JP6812365B2 - Flavor improver that imparts the cooked flavor of seafood - Google Patents

Description

INDUSTRIAL APPLICABILITY The present invention relates to a food flavor improving agent that imparts a flavor when seafood is cooked, and can be prepared from raw materials that do not use seafood, and imparts and enhances the flavor when seafood is cooked to food. The present invention relates to a flavor improving agent capable of producing the same, and a method for producing the same.

Cooking seafood produces an appetizing and palatable flavor. In particular, when cooked using the liver of seafood, that is, the internal organs, etc., complex flavors and the like are mixed, and an exquisite flavor can be produced.

Various developments have been attempted to reproduce the cooked flavor of seafood in processed foods. For example, in the field of processed foods such as seafood-based instant noodles, instant soup, pasta sauce, cooked rice, water paste, snacks, confectionery, prepared foods, and frozen foods, the seafood itself is intended to give a cooked flavor of seafood. , Seafood extract, seafood seasoning oil, etc. have been developed and used. However, it is not easy to extract and obtain cooked flavor components from seafood as a raw material. In addition, it is not easy to normally prepare high-quality products and products with sufficient titer, and there is a problem that the required amount may not be secured due to cost restrictions.

The quality of seafood extract and seafood seasoning oil largely depends on the quality of the raw material, but it is difficult to use high quality raw material for industrially produced seafood extract and seafood seasoning oil due to supply and cost restrictions. There is a problem. In addition, if the flavor is scattered or changed in the manufacturing process such as concentration, the titer of the flavor is weakened, and it becomes more difficult to prepare a quality product capable of imparting a satisfactory seafood flavor. There is also the above problem.

Therefore, in general processed foods, when enhancing or improving the seafood flavor, the seafood flavor is added with food additives such as flavors, flavor compositions utilizing the Maillard reaction, yeast extracts, protein hydrolysates, amino acids, and nucleic acids. Various methods have been tried, such as enhancement and improvement of. In the method for enhancing or improving the flavor of seafood, a flavor composition using seafood as a raw material and utilizing the Maillard reaction by heating is used.

As a method for imparting a heated flavor of seafood using a flavor composition utilizing the Maillard reaction in order to impart a more natural flavor, for example, Patent Document 1 describes (1) animals and birds and / or seafood. The step of crushing the meat to an average particle size of 10 μm to 2000 μm by a physical crushing means and / or a crushing means by a proteolytic enzyme, (2) a step of heating the crushed meat at 100 ° C. to 180 ° C., (3) the step. After cooling the heat-treated product, one or a mixture of two or more selected from amino acids, sugars, animal and plant extracts, yeast extracts and animal and plant protein hydrolysates is added and heated at 100 ° C. to 180 ° C. A method for producing a cooked flavor comprising the above steps (1) to (3) is disclosed. Further, Patent Document 2 describes heating an aqueous solution or water suspension containing a broth obtained by steaming seafood, a yeast extract containing 5'-nucleotides, a yeast extract containing glutathione, a vegetable extract, and monosaccharides. A method for producing a seasoning, which is characterized by the above, is disclosed. All of these use seafood as a raw material.

In the production of a flavor of seafood in relation to imparting a heated flavor of seafood, a method of blending each compounding component to enhance the flavor of the flavor of seafood or the like is disclosed. For example, Patent Document 3 describes (1) S-methionine sulfonium chloride as an essential component, (2) (A) hydrocarbons, (B) alcohols, (C) phenols, (D) aldehydes, etc. (E) Ketones, (F) esters, (G) lactones, (H) carboxylic acids, (I) furan compounds, (J) nitrogen-containing compounds, (K) sulfur-containing compounds, (L) natural fragrances A method for producing a seafood flavor is disclosed, which comprises blending at least one fragrance selected from the group consisting of. Specifically, it is described that the seafood flavor is mixed with bonito extract, bonito oil, and scallop extract to prepare bonito flavor and scallop flavor.

Further, in Patent Documents 4 and 5, in the method for producing shellfish flavors, (1): (A) hydrocarbons, (B) alcohols, (C) phenols, (D) aldehydes, (E) ) Ketones, (F) esters, (G) lactones, (H) carboxylic acids, (I) furan compounds, (J) nitrogen-containing compounds, (K) sulfur-containing compounds, (L) natural fragrances Described is a method for producing flavors of shellfish and seafood, which comprises blending at least one fragrance selected from the group and (2): amino acids.

However, although these flavors that enhance the flavor of seafood have a strong ability to supplement the flavor of seafood, it is difficult to adjust the sense of unity between flavor and taste, and even if the flavor itself is a natural flavor, Foods to which it is added tend to lose the balance of flavor, which is not preferable.

Further, Patent Document 6 describes a glutamic acid-containing yeast extract containing 20% by weight or more of glutamic acid in terms of sodium salt and an aqueous solution or water suspension containing sugars, or glutamic acid containing 20% by weight or more of glutamic acid in terms of sodium salt. A method for producing a seasoning produced by heat-treating a powder mixture of a contained yeast extract and sugar is described. However, the seasoning is mainly used for improving the flavor of bonito broth.

On the other hand, in relation to the imparting of the heated flavor of seafood, a method of imparting the flavor of seafood using a raw material other than seafood is disclosed. For example, Reference 7 describes a method of imparting meat-like, fish-like aroma and flavor to foods and the like by using a thiazolidine synthetic compound as an aroma and flavor-imparting component, and Reference 8 describes a thiazole derivative. Alternatively, a method of imparting a chicken flavor or a meat flavor such as beef flavor to a food by using a synthetic compound composed of a thiazolidine derivative is disclosed. These are advantageous methods from the viewpoint of preparing abundant flavor components of seafood, but in that they use synthetic compounds, seafood that aims to add or enhance flavor by taking advantage of its natural flavor. There is a difficulty in imparting a heated flavor of the same kind, and it is not satisfactory from the viewpoint of imparting a harmonious heated flavor of seafood.

As described above, various flavor improvers have been disclosed in order to reproduce the cooked flavor of seafood in processed foods, but the natural flavor and the high potency of the cooked flavor of seafood are high. There is no disclosure of a method that can provide a high quality flavor improver capable of imparting a satisfactory seafood flavor in a required and sufficient amount.

Japanese Unexamined Patent Publication No. 2001-103920 JP-A-2009-207432 Japanese Unexamined Patent Publication No. 2014-076010 Japanese Unexamined Patent Publication No. 2005-160402 Japanese Unexamined Patent Publication No. 2005-143466 Japanese Unexamined Patent Publication No. 2015-154788 Special Publication No. 57-30462 Tokukousho 48-14950

An object of the present invention is to provide a natural food flavor improver that imparts a cooked flavor of seafood that can be used to reproduce the cooked flavor of seafood (flavor when cooked seafood) in processed foods. As a flavor, high-potency, and high-quality food flavor improver, provide a sufficient supply amount of the food flavor improver, and further, provide a food flavor improver that imparts the flavor when the seafood is cooked. It is an object of the present invention to provide a method for supplying a high-quality food flavor improving agent having a natural flavor in a sufficient supply amount, which can be prepared even with non-classical raw materials.

In order to solve the above problems, the present inventors have sufficiently provided a food flavor improver having a natural flavor, high titer, and high quality as a food flavor improver for imparting a cooked flavor of seafood. As a result of studying a method for preparing a food flavor improving agent that imparts a flavor when the seafood is cooked without using the seafood as a raw material, while diligently studying the method of providing the food in a supplied amount. By coexisting an aliphatic aldehyde compound, a thiol compound, an ammonia or amine compound, and a saccharide that can be provided as a raw material and heat-treating the production raw material, it has a natural flavor and a high titer. Moreover, they have found that it is possible to prepare a food flavor improving agent that imparts a flavor when high-quality seafood is cooked, and have completed the present invention. Since it is not necessary to use seafood as a raw material for the preparation of the food flavor improving agent of the present invention, it is necessary to prepare a high quality food flavor improving agent as in the case of using seafood as a raw material. There is no risk of procuring raw materials for seafood, and there is an advantage that high-quality food flavor improvers can be provided in a sufficient supply amount.

That is, in the present invention, seafood is cooked with a heat-treated product produced by heat-treating a flavor-improving agent-producing raw material in which an aliphatic aldehyde compound, a thiol compound, an ammonia or an amine compound, and a saccharide coexist. It comprises a food flavor improving agent containing as a component for imparting a special flavor or a component for enhancing the cooked flavor of seafood, and a method for producing the food flavor improving agent. By using the food flavor improving agent of the present invention, it is possible to impart the flavor of the food and drink when the seafood is cooked, and to enhance the cooked flavor of the food and drink.

The present inventors are studying a method for providing a food flavor improving agent that imparts a flavor when cooked seafood with high quality and in a sufficient supply amount, without using seafood as a raw material. We diligently examined the methods that can be provided. As a result, the flavor of fish and shellfish when cooked is derived from a specific cyclic sulfur-containing compound, that is, a compound having a thiazole ring, a thiazolin ring, or a dithiazine ring, and those compounds are aliphatic aldehydes. It was found that it occurs when a similar compound, a thiol compound, an ammonia or amine compound, and a sugar coexist and are heat-treated, and the heat-treated product has a high titer and a flavor when seafood is cooked. It has been found that it is possible to provide a high-quality food flavor improving agent by imparting the compound, which led to the present invention. That is, the present invention uses an aliphatic aldehyde compound, a thiol compound, an ammonia or amine compound, and a sugar as raw materials for producing, which can be provided as a raw material for foods, and imparts a flavor when cooked seafood. It consists of an improving agent.

In the food flavor improving agent of the present invention, the aliphatic aldehyde compound, the thiol compound, the ammonia or amine compound, and the saccharide which are the production raw materials can be prepared as the food raw material component or the food raw material derived component.

In the food flavor improving agent of the present invention, examples of the aliphatic aldehyde compound used as a raw material for production include an aliphatic aldehyde compound having 2 to 9 carbon atoms. In addition, examples of the thiol compound include cysteine, reduced glutathione, or one or more thiol compounds selected from meat extracts and yeast extracts containing thiol compounds, and processed food production by-products.

Further, in the food flavor improving agent of the present invention, the ammonia or amine compounds used as production raw materials are selected from ammonia, organic or inorganic ammonium salts, yeast extract, protein hydrolyzate, or processed food production by-products. One or more ammonia or amine compounds to be produced can be mentioned. Examples of the saccharide include a reducing saccharide composed of a monosaccharide or a disaccharide, or one or more saccharides selected from food materials containing the saccharide.

In the food flavor improving agent of the present invention, the heat-treated product produced by heat-treating the flavor improving agent manufacturing raw material was produced by heat-treating the flavor improving agent raw material at 40 to 100 ° C. for 0.1 to 5 hours. Heat-treated products can be mentioned. The heat-treated product is characterized in that the heat-treated product contains a compound having one or more functional groups selected from the group consisting of a thiazole ring, a thiazolin ring and a dithiazine ring.

In the present invention, a flavor improving agent manufacturing raw material in which an aliphatic aldehyde compound, a thiol compound, ammonia or an amine compound, and a saccharide coexist is heat-treated at 40 to 100 ° C. for 0.1 to 5 hours. Includes the invention of a method for producing a food flavor improver, which comprises producing a heat-treated product containing a cooked flavor-imparting component of seafood. In the method for producing a food flavor improving agent, the heat treatment of the flavor improving agent manufacturing raw material can be performed in the presence of alcohol.

The present invention includes the invention of a method for improving the flavor of food and drink, which comprises adding the food and drink flavor improving agent of the present invention to the food and drink to impart the cooking flavor of seafood to the food and drink. Examples of imparting the cooking flavor of the seafood of the food and drink include enhancement of the cooking flavor of the food and drink using seafood.

The present invention also includes the invention of a seafood extract, which is characterized in that the cooking flavor of seafood is enhanced by adding the flavor improving agent of the present invention.

That is, specifically, the present invention relates to [1] (A) aliphatic aldehyde compounds, (B) thiol compounds, (C) ammonia or amine compounds, and (D) saccharides (A) to (D). The heat-treated product produced by heat-treating the flavor-improving raw material in which the above components coexist is included as a component that imparts the flavor when the seafood is cooked or a component that enhances the cooked flavor of the seafood. The food flavor improver, [2] aliphatic aldehyde compound, thiol compound, ammonia or amine compound, and sugar are prepared from food raw materials other than seafood, or derived from food raw materials. The food flavor improving agent according to the above [1] and [3] the aliphatic aldehyde compound, which is characterized by being an ingredient, is an aliphatic aldehyde compound having 2 to 9 carbon atoms. The food flavor improver according to [1] or [2] or the [4] aliphatic aldehyde compound is an oxide of an edible oil or fat containing an unsaturated fatty acid. The food flavor improver according to any one of 3] and [5] thiol compound are selected from cysteine, reduced glutathione, or meat extract containing thiol compound, yeast extract, and processed food manufacturing by-products. The food flavor improving agent according to any one of [1] to [4] above, which is characterized by being one or two or more thiol compounds, and [6] ammonia or amine compounds are ammonia, organic or inorganic. The above-mentioned [1] to [5], which are ammonium salts, yeast extracts, protein hydrolysates, or one or more ammonia or amine compounds selected from processed food production by-products. The food flavor improving agent according to any one or the [7] saccharide is a reduced saccharide composed of monosaccharides or disaccharides, or one or more saccharides selected from food materials containing the saccharides. The food flavor improving agent according to any one of the above [1] to [6], [8] (A) aliphatic aldehyde compounds, (B) thiol compounds, (C) ammonia or amine compounds, And (D) The flavor improving agent manufacturing raw materials according to the above [1] to [7] in which the components (A) to (D) of the saccharide coexist were further contained with alcohol and heat-treated to produce the food. A food flavor improving agent characterized by containing the heat-treated product as a component that imparts a flavor when the seafood is cooked or a component that enhances the heat-cooked flavor of the seafood, and [9] the heat-treated product Flavor improver raw material, 40 to 10 The food flavor improving agent according to any one of [1] to [8] above, which is a heat-treated product produced by heat-treating at 0 ° C. for 0.1 to 5 hours, or [10] flavor. The heat-treated product produced by heat-treating the improver raw material contains a compound having one or more functional groups selected from the group consisting of a thiazole ring, a thiazolin ring and a dithiazine ring in the heat-treated product. It comprises the food flavor improving agent according to any one of the above [1] to [9].

Further, in the present invention, [11] (A) aliphatic aldehyde compounds, (B) thiol compounds, (C) ammonia or amine compounds, and (D) saccharides (A) to (D) coexist. The raw material for producing a flavor improving agent or the raw material for producing a flavor improving agent further containing alcohol is heat-treated at 40 to 100 ° C. for 0.1 to 5 hours to produce seafood. The above-mentioned [1] to [10], wherein a heat-treated product containing a component that imparts a flavor when the seafood is cooked or a component that enhances the cooked flavor of seafood is produced. [12] When the seafood is cooked in the food or drink by adding the flavor improving agent according to any one of [1] to [10] to the food and drink. A method for improving the flavor of foods and drinks, which is characterized by imparting flavor or enhancing the cooked flavor of seafood, or adding the flavor improving agent according to any one of [13] above [1] to [10]. This comprises a seafood extract characterized by imparting a flavor when the seafood is cooked or enhancing the cooked flavor of the seafood.

The present invention provides a food flavor improver that imparts a cooked flavor of seafood that can be used to reproduce the cooked flavor of seafood (flavor when cooked seafood) in processed foods, with a natural flavor. As a high-potency and high-quality food flavor improver, it is provided in a sufficient supply amount. INDUSTRIAL APPLICABILITY According to the present invention, a food flavor improving agent that imparts a flavor when cooked seafood can be prepared even with raw materials that do not use seafood, and has a natural flavor, high potency, and high quality. By supplying a sufficient amount of the food flavor improving agent of the above, and enhancing the flavor of the food and drink, especially the food and drink using seafood, the cooked flavor of the seafood of the food and drink is enhanced. It is possible to provide.

FIG. 1 is a chart in which the aliphatic aldehyde compounds in the heat-oxidized sunflower oil in the examples of the present invention are analyzed by a gas chromatography / mass spectrometer. FIG. 2 shows, in the embodiment of the present invention, gas chromatography / gas chromatography / thiazole compounds in a heat-treated product of a heat-oxidized sunflower oil, a yeast extract containing a high amount of glutathione, a yeast extract containing a high ammonia content, and a mixed solution of glucose and ethanol. It is a chart figure analyzed by a mass spectrometer.

In the present invention, a heat-treated product produced by heat-treating a flavor-improving agent manufacturing raw material in which an aliphatic aldehyde compound, a thiol compound, an ammonia or an amine compound, and a saccharide coexist is cooked for food and drink. It comprises a food flavor improving agent containing as a component for imparting a flavor at the time of brewing, or a component for enhancing the cooked flavor of food and drink, and a method for producing the food flavor improving agent. The flavor improver of the present invention can be produced without using a raw material for seafood, and is used in the production of processed foods to impart or enhance a good and complex flavor obtained when the food is heated with seafood. Has the effect of

In the food flavor improving agent of the present invention, the aliphatic aldehyde compound, the thiol compound, the ammonia or amine compound, and the saccharide which are the production raw materials can be prepared as the food raw material component or the food raw material derived component. Seafood may be used as the food raw material, but in the present invention, it is not necessary to dare to use seafood.

<Alphatic aldehyde compounds>
The aliphatic aldehyde compound used in the present invention is not particularly limited, but is usually an aliphatic aldehyde compound having 1 to 18 carbon atoms, and preferably an aliphatic aldehyde compound having 2 to 9 carbon atoms. It is a compound. Further, the number of unsaturated bonds in these aliphatic aldehydes may be one or more. Furthermore, the structure of these aliphatic aldehyde compounds may be linear or branched.

Examples of aliphatic aldehyde compounds having 2 to 9 carbon atoms include etanal (acetaldehyde), n-propanal, n-butanal, 2-butenal, 2-methylpropanal, n-pentanal, 2-pentenal, 3-. Methylbutanal, 2,2-dimethylpropanal, n-hexanal, 2-hexenal, 3-hexenal, 4-hexenal, 2,4-hexadienal, 2,3-dimethylbutanal, 2-methylpentanal, n-heptanal, 2-heptenal, 4-heptenal, 2,4-heptadienal, 2,6-heptadienal, 3-methylhexanal, 2-methyl-2-pentenal, 4-methyl-2-pentenal, n-octanal, 2 -Octenal, 3-octenal, 4-octenal, 5-octanal, 2,4-octanal, 6-methylheptanal, n-nonanal, 2-nonenal, 3-nonenal, 4-nonenal, 5-nonenal, 6 -Nonenal, 8-nonenal, 2,4-nonadienal, 2,6-nonazienal, 3,6-nonadienal, 2,4,6-nonatrienal, 2-methyloctanal, 6-methyloctanal, 2,6-dimethyl Examples thereof include -5-heptenal, glyoxal, butangial, 1,5-pentandial and the like, but those that can be used for food and drink are preferable. These aliphatic aldehyde compounds may be used alone or in combination of two or more.

The aliphatic aldehyde compound may be contained in the content of the aliphatic aldehyde compound, or may be isolated, purified and used by a conventional method from the content of the aliphatic aldehyde compound.

In addition, since the flavor improving agent is used for food and drink, it is safe that the aliphatic aldehyde compound used as the raw material is derived from a raw material having eating experience including the aliphatic aldehyde compound. Is preferable. One example is an oxide of unsaturated fatty acids.

Examples of unsaturated fatty acids include oleic acid, linoleic acid, linolenic acid, docosahexaenoic acid (DHA), and eicosapentaenoic acid (EPA). The unsaturated fatty acid may be contained in edible fats and oils. Edible fats and oils include animal fats and oils such as beef fat, pork fat, chicken fat, egg yolk fat, olive oil, sesame oil, rice bran oil, safflower oil, soybean oil, salad oil, corn oil, sunflower oil, rapeseed oil, palm oil, cottonseed oil, etc. Examples include vegetable oils such as palm oil, safflower oil, cottonseed oil, and sesame oil.

As the unsaturated fatty acid-containing substance, one extracted from the fat-containing substance using an organic solvent such as hexane or ethanol may be used. In addition, fats and oils obtained as by-products during the production of processed livestock products and processed vegetable products may be used as unsaturated fatty acid-containing substances.

<Thiol compound>
The thiol compound used in the present invention may be any compound as long as it has a thiol group (SH group), and examples thereof include hydrogen sulfide, cysteine, and reduced glutathione. These thiol compounds may be used alone or in combination of two or more. Further, it may be a thiol compound obtained by chemically treating, enzymatically treating, or physically treating a compound containing a sulfur atom such as cystine, methionine, thiamine, oxidized glutathione, and allyl sulfide.

The thiol compound is also preferably a food and drink raw material having eating experience, which contains the thiol compound. For example, use meat-derived extracts, yeast-derived extracts, processed livestock products, processed vegetable products, processed fruit foods containing thiol compounds, boiled juices, steamed liquids, cooker juices, etc. obtained as by-products. Is preferable. In addition, these thiol compound-containing substances may be isolated and purified by a conventional method before use.

<Ammonia or amino acid compounds>
The ammonia used in the present invention may be free ammonia or may be in the form of ammonium salts such as ammonium carbonate, ammonium acetate, ammonium lactate, ammonium phosphate and ammonium glutamate.

It is preferable to use ammonia or ammonium salt derived from food and drink raw materials having eating experience. For example, yeast extract, protein hydrolyzate, processed livestock products, processed vegetable products, processed fruit foods containing yeast extract, steamed liquid, cooker juice, etc., which are obtained as by-products during the production of processed fruit foods, may be used. preferable. At this time, these ammonia-containing substances may be isolated and purified by a conventional method before use. Further, ammonia obtained by deamidation of proteins, peptides and amino acids may be used.

The amine compounds used in the present invention are not particularly limited, and are not particularly limited, such as primary amine compounds such as methylamine, secondary amine compounds such as dimethylamine, and tertiary amine compounds such as trimethylamine. Etc. are given as an example. These amine compounds may be used alone or in combination of two or more.

It is preferable to use these amine compounds also derived from food and drink raw materials having eating experience. For example, it is preferable to use boiled juice, steamed liquid, cooker juice, etc., which are obtained as by-products during the production of processed livestock products, processed vegetable products, and processed fruit foods, which contain amine compounds. At this time, it may be isolated, purified and used by a conventional method from the contents of these amine compounds.

The sugar used in the present invention is not particularly limited as long as it can be used in foods, but reducing sugars are preferably used. Examples of reducing sugars include monosaccharides such as ribose, xylose, arabinose, glucose, fructose, galactose, mannose and lambnorse, and disaccharides such as lactose, maltose and trehalose. These sugars may be used alone or in combination of two or more. Further, polysaccharides such as sucrose, oligosaccharide, starch and dextrin may be decomposed into monosaccharides or disaccharides by various methods and used. Furthermore, yeast extract, molasses, liquid sugar and the like containing a large amount of these sugars may be used. These sugars may be contained in boiled juice, steamed liquid, cooker juice, etc. obtained as by-products during the production of processed livestock products, processed vegetable products, processed fruit foods, and the like. From the contents of these saccharides, it may be isolated and purified by a conventional method and used.

The method for coexisting the above aliphatic aldehyde compounds, thiol compounds, ammonia or amine compounds, and sugars is not particularly limited, but for example, these compounds can be mixed to form a mixture. The mixture may be in a solid state such as powder, granules, or powder or granular material, but may be further coexisted with an appropriate solvent such as water or alcohol to be in a solution state if necessary. Of these, it is preferable to coexist with alcohol.

As the alcohol, ethanol is preferable in consideration of its use in food. As the alcohol, brewed liquor, distilled liquor, liqueur, mirin, cooking liquor, brewed seasoning, soy sauce, alcohol preparation, fermented product by microorganisms such as yeast may be used.

The amount of aliphatic aldehyde compounds, thiol compounds, ammonia or amine compounds, and sugars to coexist is difficult to specify due to the variety of raw materials. Selected from the group consisting of thiazole ring, thiazolin ring, thiazine ring and dithiazine ring, which are cyclic sulfur-containing nitrogen compounds, which are active ingredients that impart or enhance the heated flavor of fish and shellfish in the heat-treated product obtained by heating. There is no particular limitation as long as an effective amount of the compound having one or more functional groups is produced and contained.

Examples of the compound having a thiazole ring include thiazole, 2,4,5-trimethylthiazole, 2,4-dimethylthiazole, 2-acetylthiazole, 4-ethyl-5-ethylcarbonyloxyethylthiazole, and 4-butyl-5. Examples thereof include- (2-hydroxyethyl) thiazole, 4-methyl-5- (2-hydroxyethyl) thiazole, 4-methyl-5- (2-hydroxypropyl) thiazole and the like.

Examples of the compound having a thiazolin ring include 4-methyl-5- (2-hydroxyethyl) thiazolin, 2-acetyl-2-thiazolin and the like.

Examples of the compound having a dithiazine ring include 2,4,6-trimethyl-1,3,5-dithiazine, 2-isobutyl-4,6-methyldihydro-4H-1,3,5-dithiazine and 4-isobutyl. -2,6-dihydro-4H-1,3,5-dithiadin, 2-isopropyl-4,6-dimethyl-4H-1,3,5-dithiadin, 4-isopropyl-2,6-dimethyldihydro-4H- Examples thereof include 1,3,5-dithiazine and dimethylfreel-dihydro-1,3,5-dithiazine.

As an example of a raw material for heating an aliphatic aldehyde compound, a thiol compound, an ammonia or an amine compound, and a sugar in the coexistence, the aliphatic aldehyde compound is acetaldehyde, the thiol compound is hydrogen sulfide, and ammonia or amines. Taking the case where the compound is ammonia and the sugar is glucose, the amounts thereof are usually 0.01 to 1000 parts by weight, preferably 0.1 to 1000 parts by weight, based on 1 part by weight of acetaldehyde. Parts, more preferably 0.1 to 100 parts by weight, more preferably 0.5 to 10 parts by weight, ammonia 0.01 to 1000 parts by weight, preferably 0.1 to 1000 parts by weight, further. It is preferably 1 to 1000 parts by weight, more preferably 1 to 20 parts by weight, and the glucose is 10 to 10000 parts by weight, preferably 10 to 1000 parts by weight, still more preferably 10 to 1000 parts by weight, more preferably. Is 10 to 50 parts by weight. When alcohol is allowed to coexist as needed, for example, it is preferable to use an amount of alcohol of 0.1 to 10 parts by weight, preferably 1 to 8 parts by weight, with the entire raw material as 100 parts by weight.

The pH at the time of heat treatment in which an aliphatic aldehyde compound, a thiol compound, an ammonia or amine compound, and a sugar coexist is usually about pH 5 to 8, preferably pH 6 to 8, and more preferably pH 7 to 8. It is preferable to adjust as such.

The heat treatment temperature when the aliphatic aldehyde compound, the thiol compound, the ammonia or amine compound, and the sugar are coexisted and heated is composed of a thiazole ring, a thiazolin ring, and a dithiazine ring in the processed product obtained by heating. The conditions under which a compound having one or more functional groups selected from the group is produced and contained are not particularly limited, but are usually 40 to 100 ° C. for 0.1 to 5 hours, preferably 0.1 to 5 hours. It is 0.1 to 3 hours at 50 to 100 ° C., more preferably 0.3 to 3 hours at 90 to 100 ° C., and more preferably 0.3 to 2 hours at 90 to 100 ° C.

The heating means at this time is not particularly limited, and examples thereof include tank heating, IH heater heating, oven heating, extruder heating, microwave oven heating, steam heating, and hot air heating. Further, retort sterilization, joule sterilization, pressure heating, hot air drying, steam drying, smoking and the like may also be used as the heating means.

The heat-treated product obtained by heating can be used as it is as the flavor improving agent of the present invention, but if necessary, an inorganic salt such as salt, ascorbic acid, fumaric acid, malic acid, tartrate acid, citric acid and other carboxylic acids Acids such as, amino acids such as monosodium glutamate and sodium aspartate, nucleic acids such as sodium inosinate and sodium guanylate, sugars such as sucrose, glucose and lactose, soy sauce, miso, livestock meat extract, poultry extract, seafood extract, yeast It may contain additives that can be used in foods and drinks, such as extracts, natural seasonings such as protein hydrolysates, spices such as spices and herbs, and excipients such as dextrin and various starches.

When the flavor improving agent of the present invention contains an umami substance such as monosodium glutamate, aspartic acid, oxyglutamic acid, ibotenic acid, trichoromic acid, sodium inosinate, sodium guanylate, and sodium succinate, it is preferably used as a seasoning. Can be done. The flavor improving agent of the present invention may be in any shape such as liquid, powdery, and granular.

Examples of the flavor improving method of the present invention include a method of adding the flavor improving agent of the present invention as a material at the time of manufacturing food and drink, a method of adding as a cooking material at the time of cooking food and drink, a method of adding at the time of feeding, and the like. .. Foods and drinks are not particularly limited, but foods and drinks in which seafood is used as a raw material are preferable.

The fish and shellfish used as raw materials are not particularly limited, but for example, head and foot species such as squid and octopus, crustaceans such as shrimp, oyster, crab and lobster, asari, shijimi, saury, abalone and turban shell. , Crustaceans such as sardines, baigai, scallops, fish eggs such as sardines, tarako, kazunoko, salmon, tuna, bonito, sardines, saury, mackerel, tobiuo, horse mackerel, herring, curry, flatfish, tie, cod, haze, anko, Examples include fish such as shrimp, shark, pufferfish, sardines, eels, anago, and ayu, and seafood, but crustaceans and shellfish are preferable examples. Of these, crustaceans are particularly preferred, and shrimp are more preferred. Further, a processed seafood product may be used as the seafood.

Specific examples of foods and drinks in which seafood is used include, for example, dashi, miso with dashi, fish sauce, shrimp chili (fried shrimp chili sauce) sauce, fried seafood sauce, seafood fried rice seasoning, tom yum soup (tom yum kung, etc.) ) Seasoning, Nashigoren seasoning, Oyster sauce, XO soy sauce, Seafood salad dressing, Mayonnaise with mentaiko, etc., Seafood Chinese soup, Shrimp wantan soup, Fuka fin soup, Bisque, Clam chauder, Seafood potage, Tom yum soup (Tom Yum Kung, etc.), seafood miso soup, seafood soup and other soups, noodles (seafood grilled soba, seafood champon, dish udon, seafood ramen, tom yum ramen, laxa, pho, shrimp tomato cream pasta, pescatore, squid squid pasta, etc.) , Sauces, salmon ginger, seafood fried rice, shrimp pilaf, paella, shrimp doria, pear goren, crab miscellaneous dishes, rice with sardines, takoyaki, okonomiyaki, chijimi and other powders, kamaboko, mentaiko (spicy cod roe, etc.), seafood Dried fish, processed marine products such as salted fermented seafood (salt spicy, salted anchovies, etc.), processed vegetable products such as kim chi, dumplings with shrimp, shumai with shrimp, shrimp chili (fried shrimp chili sauce), shrimp tempura, fried shrimp , Frozen foods such as squid fried, fish fried, gratin with shrimp, snack seasoning used for shrimp-containing senbei, snacks with shrimp, confectionery, and other cooked foods such as seafood, fried food, grilled food, curry, etc. Be done.

By adding the flavor improving agent of the present invention to foods and drinks, the flavor of foods and drinks can be improved. When the food and drink is a food and drink in which seafood is used as a raw material, the addition enhances the flavor of the seafood used, particularly the flavor when cooked. That is, the flavor improving agent of the present invention can be used as a seafood flavor enhancing agent for foods and drinks in which seafood is used, and can be used in a method for enhancing the seafood flavor in foods and drinks in which seafood is used.

It depends on the content of the thiazole ring, thiazolin ring, or dithiazine ring-containing compound in the seafood flavor improver or seafood extract, and the type of food and drink, and may be adjusted as appropriate. These compounds can be quantified by a conventional method such as a method using gas chromatography.

The amount of the flavor improving agent of the present invention added to the food or drink may be appropriately set according to the food or drink, but when a food or drink in which seafood is used is used as the food or drink, the thiazole ring or thiazolin in the food or drink is used. The content of the compound having a ring or a dithiazine ring is preferably an amount of 10 ppb in total.

Examples of the present invention are shown below, but the present invention is not limited to these examples.

[Reference example]
In order to verify the flavor components produced in the production of the food flavor improving agent of the present invention, a flavor imparting test was conducted using the following compounds.

<Reference example 1>
2-Acetylthiazole as a compound having a thiazole ring, 2-Acetyl-2-thiazoline as a compound having a thiazolin ring, and a compound having a dithiazine ring. 2,4,6-trimethyl-1,3,5-dithiazine (2,4,6-trimethyl-1,3,5-dithiazine) was added to the shrimp tomato cream pasta sauce so as to have a content of 100 ppb. Addition was made to prepare shrimp tomato cream pasta sauce from Test Groups 1-3. Further, the shrimp tomato cream pasta sauce of Test Group 4 was prepared by adding to the shrimp tomato cream pasta sauce so that the contents of each of the three compounds were 30 ppb. The above three compounds were selected because they were available as reagents.

A sensory evaluation was performed by three trained panelists on the strength of the shrimp flavor of the additive-free shrimp tomato cream pasta sauce and the shrimp tomato cream pasta sauce of Test Groups 1 to 4. The "shrimp flavor" here is a "shrimp flavor" obtained by cooking shrimp, which is a raw material of shrimp tomato cream pasta sauce. In the evaluation, the strength of the shrimp flavor of the additive-free shrimp tomato cream pasta sauce was given as 4 points, and the strength of the shrimp flavor as compared with this was evaluated by a 7-point evaluation method according to the following criteria.
7 points: Very strong shrimp flavor compared to no additives 6 points: Very strong shrimp flavor compared to no additives 5 points: 4 points that feel a strong shrimp flavor compared to no additives : Feel the shrimp flavor as much as additive-free 3 points: Feel the shrimp flavor weaker than the additive 2 points: Feel the shrimp flavor considerably weaker than the additive 1 point: Compare the additive-free Table 1 shows the average scores of the three panelists who feel a very weak shrimp flavor.

As shown in Table 1, the shrimp tomato cream pasta sauce obtained by adding the compound having a thiazole ring, the compound having a thiazolin ring, and the compound having a dithiazine ring were all shrimp as compared with those without the addition. The flavor was enhanced. In addition, the shrimp flavor was most strongly enhanced in the shrimp tomato cream pasta sauce obtained by adding all three of each compound.

<Reference example 2>
The compounds used in Reference Example 1 are added to mentsuyu, crab juice, clam miso soup, bisque, clam chowder, seafood noodles, seafood yakisoba, paella, and tarako pasta sauce as commercially available foods and drinks using seafood. However, when the seafood flavor of each food and drink was evaluated, it was confirmed that the flavor generated when the seafood used in each food and drink was cooked was enhanced.

[Example 1]
Aldehyde (Wako Pure Chemical Industries, Ltd.) was diluted with distilled water to prepare a 5 mM acetaldehyde solution (a). Hydrogen sulfide (solid; Wako Pure Chemical Industries, Ltd.) was heated, and the generated hydrogen sulfide was dissolved in distilled water to prepare a hydrogen sulfide solution. The amount of hydrogen sulfide in the hydrogen sulfide solution was measured using a hydrogen sulfide HPLC detection kit (Dojin Kagaku), and diluted with distilled water to prepare a 5 mM hydrogen sulfide solution (a). 25% aqueous ammonia (Wako Pure Chemical Industries, Ltd.) was diluted with distilled water to prepare a 10 mM ammonia solution (c). Glucose (Wako Pure Chemical Industries, Ltd.) was dissolved in distilled water to prepare a 100 mM glucose solution (d). A solution was prepared by mixing equal amounts of (a), (b), (c), and (d), and the pH was adjusted to 7.5 with a sodium hydroxide (Wako Pure Chemical Industries, Ltd.) solution. The solution was heated in an autoclave at 100 ° C. for 30 minutes, and the produced volatile components were measured using a gas chromatography / mass spectrometer (GC / MS).

<Result>
As a result, it was confirmed that a compound having a thiazole ring, a thiazolin ring, and a dithiazine ring was produced.

[Example 2]
Samples (a) to (c) containing aliphatic aldehyde compounds were prepared by heat-oxidizing α-linolenic acid, linoleic acid, and oleic acid, which are fatty acids having 18 carbon atoms, respectively. Next, in the method described in Example 1, the same operation was performed except that samples (a) to (c) were used in place of the acetaldehyde solution (a) in an amount of about 5 mM of the aliphatic aldehyde compound. The result of heating the seeds was obtained.

<Result>
When the volatile components of each heating result were subjected to a gas chromatography / mass spectrometer, it was confirmed that a compound having a thiazole ring, a thiazolin ring, and a dithiazine ring was produced. The three types of heating results were appropriately added to the foods and drinks using the seafood used in Reference Example 2, and the seafood flavor of each food and drink was evaluated. As a result, the seafood used in all the foods and drinks was derived. It was confirmed that the flavor produced when the seafood was cooked was enhanced.

[Example 3]
Sunflower oil was heated and oxidized to prepare a sample (i) containing an aliphatic aldehyde compound. The sample (i) was subjected to a gas chromatography / mass spectrometer, and it was confirmed that an aliphatic aldehyde compound having 4 to 7 carbon atoms was produced (FIG. 1).

In addition, a sample (ii) was prepared by dissolving a commercially available yeast extract containing a large amount of glutathione in distilled water so as to have a content of 50% by weight. In addition, a commercially available yeast extract containing a large amount of ammonia was dissolved in distilled water so as to have a content of 50% by weight to prepare a sample (iii). A solution is prepared by mixing 5 parts by weight of sample (i), 30 parts by weight of sample (ii), 45 parts by weight of sample (iii), 3 parts by weight of glucose and 4 parts by weight of ethanol to prepare a solution of sodium hydroxide. The pH was adjusted to 7.3 with. The resulting solution was heated at 100 ° C. for 60 minutes. When the volatile components of the obtained heated product were subjected to a gas chromatography / mass spectrometer, it was confirmed that various compounds having a thiazole ring were produced (Fig. 2).

[Example 4]
The heat-treated product obtained in Example 3 was added to the food and drink in which the seafood used in Reference Example 2 was used so as to have the addition amounts shown in Table 2. The strength of the seafood flavor of each of the obtained foods and drinks was sensorimetrically evaluated by three trained panelists. The "seafood flavor" here is a flavor generated when each seafood is cooked.
++: The seafood flavor is very strong compared to no additives.
+: The seafood flavor is stronger than that without additives.
±: The seafood flavor is similar to that without additives.
-: The seafood flavor is weaker than that without additives.
-: The seafood flavor is very weak compared to no additives.

As shown in Table 2, the seafood flavor was enhanced by the addition of the heat-treated product in all the added foods and drinks.

[Example 5]
<Ingredient composition and heat treatment>
One or more compounds or compositions were selected from the compounds or compositions listed in the “Aliphatic aldehyde compounds” column of Table 3 and oxidized by heating to prepare a sample (i). Further, one or more compounds or compositions were selected from the compounds or compositions listed in the "thiol compound" column of Table 3 and dissolved in distilled water in an appropriate amount (for example, 50% by weight) to prepare a sample (ii). .. Further, one or more compounds or compositions are selected from the compounds or compositions listed in the "Ammonia or amine compounds" column of Table 3 and dissolved in distilled water in an appropriate amount (for example, 50% by weight) to sample (iii). Was prepared. Appropriate amounts of samples (i) to (iii), for example, 5 parts by weight sample (i), 30 parts by weight sample (ii), 45 parts by weight sample (iii), in the "sugar" column shown in Table 3. One or more compounds selected from the listed compounds and an appropriate amount (for example, 4 parts by weight) of ethanol were added and mixed to prepare a solution, which was adjusted to pH 7.5 with sodium hydroxide. The obtained solution was heated at 100 ° C. for 60 minutes, and it was confirmed that a compound having one or more functional groups selected from the group consisting of a thiazole ring, a thiazolin ring and a dithiazine ring was produced.

The present invention provides a food flavor improver that imparts a cooked flavor of seafood that can be used to reproduce the cooked flavor of seafood in processed foods, with a natural flavor, high potency, and high quality. Provided in sufficient supply as a food flavor improver. According to the present invention, a food flavor improving agent that imparts or enhances the flavor of cooked seafood can be prepared from raw materials that do not use seafood, and has a natural flavor, high titer, and high quality. By supplying a food flavor improving agent in a sufficient supply amount and imparting or enhancing the cooking flavor of the food and drink, especially the food and drink using seafood, the food and drink with excellent flavor It makes it possible to provide goods.

Claims (13)

(A) Aliphatic aldehyde compounds,
(B) Thiol compound,
(C) Ammonia or amine compounds,
And (D) a flavor improving agent manufacturing raw material in which the components (A) to (D) of the saccharide coexist , or a flavor improving agent manufacturing raw material in which the flavor improving agent manufacturing raw material further contains alcohol, is produced by heat treatment. A food flavor improving agent, which comprises the heat-treated product as a component that imparts a flavor when the seafood is cooked or a component that enhances the cooked flavor of the seafood. The first aspect of claim 1, wherein the aliphatic aldehyde compound, the thiol compound, the ammonia or amine compound, and the saccharide are a food raw material component prepared from a food raw material other than fish and shellfish, or a food raw material-derived component. Food flavor improver. The food flavor improving agent according to claim 1 or 2, wherein the aliphatic aldehyde compound is an aliphatic aldehyde compound having 1 to 18 carbon atoms. The food flavor improving agent according to any one of claims 1 to 3, wherein the aliphatic aldehyde compound is an oxide of an edible fat or oil containing an unsaturated fatty acid. A claim, wherein the thiol compound is cysteine, reduced glutathione, or one or more thiol compounds selected from meat extracts, yeast extracts, and processed food production by-products containing thiol compounds. The food flavor improving agent according to any one of 1 to 4. That the ammonia or amine compounds are ammonia, organic or inorganic ammonium salts, or one or more ammonia or amine compounds selected from yeast extracts, protein hydrolysates, or processed food manufacturing by-products. The food flavor improving agent according to any one of claims 1 to 5. The invention according to any one of claims 1 to 6, wherein the saccharide is a reduced saccharide composed of a monosaccharide or a disaccharide, or one or more saccharides selected from food materials containing the saccharide. Food flavor improver. The heat-treated product is a heat-treated product produced by heat-treating a flavor-improving agent-producing raw material in which the components (A) to (D) coexist and further containing alcohol. The food flavor improving agent according to any one of claims 1 to 7. The invention according to any one of claims 1 to 8, wherein the heat-treated product is a heat-treated product produced by heat-treating a flavor improving agent manufacturing raw material at 40 to 100 ° C. for 0.1 to 5 hours. Food flavor improver. The heat-treated product produced by heat-treating the flavor improving agent manufacturing raw material contains a compound having one or more functional groups selected from the group consisting of a thiazole ring, a thiazolin ring and a dithiazine ring in the heat-treated product. The food flavor improving agent according to any one of claims 1 to 9, wherein the food flavor improving agent is characterized. (A) Aliphatic aldehyde compounds,
(B) Thiol compound,
(C) Ammonia or amine compounds,
And (D) a flavor improving agent manufacturing raw material in which the components (A) to (D) of the saccharide coexist, or a flavor improving agent manufacturing raw material in which the flavor improving agent manufacturing raw material further contains alcohol, 40 to 100 ° C. By performing the heat treatment for 0.1 to 5 hours, it is possible to produce a heat-treated product containing a component that imparts a flavor when the seafood is cooked or a component that enhances the cooked flavor of the seafood. The method for producing a food flavor improving agent according to any one of claims 1 to 10. By adding the flavor improving agent according to any one of claims 1 to 10 to a food or drink, the food or drink may be given a flavor when the seafood is cooked, or the cooked flavor of the seafood may be enhanced. A characteristic method for improving the flavor of food and drink. A seafood extract characterized by imparting a flavor when the seafood is cooked or enhancing the cooked flavor of the seafood by adding the flavor improving agent according to any one of claims 1 to 10.