WO2024024120A1 - 香料組成物および飲食品 - Google Patents
香料組成物および飲食品 Download PDFInfo
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- WO2024024120A1 WO2024024120A1 PCT/JP2022/040383 JP2022040383W WO2024024120A1 WO 2024024120 A1 WO2024024120 A1 WO 2024024120A1 JP 2022040383 W JP2022040383 W JP 2022040383W WO 2024024120 A1 WO2024024120 A1 WO 2024024120A1
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- 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
- A23L27/84—Flavour masking or reducing agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
- A23C11/10—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins
- A23C11/103—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins containing only proteins from pulses, oilseeds or nuts, e.g. nut milk
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- 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
- A23J3/16—Vegetable proteins from soybean
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- 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
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- 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
- A23L11/60—Drinks from legumes, e.g. lupine drinks
- A23L11/65—Soy drinks
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- 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
- A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
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- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/38—Other non-alcoholic beverages
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
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- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
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- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
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- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
Definitions
- the present invention relates to a flavoring agent that masks unpleasant odor (off-flavor) components generated from food and drink products, and masked food and drink products.
- Non-Patent Document 1 N-hexanal, which is produced by oxidation of lipids, has been identified as a causative agent of grassy odor.
- Non-Patent Document 1 n-hexanal is one of the substances that cause the odor caused by the oxidation of oils and fats contained in foods derived from plants such as soybeans and various foods and drinks including processed meat products, and it is also used at manufacturing sites and distribution sites. This becomes a problem (Patent Document 1).
- Patent Document 1 describes the use of E-beta-damascone, S-(2-methyl-3-furyl)ethanethioate, beta-caryophyllene oxide, beta-ionone, 2,5 -dihydroxy-1,4-dithiane, methylanthranilate, S-furfurylthioformate, 1-isothiocyanate-3-(methylthio)propane, nootkatone, 1,4-dioxacycloheptadecane-5,17-dione
- a method of adding one or more selected from the group consisting of , sclareol, and sclareolidopineol is described.
- Non-Patent Document 1 uses the olfactory receptor OR2W1, which showed a response to n-hexanal, to screen a food component library to find a specific amount of ⁇ -pinene, which is contained in herbs and has a refreshing aroma. It describes how to do this.
- the present invention aims to provide a technology that can mask unpleasant odors (off-flavors) generated from food and drink products.
- One aspect of the present invention relates to providing a method for making (masking) the grassy smell derived from n-hexanal or the like less perceptible without affecting the flavor of food or drink products.
- the present inventors investigated various fragrance compounds to solve the above problems, and found that oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl It has been found that carbinyl butyrate and methyl 4-TERT-butylphenyl acetate suppress n-hexanal odor without impairing the flavor of foods and drinks.
- the present invention includes the following contents [1] to [26].
- [1] Selected from the group consisting of oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl carbinyl butyrate, and methyl 4-TERT-butylphenyl acetate
- An agent for suppressing unpleasant odors (off-flavors) in foods and drinks which contains one or more of the following as an active ingredient.
- the food or drink according to [1] above which may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide.
- [7] Selected from the group consisting of oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl carbinyl butyrate, and methyl 4-TERT-butylphenyl acetate
- the plant-derived plant according to [7] above which may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide.
- the flavor composition according to [9] above, wherein the legume is soybean.
- the fragrance composition according to any one of [7] to [10] above, wherein the unpleasant odor (off flavor) is an n-hexanal odor.
- [12] Selected from the group consisting of oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl carbinyl butyrate, and methyl 4-TERT-butylphenyl acetate
- the plant-derived plant according to [12] above which may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide.
- Food and drink products containing one or more types selected from the group consisting of food and drink products, processed meat foods, and edible processed oils and fats.
- the food or drink according to [12] or [13] above, wherein the plant is a legume.
- the food or drink according to [14] above, wherein the legumes are soybeans.
- a method for masking unpleasant odors (off-flavors) originating from plant-derived foods and drinks, processed meat foods, or edible processed oils and fats which comprises adding one or more of the following as active ingredients.
- the invention consists of oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT-butylphenyl acetate.
- the inhibitor of unpleasant odor (off-flavor) of food and drink products of the present invention includes oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3 -Hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT-butylphenyl acetate as an active ingredient (ie, masking ingredient).
- Masking components used in the present invention include oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT- One type of butyl phenylacetate may be used alone, or two or more types may be combined. All of these are known aroma components, and commercially available products can be used.
- the inhibitor of the present invention may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide as a masking component. .
- the masking effect can be further enhanced.
- These may be used alone or in combination of two or more, and all of them are known aroma components, and commercially available products can be used.
- the content of the masking component in the inhibitor of the present invention is not particularly limited as long as it is an effective amount against the unpleasant odor (off-flavor) of foods and drinks, but is preferably 70% by mass or more, more preferably 80% by mass or more. , more preferably 90% by mass or more, particularly preferably 95% by mass or more, still more preferably 99% by mass or more, most preferably 99.5% by mass or more, and 100% by mass when two or more masking components are used together. It may be %. In addition, when using two or more kinds of masking components together, their total amount should just be within the above range.
- oleic acid ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT-butylphenyl acetate.
- the content is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, still more preferably 99% by mass or more, and most preferably 99.5% by mass. % or more.
- Other components other than the masking component may be used as long as they do not impede the purpose and effect of the present invention, and include, but are not particularly limited to, various synthetic fragrances, natural fragrances, etc. as exemplified in the fragrance composition. Natural essential oils, plant extracts, solvents, retention agents, etc. can be used.
- the inhibitor of the present invention can be particularly suitably used in foods and drinks that have an unpleasant odor (off-flavor) derived from plant-derived foods, processed meat foods, or edible processed oils and fats.
- the inhibitor of the present invention can make unpleasant odors mainly composed of hexanal contained in foods and drinks, particularly plant-derived foods and drinks, processed meat foods, or edible processed oils and fats, less perceivable.
- plant-derived foods and beverages include foods and beverages derived from beans, and more specifically, foods and beverages derived from soybeans.
- the fragrance composition of the present invention is used to suppress unpleasant odors (off-flavors) originating from plant-derived foods and drinks, processed meat foods, or edible processed oils and fats, and contains oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl It contains one or more selected from the group consisting of -2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinyl butyrate, and methyl 4-TERT-butylphenyl acetate as an active ingredient (ie, masking ingredient).
- the flavor composition of the present invention is a composition used for the purpose of imparting or enhancing flavor to foods and drinks.
- the fragrance composition of the present invention may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide as a masking component.
- the masking effect can be further enhanced.
- These compounds may be used alone or in combination of two or more.
- Components other than the masking component that can be incorporated into the fragrance composition, food and drink, etc. of the present invention include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, etc. Examples include natural essential oils, natural fragrances, synthetic fragrances, etc. described in "Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II Food Flavors," P88-131, published January 14, 2000.
- the fragrance composition of the present invention may contain commonly used solvents, such as water and ethanol, as needed; ethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium chain It may contain a retention agent such as fatty acid triglyceride, medium chain fatty acid diglyceride, animal or vegetable oil or fat.
- solvents such as water and ethanol, as needed; ethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium chain It may contain a retention agent such as fatty acid triglyceride, medium chain fatty acid diglyceride, animal or vegetable oil or fat.
- fragrance composition of the present invention unpleasant odors (off-flavors) originating from foods and drinks, more specifically, plant-derived foods and drinks, processed meat foods, or edible processed oils and fats, particularly n-hexanal as a main component, can be obtained. Unpleasant odors can be suppressed.
- the content of the masking component in the fragrance composition of the present invention varies depending on the other ingredients blended and cannot be generalized, it is usually in a concentration range of 0.01 ppb or more and 100,000 ppm or less based on the weight of the fragrance composition.
- the concentration range is 0.1 ppb or more and 10,000 ppm or less. If the content of the masking component is less than 0.01 ppb, the masking effect of the present invention cannot be obtained, and if the content exceeds 100,000 ppm, the masking component itself will affect the flavor, which is not preferable.
- oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT-butyl account for the fragrance composition of the present invention.
- the content of phenylacetate is usually in a concentration range of, for example, 0.01 ppb or more and 100,000 ppm or less, preferably 0.1 ppb or more and 10,000 ppm or less, based on the weight of the perfume composition.
- the food/beverage products of the present invention are food/beverage products containing one or more selected from the group consisting of plant-derived food/beverage products, processed meat foods, and edible processed oils/fats, and include oleic acid, ⁇ -damascenone, 4-methyl-2- Contains one or more selected from the group consisting of phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl carbinyl butyrate, and methyl 4-TERT-butylphenyl acetate as an active ingredient (i.e., masking ingredient) do.
- the food/drink product of the present invention may further contain one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide as a masking component.
- these compounds may be used alone or in combination of two or more.
- the food and drink products of the present invention can eliminate unpleasant odors (off-flavors) originating from food and drink products, more specifically, plant-derived food and drink products, processed meat foods, or edible processed oils and fats.
- the unpleasant odor mainly composed of hexanal can be made less perceivable.
- Examples of plant-derived foods and drinks include foods and drinks derived from beans, and more specifically, foods and drinks derived from soybeans.
- Examples of the food and drink products of the present invention include those containing substances that cause unpleasant odors (off-flavors) derived from plant-derived food and drink products, processed meat foods, or edible processed oils and fats.
- Examples include foods and drinks containing one or more selected from the group consisting of plant-derived foods, processed meat foods, and edible processed oils and fats.
- plant-derived food and drink is not particularly limited as long as it is a plant itself or a food processed from a plant or a plant-derived material. Examples include legumes themselves, or foods processed from legumes or legume-derived materials. Soybeans or soybean processed foods are preferred.
- processed meat food is not particularly limited as long as it is a processed food whose main ingredient is meat.
- Examples include processed fish foods and processed livestock foods.
- "edible processed fats and oils” are not particularly limited as long as they are raw fats and oils that have been subjected to some kind of processing technology to give new functions. Examples include margarines, shortenings, refined lard, and edible refined processed fats and oils.
- the food and drink products of the present invention include beverages such as fruit drinks, vegetable drinks, soft drinks, carbonated drinks, near water, functional drinks, drink preparations, alcoholic beverages, non-alcoholic drinks, milk drinks, and protein drinks; Tea drinks and luxury drinks such as black tea, green tea, oolong tea, herbal tea, coffee, and cocoa; plant-based alternative drinks such as soy milk drinks, oat milk drinks, almond milk drinks, and milk substitutes; yogurts, cheeses, etc. Fermented dairy products; Frozen desserts such as ice cream, lacto ice, ice milk, and ice cream; Desserts such as pudding, jelly, Bavarois, and mousse; Chewing gum, candy, gummy candy, tablets, soft sweets, chocolate, chocolate sweets, snack foods, etc.
- beverages such as fruit drinks, vegetable drinks, soft drinks, carbonated drinks, near water, functional drinks, drink preparations, alcoholic beverages, non-alcoholic drinks, milk drinks, and protein drinks
- Tea drinks and luxury drinks such as black tea, green tea, oolong tea, herbal tea
- Pastes and creams such as jam, dessert sauce, flower paste, margarine, fat spread, filling cream, flower paste, and whipped cream; Agricultural foods and processed agricultural foods; Meat and processed meat foods; Processed fish and seafood foods ; Milk oil products; Rice products such as retort cooked rice and germinated brown rice; Noodles such as instant noodles, dried noodles, and chilled noodles; Bread such as bread, meat buns, and side dish bread; Soup foods; Retort food, pasta sauce, canned foods, frozen and chilled Cooked processed foods such as foods; seasonings such as sauces, soy sauce, sauces, soups, mayonnaise, ketchup, dressings, tube products, dashi base, Chinese seasonings, Western seasonings, various roux; Spices; animal and vegetable sources Edible oils and fats; Examples include plant-based alternative foods such as alternative seafood and meat.
- the content of the masking component contained in the food/beverage product of the present invention can be in a concentration range of 0.01 ppt or more and 100 ppm or less, preferably 0.1 ppt or more and 10 ppm or less, based on the weight of the food/beverage product. If the content of the masking component is less than 0.01 ppt, the masking effect of the present invention cannot be obtained, and if the content exceeds 100 ppm, the masking component itself will affect the flavor of the food or drink, which is not preferable.
- the proportion of oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT-butylphenyl acetate in the food and drink products of the present invention The content can be in a concentration range of 0.01 ppt or more and 100 ppm or less, preferably 0.1 ppt or more and 10 ppm or less, based on the weight of the food or drink.
- the present invention provides oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzyl carbinyl butyrate, and methyl 4-TERT-butylphenyl acetate.
- a method for producing a food or drink which includes adding one or more selected from the group consisting of: The concentration range of the above compound is 0.01 ppt or more and 100 ppm or less, preferably 0.1 ppt or more and 10 ppm or less, based on the weight of the food or drink.
- one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide may be further added as a masking component.
- the masking components may be used alone or in combination of two or more. When using two or more types of masking components, the total concentration range thereof only needs to satisfy the above range.
- the timing of adding the masking component is not particularly limited. It is preferable to add it in a way that does not impair the masking effect.
- the present invention also provides, as another aspect, oleic acid, ⁇ -damascenone, 4-methyl-2-phenyl-2-pentenal, menthyl 3-hydroxybutyrate, dimethylbenzylcarvinylbutyrate, and methyl 4-TERT.
- - Foods and drinks containing one or more selected from the group consisting of butyl phenylacetate as an active ingredient, specifically plant-derived foods and drinks, processed meat foods, or edible processed oils and fats. To provide a method for masking unpleasant odors (off flavors) originating from.
- a masking component one or more selected from the group consisting of 2,3-hexanedione, thymol, lauric acid, carvacrol, and isoambrettolide may be further added, thereby providing a masking effect. can be further increased.
- the amount of the masking component used is not particularly limited, but is usually 0.01 ppt or more and 100 ppm or less, preferably 0.1 ppt or more and 10 ppm or less, based on the weight of the food or drink. When using two or more types of masking components, the total concentration range thereof only needs to satisfy the above range.
- the inhibitor and fragrance composition of the present invention can be used not only in foods and drinks but also in oral products such as dentifrices, mouthwashes, mouthwashes, mouth sprays, and gargles; dishwashing detergents, and the like. This makes it possible to suppress unpleasant odors (off-flavors) of the food/beverage products remaining in the mouth or on tableware.
- Example 1 (n-hexanal odor masking effect of oleic acid) N-hexanal, which had been adjusted to a concentration of 1% by mass with 95% ethanol, was added to ion-exchanged water at a concentration of 50 ppb. Oleic acid was added to this n-hexanal-containing aqueous solution at the concentration shown in Table 1, and the strength of the n-hexanal odor (off flavor) of each sample (masking effect) and the strength of the masking component itself (food and drink) were determined. The effect on the flavor of the product itself was confirmed.
- Example 2 (n-hexanal odor masking effect of ⁇ -damascenone) Using samples prepared in the same manner as in Example 1, we investigated the strength of the n-hexanal odor (off-flavor) of ⁇ -damascenone (masking effect) and the strength of the masking component (influence on the flavor of the food and drink itself). ) was confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 2, which shows the average score of the evaluation results for each panel.
- Example 3 (n-hexanal odor masking effect of 4-methyl-2-phenyl-2-pentenal) Using a sample prepared in the same manner as in Example 1, the strength of the n-hexanal odor (off flavor) of 4-methyl-2-phenyl-2-pentenal (masking effect) and the strength of the masking component ( The effect on the flavor of the food and drink itself was confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 3, which shows the average score of the evaluation results for each panel.
- Example 4 (n-hexanal odor masking effect of menthyl 3-hydroxybutyrate) Using samples prepared in the same manner as in Example 1, we investigated the strength of the n-hexanal odor (off-flavor) of menthyl 3-hydroxybutyrate (masking effect) and the strength of the masking component (the flavor of the food/drink itself). We confirmed the impact on The evaluation method was the same as in Example 1. The results are shown in Table 4, which shows the average score of the evaluation results for each panel.
- menthyl 3-hydroxybutyrate masks the odor of n-hexanal at a concentration of 100 ppt or more and 10 ppm or less, and does not affect the flavor of the food or drink itself.
- Example 5 n-hexanal odor masking effect of dimethylbenzyl carbinyl butyrate
- the strength of the n-hexanal odor (off-flavor) of dimethylbenzyl carbinyl butyrate (masking effect) and the strength of the masking component (flavor of the food/beverage product itself) were measured.
- the evaluation method was the same as in Example 1.
- the results are shown in Table 5, which shows the average score of the evaluation results for each panel.
- dimethylbenzyl carbinyl butyrate masks the odor of n-hexanal at a concentration of 1 ppt or more and 100 ppb or less, and does not affect the flavor of the food or drink itself.
- Example 6 n-hexanal odor masking effect of methyl 4-TERT-butylphenyl acetate
- the strength of the n-hexanal odor (off-flavor) of methyl 4-TERT-butylphenyl acetate (masking effect) and the strength of the masking component (the food/drink itself) We confirmed the effect on the flavor.
- the evaluation method was the same as in Example 1. The results are shown in Table 6, which shows the average score of the evaluation results for each panel.
- Example 7 Oleic acid off-flavor masking effect of soy milk
- Oleic acid was added to commercially available soymilk at the concentration shown in Table 7, and the strength of the off-flavor of each sample of soymilk (masking effect) and the strength of the masking component (effect on the flavor of soymilk itself) were confirmed. did.
- 8 experienced panelists were selected to perform a sensory evaluation, and the strength of the off-flavor of each sample was evaluated, with the strength of the off-flavor of soy milk being ⁇ Rating: 4'' and the strength of ion exchange water being ⁇ Rating: 0.'' (Masking effect) was relatively evaluated according to the following evaluation criteria.
- Example 8 (Off-flavor masking effect of ⁇ -damascenone on soy milk) ⁇ -damascenone was added to commercially available soymilk at the concentrations listed in Table 8, and the strength of the off-flavor of each sample of soymilk (masking effect) and the strength of the masking component (effect on the flavor of soymilk itself) were investigated. confirmed.
- the evaluation method was the same as in Example 7. The results are shown in Table 8, which shows the average score of the evaluation results for each panel.
- Example 9 (Off-flavor masking effect of 4-methyl-2-phenyl-2-pentenal on soy milk) 4-Methyl-2-phenyl-2-pentenal was added to commercially available soy milk at the concentrations listed in Table 9, and the strength of off-flavor (masking effect) and the strength of masking components (soy milk) of each sample of soy milk were measured. The effect on the flavor itself) was confirmed.
- the evaluation method was the same as in Example 7. The results are shown in Table 9, which shows the average score of the evaluation results for each panel.
- Example 10 (Off-flavor masking effect of methyl 4-TERT-butylphenyl acetate on soy milk) Methyl 4-TERT-butylphenyl acetate was added to commercially available soymilk at the concentrations listed in Table 10, and the strength of off-flavor (masking effect) and the strength of masking components (flavor of soymilk itself) of each sample of soymilk were measured. We confirmed the impact on In the test, six experienced panelists were selected to perform sensory evaluation, and the evaluation method was the same as in Example 7. The results are shown in Table 10, which shows the average score of the evaluation results for each panel.
- Example 11 (n-hexanal odor masking effect of ⁇ -damascenone) 5 ppm of n-hexanal adjusted to a concentration of 1% by mass with 95% ethanol was added to commercially available shortening. To this n-hexanal-containing shortening, ⁇ -damascenone was added at the concentration shown in Table 11, and the strength of the n-hexanal odor (off flavor) (masking effect) and the strength of the masking component (shortening) of each sample were The effect on the flavor itself) was confirmed. In the test, six experienced panelists were selected to perform sensory evaluation, and the evaluation method was the same as in Example 1. The results are shown in Table 11, which shows the average score of the evaluation results for each panel.
- Example 12 n-hexanal odor masking effect of dimethylbenzyl carbinyl butyrate
- n-hexanal odor off-flavor
- masking component the flavor of the shortening itself
- dimethylbenzyl carbinyl butyrate masks the odor of n-hexanal at a concentration of 10 ppb or more and 10 ppm or less, and does not affect the flavor of the shortening itself.
- Example 13 n-hexanal odor masking effect of methyl 4-TERT-butylphenyl acetate
- n-hexanal odor masking effect of methyl 4-TERT-butylphenyl acetate Using a sample prepared in the same manner as in Example 11, we investigated the strength of the n-hexanal odor (off-flavor) of dimethyl 4-TERT-butylphenyl acetate (masking effect) and the strength of the masking component (of the shortening itself). The effect on flavor) was confirmed.
- the evaluation method was the same as in Example 11. The results are shown in Table 13, which shows the average score of the evaluation results for each panel.
- Example 14 Soybean odor masking effect of oleic acid
- Oleic acid was added to the soybean protein suspension having the composition shown in Table 14 at the concentration shown in Table 15, and the strength of the soybean odor (off flavor) (masking effect) and the strength of the masking component ( The effect on the flavor of the soybean protein suspension itself was confirmed.
- 6 experienced panelists were selected to perform a sensory evaluation, and the strength of the soy odor (off flavor) of the soy protein suspension was evaluated as 4, and the ion exchange water was evaluated as 0.
- the strength (masking effect) of soybean odor (off-flavor) of each sample was evaluated relative to each other according to the following evaluation criteria.
- Example 15 Soy odor masking effect of ⁇ -damascenone
- the evaluation method was the same as in Example 14. The results are shown in Table 16, which shows the average score of the evaluation results for each panel.
- Example 16 Soy odor masking effect of 4-methyl-2-phenyl-2-pentenal
- the strength of the soybean odor (off flavor) of 4-methyl-2-phenyl-2-pentenal (masking effect) and the strength of the masking component (soybean protein concentration) were determined.
- the influence on the flavor of the cloudy liquid itself was confirmed.
- the evaluation method was the same as in Example 14. The results are shown in Table 17, which shows the average score of the evaluation results for each panel.
- Example 17 Soy odor masking effect of menthyl 3-hydroxybutyrate
- the strength of the soybean odor (off-flavor) of menthyl 3-hydroxybutyrate (masking effect) and the strength of the masking component (the flavor of the soybean protein suspension itself) were measured.
- the evaluation method was the same as in Example 14.
- the results are shown in Table 18, which shows the average score of the evaluation results for each panel.
- menthyl 3-hydroxybutyrate masks soybean odor at a concentration of 100 ppt or more and 30 ppm or less, and does not affect the flavor of the soy protein suspension itself.
- Example 18 Soy odor masking effect by combination It was confirmed that soybean odor (off-flavor) can be better masked by adding masking ingredients in the combinations listed in Table 19 to the soybean protein suspension having the composition shown in Table 14. Note that compounds A to K in Table 19 are as follows.
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| CN202280098369.3A CN119584869A (zh) | 2022-07-26 | 2022-10-28 | 香料组合物及饮食品 |
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| JP2011223942A (ja) * | 2010-04-21 | 2011-11-10 | T Hasegawa Co Ltd | 風味改善剤 |
| JP2019170375A (ja) * | 2018-03-26 | 2019-10-10 | 三栄源エフ・エフ・アイ株式会社 | 果汁含有製品の光劣化臭マスキング剤 |
| 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 |
| WO2021193429A1 (ja) | 2020-03-26 | 2021-09-30 | 味の素株式会社 | マスキング剤 |
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| JP2011223942A (ja) * | 2010-04-21 | 2011-11-10 | T Hasegawa Co Ltd | 風味改善剤 |
| JP2019170375A (ja) * | 2018-03-26 | 2019-10-10 | 三栄源エフ・エフ・アイ株式会社 | 果汁含有製品の光劣化臭マスキング剤 |
| 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 |
| WO2021193429A1 (ja) | 2020-03-26 | 2021-09-30 | 味の素株式会社 | マスキング剤 |
Non-Patent Citations (4)
| Title |
|---|
| "Japanese Patent Office Bulletin, Collection of Well-known Prior Arts", FOOD FLAVORS, 14 January 2000 (2000-01-14), pages 88 - 131 |
| NAKA, TOSHIHITO ET AL.: "Light-induced off- flavor of citrus juice packed in PET bottles", REPORT OF TOYO INSTITUTE OF FOOD TECHNOLOGY, TOYO JUNIOR COLLEGE OF FOOD TECHNOLOGY AND TOYO INSTITUTE OF FOOD TECHNOLOGY, JP, vol. 27, 1 March 2009 (2009-03-01), JP , pages 65 - 69, XP009530753, ISSN: 0564-0296 * |
| SOY PROTEIN RESEARCH, vol. 23, 2020, pages 159 - 164 |
| YUKO TERADA, KAYANO SATO, SAKURA TSUCHIYA, KOHEI KODUKA, SHOGO NAKANO, SOHEI ITO AND KEISUKE ITO: "Identification of Human Olfactory Receptor Sensing n-Hexanal, the Causative Compound of Grassy Smell in Soybean Products", DAIZU TAMPAKUSHITSU KENKYU - SOY PROTEIN RESEARCH JAPAN, FUJI TANPAKUSHITSU KENKYU SHINKO ZAIDAN, IZUMISANO, JP, vol. 23, 1 January 2020 (2020-01-01), JP , pages 159 - 164, XP009552245, ISSN: 1344-4050 * |
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| WO2025047524A1 (ja) * | 2023-08-31 | 2025-03-06 | 高砂香料工業株式会社 | 異臭抑制剤、異臭抑制用香料組成物および飲食品中に含まれる異臭がマスキングされた飲食品 |
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| CN119584869A (zh) | 2025-03-07 |
| EP4563008A1 (en) | 2025-06-04 |
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