Taste-improving composition, taste-improving seasoning, and method for improving taste of food / beverage

Abstract

Provided is, e.g., a novel composition or seasoning with which it is possible to improve the taste of a food / beverage, or to provide a novel method for improving the taste of a food / beverage.　The present invention uses a compound represented by general formula (1) or a sitologically acceptable salt thereof. (In general formula (1), each of R1, R2, R3, and R4 independently represents a hydrogem atom, a methyl group, or a hydroxy group, and R5 represents a methyl group or a carboxy group.)

Description

Taste-improving composition, taste-improving seasoning, and method for improving the taste of food and beverages.

[0001] This disclosure relates, for example, to a taste-improving composition, a taste-improving seasoning, and a method for improving the taste of food and beverages.

[0002] Mammals, including humans, can perceive a combination of flavors when eating and drinking, including the five basic tastes (sweet, salty, sour, bitter, and umami) detected by taste buds on the tongue, as well as spiciness, astringency, bitterness, richness, and various other flavors. It is known that various components are involved in the taste of food and beverages, and all components involved in taste are sometimes referred to as taste components in a broad sense.

[0003] Various substances are used to improve, adjust, or alter the taste of food and beverages. For example, 2-aminoglutaric acid, in which an amino group is bonded to the 2-carbon of glutaric acid, is known as glutamic acid, and its sodium salt is used as an umami seasoning. Furthermore, it is known that some derivatives of glutaric acid affect the taste, such as ketoglutaric acid providing a sour taste (Japanese Patent Publication No. 2024-502150), monomenthlyl glutaric acid and dimenthlyl glutaric acid contributing to a refreshing sensation (Japanese Patent Publication No. 2017-128579), and α-ketoglutaric acid imparting good umami and richness to soy sauce-like seasonings (Japanese Patent Publication No. 2017-085937).

[0004] Japanese Patent Publication No. 2024-502150, Japanese Patent Publication No. 2017-128579, Japanese Patent Publication No. 2017-085937

[0005] With the increasing diversification of food and beverage preferences, there is a growing demand for methods that can improve the taste of food and beverages from various perspectives. This disclosure relates to providing a new composition or seasoning that can improve the taste of food and beverages, and to providing a new method for improving the taste of food and beverages.

[0006] This disclosure relates to a taste-improving composition containing a compound represented by the following general formula (1) or a food-grade salt thereof.

[0007]

[0008] (In general formula (1), R１ , R ２ , R ３ , R ４ , R each independently represents a hydrogen atom, a methyl group or a hydroxy group, and R ５ represents a methyl group or a carboxy group.)

[0009] The present disclosure also relates to a flavor-improving seasoning containing a heating reaction product of a compound represented by the general formula (1) or a food-acceptable salt thereof and a protein.

[0010] The present disclosure also relates to a method for producing a flavor-improving seasoning, which comprises a step of heating a compound represented by the general formula (1) or a food-acceptable salt thereof in the presence of a protein.

[0011] The present disclosure also relates to a method for improving the flavor of food and drink products using a compound represented by the general formula (1) or a food-acceptable salt thereof.

[0012] The present disclosure also relates to the use of a compound represented by the general formula (1) or a food-acceptable salt thereof for improving the flavor of food and drink products.

[0013] Now, it has been first found that a component obtained by heating a compound represented by the following general formula (1) or a food-acceptable salt thereof in the presence of a protein can improve the flavor of food and drink products from various viewpoints. In particular, at least a part of the compound represented by the following general formula (1) or a food-acceptable salt thereof, although having no flavor or having almost no flavor by itself, the component obtained by heating them in the presence of a protein can enhance a preferable flavor possessed by food and drink products or can reduce an unfavorable flavor. Further, it has been found that the component thus obtained can even simultaneously affect a wide variety of flavors possessed by food and drink products. All of the plurality of embodiments disclosed below are based on this new finding.

[0014]

[0015] (In the general formula (1), R １ , R ２ , R ３ , R ４Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ (This indicates a methyl group or a carboxyl group.)

[0016] If the compound represented by general formula (1) has optical isomers, either enantiomer may be used. A racemic mixture may also be used, or a mixture in which either enantiomer is present in excess may be used.

[0017] Compounds represented by general formula (1) are R １ , R ２ , R ３ , R ４ None of them have to be hydroxyl groups, R １ , R ２ , R ３ , R ４ Only one of them may be a hydroxyl group. Compounds represented by general formula (1) are R １ , R ２ , R ３ , R ４ None of them have to be methyl groups, R １ , R ２ , R ３ , R ４ Only one or two of them may be methyl groups. In a compound represented by general formula (1), R １ , R ２ , R ３ , R ４ At least one of them may be a methyl group or a hydroxyl group. In a compound represented by general formula (1), R １ and R ２ At least one of them may be a methyl group or a hydroxyl group. In a compound represented by general formula (1), R １ and R ２ One of them may be a methyl group and the other a hydroxyl group. In one embodiment, the compound represented by general formula (1) is R １ , R ２ , R ３ , R ４ It does not contain a hydroxyl group, and R ５ Is it a carboxyl group, or R １ , R２ , R ３ , R ４ At least one of them is a hydroxyl group, and R ５ is a methyl group or a carboxyl group. In one embodiment, the compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ (B) In general formula (1), R １ , R ２ , R ３ , R ４ (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

[0018] The compound represented by general formula (1) may be at least one selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol (3-hydroxy-3-methylglutaric acid), 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

[0019] The food-grade salts of the compound represented by general formula (1) may be, for example, sodium salts, potassium salts, calcium salts, magnesium salts, or other food-grade salts. "Food-grade salts" refer to salts that are acceptable for food hygiene purposes (salts acceptable for consumption), and are considered safe for human consumption under food regulations or legal systems in each country or region.

[0020] In one embodiment, the compound represented by general formula (1) or a food-grade salt thereof is meglutol or a salt thereof. Meglutol is a compound having the following structure.

[0021]

[0022] Meglutol is known as a drug for treating dyslipidemia, but it was surprising to learn that the component obtained by heating it in the presence of protein has a taste-improving effect.

[0023] In this disclosure, “taste” is a concept that includes tastes perceived by taste buds, etc., of mammals, particularly humans, and flavors that can be perceived when placed in the mouth. In this disclosure, “taste improvement” means improving the taste of food and beverages from various perspectives. For example, in one aspect, “taste improvement” means enhancing at least one selected from the group consisting of sweetness, umami, sourness, saltiness, spiciness, and richness. Here, “spiciness” may be the spiciness of chili peppers or the spiciness of ginger. Also, in another aspect, “taste improvement” means enhancing at least one selected from the group consisting of milky flavor, dashi flavor, egg flavor, fish roe flavor, soybean flavor, ginger flavor, fruit juice flavor, stewed flavor, and coolness. Also, in another aspect, “taste improvement” means reducing at least one selected from the group consisting of astringency, astringency, and bitterness. Furthermore, in some respects, "improved flavor" means reducing at least one selected from the group consisting of retort flavor, spoiled flavor, and grassy taste. "Improved flavor" may also include improving the persistence of acidity while maintaining its intensity. "Improved flavor" may also include improving the persistence of bitterness while reducing its intensity. "Improved flavor" may also include reducing unpleasant tastes derived from potassium chloride. "Improved flavor" may also include enhancing at least one selected from the group consisting of broadness, complexity, and persistence of savory flavor. "Improved flavor" may also include reducing astringent saltiness or improving the persistence of the aftertaste.

[0024] These taste-improving effects are thought to enhance or reduce the taste that food and beverages originally possess. Therefore, the taste-improving compositions or seasonings of this disclosure do not need to have a taste of their own. Furthermore, the strength of the taste-enhancing or reducing effects of the technology of this disclosure may vary depending on the food or beverage in question. For example, if the food or beverage in question has both sour and sweet tastes, such as sweet and sour sauce, the sweetness-enhancing effect may be stronger than the sourness-enhancing effect, resulting in a food or beverage that is perceived as having a strong sweet taste.

[0025] In some respects, applying the technology disclosed herein makes it possible to provide food and beverages with improved taste. In other respects, applying the technology disclosed herein makes it possible to reduce the amount of salt and sugar used in food and beverages while maintaining the saltiness or sweetness, for example, making it possible to provide health-conscious food and beverages.

[0026] [Taste-improving composition] This specification discloses a taste-improving composition (taste-improving agent) containing a compound represented by general formula (1) or a food-grade acceptable salt thereof. The compound represented by general formula (1) may be meglutol. The taste-improving composition is used to improve the taste of food and beverages. The taste-improving composition may, when added to or mixed with food and beverages and heated, cause the compound represented by general formula (1) or a food-grade acceptable salt contained in the composition to react with proteins contained in the food and beverages to exhibit a taste-improving effect. Alternatively, the taste-improving composition may be intended for adding or mixing with food and beverages a taste-improving seasoning obtained by heating the composition in the presence of proteins beforehand.

[0027] The taste-improving composition is obtained by mixing a compound represented by general formula (1) or a food-grade salt thereof with other components. The compound represented by general formula (1) or a food-grade salt thereof may be commercially available or chemically synthesized. Furthermore, the compound represented by general formula (1) or a food-grade salt thereof may be obtained by extraction or concentration from natural raw materials such as plants. The compound represented by general formula (1) or a food-grade salt thereof may also be produced by microbial culture.

[0028] The taste-improving composition may be in the form of a powder or granules, a paste, a liquid, or any other form.

[0029] The content of the compound represented by general formula (1) or its food-grade acceptable salt in the taste-improving composition is determined appropriately according to the intended use and is not particularly limited. For example, the content of the compound represented by general formula (1) or its food-grade acceptable salt in the taste-improving composition may be 50% by mass or less, 10% by mass or less, 1% by mass or less, or 0.1% by mass or less. Furthermore, the content of the compound represented by general formula (1) or its food-grade acceptable salt in the taste-improving composition may be 0.00000001% by mass or more, 0.0000001% by mass or more, 0.000001% by mass or more, or 0.00001% by mass or more. Typically, the compound represented by general formula (1) or its food-grade acceptable salt can exhibit a taste-improving effect even in very small amounts.

[0030] For example, the content of the compound represented by general formula (1) or a food-grade salt of it in the taste-improving composition may be in the range of 0.00000001% by mass or more and 50% by mass or less, in the range of 0.0000001% by mass or more and 10% by mass or less, in the range of 0.000001% by mass or more and 1% by mass or less, or in the range of 0.00001% by mass or more and 0.1% by mass or less.

[0031] The flavor-improving composition may contain, in addition to the compound represented by general formula (1) or a food-grade salt thereof, other ingredients such as water, dietary fiber, sugars, protein, flour, fruit juice, vegetables, oils and fats, seasonings, spices, pigments, flavors and enzymes.

[0032] If the taste-improving composition contains glucose, fructose, or sucrose, the taste-improving composition contains 100 × 10 parts by mass of the total of glucose, fructose, and sucrose, in addition to the compound represented by general formula (1) or a food-grade salt thereof. －６ It may contain more than parts by mass, 200 x 10 －６ It may contain more than parts by mass, 400 x 10 －６ It may contain more than 600 parts by mass, 600 x 10 －６ It may contain more than parts by mass, 800 x 10 －６ It may contain more than 1,000 parts by mass, and 1,000 × 10 －６ It may contain more than parts by mass, such as 1,500 × 10 －６ It may contain more than parts by mass, 2,000 × 10 －６ It may contain more than parts by mass. Note that all of the above conditions include the case where the taste-improving composition contains no glucose, fructose, or sucrose at all. Sugars can undergo the Maillard reaction when heated in the presence of proteins, potentially affecting the color and taste of food and beverages. Typically, the lower the content of glucose, fructose, and sucrose in the taste-improving composition, the more effectively the Maillard reaction can be suppressed. Furthermore, the presence of sugars can inhibit the reaction between the taste-improving composition and proteins. Typically, the lower the content of glucose, fructose, and sucrose in the taste-improving composition, the easier it is for the taste-improving effect to be exhibited.

[0033] The taste-improving composition may be manufactured by obtaining a compound represented by general formula (1) or a food-grade salt thereof as a pure substance or close to it, and mixing it with other components. Alternatively, the taste-improving composition may be an extract or powder produced by subjecting a natural raw material containing the compound represented by general formula (1) or a food-grade salt thereof to processes such as extraction, purification, concentration, or powdering.

[0034] Taste-improving compositions, especially when produced from natural raw materials such as plants, may be produced by a step of adjusting the content of the compound represented by general formula (1) or a food-grade salt thereof, preferably by a step of selectively adjusting the content of the compound represented by general formula (1) or a food-grade salt thereof. Taste-improving compositions may also be produced by a step of increasing the ratio of the content of the compound represented by general formula (1) or a food-grade salt thereof to other components excluding water. Alternatively, taste-improving compositions may be produced by a step of increasing the ratio of the content of the compound represented by general formula (1) or a food-grade salt thereof to glucose, fructose, or sucrose. Such a step may be a step of selectively removing glucose, fructose, or sucrose. Those skilled in the art can carry out these steps using conventional separation or purification techniques known in the field of chemical processes. Separation or purification may include, for example, filtration, distillation, fractional distillation, recrystallization, extraction, sublimation, and chromatography. Chromatography may include normal-phase chromatography, reverse-phase chromatography, adsorption chromatography, ion-exchange chromatography, size-removal chromatography, and affinity chromatography.

[0035] [Flavor-improving seasonings] This specification also discloses flavor-improving seasonings containing a heat reaction product of a compound represented by general formula (1) or a food-grade salt thereof with a protein. The compound represented by general formula (1) may be at least one selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol (3-hydroxy-3-methylglutaric acid), 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid. The compound represented by general formula (1) may also be meglutol. Such flavor-improving seasonings may be produced by heating the compound represented by general formula (1) or a food-grade salt thereof in the presence of a protein. Alternatively, such a process may be carried out by adding or mixing a protein to the above-described flavor-improving composition and then heating it. When a flavor-improving composition used in a flavor-improving seasoning contains glucose, fructose, or sucrose, the flavor-improving composition contains 100 × 10 parts by mass of the total of glucose, fructose, and sucrose, in the amount of the compound represented by general formula (1) or a food-grade salt thereof. －６ It may contain more than parts by mass, 200 x 10 －６ It may contain more than parts by mass, 400 x 10 －６ It may contain more than 600 parts by mass, 600 x 10 －６ It may contain more than parts by mass, 800 x 10 －６ It may contain more than 1,000 parts by mass, and 1,000 × 10 －６ It may contain more than parts by mass, such as 1,500 × 10 －６ It may contain more than parts by mass, 2,000 × 10 －６ It may contain parts by mass or more. The flavor-improving seasoning may be made by adding or mixing such a flavor-improving composition with protein and heating it, after which sugars including glucose, fructose, or sucrose may be added.

[0036] The protein used may be any protein that is food-grade acceptable. The protein may be derived from animal sources, plant sources, fungi, or a mixture of these.

[0037] Animal-derived ingredients may include meat, poultry, insects, seafood, milk or dairy products, eggs or egg products, or gelatin. Meat may include meat from cattle, pigs, sheep, goats, or horses. Poultry may include meat from chickens, turkeys, ducks, geese, or quail. Seafood may include fish, crustaceans, or mollusks (shellfish, octopuses, squid). Animal-derived ingredients may also include meat, organs, bones, skin, eggs, or milk from meat, poultry, or seafood, or their extracts or powders. Animal-derived ingredients may also include extracts to which fats or emulsifiers have been added, such as in a white broth. Dairy products may include milk, cream, cheese, yogurt, or butter.

[0038] The plant-based raw material may be legumes, grains, nuts, or vegetables. Legumes may be edible beans belonging to genera such as soybeans, peas, broad beans, chickpeas, cowpeas, kidney beans, lentils, or peanuts. Legumes may be soybeans, peas, broad beans, adzuki beans, chickpeas, kidney beans, or lentils. The plant-based raw material may also be processed legume products. Processed legume products may be fermented foods such as soy sauce, miso, moromi, and natto, or they may be soy milk, okara, tofu, kinako, roasted beans, etc. Grains may be wheat, barley, oats, rye, buckwheat, corn, or rice, or processed products thereof. The nuts and seeds may be almonds, peanuts, pistachios, chestnuts, walnuts, coconuts, sunflowers, ginkgo nuts, hazelnuts, sesame seeds, or chia seeds, or processed products thereof. The vegetables may be broccoli, asparagus, bracken, fiddlehead ferns, garlic, water chestnuts, Brussels sprouts, or molokhia, or processed products thereof.

[0039] The fungi may be mushrooms such as shiitake or button mushrooms, or they may be cultures of yeasts or filamentous fungi.

[0040] The proteins used may have molecular weights of, for example, 1,000 to 100,000, 2,000 to 80,000, or 3,000 to 50,000. However, the molecular weight of the protein is not limited to these ranges. Furthermore, a mixture of multiple proteins with different molecular weights may be used.

[0041] In the preparation of a flavor-improving seasoning, the mass ratio of the compound represented by general formula (1) or its food-grade salt to the protein is such that, if A is the mass of the compound represented by general formula (1) or its food-grade salt, and B is the mass of the protein, then for example, A:B = 1:10,000 (1 × 10⁻¹⁰). ４ ) ~ 1: 1,000,000,000 (1 x 10 ９ ) may also be A:B = 1:100,000 (1 × 10 ５ ) ~ 1:100,000,000 (1 x 10 ８ ) is also acceptable.

[0042] The heating reaction between a compound represented by general formula (1) or a food-grade salt thereof and a protein may be carried out in the presence of fat. The fat may be present in an emulsified state. Typically, the effect of the resulting flavor-improving seasoning tends to be enhanced when the heating reaction is carried out in the presence of fat, preferably emulsified fat.

[0043] The heating conditions for heating a compound represented by general formula (1) or a food-grade salt thereof in the presence of protein are not particularly limited. The heating temperature may be, for example, in the range of 50°C to 100°C or 80°C to 100°C under normal pressure, or in the range of 100°C to 150°C under pressure. The heating time may be, for example, 10 minutes or more, 20 minutes or more, 30 minutes or more, or 50 minutes or more. The pH during the reaction may be, for example, in the range of 4 to 10.

[0044] The flavor-enhancing seasoning may be produced by a step of adjusting the content of a heat reaction product between a compound represented by general formula (1) or a food-grade salt of a protein and a protein, preferably a step of selectively adjusting the content of the heat reaction product. The flavor-enhancing seasoning may also be produced by a step of increasing the ratio of the content of the heat reaction product to other components excluding water. Those skilled in the art can carry out these steps using conventional separation or purification techniques known in the field of chemical processes. For separation or purification, for example, filtration, distillation, fractional distillation, recrystallization, extraction, sublimation, chromatography, etc. As for chromatography, normal-phase chromatography, reverse-phase chromatography, adsorption chromatography, ion exchange chromatography, size removal chromatography, affinity chromatography, etc., may be used.

[0045] [Method for Improving the Taste of Food and Beverages] This specification also discloses a method for improving the taste of food and beverages using a compound represented by general formula (1) or a food-grade salt thereof. This specification also discloses a method for using a compound represented by general formula (1) or a food-grade salt thereof to improve the taste of food and beverages. The compound represented by general formula (1) may be at least one selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol (3-hydroxy-3-methylglutaric acid), 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid. The compound represented by general formula (1) may also be meglutol.

[0046] This method or method of use may be carried out by adding or mixing a compound represented by general formula (1) or a food-grade salt thereof to food or beverage and heating it with the protein contained in the food or beverage, or by adding or mixing a heat reaction product obtained by pre-reacting a compound represented by general formula (1) or a food-grade salt thereof with protein to food or beverage. This method or method of use may also be carried out using the above-mentioned taste-improving composition or taste-improving seasoning.

[0047] Typically, this method or use enhances or reduces the flavor inherent in food and beverages. This method or use may enhance sweetness. This method or use may enhance umami. This method or use may enhance sourness. This method or use may enhance saltiness. This method or use may enhance spiciness. This method or use may enhance richness.

[0048] This method or method of use may be intended to enhance the milk flavor. This method or method of use may be intended to enhance the dashi flavor. This method or method of use may be intended to enhance the egg flavor. This method or method of use may be intended to enhance the fish roe flavor. This method or method of use may be intended to enhance the soybean flavor. This method or method of use may be intended to enhance the ginger flavor. This method or method of use may be intended to enhance the fruit juice flavor. This method or method of use may be intended to enhance the stewed flavor. In this specification, "stewed flavor" means a state in which multiple flavors are harmonized without each individual flavor of the raw materials standing out. In stewed dishes, the state in which a sense of harmony or mellowness created by heating is felt may be expressed as "stewed flavor." This method or method of use may be intended to enhance the coolness.

[0049] This method or method of use may be intended to reduce astringency. This method or method of use may be intended to reduce bitterness. This method or method of use may be intended to reduce retort flavor. This method or method of use may be intended to reduce spoilage flavor. This method or method of use may be intended to reduce grassy odor.

[0050] In some respects, applying this method or usage method makes it possible to provide food and beverages with improved taste. In other respects, applying this method or usage method makes it possible to reduce the amount of salt and sugar used in food and beverages while maintaining the saltiness or sweetness, for example, making it possible to provide health-conscious food and beverages.

[0051] In this method or use, the compound represented by general formula (1) or a food-grade salt thereof is heated together with the protein at either the stage before or after it is added to or mixed with the food or beverage in question to form a heat reaction product. Since the effect is either absent or limited when the compound represented by general formula (1) or a food-grade salt thereof is used alone, or when the compound represented by general formula (1) or a food-grade salt thereof coexists with the protein in an unheated state, it is considered that the aforementioned heat reaction product contributes to the improvement of taste. During the heat reaction, the carboxyl group of the compound represented by general formula (1) may form peptide bonds with specific amino groups of the protein. However, the techniques of this disclosure are not bound by any speculation or theory.

[0052] The heating conditions for heating a compound represented by general formula (1) or a food-grade salt thereof in the presence of protein are not particularly limited. The heating temperature may be, for example, in the range of 50°C to 100°C or 80°C to 100°C under normal pressure, or in the range of 100°C to 150°C under pressure. The heating time may be, for example, 10 minutes or more, 20 minutes or more, 30 minutes or more, or 50 minutes or more. The pH during the reaction may be, for example, in the range of 4 to 10.

[0053] In this method or method of use, the mass of the compound represented by general formula (1) or its salt used, relative to the mass of the final food or beverage product, may be within the range of 0.1 ppb to 10,000 ppb, 0.5 ppb to 1,000 ppb, or 1 ppb to 100 ppb.

[0054] If this method or method of use is carried out using a composition containing a compound represented by general formula (1) or a food-safe salt thereof, such a composition may be produced by adjusting the content of the compound represented by general formula (1) or a food-safe salt thereof in the composition, preferably by selectively adjusting the content of the compound represented by general formula (1) or a food-safe salt thereof. Alternatively, the composition may be produced by increasing the ratio of the content of the compound represented by general formula (1) or a food-safe salt thereof to other components other than water. Alternatively, the composition may be produced by increasing the ratio of the content of the compound represented by general formula (1) or a food-safe salt thereof to glucose, fructose, or sucrose. Such a step may be a step of selectively removing glucose, fructose, or sucrose. Those skilled in the art can carry out these steps using ordinary separation or purification techniques known in the field of chemical processes. For example, filtration, distillation, fractional distillation, recrystallization, extraction, sublimation, chromatography, etc., may be used for separation or purification. Chromatographic methods such as normal-phase chromatography, reverse-phase chromatography, adsorption chromatography, ion exchange chromatography, size removal chromatography, and affinity chromatography may be used.

[0055] [Food and Beverages] This specification also discloses food and beverages containing a heat reaction product of a compound represented by general formula (1) or a food-grade salt thereof with a protein. Food and beverages may be of any kind. Examples of food and beverages include seasonings such as noodle soup and sauces; beverages such as coffee, tea, juice, and soy milk; desserts such as coffee jelly and yogurt; foods obtained by simmering such as stews, clam chowder, and soups; foods obtained by steaming such as chawanmushi; and these in the form of room temperature foods, refrigerated foods, frozen foods, freeze-dried foods, and retort foods, but are not limited to these.

[0056] In this specification, any specific feature described in any embodiment relating to each aspect of the present disclosure may be arbitrarily combined to form a new embodiment, and such new embodiments should be understood to be included in each aspect of the present disclosure.

[0057] The technology of this disclosure will be described in more detail below with reference to examples, etc., but the technology of this disclosure is not limited in any way by these examples, etc. In the following, for convenience, the terms "examples" and "comparative examples" are used, but the term "comparative examples" does not necessarily mean that the compositions, etc., relating to the comparative examples do not belong to the technology of this disclosure.

[0058] [Preparation] (Preparation of Meglutol aqueous solution) Meglutol (3-hydroxy-3-methylglutaric acid, distributor: Merck Ltd.) was dissolved in pure water to prepare a 0.001% by mass aqueous solution and a 0.01% by mass aqueous solution.

[0059] (Preparation of Milk Sample 1) Of the raw materials shown in Table 1, all except monosodium glutamate (distributor: Ajinomoto Co., Inc.) and nucleic acid-based seasoning (distributor: Ajinomoto Co., Inc., product name: Double Plus) were mixed, placed in a sealed container, and heated in a 100°C water bath for 90 minutes. After cooling to room temperature, monosodium glutamate and nucleic acid-based seasoning were added as shown in Table 1, and the mixture was placed in a sealed container again and heated in a 100°C water bath for 30 minutes to obtain Milk Sample 1-1 and Milk Sample 1-2.

[0060]

[0061] (Preparation of Milk Sample 2) The raw materials shown in Table 2 were mixed, placed in a sealed container, and heated in a 100°C water bath for 90 minutes to obtain Milk Sample 2-1 and Milk Sample 2-2.

[0062]

[0063] (Preparation of Gelatin Samples) Gelatin (manufacturer: Nitta Gelatin Co., Ltd., product name: APH-100) and pure water were mixed in the ratios shown in Table 3, and the mixture was heated in an 80°C water bath to completely dissolve the gelatin. After cooling to room temperature, the amount of Meglutol aqueous solution shown in Table 3 was added. This mixture was divided into two portions. One portion was placed in a sealed container and heated in a 100°C water bath for 90 minutes to obtain Gelatin Sample 2. The other portion was not heated and was designated as Gelatin Sample 1.

[0064]

[0065] (Preparation of Soy Milk Sample 1) The raw materials shown in Table 4 were mixed, placed in a sealed container, and heated in a 100°C water bath for 90 minutes to obtain Soy Milk Sample 1-1 and Soy Milk Sample 1-2. Unprocessed soy milk (manufacturer: Kikkoman Corporation) was used as the soy milk.

[0066]

[0067] (Preparation of Soy Milk Sample 2) The raw materials shown in Table 5 were mixed. As for the soy milk, unadjusted soy milk (manufacturer: Kikkoman Corporation) was used. Soy milk sample 2-1 was not heated, while soy milk samples 2-2 and 2-3 were placed in sealed containers and heated in a 100°C water bath for 90 minutes.

[0068]

[0069] (Preparation of Soy Sauce Samples) The raw materials shown in Table 6 were mixed. Dark soy sauce (manufacturer: Kikkoman Corporation) was used as the soy sauce. Soy sauce sample 1 was not heated. Soy sauce samples 2 and 3 were placed in sealed containers and heated in a 100°C water bath for 60 minutes.

[0070]

[0071] (Preparation of Chicken Samples) Raw materials containing chicken extract (manufacturer: Japan Ecology Thinking Co., Ltd., product name: CBC-45) were mixed in the proportions shown in Table 7. Chicken sample 1 was not heated. Chicken sample 2 was placed in a sealed container and heated in a 100°C water bath for 90 minutes.

[0072]

[0073] [Method for evaluating taste] (Evaluation in stew) Using commercially available stew mix (manufacturer: House Foods Corporation, product name: House Stew Mix Cream), the ingredients were mixed in the proportions shown in Table 8. After heating in a 50°C water bath for 5 minutes to dissolve all the powder, the mixture was heated in a 100°C water bath for 10 minutes to obtain the stews of Comparative Example 1 and Example 1.

[0074]

[0075] After cooling to room temperature, a sensory evaluation was conducted by a panel of 12 experts. Comparative Example 1 was used as the standard, and the intensity of saltiness, sweetness, umami, and richness (breadth, complexity, and persistence) of the stew from Example 1 was compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0076] (Evaluation of soy milk) Soy milk sample 1-1 was designated as Comparative Example 2, and soy milk sample 1-2 was designated as Example 2. After cooling to room temperature, sensory evaluation was conducted by a panel of 12 experts. Comparative Example 2 was used as the standard, and the saltiness, sweetness, umami, richness (breadth, complexity, persistence), and bitterness intensity of the soy milk in Example 2 were compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0077] (Evaluation of clam chowder) Using a commercially available clam chowder mix (manufacturer: House Foods Corporation, product name: Hokkaido Chowder Clam Chowder mix), the raw materials were mixed in the proportions shown in Table 9. After heating in a 55°C water bath for 5 minutes to dissolve all the powder, the mixture was heated at 100°C for 3 minutes to obtain the clam chowders of Comparative Example 3 and Example 3.

[0078]

[0079] After cooling to room temperature, a sensory evaluation was conducted by an 11-member expert panel. Comparative Example 3 was used as the standard, and the sweetness, umami, richness (breadth, complexity, and persistence), and bitterness intensity of Example 3's clam chowder were compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0080] (Evaluation of yogurt) Using a commercially available yogurt starter culture (manufacturer: Fujikko Co., Ltd., product name: Caspian Sea Yogurt Homemade Starter Culture Set), the raw materials were mixed in the proportions shown in Table 10. Fermentation was carried out in a 30°C constant temperature oven for 24 hours to obtain the yogurts of Comparative Example 4 and Example 4.

[0081]

[0082] A sensory evaluation was conducted by a panel of four experts. Comparative Example 4 was used as the standard, and the sweetness and richness (breadth, complexity, and persistence) of the yogurt in Example 4 were compared to the standard on a five-point scale (-2: clearly weaker, -1: weaker, 0: about the same as the standard, +1: stronger, +2: clearly stronger). The results are described below.

[0083] (Evaluation of curry soup) Using commercially available soup curry mix (manufacturer: Hokkai Yamato Co., Ltd., product name: Sapporo Soup Factory Soup Curry), the ingredients were mixed in the proportions shown in Table 11. The mixture was heated in a 40°C water bath for 5 minutes to dissolve all the powder and obtain the curry soups of Comparative Example 5 and Example 5.

[0084]

[0085] After cooling to room temperature, a sensory evaluation was conducted by a panel of eight experts. Comparative Example 5 was used as the standard, and the richness (breadth, complexity, and persistence) and spiciness intensity of the curry soup of Example 5 were compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0086] (Evaluation of coffee jelly) Gelatin (manufacturer: Morinaga & Co., Ltd., product name: Morinaga Cook Gelatin) was swollen with water in the proportions shown in Table 12, and the remaining ingredients, including commercially available instant coffee (manufacturer: UCC Ueshima Coffee Co., Ltd.), were mixed in. The mixture was then heated in an 80°C water bath for 3 minutes until the gelatin dissolved to prepare the coffee jelly liquid. After that, the mixture was mixed with the gelatin sample in the proportions shown in Table 13, and then chilled in a refrigerator for 3 hours to solidify, obtaining the coffee jellies of Comparative Example 6 and Example 6.

[0087]

[0088]

[0089] After cooling to room temperature, sensory evaluation was conducted by a panel of 8 or 12 experts. Comparative Example 6 was used as the standard, and the sweetness, acidity (intensity and persistence), bitterness (intensity and persistence), and body (breadth, complexity, and persistence) of the coffee jelly of Example 6 were compared to the standard on a 5-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0090] (Evaluation of coffee) Using commercially available instant coffee (manufacturer: UCC Ueshima Coffee Co., Ltd.), the raw materials were mixed in the proportions shown in Table 14. The mixture was heated in a 40°C water bath for 3 minutes to completely dissolve the powder and obtain the coffees of Comparative Example 7 and Example 7.

[0091]

[0092] After cooling to room temperature, a sensory evaluation was conducted by a panel of eight experts. Comparative Example 7 was used as the standard, and the bitterness (intensity and persistence) of the coffee in Example 7 was compared to the standard on a five-point scale (-2: clearly weaker, -1: weaker, 0: about the same as the standard, +1: strong, +2: clearly stronger). The results are described below.

[0093] (Evaluation of orange juice) Using commercially available 100% fruit juice orange juice (manufacturer: Tomoe Dairy Co., Ltd.), the raw materials were mixed in the proportions shown in Table 15 to obtain the orange juices of Comparative Examples 8 and 9 and Example 8.

[0094]

[0095] Sensory evaluation was conducted on evaluation samples at room temperature by a panel of five experts. Comparative Example 8 was used as the standard, and the sweetness intensity of the orange juice from Comparative Example 9 and Example 8 was compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0096] (Evaluation of noodle soup base) Using authentic mirin (manufacturer: Kikkoman Corporation) and granulated dashi stock (manufacturer: Ajinomoto Co., Inc., product name: Hondashi Bonito and Kombu Blended Dashi), the raw materials were mixed in the proportions shown in Table 16, and then heated in a 60°C water bath for 5 minutes to dissolve all the powder, obtaining the noodle soup bases of Comparative Examples 10 and 11 and Example 9.

[0097]

[0098] After cooling to room temperature, sensory evaluation was conducted by a panel of five experts. Comparative Example 10 was used as the standard, and the saltiness and umami intensity of the noodle soup from Comparative Example 11 and Example 9 were compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0099] (Evaluation of chicken stock) Using commercially available granulated chicken stock powder (manufacturer: Ajinomoto Co., Inc., product name: Marutori Gara Soup), the raw materials were mixed in the proportions shown in Table 17, heated in a 60°C water bath for 5 minutes to completely dissolve, and the chicken stocks of Comparative Examples 12, 13 and Example 10 were obtained.

[0100]

[0101] After cooling to room temperature, sensory evaluation was conducted by a panel of five experts. Comparative Example 12 was used as the standard, and the chicken broths of Comparative Example 13 and Example 10 were compared to the standard in terms of the intensity of umami and unpleasant taste derived from potassium chloride on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0102] (Evaluation in Chawanmushi) Using granulated bonito stock powder (manufacturer: Riken Vitamin Co., Ltd., product name: Sozai Ryoku Dashi Honkatsuo Dashi), the raw materials were mixed in the proportions shown in Table 18, then heated in a 60°C water bath for 5 minutes to completely dissolve, and broths 1 to 3 were prepared. The egg mixture obtained by mixing the raw materials in the proportions shown in Table 19 was filtered through a sieve, then dispensed into heat-resistant containers, and heated in a steamer for 13 minutes to obtain the chawanmushi of Comparative Examples 14 and 15 and Example 11.

[0103]

[0104]

[0105] After cooling to room temperature, sensory evaluation was conducted by a panel of five experts. Comparative Example 14 was used as the standard, and the chawanmushi (steamed egg custard) of Comparative Example 15 and Example 11 were compared to the standard in terms of umami, saltiness, and persistence of aftertaste, with the intensity rated on a five-point scale (-2: clearly weak, -1: weak, 0: similar to the standard, +1: strong, +2: clearly strong). The results are described below.

[0106] (Evaluation of Ponzu Sauce) Using commercially available ponzu sauce (manufacturer: Mizkan Co., Ltd., product name: Ajipon), the raw materials were mixed in the proportions shown in Table 20 to obtain the ponzu sauces of Comparative Examples 16 and 17 and Example 12.

[0107]

[0108] Sensory evaluation was conducted on evaluation samples at room temperature by a panel of five experts. Comparative Example 16 was used as the standard, and the acidity intensity of the ponzu sauces from Comparative Example 17 and Example 12 was compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0109] (Evaluation of mentaiko sauce) Using commercially available mentaiko sauce (manufacturer: Nissui Co., Ltd., product name: raw pickled spicy mentaiko sauce), the raw ingredients were mixed in the proportions shown in Table 21 to obtain the mentaiko sauces of Comparative Examples 18 and 19 and Example 13.

[0110]

[0111] Sensory evaluation was conducted on evaluation samples at room temperature by a panel of five experts. Comparative Example 18 was used as the standard, and the spiciness (chili pepper spiciness) of the mentaiko sauces of Comparative Example 19 and Example 13 was compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0112] (Evaluation of Ginger Chinese Soup) Using commercially available granulated chicken stock powder (manufacturer: Ajinomoto Co., Inc., product name: Marutori Gara Soup) and grated ginger (manufacturer: S&B Foods Co., Ltd., product name: Flavor Recommended Grated Raw Ginger), the ingredients were mixed in the proportions shown in Table 22, heated in a 60°C water bath for 5 minutes to completely dissolve, and ginger Chinese soups of Comparative Examples 20, 21 and Example 14 were obtained.

[0113]

[0114] After cooling to room temperature, sensory evaluation was conducted by a panel of five experts. Comparative Example 20 was used as the standard, and the spiciness (ginger spiciness) of the soups from Comparative Example 21 and Example 14 was compared to the standard on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0115] (Evaluation of chicken soup) After mixing the raw materials in the proportions shown in Table 23, the mixture was heated in a 60°C water bath for 5 minutes to completely dissolve the ingredients, yielding the chicken soups of Comparative Examples 22 and 23 and Examples 15 and 16.

[0116]

[0117] After cooling to room temperature, sensory evaluation was conducted by a panel of five experts. Comparative Example 22 was used as the standard, and the soups of Comparative Example 23 and Examples 15 and 16 were compared to the standard in terms of the intensity of richness (breadth, complexity, and persistence) on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong).

[0118] [Results of sensory evaluation of taste] The results of the sensory evaluation described above are shown in Tables 24 to 30.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] [Other methods for evaluating taste and flavor] (Evaluation A in stew) The raw materials were mixed in the proportions shown in Table 31. After heating in a 50°C water bath for 5 minutes to dissolve all the powder, comparative example 24 was heated in a 100°C water bath for 30 minutes, and comparative example 25 and Example 17 were heated in a 100°C water bath for 10 minutes to obtain evaluation samples.

[0127]

[0128] After cooling to room temperature, a sensory evaluation was conducted by a panel of 12 experts. Comparative Example 24 was used as the standard, and the stews of Comparative Example 25 and Example 17 were compared to the standard in terms of the intensity of the "cooked" feel (a state in which the flavors of each ingredient do not stand out, and a sense of harmony and mellowness created by heating is felt), which was evaluated on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0129] (Evaluation B for stew) The raw materials were mixed in the proportions shown in Table 32. After heating in a 50°C water bath for 5 minutes to dissolve all the powder, the mixture was heated in a 100°C water bath for 10 minutes to obtain the stews of Comparative Examples 26 and 27 and Example 18.

[0130]

[0131] After cooling to room temperature, a sensory evaluation was conducted by a panel of 12 experts. Comparative Example 26 was used as the standard, and the stews of Comparative Example 27 and Example 18 were compared to the standard. The intensity of the desirable milk flavor (the fresh flavor of raw milk) and the heat-degraded milk flavor (the undesirable flavor that occurs when milk is heated) was evaluated on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0132] (Evaluation of soy milk) Soy milk sample 2-1 was designated as Comparative Example 28, soy milk sample 2-2 as Comparative Example 29, and soy milk sample 2-3 as Example 19.

[0133] After cooling to room temperature, a sensory evaluation was conducted by a panel of 12 experts. Comparative Example 28 was used as the standard, and the soy milk of Comparative Example 29 and Example 19 were compared to the standard. The intensity of the desirable soy flavor (the desirable bean flavor and richness inherent in soybeans) and the grassy soy odor (the undesirable grassy flavor that occurs when soybeans are heated) was evaluated on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0134] (Evaluation of clam chowder) The same evaluation samples as in Comparative Example 3 and Example 3 were used. After cooling to room temperature, sensory evaluation was performed by an 11-person expert panel. Comparative Example 3 was used as the standard, and the intensity of the clam broth flavor in the clam chowder of Example 3 was evaluated on a 5-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0135] (Evaluation of Orange Juice) The same evaluation samples as in Comparative Example 9 and Example 8 were used. After the evaluation samples were brought to room temperature, sensory evaluation was performed by a panel of five experts. Comparative Example 8 was used as the standard, and the orange juice from Comparative Example 9 and Example 8 was compared and evaluated on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0136] (Evaluation of noodle soup base) The same evaluation samples as in Comparative Examples 10 and 11 and Example 9 were used. After cooling to room temperature, sensory evaluation was performed by a panel of five experts. Comparative Example 10 was used as the standard, and the intensity of the Japanese-style dashi flavor in the noodle soup bases of Comparative Example 11 and Example 9 was compared on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0137] (Evaluation of Chawanmushi) The same evaluation samples as in Comparative Examples 14 and 15 and Example 11 were used. After cooling to room temperature, sensory evaluation was performed by a panel of five experts. Comparative Example 14 was used as the standard, and the intensity of the bonito broth flavor and egg flavor of the chawanmushi from Comparative Example 15 and Example 11 was compared on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0138] (Evaluation of Mentaiko Sauce) The same evaluation samples as in Comparative Examples 18 and 19 and Example 13 were used. After the evaluation samples were brought to room temperature, sensory evaluation was performed by a panel of five experts. Comparative Example 18 was used as the standard, and the intensity of the fish roe flavor in the mentaiko sauces of Comparative Example 19 and Example 13 was compared on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results will be described later.

[0139] (Evaluation of Ginger Chinese Soup) The same evaluation samples as in Comparative Examples 20, 21 and Example 14 were used. After the evaluation samples were brought to room temperature, sensory evaluation was performed by a panel of five experts. Comparative Example 20 was used as the standard, and the ginger flavor intensity of the soups from Comparative Example 21 and Example 14 was compared on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0140] (Evaluation of vegetable juice) Using commercially available vegetable juice (manufacturer: Zen-Noh High Pack Co., Ltd., product name: Concentrated Vegetables for One Day), the raw materials were mixed in the proportions shown in Table 33 to obtain the vegetable juices of Comparative Examples 30, 31 and Example 20.

[0141]

[0142] After the evaluation samples were brought to room temperature, a sensory evaluation was conducted by a panel of five experts. Comparative Example 30 was used as the standard, and the vegetable juices of Comparative Example 31 and Example 20 were compared to the standard in terms of the intensity of the grassy odor of the vegetables on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0143] (Evaluation of Mint Tea) Mint tea was extracted using commercially available mint tea leaves (distributor: Kataoka Bussan Co., Ltd., product name: TWININGS Pure Herb Tea Peppermint) according to the manufacturer's recommended procedure. The raw materials were mixed in the proportions shown in Table 34 to obtain the mint teas of Comparative Examples 32 and 33 and Example 21.

[0144]

[0145] After the evaluation samples were brought to room temperature, a sensory evaluation was conducted by a panel of five experts. Comparative Example 32 was used as the standard, and the mint tea of ​​Comparative Example 33 and Example 21 were compared to the standard, with the intensity of the mint's cooling sensation evaluated on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0146] (Evaluation of egg soup) Using commercially available granulated chicken stock powder (manufacturer: Ajinomoto Co., Inc., product name: Marutori Gara Soup), the ingredients were mixed in the proportions shown in Table 35. The mixture was sealed in a heat-resistant and pressure-resistant pouch. Comparative Example 34 was heated in a 100°C water bath for 10 minutes, while Comparative Examples 35, 36, and Examples 22 and 23 were sterilized by pressurized heating at 121°C for 15 minutes using a retort sterilizer.

[0147]

[0148] After the evaluation samples were brought to room temperature, a sensory evaluation was conducted by a panel of five experts. Comparative Example 34 was used as the standard, and the soups of Comparative Examples 35 and 36, and Examples 22 and 23 were compared to the standard in terms of the intensity of the retort flavor (an unpleasant flavor caused by overheating characteristic of retort foods) on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong). The results are described below.

[0149] (Evaluation of chicken and onion soup) The ingredients were mixed in the proportions shown in Table 36, stir-fried in a frying pan, and then allowed to cool. The stir-fried chicken breast and onion mixture, which was 88% of the weight before heating, and commercially available granulated chicken stock (manufacturer: Ajinomoto Co., Inc., product name: Marutori Gara Soup) were used, and the ingredients were mixed in the proportions shown in Table 37. The mixtures were sealed in heat-resistant and pressure-resistant pouches. Comparative Example 37 was heated in a 100°C water bath for 10 minutes, while Comparative Examples 38, 39, and Examples 24 and 25 were sterilized by pressurized heating at 121°C for 15 minutes using a retort sterilizer.

[0150]

[0151]

[0152] After the evaluation samples were brought to room temperature, a sensory evaluation was conducted by a panel of five experts. Comparative Example 37 was used as the standard, and the soups of Comparative Examples 38 and 39, and Examples 24 and 25, were compared to the standard in terms of the intensity of the retort flavor (an unpleasant flavor caused by overheating, which is characteristic of retort foods) on a five-point scale (-2: clearly weak, -1: weak, 0: about the same as the standard, +1: strong, +2: clearly strong).

[0153] [Results of other sensory evaluations such as taste and flavor] The results of the above sensory evaluations are shown in Tables 38 to 41.

[0154]

[0155]

[0156]

[0157]

[0158] [Evaluation of each compound] (Preparation of reaction solution samples) 0.01% by mass aqueous solutions were prepared for each of the compounds represented by general formula (1) (or their salts): glutaric acid (distributor: Fujifilm Wako Pure Chemical Corporation), 2-hydroxyglutaric acid disodium salt (distributor: Fujifilm Wako Pure Chemical Corporation), 3-hydroxyglutaric acid (distributor: Fujifilm Wako Pure Chemical Corporation), meglutol (3-hydroxy-3-methylglutaric acid) (distributor: Sigma-Aldrich), 2-methylglutaric acid (distributor: Sigma-Aldrich), 3-methylglutaric acid (distributor: Sigma-Aldrich), 3,3-dimethylglutaric acid (distributor: Sigma-Aldrich), 2,2-dimethylglutaric acid (distributor: Sigma-Aldrich), and 3-hydroxy-3-methylpentanoic acid (distributor: Sigma-Aldrich). For the sodium salt, the concentration of the portion excluding sodium was prepared to be 0.01% by mass. Gelatin (manufacturer: Nitta Gelatin Co., Ltd., product name: APH-100) and pure water were mixed in the proportions shown in Table 42, heated in an 80°C water bath for 5 minutes to completely dissolve the gelatin, then returned to room temperature, and 0.01% by mass aqueous solutions of the compound represented by general formula (1) were added in the proportions shown in Table 42. These were heated at 100°C for 90 minutes to obtain each reaction solution sample.

[0159]

[0160] (Sensory evaluation) Each aqueous solution for sensory evaluation was prepared by mixing each reaction solution sample, sodium chloride, and pure water in the proportions shown in Table 43.

[0161]

[0162] Using each aqueous solution for sensory evaluation that had returned to room temperature, a panel of 12 experts who had received sufficient training in identifying the intensity of umami flavor evaluated the intensity of umami on a five-point scale (0: no umami flavor, 1: slight umami flavor, 2: umami flavor, 3: strong umami flavor, 4: very strong umami flavor). The results are shown in Table 44.

[0163]

[0164] [Study using meglutol-containing extract derived from natural raw materials] An extract was produced by selectively concentrating meglutol using vegetables as raw materials. The produced extract contained 100 x 10⁶ meglutol per 1 mass of glucose, fructose, and sucrose. －６ It contained more than parts by mass. When a heat reaction product with protein was prepared using such an extract, the same effects were observed as when using each sample in the above-described examples: enhancement of sweetness, umami, sourness, saltiness, spiciness, and richness; enhancement of milky flavor, dashi flavor, egg flavor, stewed flavor, and coolness; reduction of astringency and bitterness; and reduction of retort odor, soybean odor, spoiled odor, and grassy odor.

[0165] Each exemplary embodiment of the present disclosure is described below: [1] A taste-improving composition comprising a compound represented by the following general formula (1) or a food-grade salt thereof. (In general formula (1), R １ , R ２ , R ３ , R ４ Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ (wherein R represents a methyl group or a carboxyl group.) [2] A taste-improving composition according to [1] that enhances at least one selected from the group consisting of sweetness, umami, sourness, saltiness, spiciness, and richness. [3] A taste-improving composition according to [1] or [2] that enhances at least one selected from the group consisting of milk flavor, dashi flavor, egg flavor, fish roe flavor, soybean flavor, ginger flavor, fruit juice flavor, stewed taste, and cool taste. [4] A taste-improving composition according to any of [1] to [3] that reduces astringency or bitterness. [5] A taste-improving composition according to any of [1] to [4] that reduces at least one selected from the group consisting of retort flavor, spoiled flavor, and grassy taste. [6] In a compound represented by general formula (1), R １ , R ２ , R ３ , R ４ It does not contain a hydroxyl group, and R ５ Is it a carboxyl group, or R １ , R ２ , R ３ , R ４At least one of which is a hydroxy group, and R ５ The taste-improving composition according to any one of [1] to [5], wherein is a methyl group or a carboxy group. [7] The taste-improving composition according to any one of [1] to [5], wherein the compound represented by the general formula (1) satisfies at least one of the following (A) to (C). (A) In the general formula (1), R ５ is a carboxy group. (B) In the general formula (1), R １ , R ２ , R ３ , R ４ Any one of is a hydroxy group. (C) The compound represented by the general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid. [8] The taste-improving composition according to any one of [1] to [7], wherein the compound represented by the general formula (1) is meglutol.

[0166] [9] The taste-improving composition according to any one of [1] to [8], which contains 100×10 －６ parts by mass or more of the compound represented by the general formula (1) or a food-acceptable salt thereof with respect to 1 part by mass in total of glucose, fructose, and sucrose.

[10] The taste-improving composition according to any one of [1] to [8], which contains 200×10 －６ parts by mass or more of the compound represented by the general formula (1) or a food-acceptable salt thereof with respect to 1 part by mass in total of glucose, fructose, and sucrose.

[11] The taste-improving composition according to any one of [1] to [8], which contains 400×10 －６ parts by mass or more of the compound represented by the general formula (1) or a food-acceptable salt thereof with respect to 1 part by mass in total of glucose, fructose, and sucrose.

[12] The taste-improving composition according to any one of [1] to [8], which contains 600×10 －６A flavor-improving composition according to any one of [1] to [8], containing at least the mass part. For 1 mass part in total of glucose, fructose, and sucrose, the compound represented by the general formula (1) or its food-acceptable salt is 800×10 －６ A flavor-improving composition according to any one of [1] to [8], containing at least the mass part. For 1 mass part in total of glucose, fructose, and sucrose, the compound represented by the general formula (1) or its food-acceptable salt is 1,000×10 －６ A flavor-improving composition according to any one of [1] to [8], containing at least the mass part. For 1 mass part in total of glucose, fructose, and sucrose, the compound represented by the general formula (1) or its food-acceptable salt is 1,500×10 －６ A flavor-improving composition according to any one of [1] to [8], containing at least the mass part. For 1 mass part in total of glucose, fructose, and sucrose, the compound represented by the general formula (1) or its food-acceptable salt is 2,000×10 －６ A flavor-improving composition according to any one of [1] to [8], containing at least the mass part.

[0167]

[17] A method for producing a flavor-improving composition according to any one of [1] to

[16] , having a step of adjusting the content of the compound represented by the general formula (1) or its food-acceptable salt.

[18] A production method according to

[17] , having a step of increasing the ratio of the content of the compound represented by the general formula (1) or its food-acceptable salt to other components excluding water.

[19] A production method according to

[17] or

[18] , having a step of increasing the ratio of the content of the compound represented by the general formula (1) or its food-acceptable salt to glucose, fructose, or sucrose.

[0168]

[20] A flavor-improving seasoning containing a heat reaction product of a compound represented by general formula (1) or a food-grade salt thereof and a protein.

[21] A method for producing a flavor-improving seasoning, comprising the step of heating a compound represented by general formula (1) or a food-grade salt thereof in the presence of a protein.

[22] In the heating step, the composition to be heated contains 100 × 10 parts by mass of glucose, fructose, and sucrose in total, with the compound represented by general formula (1) or a food-grade salt thereof being added. －６ A method for producing

[21] , comprising parts by mass or more of

[21] .

[23] In the heating step, the composition to be heated contains, with a total of 1 part by mass of glucose, fructose, and sucrose, a compound represented by general formula (1) or a food-grade salt thereof, comprising 200 × 10 －６ A method for producing

[21] , comprising parts by mass or more of

[21] .

[24] In the heating step, the composition to be heated contains, with a total of 1 part by mass of glucose, fructose, and sucrose, a compound represented by general formula (1) or a food-grade salt thereof, comprising 400 × 10 －６ A method for producing

[21] , comprising parts by mass or more of

[21] .

[25] In the heating step, the composition to be heated contains, with a total of 1 part by mass of glucose, fructose, and sucrose, a compound represented by general formula (1) or a food-grade salt thereof, comprising 600 × 10 －６ A method for producing

[21] , comprising parts by mass or more of

[21] .

[26] In the heating step, the composition to be heated contains, with a total of 1 part by mass of glucose, fructose, and sucrose, a compound represented by general formula (1) or a food-grade salt thereof, comprising 800 × 10 －６ A method for producing

[21] , comprising parts by mass or more of

[21] .

[27] In the heating step, the composition to be heated contains, with respect to 1 part by mass of glucose, fructose, and sucrose, 1,000 × 10 －６ A method for producing

[21] , comprising parts by mass or more.

[28] In the heating step, the composition to be heated contains, with respect to 1 part by mass of glucose, fructose, and sucrose, 1,500 × 10－６ A method for producing

[21] , comprising parts by mass or more.

[29] In the heating step, the composition to be heated contains, with a total of 1 part by mass of glucose, fructose, and sucrose, 2,000 × 10⁻¹⁶ parts by mass of a compound represented by general formula (1) or a food-grade salt thereof. －６ A method for producing

[21] , comprising parts by mass or more.

[0169]

[30] A method for improving the taste of food and beverages using a compound represented by general formula (1) or a food-grade salt thereof.

[31] The method for improving the taste of food and beverages according to

[30] , further comprising the step of heating a compound represented by general formula (1) or a food-grade salt thereof in the presence of protein.

[32] Use of a compound represented by general formula (1) or a food-grade salt thereof for improving the taste of food and beverages.

Claims

1. A taste-improving composition containing a compound represented by the following general formula (1) or a food-acceptable salt thereof. (In general formula (1), R １ , R ２ , R ３ , R ４ each independently represents a hydrogen atom, a methyl group or a hydroxy group, and R ５ represents a methyl group or a carboxy group. However, the compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ is a carboxy group. (B) In general formula (1), any one of R １ , R ２ , R ３ , R ４ is a hydroxy group. (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.) 2. The taste-improving composition according to claim 1, which enhances at least one selected from the group consisting of sweetness, umami, sourness, saltiness, spiciness, and richness.

3. The flavor-improving composition according to claim 1, which enhances at least one selected from the group consisting of milk flavor, dashi flavor, egg flavor, fish roe flavor, soybean flavor, ginger flavor, fruit juice flavor, stewed flavor, and coolness.

4. The taste-improving composition according to claim 1, which reduces astringency or bitterness.

5. The taste-improving composition according to claim 1, which reduces at least one selected from the group consisting of retort flavor, spoiled flavor, and grassy odor.

6. The taste-improving composition according to claim 1, wherein the compound represented by general formula (1) is meglutol.

7. For every 1 part by mass of glucose, fructose, and sucrose, add 100 × 10¹⁶ of the compound represented by general formula (1) or a food-grade salt thereof. －６ A taste-improving composition according to any one of claims 1 to 6, comprising parts by mass or more.

8. A method for producing a taste-improving composition according to any one of claims 1 to 6, comprising the step of adjusting the content of a compound represented by general formula (1) or a food-grade salt thereof.

9. The manufacturing method according to claim 8, comprising the step of increasing the ratio of the content of the compound represented by general formula (1) or a food-grade salt thereof to other components other than water.

10. The method for producing a food product according to claim 8, comprising the step of increasing the ratio of the content of a compound represented by general formula (1) or a food-safe salt thereof to glucose, fructose, or sucrose.

11. A flavor-enhancing seasoning containing a heat reaction product of a compound represented by the following general formula (1) or a food-grade salt thereof with a protein. (In general formula (1), R １ , R ２ , R ３ , R ４ Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ R represents a methyl group or a carboxyl group. However, a compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ (B) In general formula (1), R １ , R ２ , R ３ , R ４ (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

12. The flavor-improving seasoning according to claim 11, wherein the compound represented by general formula (1) is meglutol.

13. A method for producing a flavor-improving seasoning, comprising the step of heating a compound represented by the following general formula (1) or a food-grade salt thereof in the presence of protein. (In general formula (1), R １ , R ２ , R ３ , R ４ Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ R represents a methyl group or a carboxyl group. However, a compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ (B) In general formula (1), R １ , R ２ , R ３ , R ４ (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

14. The manufacturing method according to claim 13, wherein the compound represented by general formula (1) is meglutol.

15. In the heating step, the composition to be heated contains, for every 1 part by mass of glucose, fructose, and sucrose, a compound represented by general formula (1) or a food-grade salt thereof, in a quantity of 100 × 10 －６ The manufacturing method according to claim 13 or 14, comprising parts by mass or more.

16. A method for improving the taste of food and beverages using a compound represented by the following general formula (1) or a food-grade salt thereof. (In general formula (1), R １ , R ２ , R ３ , R ４ Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ R represents a methyl group or a carboxyl group. However, a compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ (B) In general formula (1), R １ , R ２ , R ３ , R ４ (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

17. The method according to claim 16, wherein the compound represented by general formula (1) is meglutol.

18. The method according to claim 16 or 17, comprising the step of heating a compound represented by general formula (1) or a food-safe salt thereof in the presence of a protein.

19. Use of a compound represented by the following general formula (1) or a food-grade salt thereof for improving the taste of food and beverages. (In general formula (1), R １ , R ２ , R ３ , R ４ Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group, R ５ R represents a methyl group or a carboxyl group. However, a compound represented by general formula (1) satisfies at least one of the following (A) to (C): (A) In general formula (1), R ５ (B) In general formula (1), R １ , R ２ , R ３ , R ４ (C) The compound represented by general formula (1) is selected from the group consisting of glutaric acid, 2-hydroxyglutaric acid, 3-hydroxyglutaric acid, meglutol, 2-methylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 2,2-dimethylglutaric acid, and 3-hydroxy-3-methylpentanoic acid.

20. The use according to claim 19, wherein the compound represented by general formula (1) is meglutol.

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