WO1995004478A1

WO1995004478A1 - Method of increasing bitterness and/or astringency

Info

Publication number: WO1995004478A1
Application number: PCT/JP1994/001272
Authority: WO
Inventors: Takashi Oonishi; Hiroaki Koiso; Toshinaga Tamiya; Toshihiro Ishii
Original assignee: San-Ei Gen F.F.I., Inc.
Priority date: 1993-08-05
Filing date: 1994-08-01
Publication date: 1995-02-16
Also published as: JP3481246B2; AU7239494A

Abstract

A method of increasing bitterness and/or astringency characterized by adding a phenoxyalkanoic acid derivative represented by general formula (I) or a salt thereof in an amount available for increasing bitterness and/or astringency to the products to be used in the oral cavity or perorally ingestible products wherein R's represent each independently hydrogen, halogen, hydroxy, lower alkyl, lower alkanoyl or lower alkoxy; n represents an integer of 0 to 4; and A represents C1-C5 linear or branched lower alkylene. This method serves to increase the bitterness and/or astringency of the products to be used in the oral cavity or perorally ingestible products without detriment to the taste inherent in the tasting substances contained in the raw materials of those products and without affecting the liquidity and physicochemical properties thereof. It is also possible to reduce the amount of use of the bitter and/or astringent ingredient(s).

Description

Melancholy

The present invention relates to a method for enhancing bitterness and astringency. More specifically, the present invention comprises adding a bitter or astringent enhancing effective amount of a phenolic carboxylic acid derivative or a salt thereof to a product used in the oral cavity or a product that can be taken orally. Bitter · Astringency enhancement method. The present invention also relates to a product used in the oral cavity with enhanced bitterness and astringency, but which can be taken orally. Background art

Bitterness and astringency may come from the raw materials used. For example, bitterness comes from cocoa, cocoa, beer, sherry, etc., and astringency comes from tea, black tea, etc. On the other hand, taste-imparting substances or natural extracts are used to artificially impart bitterness. For example, as for bitterness, bitterness peptides, naringin, potato fin, nicotine, polyvinyl thiourea, picric acid, magnesium sulfate, brucine, urea and the like can be mentioned. As for the astringency, tannic acid and persimmon astringent are listed.

In general, bitterness and astringency tended to be disliked as inhibiting the flavor of oral products. However, recently its irritation, astringency and taste Attention has been paid to the various effects brought about by this. For example, it is said that its irritating and astringent properties act on the gastrointestinal mucosa and are effective in improving the stomach and appetite, and are also effective in recovering from fatigue and eliminating stress. It helps to enhance and improve the flavor of things. However, there are few studies on methods to enhance bitterness and astringency, and most of them are researches on suppression methods, and no effective method for enhancing bitterness and astringency has been established at present. is there.

As a method for enhancing bitterness and astringency, a method is used in which a raw material exhibiting these tastes, bitterness, astringency substances, animal and plant extracts, and the like are used at a high concentration. However, excessive addition of these taste substances may result in changes in physical properties such as protein aggregation, and • expression of other off-taste other than the original taste to be obtained.

On the other hand, it is known that phenoxyalkanoic acid derivatives are added to suppress the sweetness of ingestible products containing sugars or sugar alcohols having sweetness (US Patent No. 4567053 and US Patent No. 5045336). In addition, in producing salt substitute granules, a phenolic carboxylic acid derivative is used to reduce the sweetness of sugar or sugar alcohol as an excipient thereof (see Japanese Patent No. 0414550A2). No.) ,,,

In addition, phenolic alkanoic acid derivatives have been used as bitterness inhibitors such as potassium chloride (US Pat. No. 5,232,735). Disclosure of the invention

In view of the above problems, the inventors of the present invention have proposed a While examining the carboxylic acid derivative, it was surprisingly found that, besides suppressing the sweetness and bitterness of sugar or sugar alcohol, bitterness and astringency were enhanced, and the present invention was completed.

According to the present invention, the general formula (I)

Wherein R is the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a lower alkyl group, a lower alkanol group or a lower alkoxy group, n is an integer of 0 to 4, and A is the number of carbon atoms. Or a lower alkylene group of 1 to 5 straight-chain or branched chains) or a salt thereof. A method for enhancing bitterness and astringency is provided, which is characterized by being added to an orally ingestible product. <The term “bitterness and astringency” used in the present invention refers to bitterness or astringency and those two It means bitterness with mixed taste.

The bitterness / astringency enhancement in the present invention means that the product used in the oral cavity or the product that can be ingested orally does not change the liquid properties or physicochemical properties, Perceived bitterness · It means that the astringency is enhanced and felt.

Details of each definition of the above general formula (I) are as follows. First, each definition of R will be described.

Preferred examples of “halogen” include fluorine, chlorine, and odor. Element and iodine.

Preferred examples of the "lower alkyl group" include a straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms, for example, methyl, ethyl, propyl and isopropyl. And so on. Of these, methyl and ethyl groups are preferred.

Preferred examples of the "lower alkanol group" include alkanoyl groups having 2 to 4 carbon atoms, and specific examples include acetyl. Propionyl and butylyl.

Preferred examples of the "lower alkoxy group" include a straight-chain or branched-chain alkoxy group having 1 to 3 carbon atoms, and specifically, for example, methoxy, ethoxyquin, propoxy and isopropoxy. And so on. Of these, methoxy and ethoxy groups are particularly preferred.

—In the general formula (I), R is preferably a lower alkyl group or a lower alkoxy group, particularly preferably a methyl, ethyl, methoxy or ethoxy group.

Next, the definitions of A and n will be described.

Preferred examples of the "lower alkylene group" include a linear or branched alkylene group having 1 to 5 carbon atoms, and specifically, for example, methylene, ethylene, trimethylene, tetramethylene, Examples include ntamethylene, butylene and amylene. Of these, methylene, ethylene and trimethylene are particularly preferred.

n is an integer from 1 to 4, and n is preferably 1. —In the general formula (I), it is preferable that n is 1 and the substituent R is bonded to the para position, and particularly that n is 1 and the scale is bonded to the para position and R Is preferably a methyl, ethyl, methoxy or ethoxy group.

— As the salt of the functional carboxylic acid derivative represented by the general formula (I), all salts that are non-toxic and are acceptable in the fields of foods, pharmaceuticals and quasi-drugs can be used, Examples thereof include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, and ammonium salts. Among these, preferred salts are alkali metal salts such as sodium and potassium.

—Many compounds of the general formula (I) usually have two optical isomers because of having a chiral center at the carbon adjacent to the carboxyl group. The present invention also includes these optical isomers and racemic mixtures. These isomers may have one with strong activity and the other with weak activity. In addition, a lasemi mixture of the above compounds usually shows an intermediate activity between two optical isomers. In the present invention, one of the optical isomers may be separated and either one of them may be used. A compound having a stronger activity is separated by optical resolution and the compound is used to reduce the difficulty. It can enhance the taste enhancing effect.

Examples of the compounds belonging to the general formula (I) include the following.

(Sat) I 2 —Phenoxypropionic acid, S— (I) 1 2— Phenoxypropionic acid, (Sat) 1-2—Phenoxybutyric acid, S— (I) 1-2—Phenoxybutyric acid, (Sat) 1-2—p—Methoxyphenoxybutyric acid, (Sat) ) 1-2-p-methylphenoxypropionic acid. S-(1) 1-2-p-Methylphenoxypropionic acid, (Sat) 1-2-p-Ethylphenoxypropionic acid, (±)- 2-p-Methoxypropionic acid, S- (1-) 1 2-p-Methoxyphenoxypropionic acid, 2-p-Methoxypropionic 2- 2-methylpropionic acid, (Sat) 1-p —Ethoxyethoxypropionic acid, p-methylbenzoic acetic acid, phenoxyacetic acid, p-methoxyphenyloxyacetic acid, p-ethoxyquinoxyacetic acid, (Sat) 1 2 — p — Black mouth phenoxypropionic acid, S — '(one)-2-ρ 1-mouth phenoxypropionic acid, (sat) 1-2-phenoxy-12-methylpropionic acid, 2,4—dimethylphenoxyacetic acid, p-isopropylphenoxyacetic acid, p— 2- (p-chlorophenoxy) -l-methylpropionic acid, 3,4-dichlorophenoxyacetic acid, p-chlorophenoxyacetic acid, 2 1- (2-Methyl-141-chloro-hydroxy) mono-acetic acid, 2- (3-chloro-oxy-oxy) mono-propionic acid, 4-fluoro-fluoro-oxy-acetic acid, 2,3-Di- Lolobenzoic acetic acid, 3-Methylphenoxyacetic acid, 2— (3,4—Dimethoxyphenoxy) monopropionic acid, 2— (2,3,4-Trimethoxyphenoxy) ) Monobutyric acid, 2-methyl ethoxy acetic acid, 2-formyl oxy oxy Acid, [rho - Echirufu et Bruno carboxymethyl acid, 2-arsenide Dorokishifu et Bruno carboxymethyl acid, 4 one ® over Zadoff We Bruno carboxymethyl acid, 2 - main Tokishifu We Roh carboxymethyl acid, 2 - E Tilphenoxyacetic acid, diphenylacetic acid, diphenylhydroxyacetic acid (diphenyldaricholic acid), 2-p-clophenylphenylpropionic acid, 2-p-isopropylphenylphenylpropionic acid, 2- (2,4-dimethoxyphenyl) 1-2 —Methoxyacetic acid, 2— (2,4-dimethylphenyl) monopropionic acid, 2— (2-methylphenyl) monopropionic acid, 2- (2-methylphenyl) -13-methylbutyric acid, and the like.

Among these preferred compounds are phenoxyacetic acid, 2-phenoxypropionic acid, 2-phenoxybutyric acid, p-methylphenoxyacetic acid, p-ethylphenoxyacetic acid, p-methoxyphenoxyacetic acid, and p-ethoxyphenoxyacetic acid. , 2 — p-Methylphenoxypropionic acid, 2 — p-Ethylphenoxypropionic acid, 2 — ρ-Methoxyphenoxypropionic acid, 2 — P-Ethoxyphenoxypropionic acid, 2 — Examples include ρ-methylphenoxybutyric acid, 2-p-ethylphenoxybutyric acid, 2-p-methoxyphenoxybutyric acid, 2-p-ethoxyquinoxybutyric acid, and their sodium or potassium salts. By combining one or more of these compounds, a desired bitter and astringent enhancing effect can be obtained.

—The compound of the general formula (I) can be synthesized by a known method such as condensation. For example, the journal 'Ob-American' Chemical 'Society (J. Anier. Chem. Soc.), 53, 304 (1 931) or the journal' Ob. ), 1891 (1956). Further, among the compounds of the general formula (I), there are also compounds that can be obtained from Aldrich, and in the present invention, such commercially available phenoxy di-lucanoic acid derivatives can also be used.

The product used in the oral cavity according to the present invention means a solid, liquid or semi-solid product which is used in the oral cavity and which is discharged from the mouth after use and is non-toxic to the human body. Those which are taken orally are also included in products used in the oral cavity.

Examples of products used in the oral cavity include cosmetics such as dentifrice, medicated dentifrice, mouthwash, mouthwash, mouthwash and oral tablets, quasi-drugs, and pharmaceuticals.

The orally ingestible product in the present invention means a solid, liquid or semi-solid product that can be ingested orally and is nontoxic to the human body, for example, a part thereof such as chewing gum. Those which are excreted from the mouth are also included in the orally ingestible products.

These products used in the oral cavity or products that can be ingested orally are products containing bitter and astringent taste substances, but bitterness and astringency are felt in the oral cavity of the human body. • It may have little or no bitterness. In the present invention, when a product used in the oral cavity or an orally ingestible product exhibits bitterness and astringency, it acts to further enhance the bitterness and astringency, and the product is completely or almost completely bitter. When it does not exhibit astringency, it acts to make bitterness / astringency more sensible. The amount of the phenoxyalkanoic acid derivative or the salt thereof is appropriately set so that the concentration can enhance the bitterness and astringency of each product. Generally, it is difficult to use 0.000001 to 0.02 parts by weight, preferably 0.0001 to 0.011 parts by weight for 100 parts by weight of a product used in the oral cavity or an orally ingestible product. Astringency can be enhanced. Outside this range, the effect of enhancing bitterness and astringency cannot be obtained, or conversely, bitterness and astringency are suppressed. Further, as the amount of the phenolic carboxylic acid derivative or its salt exceeds 0.02 parts by weight, bitterness and astringency are suppressed, and the inherent taste of the phenolic carboxylic acid derivative or its salt is reduced. Not preferred. However, the amount of the phenoxyalkanoic acid derivative or its salt that enhances bitterness / astringency differs depending on the target taste and content of bitterness / astringency, so if it is selected according to its type, Good.

Taste substances exhibiting bitterness and astringency are, for example, inorganic and organic compounds such as aluminum sulfate, aluminum sulfate, zinc sulfate, magnesium sulfate, ferric chloride, potassium chloride, calcium chloride, and magnesium chloride. , Calcium lactate, urea, phenylthiourea, picric acid, brucine, codins, ephedrines, deoxycholates, vitamins, peptides, amino acids, animal protein degradants, caffeine, Polyphenols such as depromin; pericarp such as naringin and hesperidin Fruits and their juices or extracts, spices, hops, opaque, colombo, riyutan, gentian, daipo, oren, mizugashi, sempuri, _c the taste substance such as extracts such as Koupoku the like Products containing these flavoring substances include green tea, oolong tea, black tea, mate tea, barley tea, brown rice tea, hatomugi tea, dokudami tea, kukucha, persimmon tea, ukoncha, herbal tea, jasm tea, Gymnemati, Rooibosti, Spicei, Flavoring Tea, Spice Blended Tea, Guarana, Coffee, Cocoa. Chocolate.

Products containing bitter taste substances include, for example, foods such as beer, cocoa, coffee, alcoholic beverages, soft drinks, feeds such as compound feed for broiler fattening, and pets such as birds for birds. There are drugs such as tofu, antipyretic, analgesic, anti-inflammatory, diuretic, quasi-drugs such as lozenges, and cosmetics such as lipstick. The amount of the phenoxyl carboxylic acid derivative or salt thereof varies depending on the product to be added. However, the amount of the phenoxy alkanoic acid derivative or salt thereof is 0.0000 to 100 parts by weight of the product. By adding up to 0.02 parts by weight, a product with enhanced bitterness can be provided.

Products containing astringent taste substances include green tea, oolong tea, black tea, yerba mate, barley tea, brown rice tea, hatomugi tea, dokudami tea, kukucha, ukoncha, herbal tea. Foods such as Jas Minty, Gymnemati, Rooibosty, Spicey, Flavoring Tea, Spice Blend Tea, Feeds such as Combined Feed for Beef Cattle Feeding, Pet Food for Birds, etc. No. of foods, antidiarrheal agents, gargles, astringents, bitter stomachs, troches, etc., quasi-drugs such as mouthwash, dentifrices, etc. There are goods. The amount of the phenoxy alkanoic acid derivative or salt thereof varies depending on the product to be added, but the amount of the phenoxy alkanoic acid derivative or salt thereof is preferably 0.001 to 0.02 with respect to 100 parts by weight of the product. By adding parts by weight, products with enhanced astringency can be provided.

The phenoxyalkanoic acid derivative or a salt thereof can be usually added to the taste substance or a product having the same as it is or as a solution or suspension.

Examples of the medium used for the solution or suspension include water, alcohols such as ethanol, oryzanol and octacosanol; oligosaccharides such as liquid sugar, homooligosaccharide and heterooligosaccharide; Saccharides such as starch syrup and starch hydrolyzate; sorbitol, maltitol, erythritol, reduced palatinose, reduced xylooligosaccharide, reduced gentiooligosaccharide and reduced lactose; sugar alcohols such as glycerin and propylene glycol Polyhydric alcohols: fatty acid esters such as glycerin, polyglycerin, sorbitan, polyoxyethylene, propylene glycol and sucrose; and emulsifiers such as lecithin, and hydrophilic organic compounds such as acetone Solvents and the like can be mentioned. .

The method for adding the fuunoxyalkanoic acid derivative or a salt thereof to a product used in the oral cavity or a product that can be ingested orally is not particularly limited. As the stage of addition, it may be added at the same time as the main raw material and the auxiliary raw material when producing the target product, or may be used by previously dissolving it in the liquid main raw material and the auxiliary raw material. Good _c It may be added, mixed, or dissolved in the finished product. As an addition method, it may be added as it is, or may be used by dissolving or suspending it in the above-mentioned medium. The addition method is appropriately selected depending on the product to be added and the amount added.

The specific addition method is as follows. First, when added to tea, the fuunoxyalkanoic acid derivative or salt thereof is sprayed with an aqueous solution or an aqueous alcohol solution before the final drying step during production, or dissolved in a medium during leaching or extraction. May be. Further, the tea extract may be added to water added to food used as a raw material.

Next, when it is added to coffee, the roasted coffee beans before spraying are roasted by spraying an aqueous solution or alcohol solution of a phenoxyl carboxylic acid derivative or a salt thereof, or spraying the roasted coffee beans. Can be added by fog. Alternatively, the coffee may be dissolved in the water extracted when extracting with water. Further, the coffee extract may be added to water added to food used as a raw material.

Next, when added to cocoa, the roasted cocoa beans are sprayed with an aqueous or alcoholic solution of a phenolic carboxylic acid derivative or a salt thereof, or the roasted cocoa! : Can be added by spraying. Alternatively, it may be added directly to the cocoa powder or a solution added and dissolved in an emulsifier. Further, the cocoa may be dissolved in a medium when extracting the cocoa, or may be dissolved in water added to an oral substance using the cocoa. The mechanism of action of the phenoxyalkanoic acid derivative or salt thereof for reducing the sweetness of sugar or sugar alcohol is probably as follows. The sweetness is determined by the fact that sugars having AH (hydrogen donating group) and B (hydrogen accepting group) or sugar alcohol form hydrogen bond between sweet acceptor protein having AH and B on the receptor membrane of taste cells of taste buds. It can be felt by forming. However, when the phenoxycarboxylic acid derivative or a salt thereof binds to a site of the sweet receptor protein and / or receptor membrane, the structure of the sweet receptor protein is changed, and the sweet receptor protein and sugar or sugar alcohol are converted. It is thought that the bond between the two is hindered and the sweetness cannot be felt.

On the other hand, if the structure of the sweet taste receptor protein changes, the sweetness will not be felt, but it will not affect the perception of bitterness and astringency at all. Is thought to be completely different from the mechanism of action for reducing sweetness. In other words, the taste substance having bitterness and astringency is adsorbed on the receptor membrane of the taste cells, thereby changing the potential of the taste cells, changing the conformation of the receptor membrane, and electrically connecting the taste nerve. The target signal is generated. With this electrical signal, the stimulus information is transmitted to the cerebrum, and the bitterness and astringency are felt. However, when Ca ²⁺ (which controls the conformational change of the receptor membrane) bound to the receptor membrane binds to the taste receptor membrane, the conformational change of the receptor membrane becomes less likely to occur and the bitterness Sensitivity to taste is significantly reduced. Therefore, an action mechanism that enhances the bitterness and astringency of the funinoxylated acid derivative or its salt The structure, it alters the Konhome one to emissions of C a ^{2 +} bound to the taste receiving membrane bound taste receptor membranes, or significantly increase the sensitivity to feel the bitter-astringent or modified It is thought that it may be done. In this respect, it is considered that the mechanism for suppressing sweetness by the phenoxyl succinic acid derivative or its salt is completely different from the mechanism for enhancing bitterness and astringency.

As mentioned above, it is an extremely rare phenomenon that the same substance exhibits such different effects.

Further, the phenoxyalkanoic acid derivative or salt thereof of the present invention is almost tasteless and odorless in the case of a free acid, except that it exhibits a slight acidity.

The effects of the present invention are illustrated in Test Examples and Examples. However, the present invention is not limited to these.

Test example 1

Cutlet 0.00 0 0 0 5% (wZv) solution 0.00 0 0 0 0 1%, 0.00 0 0 0 1%, 0.00 0 0 1%, 0.00.01% and 0 A mixed solution to which 0.1% (/ v) of p-ethoxyphenoxyacetic acid was added and a 0.005% (w / v) single-solution solution without added force were prepared. .

The following method was used to determine the bitterness enhancement of the forceps due to the addition of p-ethoxyphenoxyacetic acid.

Bitter taste sensory test method for rikza

a: Preparation of bitter standard solution

0.0 0 0 0 0 0 0 0 0 5 0 at 0% density interval (w / v) A 0.4-0.00.07% (/ v) cutlet bitter standard solution was prepared.

b: Sensory test method

0 0 0 0 0 0 4%, 0. 0 0 0 0 0 4 5%, 0. 0 0 0 0 0 7% (w / V) The bitterness of cutlet is 80, 90, …… 1 A bitterness of 20 was defined.

The degree of bitterness was determined in the same manner as in Test Example 1, and the results are shown in Table 1.

The panelists consisted of 10 men and 10 women.

Instructed to select bitterness of the mixed sample · bitterness same as astringency · bitterness exhibiting astringency · astringent standard solution. The results were totaled and tested by a pair test, and the bitterness / astringency that was significant at P <0.05 was determined as the bitterness / astringency of the mixed sample solution. Table 1 shows the results.

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table 1

When these sample solutions were sterilized at 120 for 20 minutes and tested after cooling, results similar to those described above were obtained. ,

Tests were also conducted on quinine, naringin, caffeine, coffee, and grapefruit juice, with similar results.

Test example 2

Epicatechin gallate 0.0 1 in 1% (W / V) solution 0 0 0 1%, 0. 0 0 0 0 1%, 0.0. 0 0 0 1%, 0.0. 0 1% and 0.0 1% (/ v) of 1-p-methylphenoxy A mixed sample solution containing butyric acid and a single solution of 0.01% (w / v) epicatechin gallate without (2-)-p-methylphenoxybutyric acid were added.

The following method was used to determine the degree of increase in the astringency of epicatechin galle by the addition of (sat) 12-p-methylphenoxydibutyric acid.

a: Preparation of astringent standard solution

A concentration of 0.08% to 0.014% (w / V) of epicatechin gallate astringent standard solution was prepared at 0.01% (w / v) concentration intervals.

b: Sensory test method

0.08%, 0.09%, 0.01%, …… 0. 13%, 0.014% (wZv) 8 0, 9 0, 1 0 0,… 1 3 0, 1 4 0

<3 and ¾ 1

Astringency was determined in the same manner as in Test Example 1, and the results are shown in Table 2.

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One one Table 2

The samples was sterilized 1 2 0 ^e C 2 0 minutes, it was tested after cooling, the similar results were obtained.

When tannic acid, catechin, and black tea were tested, similar results were obtained.

Test example 3 '

1 part by weight of commercially available oolong tea was added to each part by weight of (sat) -sodium-2-ethoxy-poxyethoxypropionate shown in Table 3 and dissolved in hot water at 70 ° C ± 3 100 parts by weight Leached for 3 minutes, filtered A leachate was prepared and subjected to a sensory test with P <0.05 compared to the bitter and astringent standard solution by 10 specialized panelists, and the results shown in Table 3 were obtained.

a: Bitter, astringent standard solution

Oolong tea 0.5, 0.55, 0. 0 to 100 parts by weight of hot water.

6, 0.65, 0.7, 0.75, 0.8, 0.85, 0.9,

0.95, 1.0, 1.05, 1.1, 1.1, 1.2, 1.25, and 1.3 parts by weight of leachate were prepared, and the bitter, astringent standard solution was prepared. And

b: Sensory test

The bitterness and astringency of the above bitter and astringent standard solutions were 80, 90, 100,

The bitterness was defined as 110, 120, 130, 140, and 150.

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Table 3

The oolong tea leachate was Takashi塡the can was sterilized 1 2 0 ^e C 1 0 minutes, even when stored at room temperature 1 2 0 day was the result similar to that described above. In addition, the results of similar tests conducted on sencha and roasted green tea were the same as above.

Test example 4

0.15% (wZw) solution To 100 parts by weight of sodium (Sat) 12-p-methoxyphenyloxybutyrate in each part by weight as shown in Table 4 was added. By comparing the strength with the bitter standard solution The results shown in Table 4 were obtained.

Caffeine bitterness sensory test

a: Bitter standard solution

Cuff X-in solutions of 0.105% to 0195% (w / w) were prepared at a concentration interval of 0.015% (w / w) and used as a bitter standard solution.

b: Sensory test method

0.15%, 0.12, 0.135 to 0.165, 0.18 and 0.1ISS ^ WZW), the bitterness of caffeine was 70, 80, 9 respectively. The degree of bitterness was defined as 0 to 110, 120 and 130, and 10 specialized panelists were instructed to select a bitter standard solution that exhibited the same bitterness as that of each sample.

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Table 4

Test example 5

90 parts of medium-roasted coffee beans 4 parts by weight of each of the parts shown in Table 5 were added and dissolved in each part by weight of sodium (soil) 12-ρ-methoxyphenoxypropionate. The extract was drip extracted with 0 parts by weight and filtered to prepare an extract. About the bitterness of this extract, The sensory test was performed in the same manner as in Test Example 1 in comparison with the bitter standard solution, and the results shown in Table 5 were obtained.

a: Bitter standard solution

A leachate was prepared by adding 2.8 to 5.2 parts by weight of medium-roasted coffee bean ground powder to 100 parts by weight of hot water at a concentration interval of 0.2 part by weight, and used as a standard bitter solution.

b: Sensory test method

2.8, 3.0, 3.2, 3.4, 3.6, 3.8, 4.0, 4.2, 4.4, 4.6, 4.8, 5.0, 5. 2 parts by weight of bitterness were reduced to 70, 75, 80, 85, 90, 95, 100, 100, 110, 115, 122, 125 and It was assumed that the degree of bitterness was 130.

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Table 5

Example 1

After adding 100 ml of 100% ethanol to 100 g of crude powder of Homica, the mixture was allowed to stand at room temperature for 5 days, and then filtered to obtain a clear Hinika tincture. To 100 parts by weight of this tincture, 0.01 parts by weight of sodium (sodium) and 0.01 parts by weight of sodium 2- (p-ethylphenyloxybutyrate) were added. 2 — Addition of 0.001 part by weight of sodium p-methylphenoxypropionate to dissolve yielded Homica extract with enhanced bitterness, and promoted secretion of saliva and gastric juice due to bitterness , Example 2

After adding 70 ν セン ν% ethanol 100 000 ml to 100 g of the asphalt powder, the mixture was allowed to stand at room temperature for 5 days, and then a filtered clear asyaku extract was obtained. By adding and dissolving 0.005 parts by weight of sodium p-ethylphenoxyacetate and 0.050 parts by weight of sodium p-ethylphenoxyacetate to 100 parts by weight of this assenjak extract, A raw material for antidiarrheal and intestinal medicine was also obtained as an oral freshener with enhanced taste.

Example 3

Fructose-glucose liquid sugar 10 parts by weight, grapefruit juice 10 parts by weight, citric acid 0.1 part by weight, grapefruit flavor 0,1 part by weight, 2-p-sodium methoxyphenoxyacetate 0.005 parts by weight Grapefruit juice was prototyped by adding the required amount of water to make the total amount 100 parts by weight. 2 — p-Methoxy phenoxy acetate in the non-added area had a weak bitterness derived from grapefruit juice and had a soft, non-punched flavor, but the added area had an increased bitterness, and grapefruit fruit had its own peculiarity. It had a good flavor similar to that of.

Example 4

Extract of 100 parts by weight of coffee beans (L value 27.5) extracted with boiling water (Brix, 2.2) 64.8 parts by weight, sugar 8.5 parts by weight Parts, milk 13 parts by weight, sodium p-ethoxyphenoxyacetate 0.008 parts by weight, and the necessary amount of water to make the total amount 100 parts by weight, and a canned coffee beverage as usual. Was manufactured and sterilized for 12 minutes and 30 minutes. The coffee-specific bitterness was enhanced and had a strong roasted odor.

Example 5

100 parts by weight of water was added to 5 parts by weight of opaque, 1.5 parts by weight of sempuri, and 0.007 parts by weight of 2-p-methylphenoxybutyric acid, and the mixture was lightly boiled for 2 hours to obtain a decoction. This product was a good bitter stomach medicine because the bitterness derived from oak and sempuri was enhanced in the group without addition of 2-p-methylphenoxybutyric acid.

Example 6

100 parts by weight of water was added to 0.05 parts by weight of genoshoko and 0.005 parts by weight of 2-p-ethylphenoxypropionic acid, and the mixture was lightly boiled for 2 hours to obtain a decoction. This product had a stronger astringency derived from genoshoko than the 2-p-ethylpyroxypropionate-free group, and was a good anti-gatagata drug.

Example 7

Hops (dried product) 0.11 part by weight, roasted malt 9 parts by weight, 2-p-ethoxyquinoxybutyrate 0.02 parts by weight, water is added to make 100 parts by weight, The extract obtained by holding for 800 minutes and then for 60 minutes and then for 50 minutes was filtered, and hops were obtained from the extract obtained by the same treatment without addition of potassium 2-p-ethoxyphenoxybutyrate. And the bitterness inherent in roasted malt was enhanced. Example 8

In the case of teas such as sencha, houjicha, and oolong tea, the extracted extract (tea 1: boiling water: 100 parts by weight) is added to 100 parts by weight of phenoxyalkanoic acid or its salt. The addition of 0.01 parts by weight of phenol increased the bitterness and astringency and enhanced the unique rich aroma of each tea. Even when this extract was filled in a can and sterilized at 120 ° C for 10 minutes, the same bitterness and astringency as before sterilization could be maintained. When the phenoxyl carboxylic acid derivative or a salt thereof was added in an amount of 0.1 part by weight or more, bitterness and astringency were suppressed, and the mellow aroma inherent to tea was inhibited.

Example 9

Black tea intake extract (black tea 1.5: 100 parts by weight of hot water) To 100 parts by weight of phenolic acid derivative or its salt is added 0.001 part by weight to 100 parts by weight, The taste was enhanced and the rich flavor of the tea was also enhanced.

The extract was Takashi塡the can, it is possible to maintain the 1 2 0 ^e C 1 0 minute sterilized even disinfecting before astringency after. When 0.05% by weight or more of the phenoxycarboxylic acid derivative or its salt was added, the astringency was suppressed, and the flavor characteristic of black tea was inhibited.

Example 10

0.005 parts by weight of a phenoxyalkanoic acid derivative or a salt thereof to 100 parts by weight of coffee extract (roasted coffee beans 4: 100 parts by weight of boiling water) This enhances the bitterness and makes it possible to obtain coffee with a strong roasted odor. Came. And Takashi塡The extract the can, sterilized 1 2 0 ° C 1 5 minutes, 6 0 be stored ^e C in 3 0 minutes enhanced 'was bitterness is held, holding a thick roasted stink We were able to. Addition of at least 0.1 part by weight of the X-noxy carboxylic acid derivative or its salt suppressed the bitterness of coffee and reduced the inherent flavor of coffee.

Example 1 1

Cocoa ingestion dispersion (cocoa powder 2: 100 parts by weight of boiling water) By adding 0.01 parts by weight of X-noxy carboxylic acid derivative or a salt thereof to 100 parts by weight, the bitterness is reduced. And a rich roasted odor unique to cocoa could be produced. Filling the extract into a can, sterilizing at 120 ° C for 20 minutes, and storing for an additional 60 ° C for 30 days retains the enhanced bitterness and retains a strong roasted odor We were able to. When 0.05 parts by weight or more of the phenoxyl carboxylic acid derivative or a salt thereof was added, the bitterness was removed and the inherent flavor of cocoa disappeared.

Example 1 2

Grapefruit juice is added to grapefruit juice by adding 0.01 part by weight of a phenoxyalkanoic acid derivative or a salt thereof to 100 parts by weight of grapefruit juice containing 50% (c / w). The flavor was accentuated by its bitterness, and the use of grapefruit juice was reduced by more than 20%.

In addition, it can be used for caffeine, naringin, quinine, tannin, hops, etc. The derivative or its salt enhanced its bitter and astringent taste, and the amount of these bitter and astringent substances used could be reduced by the increased amount.

Example 13

By adding 0.0005 parts by weight of the phenoxyalkanoic acid derivative or its salt to 100 parts by weight of the feed, bitterness and astringency were enhanced. The bitter and astringent taste thus enhanced removes other sweet, sour, umami, and salty tastes, so that a highly palatable feed was obtained.

Example 14

By adding 0.0001 parts by weight of a phenoxyalkanoic acid derivative or a salt thereof to 100 parts by weight of a bitter stomach medicine, the bitterness is enhanced and digestion of the stomach is increased. The secretion of gastric juice, which activated the activity, could be promoted.

Example 15

By adding 0.0005 parts by weight of a phenoxyalkanoic acid derivative or a salt thereof to 100 parts by weight of a troche, bitterness and astringency are enhanced and the feeling of inflammation in the throat is further alleviated. I was able to do it.

Example 16

With respect to 100 parts by weight of dentifrice, the bitterness of phenoxyalkanoic acid derivative is increased by adding 0.01 part by weight of its salt, and foreign taste remaining in the oral cavity is removed. I was able to.

Example 17

For 100 parts by weight of oral freshener, phenoxyalkanoic acid By adding 0.0001 parts by weight of the derivative or a salt thereof, bitterness was enhanced, and off-flavors and off-flavors remaining in the oral cavity could be removed.

Example 18

With respect to 100 parts by weight of a mouthwash, by adding 0.0001 parts by weight of a phenolic carboxylic acid derivative or a salt thereof, the bitterness can be enhanced and a foreign taste can be blocked. did it.

Reduces bitterness and bitterness in products used in the oral cavity or products that can be taken orally without disturbing the original taste of the taste substance contained in the raw material, and its liquidity and physicochemical properties It can be enhanced without altering its properties. It can also reduce the use of bitter-astringents.

Claims

The scope of the claims

'General formula (I)

〇一 A—COOH (I)

Wherein R is the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a lower alkyl group, a lower alkanol group or a lower alkoxy group, n is an integer of 0 to 4, and A is the number of carbon atoms. 1 to 5 is a lower alkylene group of a linear or branched chain) or a phenolic alkanoic acid derivative represented by the formula (1) or a salt thereof. A bitter and astringent enhancement method characterized by being added to ingestible products.

2. The method of claim 1, wherein A is methylene, ethylene or trimethylene in the general formula (I).

3. In the general formula (I), n is 1, R is bonded to the para-position, and R is a methyl, ethyl, methoxy or ethoxy group. Law.