JP7210935B2 - masking agent - Google Patents

Description

The present invention relates to a taste and odor masking agent for an edible product, a method for masking the taste and odor, and a method for producing a taste and odor masked edible product.

In recent years, there has been an increase in the development of foods containing amino acids, soy protein, etc., to enhance nutrition and maintain health. There is a need for technology to
For example, valine, leucine and isoleucine (branched chain amino acids: BCAAs) are known to exhibit bitterness, and it has been reported that γ-glutamyl peptide suppresses the bitterness of BCAAs (Patent Document 1).
It is also known that γ-glutamyl peptide suppresses the heat deterioration odor of extracted tea beverages (Patent Document 2). However, the effect of masking off-flavours and odors of amino acids, protein odors, grain odors, and the like is not known.

Japanese Patent Application Laid-Open No. 2016-171761 WO 2015/136841

An object of the present invention is to provide a masking agent capable of suppressing various unpleasant tastes and odors of edible products.

The present inventors have conducted intensive research to solve the above problems, and found that simply adding γ-glutamyl peptide to an edible product masks various tastes and odors of the edible product. The inventors have found that and completed the present invention.

That is, the present invention includes the following aspects.
[1] A compound represented by the following general formula (I) and a salt thereof:
γ-Glu-X-Gly (I)
(Wherein, X represents an amino acid or an amino acid derivative) and a compound represented by the following general formula (II) and a salt thereof:
γ-Glu-Y (II)
(Wherein, Y represents an amino acid or amino acid derivative)
A taste or odor masking agent for an edible product comprising at least one γ-glutamyl peptide selected from the group consisting of:
[2] The masking agent of [1], wherein the γ-glutamyl peptide is γ-Glu-Val-Gly or a salt thereof.
[3] The taste of the edible product is an off-taste or off-taste of amino acids, off-taste of vitamins, off-taste derived from additives, sour, off-taste of meat or fish, or off-taste of vegetable protein or animal protein [1] Or the masking agent according to [2].
[4] The masking agent according to [1] or [2], wherein the odor of the edible product is animal odor, vegetable protein odor, animal protein odor or vitamin odor.
[5] A compound represented by the following general formula (I) and a salt thereof:
γ-Glu-X-Gly (I)
(Wherein, X represents an amino acid or an amino acid derivative) and a compound represented by the following general formula (II) and a salt thereof:
γ-Glu-Y (II)
(Wherein, Y represents an amino acid or amino acid derivative)
A method for masking the taste or odor of an edible product, comprising the step of adding 0.001 to 10% by weight of at least one γ-glutamyl peptide selected from the group consisting of the edible product.
[6] A compound represented by the following general formula (I) and a salt thereof:
γ-Glu-X-Gly (I)
(Wherein, X represents an amino acid or an amino acid derivative) and a compound represented by the following general formula (II) and a salt thereof:
γ-Glu-Y (II)
(Wherein, Y represents an amino acid or amino acid derivative)
A method for producing an edible product with suppressed taste or odor, comprising the step of adding 0.001 to 10% by weight of at least one γ-glutamyl peptide selected from the group consisting of the edible product.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide foods, medicines, etc., in which the taste and odor are well suppressed, and to take them for a long period of time.

The present invention provides compounds represented by the following general formula (I) and salts thereof:

(Wherein, X represents an amino acid or an amino acid derivative) and a compound represented by the following general formula (II) and a salt thereof:

(Wherein, Y represents an amino acid or amino acid derivative)
A taste or odor masking agent for edible products (hereinafter abbreviated as the masking agent of the present invention) containing at least one γ-glutamyl peptide (hereinafter sometimes abbreviated as γ-glutamyl peptide) selected from the group consisting of in some cases).

The γ-glutamyl peptide in the present invention includes γ-glutamyl tripeptide represented by the general formula (I) and γ-glutamyl dipeptide represented by the general formula (II). In the general formula above, "γ-" means that X or Y is bound via the carboxyl group at the γ-position of glutamic acid. As the γ-glutamyl peptide, one of the above γ-glutamyl peptides may be used, or two or more γ-glutamyl peptides may be used in combination.

X or Y in general formulas (I) and (II) represents an amino acid or amino acid derivative, and amino acids include glycine (Gly), alanine (Ala), valine (Val), leucine (Leu), isoleucine (Ile). , Serine (Ser), Threonine (Thr), Cysteine (Cys), Methionine (Met), Asparagine (Asn), Glutamine (Gln), Proline (Pro), Neutral amino acids such as Hydroxyproline (Hyp), Aspartic acid ( Asp), acidic amino acids such as glutamic acid (Glu), basic amino acids such as lysine (Lys), arginine (Arg), histidine (His), etc., aromatics such as phenylalanine (Phe), tyrosine (Tyr), tryptophan (Trp), etc. Amino acids, ornithine (Orn), sarcosine (Sar), citrulline (Cit), norvaline (Nva), norleucine (Nle), α-aminobutyric acid (Abu), taurine (Tau), tert-leucine (t-Leu), cyclo Other amino acids such as leucine (Cle), α-aminoisobutyric acid (2-methylalanine) (Aib), penicillamine (Pen), homoserine (Hse) and the like.

The amino acid derivative refers to various derivatives of the above amino acids. Examples of amino acid derivatives include special amino acids, unnatural amino acids, amino alcohols, and amino acids in which one or more of functional groups such as a terminal carbonyl group, a terminal amino group, and a cysteine thiol group are substituted with various substituents. mentioned. Specific examples of substituents include alkyl groups, acyl groups, hydroxyl groups, amino groups, alkylamino groups, nitro groups, sulfonyl groups, and various protective groups.
Examples of amino acid derivatives include Arg(NO ₂ ): N-γ-nitroarginine, Cys(SNO): S-nitrocysteine, Cys(S-Me): S-methylcysteine, Cys(S-allyl): S- Allylcysteine, Val-NH ₂ : Valinamide, Val-ol: Valinol (2-amino-3-methyl-1-butanol), Met(O): Methionine sulfoxide, and Cys(S-Me)(O): S- and methylcysteine sulfoxide.

γ-glutamyl peptides include, for example, γ-Glu-Val-Gly, γ-Glu-Nva-Gly, γ-Glu-Abu, γ-Glu-Nva, among which γ-Glu-Val-Gly is preferred.

In the present invention, all amino acids and amino acid derivatives constituting γ-glutamyl peptides are L-configuration unless otherwise specified.

In the present invention, the salt of γ-glutamyl peptide is not particularly limited as long as it can be orally ingested. For example, salts for acidic groups such as carboxyl groups include ammonium salts, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, aluminum salts, zinc salts, triethylamine, and ethanolamine. , morpholine, pyrrolidine, piperidine, piperazine, dicyclohexylamine and the like, and salts with basic amino acids such as arginine and lysine. Examples of salts for basic groups such as amino groups include salts with inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, acetic acid, citric acid, benzoic acid, maleic acid, and fumaric acid. , tartaric acid, succinic acid, tannic acid, butyric acid, hibenzic acid, pamoic acid, enanthic acid, decanoic acid, teocuric acid, salicylic acid, lactic acid, oxalic acid, mandelic acid, malic acid, salts with organic carboxylic acids such as methylmalonic acid , methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. As the salt, one kind of salt may be used, or two or more kinds of salts may be used in combination.

As the γ-glutamyl peptide and its salt, commercially available products or appropriately produced products may be used.

A method for producing a peptide is not particularly limited, and for example, a known method can be used. Known methods include, for example, (1) a method of chemically synthesizing a peptide and (2) a method of synthesizing a peptide by an enzymatic reaction. For the synthesis of relatively short peptides having 2 to 3 amino acid residues, it is particularly convenient to use a chemical synthesis method.

When chemically synthesizing a peptide, a peptide synthesizer can be used to synthesize or semi-synthesize the peptide. Methods for chemically synthesizing peptides include, for example, peptide solid-phase synthesis. Synthesized peptides can be purified by conventional means such as ion exchange chromatography, reverse phase high performance liquid chromatography, affinity chromatography. Such methods of solid phase peptide synthesis and subsequent peptide purification are well known in the art.

When synthesizing a peptide by an enzymatic reaction, for example, the method described in WO2004/011653 can be used. Specifically, for example, an amino acid or dipeptide whose carboxyl group is esterified or amidated and an amino acid whose amino group is in a free state (for example, an amino acid whose carboxyl group is protected) are treated in the presence of a peptide-synthesizing enzyme. Dipeptides or tripeptides can be synthesized by reacting with . The synthesized dipeptides or tripeptides can be purified as appropriate. Peptide-producing enzymes include, for example, cultures of microorganisms capable of producing peptides, culture supernatants isolated from the cultures, cells isolated from the cultures, processed cells of the microorganisms, and isolates from them. and peptide synthesizing enzymes. Appropriately purified peptide-forming enzymes can be used as necessary.

In addition, γ-glutamyl peptides can be produced, for example, by culturing microorganisms capable of producing the γ-glutamyl peptides and recovering the γ-glutamyl peptides from the culture solution or cells. Specifically, yeast containing a high concentration of γ-glutamyl peptides such as γ-Glu-Abu can be obtained, for example, by the method described in JP-A-2012-213376. In addition, γ-glutamyl peptides can be produced, for example, by recovering them from agricultural, aquatic and livestock products containing the γ-glutamyl peptides.

The γ-glutamyl peptide may or may not be purified. That is, as the γ-glutamyl peptide, a material containing a large amount of the peptide may be used. “Highly containing γ-glutamyl peptide” means that the content of γ-glutamyl peptide is 100 ppm (w/w) or more. That is, "adding (adding) a γ-glutamyl peptide" is not limited to adding the peptide itself, but also includes adding a material containing a high content of the peptide. Specific examples of materials that contain a large amount of γ-glutamyl peptide include, for example, fermentation products obtained by culturing microorganisms capable of producing the peptide, microbial cells, culture supernatants, and the like. processed products. Processed products include those obtained by subjecting the above fermentation products to treatments such as concentration, dilution, drying, fractionation, extraction, and purification. Examples of such processed products include yeast extracts containing γ-glutamyl peptides such as γ-Glu-Abu (JP-A-2012-213376). In addition to the yeast extract, foods and drinks (including foodstuffs and seasonings) may naturally contain γ-glutamyl peptides. ) itself may be excluded from the "material containing a large amount of γ-glutamyl peptide" in the method of the present invention. The γ-glutamyl peptide may be purified to the desired degree. For example, the γ-glutamyl peptide has a purity of 50% (w/w) or higher, 70% (w/w) or higher, 90% (w/w) or higher, or 95% (w/w) or higher. may be used.

The masking agent of the present invention is capable of masking the taste or odor of edible products.
By "masking agent" is meant an agent that reduces or suppresses the taste or odor (off-taste, unpleasant taste or odor) of an edible product. Reducing or suppressing the taste or odor means reducing or suppressing the intensity of the taste or odor below the perceptible limit. Taste or odor intensity can be determined, for example, by sensory evaluation by an expert panel. In the present invention, a masking effect can be obtained without imparting an off-taste.

The taste or odor of the edible product to be masked in the present invention is not particularly limited as long as it is a taste or odor that makes one feel uncomfortable when ingesting or taking the product.
For example, the tastes of edible products to be masked include offensive tastes and unpleasant tastes derived from amino acids, offensive tastes derived from vitamins, offensive tastes derived from additives, sour tastes, unpleasant tastes derived from livestock meat (such as glass smell), and unpleasant tastes derived from fish meat ( fishy smell), unpleasant taste derived from vegetable protein or animal protein, and the like.
In the present invention, the term "unusual taste" means a taste different from ordinary taste, and is also called a rare taste.
In the present invention, the "unpleasant taste" is a taste that affects the taste of edible products, such as bitterness and astringency.
Offensive tastes derived from additives include offensive tastes derived from minerals, dietary fibers, lipids, and the like. The additives also include additives that are necessary for formulations of pharmaceuticals and supplements and that cause off-taste. Pharmaceuticals include orally disintegrating tablets, troches, chewable tablets and the like.
Examples of sourness include yogurt such as low-fat yogurt, vinegar, and acidulant.
The unpleasant taste of vegetable proteins is the unpleasant taste derived from vegetable proteins or their degradation products, and examples thereof include those derived from soybeans, grains, lecithin, and the like.
The unpleasant taste of animal protein is an unpleasant taste derived from animal protein or its decomposition products, and examples thereof include those derived from milk, whey, lecithin, gelatin, collagen, and the like.

The odors of edible products to be masked include animal odors, vegetable protein odors, animal protein odors, vitamin odors, and the like.
Animal odors include, for example, grass-fed odors.
The vegetable protein odor is an odor derived from a vegetable protein or its decomposition product, and examples thereof include soybean odor and lecithin odor.
Animal protein odors are odors derived from animal proteins or decomposition products thereof, and include whey protein odors, lecithin odors, gelatin odors, collagen odors, and the like.

Furthermore, the masking agent of the present invention is effective against an offensive taste, unpleasant taste, or unpleasant odor (e.g., retort odor, deteriorated odor) generated during the cooking or heat sterilization process during the production of edible products and the storage of edible products. is also preferably used.

In the present invention, the edible product is a composition to be orally ingested or a composition to be used in the oral cavity, and is not particularly limited as long as it contains the component responsible for the above taste and odor. , pharmaceuticals, quasi-drugs, and cosmetics.

Foods include, for example, milk drinks, lactic acid drinks, soft drinks (including fruit juices), carbonated drinks, fruit juice drinks, vegetable drinks, vegetable/fruit drinks, sports drinks, jelly drinks, powdered drinks, and other beverages; alcoholic beverages Tea beverages such as coffee beverages and black tea beverages; Soups such as consommé soup and potage soup and instant powdered foods thereof; Desserts such as jelly, bavarois and yogurt; Processed meat foods such as hamburgers, hams, and sausages; Processed marine products such as kamaboko and fish cakes; Dairy products such as cheese; Dairy products such as butter, fermented milk and powdered milk; Frozen desserts; breads; noodles such as udon, cold barley, somen, buckwheat, Chinese noodles, spaghetti, macaroni, rice vermicelli, vermicelli and wonton (including instant noodles such as fried noodles and non-fried noodles); gummy, candy, gum, confectionery such as tablets and snacks; nutritional bars;

Foods are not limited to general foods, but also include so-called health foods and medical foods such as dietary supplements, foods with nutrient function claims, and foods for specified health uses. For example, foods such as those exemplified above may be provided as general foods, or may be provided as health foods or medical foods.

Seasonings include solid seasonings such as sugar and salt; liquid seasonings such as dressings, ketchup, mayonnaise, sauces and sauces; and semi-solid seasonings such as miso.

Pharmaceuticals are not particularly limited as long as they contain components that cause the above tastes and odors, and include all oral pharmaceuticals. Examples include vitamins, nutritional tonics, nutrients, supplements, and various pharmaceutical preparations. Any of these may be in any form, such as powders, granules, pills, tablets, liquids, syrups, and the like. Among others, the masking agent of the present invention is preferably used for orally disintegrating tablets, troches, chewable tablets, etc., which are dissolved in the mouth and taken.

Quasi-drugs include toothpastes, mouth fresheners, halitosis preventives, halitosis removers, mouthwashes, gargles, and the like.

Lipstick etc. are mentioned as cosmetics.

The masking agent of the present invention can be produced by adding only γ-glutamyl peptide or a salt thereof, or by adding "other ingredients" by a method commonly used in the field of food production and the like.
The "other component" is not particularly limited as long as it does not impair the effects of the present invention, but for example, amino acids such as alanine, glutamic acid and glycine, and salts thereof; organic acids such as acetic acid, citric acid and tartaric acid; salts thereof; inorganic salts such as common salt, sodium chloride and potassium chloride; dietary fibers such as indigestible dextrin; sugar alcohols such as erythritol; high-intensity sweeteners; nucleic acids such as inosinic acid, guanylic acid, xanthylic acid and salts thereof; pH buffers, excipients, bulking agents, flavors, edible oils, ethanol and water be done.
As the "other component", one component may be used, or two or more components may be used in combination.

The form of the masking agent of the present invention is not particularly limited, but it is a form that can be easily added to edible products, and examples thereof include powder, granule, liquid, syrup, and jelly. Formulation can be performed by a conventional method.

The amount of the masking agent of the present invention added to the edible product can be appropriately adjusted depending on the type of the target edible product. Specifically, the concentration at the time of eating is usually 0.001 to 10% by weight, preferably 0.005 to 5% by weight, more preferably 0.005 to 5% by weight, based on the weight of free form of γ-glutamyl peptide with respect to edible products. is contained so as to be 0.01 to 3% by weight. Within the above range, a masking effect can be obtained. Here, the concentration at the time of eating means the concentration of γ-glutamyl peptide at the time of ingestion of the edible product (when taken orally, when used in the oral cavity). For example, if the edible product is a concentrated beverage, it means the γ-glutamyl peptide concentration of the beverage when diluted and drunk, and if the edible product is a powdered beverage, it is dissolved in drinking water means the γ-glutamyl peptide concentration in the beverage when the beverage is drunk as

Another aspect of the present invention includes a method of taste or odor masking an edible product comprising the step of adding 0.001-10% by weight of at least one γ-glutamyl peptide or salt thereof.
Addition of γ-glutamyl peptide or a salt thereof may be performed at any stage. That is, the γ-glutamyl peptide or its salt may be added to the raw material of the edible product, added to the edible product during production, or added to the finished edible product. The γ-glutamyl peptide may be added only once, or may be added in two or more divided doses.
Various definitions and preferred ranges conform to the above description.

As another aspect of the present invention, an edible product with suppressed taste or odor, comprising the step of adding 0.001 to 10% by weight of at least one γ-glutamyl peptide or a salt thereof to the edible product. A manufacturing method of
Addition of γ-glutamyl peptide or a salt thereof may be performed at any stage of the manufacturing process of the edible product. That is, the γ-glutamyl peptide may be added to the raw material of the edible product, to the edible product during manufacture, or to the finished edible product. The γ-glutamyl peptide may be added only once, or may be added in two or more divided doses.
The production method of the present invention includes processes and steps that are usually included in the production process of edible products, such as mixing and dissolving food additives as necessary, filling a container, and sterilizing. can be included. Various definitions and preferred ranges conform to the above description.

The present invention will be described in more detail below with reference to examples. In addition, hereinafter, "%" means "% by weight" unless otherwise specified.

(Example 1) Whey protein drink1. Preparation of Samples The amount of protein drink and water shown in Table 1 and the sports drink are weighed and put into a standing pouch, and the amount of γ-Glu-Val-Gly shown in the table is added and stirred well.

2. Evaluation Sensory evaluation was performed by 5 expert panelists on the various beverages obtained. Table 1 shows the results.

Example 2 Low-fat and low-calorie yogurt1. Preparation of Samples After adding the amount of γ-Glu-Val-Gly shown in Table 2-1 to low-fat yogurt, mix with a spoon 20 times and then swirl 20 times. Controls are similarly agitated.
After adding the amount of γ-Glu-Val-Gly shown in Table 2-2 to the low-sugar/low-calorie yogurt drink, mix by inverting about 5 to 6 times. Controls are similarly agitated.

2. Evaluation Sensory evaluation was performed by 5 expert panelists on the various beverages obtained. Table 2 shows the results.

(Example 3) Nutrient drink1. Preparation of Sample The amounts of γ-Glu-Val-Gly shown in Table 3 and a drink-type nursing care nutritional food are weighed into a standing pouch and stirred. After the pouch is heated at 85°C for 10 minutes, it is rapidly cooled and stored in a refrigerator.

2. Evaluation Sensory evaluation was performed by 5 expert panelists on the various beverages obtained. Table 3 shows the results.

(Example 4) Gummies1. Preparation of Samples All materials in the amounts shown in Table 4 were mixed and dissolved in hot water.

2. Evaluation Sensory evaluation was performed by 5 expert panelists in the state of solution. Table 4 shows the results.

(Example 5) Jelly drink1. Sample Preparation The amounts of γ-Glu-Val-Gly and jelly drink shown in Table 5 are weighed into a standing pouch and stirred.

2. Evaluation Sensory evaluation was performed by 5 expert panelists on the various jelly beverages obtained. Table 5 shows the results.

(Example 6) Protein powder1. Preparation of Sample 7 scoops of soybean protein were weighed out with a special spoon, 340 ml of water was added and dissolved, and then γ-Glu-Val-Gly was added at the ratio shown in Table 6-1 and stirred. Five cups of the protein drink were weighed out with a special spoon, and 340 ml of water was added and dissolved.

2. Evaluation Sensory evaluation was performed by 5 expert panelists on the various protein drinks obtained. Table 6 shows the results.

(Example 7) Hamburg steak1. Preparation of sample Australian beef (grass-fed beef, purchased from Tokyo Packer) ground meat (80% lean meat, 20% fat, 3.2 mm ground) was mixed with salt, and γ-Glu-Val was added at the ratio shown in Table 7. -Gly was added and mixed further. The minced meat was subdivided into 100g portions and molded into hamburger steaks, which were baked at 250°C for 7 minutes and heated to a core temperature of 80°C to complete.

2. Evaluation Sensory evaluation was performed by five expert panelists on the various hamburger steaks obtained. Table 7 shows the results.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide an easily ingestible edible product with reduced unpleasant taste and unpleasant odor.

Claims (6)

A taste or odor masking agent for an edible product comprising γ-Glu-Val-Gly or a salt thereof,
The taste of the edible product has an offensive or unpleasant taste of amino acids other than the bitterness of branched-chain L-amino acids, an offensive taste of vitamins, an offensive taste derived from additives, sourness, an unpleasant taste of meat or fish, or an unpleasant taste of vegetable protein or animal protein. and
The masking agent, wherein the odor of the edible product is animal odor, vegetable protein odor, animal protein odor or vitamin odor. The edible product has an off-taste of vitamins, an off-taste of minerals, dietary fiber or lipids, a sour taste of yogurt or an acidulant, an unpleasant taste of meat or fish, or an off-taste of soybeans, grains, lecithin, milk, whey, lecithin, gelatin or 2. The masking agent according to claim 1, which is an unpleasant taste of collagen. 2. Masking agent according to claim 1, which is an odor masking agent for edible products. A method for masking the taste or odor of an edible product, comprising the step of adding 0.001 to 10% by weight of γ-Glu-Val-Gly or a salt thereof to the edible product. The taste is off-taste or unpleasant taste of amino acids other than the bitterness of branched-chain L-amino acids, off-taste of vitamins, off-taste derived from additives, sour taste, off-taste of livestock or fish meat, or off-taste of vegetable protein or animal protein;
A masking method, wherein the odor of the edible product is animal odor, vegetable protein odor, animal protein odor or vitamin odor. The edible product has an off-taste of vitamins, an off-taste of minerals, dietary fiber or lipids, a sour taste of yogurt or an acidulant, an unpleasant taste of meat or fish, or an off-taste of soybeans, grains, lecithin, milk, whey, lecithin, gelatin or 5. The method of masking according to claim 4, wherein the masking is an unpleasant taste of collagen. 5. A method of masking according to claim 4, which is a method of masking the odor of edible products.