins such as soybeans are excellent in digestibility and nutrition, are excellent in nutrition, are low in calories, and have excellent physiological functions such as reducing neutral fat and cholesterol. It is used for various health foods.
  • Patent Document 1 a method of blending maltitol and arginine
  • Patent Document 2 a method of blending spices
  • Patent Document 3 a method of blending thaumatin
  • Patent Document 4 method of blending malt extract
  • Patent Document 5 method of blending trehalose
  • Patent Reference 6 method of blending whey protein
  • Patent Document 8 a method of blending polyphenols extracted from teas
  • Patent Document 11 a flavor oil extracted by heating by adding vegetables to cooking oil
  • Patent Document 9 a method of blending ethyl decanoate
  • Patent Document 11 a method of blending melanoidin and an egg white decomposition product
  • An object of the present invention is to suppress the bean-derived odor perceived when a processed food, a medicine or a quasi-drug is prepared using a bean-derived protein, which is the conventional problem.
  • bean-derived odor perceived when a processed food, pharmaceutical product, or quasi-drug is prepared using bean-derived protein, and the odor that requires masking is collectively referred to as bean odor.
  • the bean odor is not limited to a so-called unpleasant odor, and includes an odor that requires masking in order to feel that a bean-derived protein is blended in food or the like.
  • the bean odor is mainly a protein component in bean protein (and / or a decomposed product thereof by heat processing, etc.) and / or a fat component (and / or decomposed by heat processing or the like) usually contained in a small amount in bean protein powder. It is thought that it originates in Accordingly, an object of the present invention is to provide a masking agent for bean odor and its use. It is another object of the present invention to provide a bean odor masking method using the bean odor masking agent.
  • the present inventors have identified a main odor substance that constitutes a bean odor perceived when a processed food or the like is prepared using a bean-derived protein.
  • the present inventors have identified a masking agent component that has not been known to have a masking effect on the odorous substances constituting these bean odors.
  • the present invention has been completed by further studies based on such knowledge, and includes the following embodiments.
  • a bean protein-derived bean odor masking agent containing at least one compound selected from the group consisting of the following groups A to F; (Group A) 1,4-cineole, ⁇ -heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, (Group B) 1,4-cineole, ⁇ -heptalactone, menthyl lactate, ethyl lactate, ⁇ -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 ⁇ -butyrolactone, (Group E) ethyl lactate, 2-butanone, and
  • the bean odor is hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5- Item 2.
  • the bean odor masking agent according to Item 1 which is an odor caused by at least one compound selected from the group consisting of dimethylpyrazine.
  • Item 3. The bean odor masking agent according to item 1 or 2, further comprising one or more fragrance components.
  • Item 4. The bean odor masking agent according to any one of Items 1 to 3, which is a fragrance composition.
  • Item 5 A fragrance composition comprising the bean odor masking agent according to any one of Items 1 to 4 and a fragrance component.
  • Item 6. A method for masking bean odor, comprising the step of blending the bean odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5 into a composition containing bean protein.
  • the bean odor is hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5 Item 7.
  • Item 8 The step of blending the bean odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5 into a food, pharmaceutical or quasi-drug containing a bean protein, or a raw material thereof.
  • Item 9 The above food, medicine or quasi-drug is hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3-methoxypyrazine Item 9.
  • Item 10 A food, pharmaceutical or quasi-drug containing legume protein, A food, a pharmaceutical product or a quasi-drug, comprising the bean odor masking agent according to any one of Items 1 to 4 or the fragrance composition according to Item 5.
  • a novel masking agent for bean odor a novel masking method using the novel masking agent and a method for producing a food, drug or quasi-drug, and a food, drug or quasi-drug obtained by the production method Goods can be provided.
  • “to suppress bean odor” or “mask bean odor” means adding the masking compound of the present invention to the composition having the bean odor before adding the masking compound. This means that the bean odor is reduced or disappears.
  • the present invention can also be applied to a composition that generates the bean odor over time or by a predetermined treatment (heating, light irradiation, etc.). In this case, the present invention is applied to the composition. If the masking compound is added, the bean odor is suppressed (reduced) even after the prescribed treatment (heating, light irradiation, storage, etc.) compared to the case where the masking compound is not added. Means.
  • the phrase “comprising” or the phrase “containing” is intended to encompass the phrase “consisting of” and the phrase “consisting of only”.
  • the operations and processes described herein can be performed at room temperature unless otherwise specified.
  • room temperature is understood according to common general technical knowledge and can mean, for example, a temperature in the range of 10 ° C. to 35 ° C.
  • a composition containing legume protein includes legume protein and / or a degradation product thereof, and further, legume protein.
  • composition foodstuffs, a pharmaceutical, a quasi-drug, etc.
  • a composition containing the fats and oils and / or its degradation product normally contained in powder etc.
  • the term “bean odor derived from legume protein” includes a fat protein component, a decomposition product thereof, a fat component contained in a small amount of legume protein powder, and / or its The bean odor derived from the decomposition product is included.
  • bean odor masking agent which is the odor targeted by the bean odor masking agent of the present invention is, as described above, when a processed food, a pharmaceutical product or a quasi-drug is prepared using a bean-derived protein.
  • Perceived bean-derived odor meaning odor that requires masking.
  • bean protein (sometimes referred to as bean-derived protein in the present specification) means a food material mainly comprising a legume protein component, and this is contained in a small amount in protein powder or the like.
  • the food material containing a bean-derived oil and fat component and the like is also included.
  • limit as a protein derived from a bean,
  • the protein derived from a soybean, a pea, a chickpea, a lentil (lentil), a kidney bean, a broad bean etc. can be illustrated without a restriction
  • the production method of the bean-derived protein and / or its degradation product is not particularly limited as long as the protein and / or its degradation product contained in the bean are separated and purified. Moreover, what can be obtained commercially can also be used for bean origin protein and / or its degradation product.
  • Soy protein is, for example, defatted soybeans obtained by defatting whole soybeans or the like with an organic solvent such as hexane, ethanol, soy milk obtained by water extraction of protein from the defatted soybeans, and separated soy protein obtained from the soy milk by a method such as acid precipitation or alcohol precipitation. And concentrated soy protein.
  • the pea protein includes, for example, a product obtained by removing the shell of the bean seed and then pulverizing, extracting the protein with water, concentrating and drying.
  • chickpea protein for example, those separated and purified in the same manner as soybeans and peas can be used.
  • the above-mentioned bean-derived proteins including commercially available ones, are usually not 100% protein components but a small amount of oils and fats and the like, and can 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.
  • the present inventors have identified the main odor substance in the bean odor attributed to the bean-derived protein in the present invention.
  • Suitable specific examples of such a main odor substance include hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3 -Includes methoxypyrazine and 2,5-dimethylpyrazine.
  • the bean odor masking agent of the present invention utilizes the masking action (bean odor suppressing action) against the above-mentioned bean odor possessed by compounds belonging to the group consisting of the following groups A to F, and is selected from these compounds At least one compound as an active ingredient: (Group A) 1,4-cineole, ⁇ -heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide, (Group B) 1,4-cineole, ⁇ -heptalactone, menthyl lactate, ethyl lactate, ⁇ -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
  • “masking compounds”) are known compounds that are commercially available.
  • “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.
  • the latter is used in an amount of 0.01 to 100 parts by weight, preferably 0.1 to 10 parts by weight with respect to 1 part by weight of the former. can do.
  • flavor containing the said compound can be used as a masking agent of this invention in the range which does not impair the effect of this invention.
  • natural fragrances include, but are not limited to, for example: lime fragrance as a natural fragrance containing 1,4-cineole; apricot fragrance as a natural fragrance containing ⁇ -hexalactone; heliotropin
  • natural fragrances to be contained include vanilla fragrances
  • examples of natural fragrances containing furfural include coffee fragrances. Any of these masking compounds can be suitably used as an active ingredient of the bean odor masking agent of the present invention.
  • the bean 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.
  • the compounds described in Group A 1,4-cineol, ⁇ -heptalactone, 6-methyl-5-hepten-2-one, menthyl lactate, and rose oxide function effectively as bean odor masking agents. It functions as a masking agent for hexanal, which is a compound and in particular, one of the main odor substances of the above-mentioned bean odor. Therefore, when using a compound belonging to Group A, the masking agent of the present invention is for masking the bean odor of processed foods, pharmaceuticals or quasi drugs containing bean-derived proteins by suppressing the odor caused by hexanal. Can be used. These compounds described in Group A can be used singly or in combination of two or more.
  • the compounds described in Group B 1,4-cineol, ⁇ -heptalactone, menthyl lactate, ethyl lactate, ⁇ -hexalactone, acetaldehyde diethyl acetal, and methyl salicylate, function effectively as a bean odor masking agent. It functions effectively as a masking agent for (E, E) -2,4-decadienal, which is a compound, and in particular, one of the main odor substances of the bean odor described above.
  • the masking agent of the present invention provides a processed food, pharmaceutical product or pharmaceutical part containing a bean-derived protein by suppressing the odor caused by (E, E) -2,4-decadienal. It can be used to mask the bean odor of foreign products.
  • These compounds described in Group B can be used singly or in combination of two or more.
  • the compounds described in Group C are compounds that function effectively as bean odor masking agents, and in particular, are one of the main odor substances of bean odor described above. It effectively functions as a masking agent for guaiacol. Therefore, when using a compound belonging to Group C, the masking agent of the present invention is for masking the bean odor of processed foods, pharmaceuticals or quasi drugs containing bean-derived proteins by suppressing the odor caused by guaiacol. Can be used.
  • These compounds described in Group C can be used singly or in combination of two or more.
  • the compounds described in Group D are compounds that function effectively as bean odor masking agents. Yes, and in particular, it effectively functions 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.
  • the masking agent of the present invention is a processed food containing a bean-derived protein by suppressing odor caused by trans-4,5-epoxy- (E) -2-decenal, It can be used to mask the bean odor of drugs or quasi drugs.
  • at least one selected from the group consisting of methyl jasmonate, heliotropin, butyryl butyl lactate, and stearic acid may be used.
  • the compounds described in Group E are compounds that function effectively as a bean odor masking agent, and in particular, are one of the main odor substances of the aforementioned bean odor. It effectively functions as a masking agent for 2-isobutyl-3-methoxypyrazine. Therefore, when a compound belonging to Group E is used, the masking agent of the present invention can be used for processed foods, pharmaceuticals or quasi-drugs containing beans-derived protein by suppressing the odor caused by 2-isobutyl-3-methoxypyrazine. It can be used to mask the bean odor.
  • These compounds described in Group E can be used singly or in combination of two or more.
  • the compounds described in Group F are compounds that function effectively as a bean odor masking agent, and in particular, the main smell of the bean odor described above. It effectively functions as a masking agent for one of the substances, 2,5-dimethylpyrazine. Therefore, when a compound belonging to Group F is used, the masking agent of the present invention suppresses the odor caused by 2,5-dimethylpyrazine, thereby suppressing the bean odor of processed foods, pharmaceuticals or quasi drugs containing bean-derived proteins. Can be used for masking.
  • These compounds described in Group F can be used singly or in combination of two or more.
  • the deteriorated odor masking agent of the present invention is a compound selected from the group consisting of the groups A to F (that is, a compound belonging to the group A, a compound belonging to the group B, a compound belonging to the group C, a compound belonging to the group D, the group E 1 type or 2 types or more of the compound which contains all the compounds which belong to the compound which belongs to F, and F group), It is characterized by the above-mentioned.
  • “two or more compounds selected from the group consisting of groups A to F” include two or more compounds including compounds belonging to different groups, unless otherwise specified.
  • the case where two or more kinds of compounds belonging to the same group are included is also included.
  • 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 three or more of the compounds can be used. A better effect can be obtained.
  • the masking agent in which one of the compounds belonging to these two groups is blended is a mode in which compounds belonging to the two groups to which the compound belongs are blended. It is included in “a masking agent comprising a combination of one or more (total of two or more) compounds selected from two or more groups”. For example, when 1,4-cineole is added to the masking agent, the masking agent contains compounds belonging to two groups, Group A and Group B.
  • the masking agent containing 1,4-cineole alone is It is included in “a masking agent containing a combination of one or more compounds (two or more in total) selected from two of A to F”.
  • the masking agent compound when a compound belonging to a plurality of groups is used as the masking agent compound, the compound may be used alone, or a masking agent compound other than the compound may be used in combination.
  • the masking agent of the present invention is a masking agent compound having a plurality of compounds that belong to different groups (belonging to different groups) (for example, 2 or more, preferably 3 or more, more preferably 4 or more, more preferably It is preferable to include a combination of 5 or more, more preferably 6).
  • groups that do not belong to each other (belong to different groups) includes a case where some of the groups to which these compounds belong partially overlap but do not match. Therefore, in the present invention, the combination of the “groups that do not belong to each other (belonging to different groups)” includes 1,4-cineole (Group A, Group B) and ethyl lactate (Group B, Group E). A case where some of the overlapping parts do not match, such as a combination of.
  • the masking agent of the present invention preferably contains one or more compounds selected from at least one of the A to D groups among the A to F groups. Further, in the embodiment used for soybeans, chickpeas and the like among beans, it is preferable to use one or more compounds selected from at least one of the groups A to D. It is preferable to use a combination of one or more (total of two or more) compounds selected from two or more of the A to D groups, It is more preferable to use a combination of one or more (total of 3 or more) compounds selected from 3 or more of groups A to D, It is even more preferable to use a combination of one or more (total of four or more) compounds selected from four or more of the A to D groups.
  • the masking agent composition may contain one or more compounds selected from at least one of groups A to D, and E to One or more kinds of compounds selected from at least one of the F groups may be included.
  • the masking agent of the present invention in its preferred embodiment, is hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3.
  • odorous substances such as methoxypyrazine and 2,5-dimethylpyrazine (preferably 2 or more, more preferably 3 or more, more preferably 4 or more, more preferably 5 or more, more
  • the masking agent compound which has a masking effect with respect to all preferably 6 types) is included.
  • the masking agent of the present invention includes a bean odor of hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E)- Odor resulting from at least one selected from the group consisting of 2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine, and at least one selected from the group (preferably And at least 2 types, more preferably at least 3 types, more preferably at least 4 types, more preferably at least 5 types, and more preferably 6 types).
  • odorous substances at least selected from the group consisting of hexanal, (E, E) -2,4-decadienal, guaiacol, and trans-4,5-epoxy- (E) -2-decenal.
  • the odor resulting from one kind which masks at least one kind of bean odor selected from the above group (preferably at least two kinds, more preferably at least three kinds, more preferably four kinds) is preferred.
  • those masking any bean odor among the above-mentioned six kinds of odorous substances can be suitably used.
  • the amount of the masking compound used in the present invention may be any amount that exhibits the masking effect of bean odor, specifically the compound. Concentrations for each bean-derived protein-containing food, etc. It is preferable to use it in the range of 0.00001 ppb to 10,000 ppb, More preferably, it is used so that it falls within the range of 0.0001 ppb to 1000 ppb, and further preferably used so that it falls within the range of 0.001 ppb to 100 ppb.
  • the masking effect of the bean odor is sufficiently suppressed while suppressing the fragrance and / or taste of the masking agent compound itself from undesirably affecting the scent and / or taste of the bean-derived protein-containing food, medicine or quasi-drug. From the viewpoint of bringing about this, it is preferable that the amount of the masking compound used is within the above range.
  • the odor substance in which the total mass (or total concentration) of each group of compounds in groups A to F is a suitable target for masking of each group ie, a target that effectively functions as a masking agent
  • a suitable target for masking of each group ie, a target that effectively functions as a masking agent
  • Ie hexanal for compounds described in Group A, (E, E) -2,4-decadienal for compounds described in Group B, guaiacol for compounds described in Group C, compounds described in Group D
  • the compound belonging to the plurality of groups is any group of compounds to which the compound belongs (for example, 1, 4 -Cineol is also a Group A compound and a Group B compound).
  • the present invention uses one or more compounds selected from the group consisting of groups A to F to manufacture, distribute, store, and sell bean-derived protein-containing foods, pharmaceuticals, or quasi drugs. At each stage, the bean odor can be masked easily and safely, and without affecting the scent and / or taste of the final product.
  • the bean odor masking agent of the present invention may contain a compound other than the masking agent compound.
  • the form of the bean odor masking agent of this invention and the kind and quantity of the said other compound can be suitably set according to the usage aspect of the bean odor masking agent of this invention, etc.
  • the bean odor masking agent of the present invention may consist only of the masking agent compound, or may contain an appropriate diluent (thickening agent) or carrier in addition to the masking agent compound. Good.
  • the ratio of the masking agent compound in the bean odor masking agent is 0.00000001 to 99% by mass (0.0001 to 99%) so that the bean odor masking agent exhibits the effect of suppressing the bean odor derived from the bean protein. It can be appropriately set and adjusted from the range of 990000 ppm).
  • 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 inhibiting action derived from the legume protein of the masking agent compound.
  • a solid diluent or carrier such as gum arabic, dextrin, cyclodextrin, glucose, sucrose; or a liquid diluent such as water, ethanol, propylene glycol, glycerin, glycerin fatty acid ester, edible oil or fat, or A carrier can be mentioned.
  • additives used to prepare the bean odor masking agent of the present invention in a desired shape such as excipients, binders, disintegrants, emulsifiers, and solubilizers. , Thickeners, lubricants, flavoring agents, coloring agents and the like.
  • an emulsifier can be preferably used for preparing an aqueous solution (dispersion, suspension) or an emulsion bean odor masking agent by dispersing a masking agent compound in a liquid diluent.
  • the emulsifier examples include, but are not limited to, sucrose fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, lecithin, enzymatically decomposed lecithin, quilla extract, saponin, polysorbate, gum arabic, and gati gum.
  • the bean odor masking agent of the present invention can be made into a liquid, suspension, emulsion, paste, powder, granule, or any other dosage form.
  • the dosage form of the bean odor masking agent of the present invention can be appropriately set according to the type, shape, and the like of an object that suppresses the bean protein-derived bean odor.
  • the bean odor masking agent of the present invention is prepared as a powder formulation by blending an excipient such as dextrin in an aqueous solution in which the aforementioned masking agent compound is dissolved or dispersed, and powdered according to a conventional method such as spray drying or freeze drying. Alternatively, it may be further granulated and prepared as a granule preparation.
  • the bean odor masking agent of the present invention contains a food containing bean-derived protein (including beverages, the same in the present specification), a pharmaceutical product, or a quasi-drug (typically containing at least one of the odor substances described above).
  • the above-mentioned bean odor can be suppressed by being used by being added to foods, pharmaceuticals, or quasi drugs.
  • the bean odor masking agent of the present invention is effective as an additive (food additive, pharmaceutical additive, quasi-drug additive) for foods, pharmaceuticals, or quasi-drugs containing the aforementioned bean-derived protein.
  • Such additives include additives that are used by being added to and mixed with these raw materials in the manufacturing stage of foods, pharmaceuticals or quasi drugs, and these additives include, for example, fragrance compositions. It is.
  • the ratio of the bean odor masking agent of the present invention to foods, pharmaceuticals, or quasi-drugs (target compositions) containing proteins is the type and amount of the odorous substance contained in the target composition, and
  • the bean odor masking agent can be appropriately selected and adjusted according to the type and amount of the masking compound used as an active ingredient.
  • the masking effect is exhibited while suppressing the influence of the flavor of the masking compound itself. be able to.
  • the masking compound used in the present invention since the masking compound used in the present invention has little influence on the fragrance of other fragrance ingredients, it is prepared as a fragrance composition having an action of masking the above-mentioned bean odor by using in combination with other fragrance ingredients. Can be used preferably.
  • each of the bean odor masking agents of the present invention with respect to 10000 parts by mass of the bean protein contained in the target composition containing the bean protein (bean protein-containing composition).
  • the ratio of the masking compound can also be set as follows. However, this is an example, and the ratio is not limited.
  • Compound 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 with respect to 10,000 parts by mass of legume protein;
  • Compound 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 with respect to 10000 parts by mass of legume protein;
  • Compound 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 with respect to 10000 parts by mass of pulse protein;
  • Compound 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 with respect to 10000 parts by mass of legume protein;
  • Compound belonging to Group E 0.000002 parts by mass or more, preferably 0.000002 to
  • the amount of protein contained in the bean protein-containing composition is analyzed by the “nitrogen quantitative conversion method” described in the third column of Appendix 9 of the food labeling standards based on Article 4 Paragraph 1 of the Food Labeling Law. (Refer to Consumer Affairs Agency website / Food Labeling Law, etc. (laws and centralized information)).
  • nitrogen quantitative conversion method refers to “1 Protein (Notification of Food Labeling Standards, Analytical Methods for Nutrients, etc.” (Notified by the Deputy Director of the Consumer Affairs Agency, March 30, 2015). 1) Nitrogen quantitative conversion method ”.
  • the bean odor masking agent of the present invention has a form of a fragrance preparation and can also be used as a fragrance composition. For this reason, this invention also provides the use as a fragrance composition of the said bean odor masking agent of the said invention, and the fragrance
  • the perfume composition may contain one or more of the above-described masking compounds, and may further contain the above-described diluent or carrier according to the form of the perfume preparation. You may contain 2 or more types of other fragrance
  • Such other perfume ingredients may be used in combination with the above-described masking compound as long as they do not impair the effects of the present invention, and in combination with the masking compound, the aroma of other perfume ingredients may not be suppressed. preferable.
  • a fragrance component for example, a natural substance described in “Patent Office Gazette, well-known / conventional technology collection (fragrance) Part II food fragrance” (issued on January 14, 2000) edited by the Japan Patent Office.
  • flavor, etc. can be mentioned.
  • citrus fragrances p.
  • the perfume composition of the present invention only needs to contain 0.0000001 to 99% by mass of the above-mentioned one or more masking compounds, as long as the effects of the present invention are exhibited.
  • the blending ratio of the other fragrance components is not limited, but is 0.0000001 to 99% by mass, preferably 0.000001 to 50%. The ratio of mass% can be illustrated. 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 of other fragrance components blended separately.
  • the target legume protein-containing composition is a composition containing the legume protein described in (I) above, and typically includes hexanal, (E, E) -2,4-decadienal, guaiacol, Bean odor caused by at least one compound selected from the group consisting of trans-4,5-epoxy- (E) -2-decenal, 2-isobutyl-3-methoxypyrazine, and 2,5-dimethylpyrazine Specifically, foods, pharmaceuticals or quasi drugs can be exemplified.
  • processed meat products hamburger, sausage, patty, nugget, etc.
  • processed fish products fish sausage, kamaboko, Chikuwa etc.
  • processing seasoning or seasoning pickling liquid, dressing, mayonnaise, etc.
  • processed milk products milk drinks, yogurt, ice cream, etc.
  • processed egg products thin baked eggs, pudding, etc.
  • nutritional supplements Purified protein foods, etc.
  • beverages soy milk, milk substitute milk, protein-containing jelly beverages, nourishing tonic drinks, etc.
  • the protein content of the bean protein-containing composition may be 0.1 to 100% by mass, preferably 0.5 to 90% by mass.
  • the amount of the odorous substance contained in the bean protein-containing composition is, for example, hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2-decenal,
  • Examples of the total amount of 2-isobutyl-3-methoxypyrazine and 2,5-dimethylpyrazine are 0.0001 ppm or more, preferably 0.0005 to 10 ppm, more preferably 0.001 to 1 ppm.
  • the blending ratio of the bean odor masking agent or fragrance composition of the present invention to the bean protein-containing composition is the kind and amount of the odor substance contained in the bean protein-containing composition, and the bean odor masking agent and fragrance composition of the present invention. Can be appropriately selected and adjusted in accordance with the type and amount of the masking compound contained in.
  • the timing and method of blending the bean odor masking agent or the fragrance composition of the present invention with these bean protein-containing compositions are not particularly limited, and can be carried out according to a conventional method at any stage of producing these products.
  • the bean odor masking agent or fragrance composition of the present invention is added to the raw material of food, medicine or quasi-drug, and a method for producing food, medicine or quasi-drug according to a conventional method can be mentioned.
  • legume proteins to be incorporated into foods, pharmaceuticals or quasi drugs.
  • examples of the legume protein include those described in (I) above, and the description can be used here.
  • various ingredients can be used as raw materials according to various products such as foods, pharmaceuticals, and quasi-drugs to be used, and are not particularly limited.
  • bean odor masking method comprising the step of blending the aforementioned bean odor masking agent or fragrance composition into a composition containing legume protein.
  • the method can be carried out according to the method described in the column of “(III) Method for producing a composition (food, pharmaceutical, quasi-drug, etc.) masked with bean odor”, which is incorporated herein by reference. can do.
  • soybean protein powder and chickpea defatted powder hexanal, (E, E) -2,4-decadienal, guaiacol, trans-4,5-epoxy- (E) -2 are the main odorous substances in the bean odor. -Identified four compounds of desenal.
  • Experimental example 2 (Verification of identified bean odor components) ⁇ Preparation of evaluation solution> (1) A 5% solution of pea protein powder was diluted 5-fold with ion-exchanged water to prepare a 1% solution of pea protein powder. (2) The following 6 types of compounds were added to a 1% solution of pea protein powder to prepare a bean odor component verification evaluation solution. The addition amount of the six kinds of compounds was such that the amount after addition was equivalent to the amount of the six kinds of compounds in the 5% solution of the pea protein powder (ie, the amount of the six kinds of compounds for the 4% solution).
  • Bean odor component of pea protein (six compounds) Hexanal: 80 ppb (E, E) -2,4-Decadienal: 8 ppb Guaiacol: 0.1ppb trans-4,5-epoxy- (E) -2-decenal: 0.5 ppb 2,5-dimethylpyrazine: 5ppb 2-isobutyl-3-methoxypyrazine: 0.01 ppb.
  • a soybean protein bean odor component verification evaluation solution was also prepared by the same procedure except that the following four compounds were added in place of the six pea protein compounds: Bean odor component of soy protein (4 compounds) Hexanal: 80 ppb (E, E) -2,4-Decadienal: 8 ppb Guaiacol: 0.1ppb trans-4,5-epoxy- (E) -2-decenal: 0.5 ppb.
  • Soy protein bean odor verification solution Hexanal, (E, E) -2,4-Decadienal, Guaiacol, trans-4,5-epoxy- (E) -2-decenal in 95% ethanol It was prepared and added to a 1% solution of soy protein powder so that the concentration of each component was the above amount.
  • Hexanal odor is strongly felt: 4 points Hexanal odor is felt: 3 points Hexanal odor is felt a little: 2 points Hexanal odor is hardly felt: 1 point Hexanal odor is not felt at all: 0 points
  • 6-methyl-5-hepten-2-one has the lowest evaluation score (average) (no hexanal odor) as long as the taste of 6-methyl-5-hepten-2-one is not felt.
  • the test was a 2-one concentration of 1 ppb. From the above results, it was found that the masking effect of the group A compound tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 0.5-5.
  • Experimental Example 4 (Masking effect of group B compounds on (E, E) -2,4-decadienal)
  • the group A compound was converted into the group B compound (1,4-cineole, ⁇ -heptalactone, menthyl lactate, ethyl lactate, ⁇ -hexalactone, acetaldehyde diethyl acetal, or methyl salicylate), and hexanal (E, (E) -2,4-decadienal and (E, E) -2,4-decadienal in a 95% ethanol concentration of 0.001% by mass, (E, E) -2, Except that the concentration of 4-decadienal was changed to 2 ppb, the masking effect on the (E, E) -2,4-decadienal of the group B compound and the masking effect on the added amount of ethyl lactate were the same as in Experimental Example 3.
  • the masking effect of the group B compound tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 0.5-5.
  • Experimental Example 5 (Masking effect of group C compounds on guaiacol)
  • the group A compound was changed to a group C compound (ethyl acetoacetate, maltol isobutyrate, and diethyl malonate), hexanal to guaiacol, and the concentration of guaiacol in 95% ethanol to 0.001% by mass.
  • the masking effect of the group C compound on guaiacol and the masking effect on the added amount of diethyl malonate were evaluated in the same manner as in Experimental Example 3, except that the concentration of guaiacol in the test solution was changed to 1 ppb.
  • the masking effect of the group C compound tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 0.1.
  • Experimental Example 6 (Masking effect of group D compounds on trans-4,5-epoxy- (E) -2-decenal)
  • Group A compound was converted to Group D compound (methyl jasmonate, methyl dihydrojasmonate, heliotropin, ethyl pyruvate, butyryl butyl lactate, stearic acid, or ⁇ -butyrolactone), and hexanal to trans-4,5.
  • -Trans-in the test solution by setting the concentration of epoxy-4 (5-E) -2-decenal and the concentration of trans-4,5-epoxy- (E) -2-decenal in 95% ethanol to 0.0001% by mass.
  • the masking effect of the group D compound tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 5/3.
  • Experimental Example 7 (Masking effect of group E compounds on 2-isobutyl-3-methoxypyrazine)
  • group A compound was converted into a group E compound (ethyl lactate, 2-butanone, or nerol), hexanal was converted into 2-isobutyl-3-methoxypyrazine, and 2-isobutyl-3-methoxypyrazine in 95% ethanol.
  • concentration in the test solution was changed to 0.001% by mass and the concentration of 2-isobutyl-3-methoxypyrazine in the test solution was changed to 1 ppb, the 2-isobutyl group E compound was tested.
  • the masking effect of the group E compound tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 10-100.
  • Experimental Example 8 (Masking effect of group F compounds on 2,5-dimethylpyrazine)
  • group A compound was converted to a group F compound (furfural, methyl cinnamate, or 5 (6) -decenoic acid), hexanal to 2,5-dimethylpyrazine, and 95% of 2,5-dimethylpyrazine.
  • the masking effect of the group F compound tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 2.5.
  • ⁇ Evaluation criteria> Prepare a bean protein solution with a bean protein concentration of 1% to 4% by adding ion-exchanged water to a 5% solution of the above three types of bean proteins, and set the following evaluation points to determine the bean odor evaluation criteria.
  • Experimental Example 10 (Maize odor masking effect 2 by masking agent for 5% bean protein solution) A masking agent shown in Table 15 below was added to a 5% aqueous solution of pea protein powder prepared by the method described in Experimental Example 9 so as to have the amount in the table. About the obtained 5% bean protein solution, the masking effect by the difference in masking agent addition density
  • ⁇ Evaluation criteria> The evaluation of the odor equivalent to the bean odor of the control product (hamburger containing no soy protein added to the masking agent) is "4 points strongly feels the bean odor", and the standard product (hamburger not containing bean protein) is "0 points bean odor"
  • the following evaluation score was set as the evaluation standard for bean odor: 4 points I strongly feel the bean smell 3 points I feel the bean smell 2 points 1 point 0 points No bean odor at all ⁇ Evaluation results> 4 panelists (persons who were well trained in sensory evaluation of odors) for the hamburger with masking agent prepared in ⁇ Preparation of soybean protein-containing hamburger> and ⁇ Preparation of pea protein-containing hamburger> based on the above evaluation criteria
  • the bean odor was evaluated. Evaluation points (average) are shown in Table 18 below. In any test, the smell of the masking compound itself did not impair the hamburger flavor.
  • the mixture was homogenized with stirring and heated to 93 ° C.
  • a masking agent solution was added, filled into a container, cooled and hardened to prepare a pudding.
  • surface shows a mass part.
  • ⁇ Evaluation criteria> The evaluation of the odor equivalent to the bean odor of the control product (masking agent-free soy protein-containing pudding) is "4 points strongly feel the bean odor", and the standard product (pudding not containing bean protein) is "0 points bean odor"
  • the following evaluation score was set as the evaluation standard for bean odor: 4 points 3 points 2 points 1 point 0 points No bean odor at all ⁇ Evaluation results>
  • the bean odor was evaluated by four panelists (those who were well trained in sensory evaluation of odors) for the pudding containing the masking agent prepared in ⁇ Preparation of pea protein-containing pudding>. Evaluation points (average) are shown in Table 20 below. In any test, the odor of the masking compound itself did not impair the purine flavor.

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  • Food Science & Technology (AREA)
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  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention inhibe une odeur dérivée d'une fève qui est perçue lorsqu'un aliment transformé, un médicament ou un quasi-médicament traité est formulé à l'aide d'une protéine dérivée d'une fève. La présente invention utilise, en tant qu'agent pour masquer une odeur de fève dérivée d'une protéine de fève, au moins un composé choisi dans les groupes A à F : (groupe A) 1,4-cinéole, γ-heptalactone, 6-méthyl-5-heptèn-2-one, lactate de menthyle et oxyde de rose ; (groupe B) 1,4-cinéole, γ-heptalactone, lactate de menthyle, lactate d'éthyle, γ-hexalactone, acétaldéhyde diéthylacétal et salicylate de méthyle ; (groupe C) acétoacétate d'éthyle, isobutyrate de maltol et malonate de diéthyle ; (groupe D) jasmonate de méthyle, dihydrojasmonate de méthyle, héliotropine, pyruvate d'éthyle, lactate de butylbutyryle, acide stéarique et γ-butyrolactone ; (groupe E) lactate d'éthyle, 2-butanone et acide 5(6)-décénoïque.
PCT/JP2019/021584 2018-05-31 2019-05-30 Agent pour masquer une odeur de fève provenant d'une protéine de fève Ceased WO2019230903A1 (fr)

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JP2020156473A (ja) * 2019-03-22 2020-10-01 三栄源エフ・エフ・アイ株式会社 油脂劣化臭マスキング剤
JP2021078497A (ja) * 2019-11-18 2021-05-27 三栄源エフ・エフ・アイ株式会社 不飽和脂肪酸の酸化成分に起因する臭いのマスキング
JPWO2021193429A1 (fr) * 2020-03-26 2021-09-30
WO2022209861A1 (fr) * 2021-03-29 2022-10-06 味の素株式会社 Agent masquant les odeurs désagréables
WO2022270560A1 (fr) * 2021-06-22 2022-12-29 不二製油グループ本社株式会社 Agent aromatisant de masquage
WO2023190844A1 (fr) 2022-03-31 2023-10-05 不二製油グループ本社株式会社 Agent de masquage
JP2023546123A (ja) * 2020-10-15 2023-11-01 ジボダン エス エー 消費物におけるオフノートをマスクするための組成物および方法
WO2024058111A1 (fr) 2022-09-12 2024-03-21 高砂香料工業株式会社 Procédé de criblage pour matériau anti-odeurs désagréables
JP7742966B1 (ja) * 2025-03-28 2025-09-22 小川香料株式会社 テクスチャー改善剤

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020156473A (ja) * 2019-03-22 2020-10-01 三栄源エフ・エフ・アイ株式会社 油脂劣化臭マスキング剤
JP2021078497A (ja) * 2019-11-18 2021-05-27 三栄源エフ・エフ・アイ株式会社 不飽和脂肪酸の酸化成分に起因する臭いのマスキング
JP7731663B2 (ja) 2019-11-18 2025-09-01 三栄源エフ・エフ・アイ株式会社 不飽和脂肪酸の酸化成分に起因する臭いのマスキング
CN115334906B (zh) * 2020-03-26 2024-09-13 味之素株式会社 掩蔽剂
JPWO2021193429A1 (fr) * 2020-03-26 2021-09-30
WO2021193429A1 (fr) * 2020-03-26 2021-09-30 味の素株式会社 Agent masquant
CN115334906A (zh) * 2020-03-26 2022-11-11 味之素株式会社 掩蔽剂
JP7754087B2 (ja) 2020-03-26 2025-10-15 味の素株式会社 マスキング剤
JP2023546123A (ja) * 2020-10-15 2023-11-01 ジボダン エス エー 消費物におけるオフノートをマスクするための組成物および方法
WO2022209861A1 (fr) * 2021-03-29 2022-10-06 味の素株式会社 Agent masquant les odeurs désagréables
WO2022270560A1 (fr) * 2021-06-22 2022-12-29 不二製油グループ本社株式会社 Agent aromatisant de masquage
CN117479844A (zh) * 2021-06-22 2024-01-30 不二制油集团控股株式会社 掩蔽用风味材料
WO2023190844A1 (fr) 2022-03-31 2023-10-05 不二製油グループ本社株式会社 Agent de masquage
WO2024058111A1 (fr) 2022-09-12 2024-03-21 高砂香料工業株式会社 Procédé de criblage pour matériau anti-odeurs désagréables
JP7742966B1 (ja) * 2025-03-28 2025-09-22 小川香料株式会社 テクスチャー改善剤

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