JP3419945B2 - Bitter taste reducing agent - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a bitterness reducing agent,
In particular, it relates to a bitterness-reducing agent that effectively reduces bitterness by adding it to an oral drug, food or cosmetic having a bitterness.

[0002]

2. Description of the Related Art There are five basic tastes (sweetness,
It is classified as salty, sour, umami, and bitter). Among them, bitterness often gives an unpleasant feeling, and most medicines have a bitterness, as the saying goes, "good medicines bite in the mouth", especially in the field of pharmaceuticals. Therefore, masking bitterness has become an important issue in the formulation process.

Conventionally, as a bitterness masking method in pharmaceuticals, sugar coating has been mainly carried out in the case of tablets, and sugar coating or polymer film coating has been mainly carried out in the case of tablets, granules and fine granules. For solid agents in general, microencapsulation or a method using an inclusion compound (JP-A-3-
No. 236316) or a method of insolubilizing a drug by chemically modifying it. However, each method has problems that it cannot completely mask the bitterness, complicates the process, and can be used only for a limited drug. In the case of liquid agents, the reduction of bitterness is more serious, and since coating agents cannot be used, formulation is carried out by adding high-concentration sugar or organic acid or adding flavors. Perfect. Especially for infants and children, it is difficult to take solid preparations such as tablets and granules, and therefore liquid preparations or dry-solution syrups for business use are often prescribed, and bitterness masking in liquid preparations is an important issue. ing.

[0004] Regarding foods, there are problems of bitterness in various foods such as a bitter taste mainly due to the bitterness of peptides and amino acids obtained from protein hydrolysates and a bitterness of fruit juice. In recent years, various health foods have been marketed for their health preference. For example, plant-derived extracts such as gymnematic acid and aloe have a strong bitterness. The presence of off-tastes in foods deteriorates the quality of the foods themselves, so removal is often an essential condition. Examples of the method for removing the off-taste component centering on bitterness in foods include a method using an adsorbent (Japanese Patent Laid-Open Nos. 55-108254 and 60-60).
No. 91969), a method using an inclusion compound (JP-A 61-40260, JP-A 2-283246), a method of adding a sweetener (JP-A 60-9774), peptides and the like. And a method of decomposing and removing the bitterness component of (2) by JP-A-2-207768. Further, as an improvement of the raw material for foods, a method of previously removing a tissue containing an off-taste component such as bitterness has been adopted. However, there are problems that the above-mentioned method cannot completely suppress the bitterness and changes the taste of food. In the case of food, in addition to completely masking the off-taste centering on bitterness, for example, coffee, tea, alcoholic beverages such as beer and whiskey, alcoholic beverages such as whiskey, some beverages such as vegetable juice, and edible wild plants There are foods such as flavored vegetables that require adjustment of bitterness, and these foods require adjustment of bitterness.

[0005] In the case of cosmetics, it is preferable that the content components thereof do not have a bitter taste particularly in lotions, mouthwashes, toothpastes, etc. used for the face and oral cavity. However, some of the components, such as surfactants and fragrances (flavors), have a bitter taste, and their types and amounts may be limited when used. Conventionally, bitterness is removed by adding a sweetening agent or adding a specific flavor to alleviate the bitterness, but such a means does not provide a sufficient effect for a component exhibiting a strong bitterness. There is.

[0006]

Therefore, an object of the present invention is to exhibit an excellent bitterness-reducing action in medicines, foods or cosmetics containing a bitter taste ingredient such as bitterness, and to safely
Another object of the present invention is to provide a bitterness-reducing agent which can be used for foods without changing its taste, and an oral pharmaceutical composition, food or cosmetics containing the same.

[0007]

Under such circumstances, the inventors of the present invention have conducted extensive studies and found that an ester of a mono- or diglyceride and a polycarboxylic acid has a great effect on bitterness reduction. It came to completion.

That is, the present invention provides a bitterness-reducing agent for use in foods other than soft candy, oral drugs or cosmetics, characterized by containing an ester of mono- or diglyceride and polycarboxylic acid. Is.

The ester of mono- or diglyceride and polycarboxylic acid used in the present invention is produced, for example, by reacting mono- or diglyceride with polycarboxylic acid or its reactive derivative.

The fatty acid residue constituting the monoglyceride in the present invention is not particularly limited, but is preferably a saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms, particularly preferably 12 to 18 carbon atoms.

The fatty acid residue constituting the diglyceride is not particularly limited, but may be a fatty acid residue constituting the above monoglyceride, or one or a mixture of two or more of the polycarboxylic acid residues described below. Can be mentioned. Particularly preferred fatty acid residues of mono- or diglycerides include lauric acid, stearic acid, oleic acid, linoleic acid and linolenic acid. In the case of diglyceride, two kinds of the above fatty acid residues may be combined. The mono- or diglyceride may be a monoglyceride, a diglyceride or a mixture thereof,
It may also contain triglycerides.

As the polycarboxylic acid in the present invention,
Although not particularly limited, oxalic acid, malonic acid, succinic acid,
Saturated dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, and azelaic acid; unsaturated dicarboxylic acids such as maleic acid, methylmaleic acid, fumaric acid, and methylfumaric acid; hydroxypoly acids such as malic acid, tartaric acid, and citric acid. Carboxylic acid; Examples thereof include esterified polycarboxylic acids such as diacetyltartaric acid in which the hydroxyl groups of hydroxycarboxylic acid are wholly or partially esterified with the above-mentioned carboxylic acids such as acetic acid and oxalic acid.

The reactive derivative of polycarboxylic acid is preferably an acid anhydride, and the acid anhydride is preferably diacetyltartaric acid anhydride, maleic anhydride, phthalic anhydride or succinic anhydride, and particularly preferably anhydrous. Examples include diacetyl tartaric acid and succinic anhydride.

Mono- or diglycerides and polycarboxylic acids or their reactive derivatives (hereinafter referred to as polycarboxylic acids)
The esterification reaction with is not particularly limited, and a mono- or diglyceride and a polycarboxylic acid are mixed, and the temperature is 85 to 200 ° C.
The temperature may be 0.1 to 3 hours. Further, the ratio of mono- or diglyceride to polycarboxylic acid is such that the polycarboxylic acid is 0.1 to 10 with respect to 1 part of mono- or diglyceride.
It is preferably doubled (molar ratio). Further, when carrying out the esterification reaction, amines such as pyridine and a basic catalyst may be added. In this case, the reaction can be completed at a lower temperature and in a shorter time.

The ester obtained by the above reaction can be used as it is as a bitterness reducing agent, and may contain both an ester of monoglyceride and polycarboxylic acid and an ester of diglyceride and polycarboxylic acid. The content ratio is also not particularly limited. Unreacted polycarboxylic acids and mono- or diglycerides may be further contained, but the content of components other than the ester of mono- or diglyceride and polycarboxylic acid in the reaction product is preferably 80% by weight or less. , More preferably 50% by weight or less, further preferably 30% by weight or less, particularly preferably 5% by weight or less.

As the purification method, a purification method using a hydrophobic adsorption column such as silica gel chromatography or a molecular weight fractionation column such as gel chromatography can be used.

The ester of mono- or diglyceride and polycarboxylic acid used in the present invention does not include its salt.

The above ester contained in the bitterness reducing agent of the present invention can be used as it is if the obtained ester is in powder form. If the obtained ester is a liquid ester, it can be used by pulverizing it by mixing with protein, starch, saccharides, high molecular weight cellulose and the like. Further, among the above-mentioned esters, when it has an unsaturated fatty acid residue, an antioxidant can be added for the purpose of preventing oxidation. Examples of the antioxidant include tocopherol acetate (trade name: Sankatol, manufactured by Taiyo Kagaku Co .;
Sancanon, manufactured by Maruzen Kasei Co., Ltd .; trade name: Sunmelin, manufactured by San-ei Gen.

It is also possible to dissolve the above ester in edible oil (triglyceride) and use it, for example, soybean oil, rapeseed oil, corn oil, palm oil, cottonseed oil, coconut oil,
Vegetable oils such as palm kernel oil, rice oil, sesame oil, safflower oil, high oleic safflower oil, sunflower oil and high oleic sunflower oil; animal oils and fats such as beef tallow, lard, fish oil, whale oil and milk fat; these Fractionated oils; also hydrogenated; and transesterified 1
A combination of two or more species can be used.

Further, when the above ester is used as a bitterness reducing agent, it can be used in combination with a surfactant. Examples of the surfactant include sucrose fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, Examples thereof include polyglycerin condensed ricinoleic acid ester, lecithin, polyoxyethylene hydrogenated castor oil, polyethylene glycol fatty acid ester, glycerin fatty acid ester, and polyoxyethylene nonionic surfactant.

The bitterness-reducing agent of the present invention can reduce the bitterness by being mixed with an oral pharmaceutical composition having a bitterness, food or cosmetics.

The oral pharmaceutical composition having a bitterness, the food and the cosmetic containing the bitterness-reducing agent of the present invention may be in the form of a liquid such as an aqueous solution, suspension or emulsion, or a solid such as a paste or powder. Either is fine. The mixing method is also not particularly limited, and in the case where these forms are a liquid or a paste such as an aqueous solution, suspension, or emulsion, a method of sufficiently stirring and dispersing after adding the bitterness-reducing agent of the present invention. A homogenizer, an emulsifier, an ultrasonic treatment device, etc. can be used for stirring and dispersion. The obtained dispersion is
After drying with a spray drier, a freeze drier, etc., it may be a powdery or granular solid substance. Further, when the forms of the pharmaceutical composition, food and cosmetic having bitterness are solids such as powder, the method of adding and mixing the bitterness reducing agent of the present invention can be used. Further, a method of dispersing the above-mentioned bitterness-reducing agent in water or the like, mixing this with a pharmaceutical composition having a bitterness in the form of a solid, food or cosmetics, homogenizing and then dehydrating it is utilized. Good. Incidentally, the pharmaceutical composition having a bitter taste, food or cosmetics, if poorly soluble in water, after using an organic solvent such as hexane and ethyl acetate or alcohols such as ethanol, to dissolve these components, The bitterness reducing agent of the present invention may be added.

The bitterness-containing pharmaceutical composition containing the bitterness-reducing agent of the present invention is not particularly limited, and examples thereof include basic drugs such as promethazine, propranolol, berberine, chlorpromazine, chlorpheniramine, papaverine, thiamine, quinine and the like; Mineral salts of basic drugs such as hydrochloride, nitrate, sulfate, acetate, citrate and carbonate;
Organic acid salts such as maleic acid salts of basic drugs; Oren, Assemblies, Keihi, Kujin, Yellowfin, Kouka, Daioh,
All of pharmaceutical compositions containing bitter-tasting ingredients such as Chinese herbs or galenical preparations such as ogon, psyllium, gymnema, rogai, ginkgo, chlorella, and jujube are included.

The dosage form of the pharmaceutical composition containing the bitterness reducing agent of the present invention is not particularly limited, and various dosage forms can be used. The dosage form includes, for example, solid preparations such as capsules, granules, fine granules, pills, powders, tablets, troches, chewable preparations and dry syrups, liquid preparations, extracts, elixirs, spirits, syrups, Liquid preparations such as fragrance water solutions, limonade agents and flow extract agents can be mentioned.

Known methods can be used for the above formulation,
For example, excipients, binders, disintegrants, lubricants, superplasticizers,
One or more kinds of additives such as coating agents, flavoring agents, masking agents and flavors are combined, a planetary mixer, a stirring granulator, a constrained mixing granulator, an extrusion granulator, a fluidized bed granulator, It can be performed by using a granulator such as a centrifugal tumbling granulator and a roller compactor.

The content of the bitterness-reducing agent of the present invention in the pharmaceutical composition is preferably 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, further preferably 0.1 to 3% by weight. %: It is preferably 0.01 to 1000 parts by weight, particularly preferably 0.1 to 100 parts by weight, relative to 1 part by weight of the component exhibiting a bitter taste in the pharmaceutical composition.

The bitterness-containing food containing the bitterness-reducing agent of the present invention is not particularly limited, and citrus fruits such as grapefruit, orange and lemon and fruit juices containing them; tomato, pepper, celery, cucumber, carrot, potato,
Vegetables such as asparagus, vegetable juice and vegetable juice containing the same; sauces, soy sauce, miso, seasonings such as umami seasoning and peppers; soybean milk, soybean food including soymilk; cream, dressing, mayonnaise, margari etc. Emulsified foods; Processed seafood products such as fish meat, surimi and fish eggs; Nuts such as peanuts; Fermented products such as natto; Meat and processed meat products; Beer, whiskey, coffee, cocoa, tea, green tea, fermented tea, semi-fermented Beverages such as tea, soft drinks and functional beverages; pickles; noodles; soups including powdered soup; dairy products such as cheese and milk; bread and cakes; snacks such as snacks, chewing gum and chocolate; candies Cigarettes; health foods and the like. Further, the bitterness of the flavor can be reduced by adding it to the flavor used in foods. Furthermore, leucine,
It can also be used to reduce the bitterness of bitter amino acids such as isoleucine and phenylalanine, peptides and oligosaccharides. Furthermore, the bitterness-reducing agent of the present invention is a palatable beverage such as coffee, black tea, or green tea; an alcohol-containing beverage such as beer or whiskey; some beverages such as vegetable juice; flavored vegetables such as edible wild plants, root vegetables, etc. It can be added to foods that enjoy bitterness for the purpose of adjusting the bitterness. It can also be used in the lye removal process performed when processing flavored vegetables and root vegetables.

The content of the bitterness reducing agent of the present invention in the food is preferably 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, further preferably 0.1 to 3% by weight; It is preferably 0.1 to 1000 parts by weight, particularly preferably 0.1 to 1000 parts by weight, based on 1 part by weight of the component exhibiting bitterness in food.
It is 50 parts by weight.

The bitterness-containing cosmetic containing the bitterness-reducing agent of the present invention is not particularly limited, and examples thereof include lotion, emulsion, cream, pack, lipstick, foundation, beard shaving agent, aftershave lotion, cleansing foam and Facial cosmetics such as cleansing gel; oral cosmetics such as toothpaste, mouthwash and mouthrinse.

Examples of the component exhibiting bitterness include surfactants such as sodium alkylsulfate and sodium monoalkylphosphate, menthol, linalool, phenylethyl alcohol, ethyl propionate, geraniol, linalyl acetate, benzyl acetate and the like. Perfume, bactericides such as methylparaben, propylparaben and butylparaben, moisturizers such as lactic acid and sodium lactate, 8
-Acetylated sucrose, alcohol modifiers such as pursin, and astringents such as aluminum lactate.

The content of the bitterness reducing agent of the present invention in the cosmetic is preferably 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, and further preferably 0.1 to 3% by weight. ; 0.1 to 1000 parts by weight, particularly preferably 0.1, relative to 1 part by weight of the component exhibiting bitterness in cosmetics
˜50 parts by weight.

[0032]

EFFECT OF THE INVENTION The bitterness-reducing agent of the present invention can be obtained by a simple method, is excellent in reduction of bitterness, and can be incorporated into oral pharmaceutical compositions, foods and cosmetics having a bitterness component.

[0033]

EXAMPLES The present invention will now be described in more detail by way of examples, which are merely examples and do not limit the present invention. In addition, the compounding amount indicates% by weight unless otherwise specified.

Reference Example 1 High-purity glyceryl monostearate (purity 93% or more,
Product name: EXCEL T-95, manufactured by Kao Corporation) and succinic anhydride are mixed at a ratio of 1: 1 (molar ratio), and the mixture is heated at 95 to 120 ° C.
The esterification is carried out while stirring for 1 hour under the temperature conditions of
Component A containing an ester of monoglyceride and succinic anhydride
Got

Reference Example 2 High-purity glyceryl dilaurate (purity 75%) and succinic anhydride were mixed in a ratio of 1: 1 (molar ratio), and esterification was carried out under stirring at 95 ° C. for 1 hour to give diglyceride. A component B containing an ester of succinic anhydride and was obtained.

Reference Example 3 Medium Purity Glycerin Monostearate (Purity of 50% or more,
Product name: Exel 150, manufactured by Kao Co., Ltd.) and succinic anhydride are mixed at a ratio of 1: 1 (molar ratio), and the mixture is esterified under a temperature condition of 95 ° C. for 1 hour while stirring to diglyceride and succinic anhydride. A component C containing an ester of an acid, a monoglyceride and an ester of succinic anhydride was obtained.

Reference Example 4 A component D containing an ester was obtained in the same manner as in Reference Example 2 except that diacetyltartaric anhydride was used instead of succinic anhydride.

Reference Example 5 A component E containing an ester was obtained in the same manner as in Reference Example 2 except that maleic anhydride was used instead of succinic anhydride.

Reference Example 6 A component F containing an ester was obtained in the same manner as in Reference Example 2 except that citric acid was used instead of succinic anhydride.

Reference Example 7 The component C obtained in Reference Example 3 was adjusted to pH 7-9 with sodium bicarbonate to obtain G.

Reference Example 8 The C component obtained in Reference Example 3 was purified by silica gel chromatography to obtain a highly pure ester component H.

Example 1 A liquid preparation having the composition shown in Table 1 containing propranolol hydrochloride having a strong bitterness was prepared, and then pH was adjusted with a citrate buffer solution.
Was adjusted to 5.5 and water was added so that the total amount became 50 ml. In addition, as a comparative example, a liquid formulation was similarly prepared by using monoglyceride, diglyceride and soybean lecithin instead of the product of the present invention. In addition, the bitterness of the obtained liquid preparations was evaluated by using the one containing no bitterness-reducing agent as a control (the same applies to the following Examples). The results are shown in Table 2.

[Evaluation Method] The bitterness was evaluated by a sensory evaluation by 10 men and women in their 20s to 40s, and evaluated according to the following 6-point scale, and the average value thereof was shown. Bitterness intensity 6: I feel a very strong bitterness. Bitterness intensity 5: A strong bitterness is felt. Bitterness intensity 4: Not very strong, but bitterness is felt. Bitterness intensity 3: Slight bitterness is felt. Bitterness intensity 2: The bitterness is perceptible. Bitterness intensity 1: No bitterness is felt.

[0044]

[Table 1]     Propranolol hydrochloride 10mg     Sucrose 15mg     Butyl paraoxybenzoate 4mg     Emanone CH60K (manufactured by Kao Corporation) 100 mg     Acetic acid d-α-tocopherol 100 mg     Bitterness reducing agent A to H 0.5 or 1.5%

[0045]

[Table 2]       Additive sample name Bitterness intensity (average value)                                     Addition amount                           0.5% 1.5%     Bitterness reducing agent A 4.6 3.8     Bitterness reducing agent B 3.8 2.4     Bitterness reducing agent C 4.2 3.1     Bitterness reducing agent D 3.9 2.6     Bitterness reducing agent E 3.4 2.1     Bitterness reducing agent F 4.0 2.9     Bitterness reducing agent G 4.4 3.0     Bitterness reducing agent H 4.1 2.3     Monoglyceride 5.7 5.4     Diglyceride 5.4 5.0     Soy lecithin 5.0 4.6     Control 5.9

From the results shown in Table 2, it is clear that bitterness can be reduced by using the bitterness reducing agent of the present invention.

Example 2 A drug containing the following drug was prepared in the same manner as in Example 1 instead of propranolol hydrochloride. All of the liquids had their inherent unpleasant bitterness disappeared, and became liquids that could be taken orally.

Drugs used: quinine, promethazine,
Papaverine, chlorpromazine, berberine, brucine, strychnine, vitamins, herbal medicine, herbal medicine

Example 3 Granules containing quinine hydrochloride and having the composition shown in Table 3 were prepared by an extrusion granulation method. Moreover, what used monoglyceride and lecithin instead of the bitterness reducing agent of this invention product was made into the comparative example. The lactose content of the unblended (control) was 60 parts. The results are shown in Table 4.

[0050]

[Table 3] Quinine hydrochloride (main ingredient) 1 part Pregelatinized starch 7 parts 32 parts of corn starch Lactose 55 parts Bitterness reducing agent A to H 5 parts

[0051]

[Table 4]     Granules Bitterness intensity (average value)     Control 6.0     Bitterness reducing agent A 4.7     Bitterness reducing agent B 3.6     Bitterness reducing agent C 3.9     Bitterness reducing agent D 3.7     Bitterness reducing agent E 3.4     Bitterness reducing agent F 4.0     Bitterness reducing agent G 4.1     Bitterness reducing agent H 3.8     Monoglyceride 5.5     Lecithin 5.2

By using the bitterness-reducing agents A to H of the present invention, the bitterness of the granules containing the bitterness component could be further reduced.

Example 4 A granule containing the following drug was prepared in the same manner as in Example 3 in place of quinine hydrochloride. The bitterness was reduced by using the bitterness-reducing agent of the present invention.

Drugs used: promethazine, chlorpromazine, papaverine, propranolol, berberine,
Vitamins, Chinese herbs, crude drugs

Example 5 Tablets were prepared in the same manner as in Example 3 except that promethazine, chlorpromazine, papaverine, propranolol, or berberine were used in place of quinine hydrochloride to form tablets instead of granules.

As a result, bitterness was further reduced by using the bitterness-reducing agent of the present invention.

Example 6 Granules containing quinine hydrochloride and having the composition shown in Table 5 were prepared according to the rolling granulation method. Moreover, what used monoglyceride instead of the bitterness reducing agent of this invention was made into the comparative example.
The mannitol content of the unblended (control) was 59 parts.

[0058]

[Table 5]     Quinine hydrochloride (main ingredient) 1 part     33 parts of corn starch     58 parts mannitol     Hydroxypropyl cellulose (15%) 3.5 parts     Bitterness reducing agent A to H 1 part

The composition containing the bitterness reducing agent of the present invention is
The bitterness was reduced as compared to the comparative example and the control. Further, instead of quinine hydrochloride, promethazine, chlorpromazine, papaverine, propranolol, berberine, vitamins, herbal medicines, and herbal medicines were similarly used to prepare granules, but similar results were obtained.

Example 7 The bitterness-reducing agents A to G were blended into a dry syrup of the solubilized type containing quinine hydrochloride as the main ingredient. Also, instead of quinine hydrochloride, promethazine, chlorpromazine, papaverine, propranolol, berberine, vitamins, herbal medicines, and herbal medicines were used to prepare a dry syrup in the same manner.

The composition containing the bitterness-reducing agent of the present invention is
The bitterness was reduced in all cases compared to the unblended ones.

Example 8 Regular coffee was mixed with a bitterness-reducing agent B to prepare coffee with suppressed bitterness. A mixture containing lecithin in place of the bitterness-reducing agent B was used as a comparative example. The results are shown in Table 6.

[0063]

[Table 6]                                                 Bitterness     Control 3.8     Bitterness reducing agent B added 0.01% 3.3     Addition of 0.1% bitterness reducing agent B 2.6     Addition of 1.0% bitterness reducing agent 1.7     Lecithin 0.1% added 3.4

From the results of Table 6, it was revealed that the bitterness can be further reduced by using an effective amount of the bitterness-reducing agent B, and coffee having a mild feeling was obtained.

Example 9 The procedure of Example 8 was repeated except that the bitterness reducing agent G was used in place of the bitterness reducing agent B. The bitterness could be reduced by using the bitterness reducing agent G.

Example 10 A bitterness reducing agent C was added to vegetable jars, orange juice, and grapefruit juice. The results are shown in Table 7.

[0067]

[Table 7]                                                             Bitterness     Vegetable juice 3.8     Vegetable juice with 0.1% bitterness reducing agent C 3.0     Vegetable juice with 0.5% bitterness reducing agent C added 1.7     Orange juice 3.5     Orange juice with 0.1% bitterness reducing agent C 3.0     Orange juice with 0.5% bitterness reducing agent C added 1.1     Grapefruit juice 4.0     Add 0.1% of bitterness reducing agent C to grapefruit juice       What I did 3.2     Add 0.5% of bitterness reducing agent C to grapefruit juice       What I did 1.4

From Table 7, juice and fruit juice with reduced bitterness were obtained.

Example 11 A whipped cream was prepared by dissolving 0.3% of the bitterness-reducing agent B in rapeseed oil and using the rapeseed oil to obtain a whipped cream with improved flavor.

Example 12 0.1% of a bitterness-reducing agent G was added to water and dispersed, and the burdock root, lotus root, bamboo shoot, and bracken were subjected to lye removal. In both cases, the flavor was improved.

Example 13 A bitterness reducing agent H was added to a cookie containing corn peptide which is a hydrolyzate of corn protein. The results are shown in Table 8.

[0072]

[Table 8]                                                     Bitterness     Cookie 4.3     Cookie with 0.5% bitterness reducing agent H added 3.1     Cookie with 2.0% bitterness reducing agent 1.4 added 1.4

From Table 8, cookies with reduced bitterness were obtained.

Example 14 A candy containing caffeine and menthol was mixed with bitterness-reducing agents E, F and G. In addition, a monoglyceride and citric acid were used in place of the bitterness-reducing agent to give a comparative example. The results are shown in Table 9.

[0075]

[Table 9]                                                         Bitterness     Candy 5.1     A candy containing 1.0% of a bitterness reducing agent E 3.1     A candy containing 1.0% of a bitterness reducing agent F 3.4     Bitterness reducing agent G 1.0% added to candy 3.3     Candy with 1.0% monoglyceride added 4.8     Candy with 1.0% citric acid added 4.4

From Table 9, candy with reduced bitterness was obtained.

Example 15 Toothpaste having the composition shown in Table 10 was prepared by a conventional method.

[0078]

[Table 10] Dicalcium phosphate 2H ₂ O 45.0% Silicic anhydride 2.0% Sorbitol 15.0% Carboxymethyl cellulose 1.5% Sodium monolauryl phosphate 2.0% Flavoring agent Suitable amount Bitterness reducing agent A 3.0% water balance

This toothpaste had a reduced bitterness derived from sodium monolauryl phosphate.

Example 16 The mouthwash shown in Table 11 was prepared by a conventional method.

[0081]

[Table 11]     Ethanol 15.0%     Sorbitol 10.0%     Saccharin sodium 0.15%     L-menthol 0.10%     Sodium lauryl sulfate 0.10%     Bitterness reducing agent B 1.0%     Water balance

This mouthwash had a reduced bitterness derived from L-menthol and sodium lauryl sulfate.

Example 17 A lotion having the composition shown in Table 12 was prepared by a conventional method.

[0084]

[Table 12]     Glycerin 5.0%     1,3-butanediol 5.0%     Denatured ethanol (8-acetylated sucrose 0.1%     Included) 10.0%     Polyoxyethylene (20) octyl dodecyl ether 1.0%     Fragrance suitable amount     Bitterness reducing agent C 0.5%     Methylparaben 0.1%     Water balance

The lotion had a reduced bitterness derived from 8-acetylated sucrose, and the presence of the lotion remaining around the mouth was not a concern even after the lotion was used.

Example 18 An emulsion having the composition shown in Table 13 was prepared by a conventional method.

[0087]

[Table 13]     Cyclic silicone (pentamer) 20.0%     Squalane 5.0%     Polyoxyethylene modified silicone 5.0%     Sodium lactate 4.0%     Methylparaben 0.1%     Fragrance suitable amount     Bitterness reducing agent G 2.0%     Water balance

This emulsion had a reduced bitterness derived from sodium lactate, and the bitterness was not noticeable even when applied around the mouth.

Example 19 A face wash having the composition shown in Table 14 was prepared.

[0090]

[Table 14]     Monolauryl phosphate triethanolamine 20.0%     Lauryl betaine 5.0%     Glycerin 5.0%     Polyoxyethylene (100) oleyl ether 2.0%     Bitterness reducing agent E 5.0%     Water balance

This facial cleanser did not cause bitterness even if it accidentally entered the mouth during face washing.

Example 20 Mouth fresheners having the compositions shown in Table 15 were prepared.

[0093]

[Table 15]     Ethanol 35.0%     Glycerin 10.0%     Polyoxyethylene hydrogenated castor oil 1.0%     L-menthol 0.5%     Chlorhexidine gluconate 0.02%     Bitterness reducing agent H 1.0%     Water balance

This mouth freshener had little bitterness and had a strong refreshing feeling despite containing a large amount of L-menthol.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI A23L 1/19 A23L 1/19 1/212 1/212 A 2/00 A61K 7/00 C A61K 7/00 A23L 2/00 B (72) Inventor Shigeyuki Ono 1-8762-23, Doihoncho, Hasaki-cho, Kashima-gun, Ibaraki Prefecture (72) Inventor Kazuya Otsuji 466-14, Hiramatsumoto-cho, Utsunomiya-shi, Tochigi Prefecture (56) Reference JP 1-210029 (JP) , A) JP 3-47028 (JP, A) JP 1-171430 (JP, A) JP 7-39347 (JP, A) JP 4-51875 (JP, A) JP 5-168403 (JP, A) JP-A-2-16959 (JP, A) JP-A-3-94660 (JP, A) JP-A-6-113742 (JP, A) JP-A-5-227893 (JP, A) A) JP 62-215376 (JP, A) JP 62-95133 (JP, A) JP 60-6161 (J , A) JP 59-160523 (JP, A) JP 59-25644 (JP, A) JP 58-209937 (JP, A) JP 61-152226 (JP, A) JP 64-63337 (JP, A) JP 58-201964 (JP, A) JP 61-56061 (JP, A) JP 60-25934 (JP, A) JP 59-45854 (JP, A) JP 61-134308 (JP, A) JP 8-205823 (JP, A) JP 8-196233 (JP, A) JP 8-140620 (JP, A) JP 8 -140629 (JP, A) JP-A-7-313107 (JP, A) JP-A-7-203905 (JP, A) JP-A-7-203903 (JP, A) JP-A-7-170942 (JP, A) ) Japanese Patent Publication Sho 53-45373 (JP, B1) (58) Fields investigated (Int.Cl. ⁷ , DB name) A23L 1/22-1/237 A23L 1/24 A61K 47/00 A61K 7/00

Claims (4)

(57) [Claims] 1. A bitterness reducing agent for use in foods other than soft candy, oral pharmaceuticals, or cosmetics, which comprises an ester of a mono- or diglyceride and a polycarboxylic acid. 2. The polycarboxylic acid is diacetyl tartaric acid,
The bitterness reducing agent according to claim 1, which is selected from maleic acid, phthalic acid, citric acid and succinic acid. 3. A fatty acid residue of mono- or diglyceride,
The bitterness reducing agent according to claim 1, which is one or more kinds of saturated or unsaturated fatty acid residues having 8 to 22 carbon atoms. 4. An oral pharmaceutical composition containing the bitterness-reducing agent according to any one of claims 1 to 3.