Masking composition

Isoliquiritigenin glycosides are used to create a masking composition that effectively masks unpleasant tastes and odors in oral compositions, addressing the inadequacies of existing technologies by reducing or eliminating such flavors and aromas in foods like beans, seafood, and meat.

JP2026042702AActive Publication Date: 2026-03-11IKEDA SHOKKEN KK
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Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2025-05-20
Publication Date
2026-03-11

AI Technical Summary

Technical Problem

Existing technologies are inadequate in effectively masking unpleasant tastes and odors in oral compositions, particularly those derived from beans, seafood, meat, and other food sources.

Method used

The use of isoliquiritigenin glycosides, specifically isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside, as active ingredients in a masking composition to mask unpleasant tastes and odors in oral compositions.

Benefits of technology

The masking composition effectively reduces or eliminates unpleasant tastes and odors in various oral compositions, including those from beans, seafood, meat, and other food sources, by incorporating isoliquiritigenin glycosides at specific concentrations.

✦ Generated by Eureka AI based on patent content.

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Abstract

An object of the present invention is to mask an unpleasant taste or odor of an oral composition, particularly an unpleasant taste or odor derived from beans, and further to provide a method for masking an oral composition having an unpleasant taste or odor, an oral composition in which an unpleasant taste or odor is masked, and a method for producing the same. [Solution] Isoliquiritigenin glycosides, more specifically, isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside, can mask unpleasant tastes or odors, so the above problem can be solved by preparing a composition containing one or more of these isoliquiritigenin glycosides as active ingredients and using this as a masking composition.
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Description

[Technical Field]

[0001] The present invention relates to a masking composition, a masking method, an oral composition in which an unpleasant taste or odor is masked, and a method for producing the same. [Background technology]

[0002] To date, compounds that modify tastes and flavors using various materials have been developed. For example, the Examples (Table 2) of Patent Document 1 disclose that, as flavor-modifying compounds, liquiritin, liquiritin apioside, isoliquiritin, isoliquiritigenin, and isoliquiritin apioside each enhance the sweetness of sucrose, and liquiritin and liquiritigenin each enhance the sweetness of steviol glycoside (SG), as well as mask the aftertaste of licorice and the lingering aftertaste of SG, and the bitterness and astringency of a mixture of limonin, naringin, and normilin. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2024-525502 Summary of the Invention [Problem to be solved by the invention]

[0004] The object of the present invention is to provide a masking composition capable of masking an unpleasant taste or odor, and further to provide a method for masking an oral composition having an unpleasant taste or odor, an oral composition in which an unpleasant taste or odor is masked, and a method for producing the same. [Means for solving the problem]

[0005] The inventors have conducted various studies to solve this problem and have found that isoliquiritigenin glycoside has the effect of masking the unpleasant taste or odor of oral compositions, thereby completing the present invention.

[0006] That is, the present invention relates to the following [1] to

[10] . [1] A composition for masking unpleasant tastes or odors in oral compositions, comprising isoliquiritigenin glycoside as an active ingredient. [2] The masking composition according to [1], wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside. [3] The masking composition according to [1] or [2], wherein the unpleasant taste or odor is derived from beans. [4] A method for masking an unpleasant taste or odor of an oral composition, characterized by comprising adding isoliquiritigenin glycoside to the oral composition. [5] The masking method described in [4], wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside. [6] A masking method according to [4] or [5], wherein the unpleasant taste or odor is derived from beans. [7] A bean protein-containing oral composition containing 0.0002 to 2 parts by weight of isoliquiritigenin glycoside per 100 parts by weight of bean protein. [8] The bean protein-containing oral composition described in [7], wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside. [9] A method for producing a soy protein-containing oral composition, characterized in that isoliquiritigenin glycoside is contained in an amount of 0.0002 to 2 parts by weight per 100 parts by weight of soy protein.

[10] A method for producing a bean protein-containing oral composition described in [9], wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside. [Effects of the Invention]

[0007] According to the present invention, the unpleasant taste or odor of an oral composition can be suppressed, and therefore an oral composition with a reduced unpleasant taste or odor can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0008] The isoliquiritigenin glycoside of the present invention is a compound in which a sugar is bound to the phenolic hydroxyl group of isoliquiritigenin (CAS RN: 961-29-5) via a glycosidic bond, and examples thereof include isoliquiritin (CAS RN: 5041-81-6), neoisoliquiritin (CAS RN: 59122-93-9), isoliquiritin apioside (CAS RN: 120926-46-7), liculaside (CAS RN: 29913-71-1), etc. Here, the chemical formula of isoliquiritin is shown as [Chemical Formula 1], and the chemical formula of its aglycone, isoliquiritigenin, is shown as [Chemical Formula 2].

[0009] [ka]

[0010] [ka]

[0011] One aspect of the present invention is a composition for masking an unpleasant taste or odor of an oral composition, containing isoliquiritigenin glycoside as an active ingredient. Commercially available, highly purified isoliquiritigenin glycosides or plant extracts containing isoliquiritigenin glycosides may be used. However, it is preferable to use purified products with an increased isoliquiritigenin glycoside content. This is because the use of purified products can reduce the unpleasant odors and tastes inherent in the plant material. Once a purified product is obtained, the purification method is not particularly limited and can be performed using a conventional method. For example, purification can be performed using a preparative ODS column. The elution is performed appropriately with a 10% to 50% (v / v) aqueous ethanol solution, preferably a 20% (v / v) or 30% (v / v) aqueous ethanol solution. After separation, the isoliquiritigenin glycoside concentration of each fraction is analyzed, and fractions rich in isoliquiritigenin glycoside are collected and purified. This process can be repeated. The masking composition of the present invention has the effect of masking one or more of the unpleasant flavors of the initial taste, middle taste, and aftertaste that are felt in that order from the time an oral composition is placed in the mouth until after it is swallowed, and one or more of isoliquiritin, neoisoliquiritin, and isoliquiritin apioside are particularly effective against the unpleasant initial taste, one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside are particularly effective against the unpleasant middle taste, and one or more of isoliquiritin, neoisoliquiritin, and liclaside are particularly effective against the unpleasant aftertaste. The masking composition of the present invention may be a mixture or emulsion obtained by dispersing or emulsifying the active ingredient of the present invention or a licorice root extract containing the active ingredient in a solution of a dispersant or emulsifier, or may be a concentrated or dried product obtained by vacuum concentration, membrane concentration, drum drying, air drying, spray drying, vacuum drying, freeze drying, granulation, or a combination thereof. During spray drying or granulation, dextrin, starch, modified starch, thickening polysaccharides, etc. can be used as an excipient. The masking composition of the present invention may contain isoliquiritigenin glycoside as an active ingredient, more preferably one or more selected from isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside, and the concentration of the active ingredient is not particularly limited, but may be 0.01 to 100% by weight, preferably 0.05 to 80% by weight, more preferably 0.1 to 70% by weight, so that the amount required to achieve the effects of the present invention described below can be efficiently contained in the oral composition.

[0012] Examples of the dispersion or emulsification treatment include treatment using a device such as a high-pressure homogenizer, a colloid mill, an ultrasonic emulsifier, a homomixer, or a homodisper, and two or more types of devices may be combined. Heating during the treatment is preferably performed at a temperature of, for example, 40 to 200°C, or 50 to 150°C, preferably 120°C or lower, more preferably 100°C or lower, and even more preferably 95°C or lower.

[0013] When added to an oral composition having an unpleasant taste or odor, the masking composition of the present invention can mask the unpleasant taste or odor of the oral composition, and in particular can mask the unpleasant taste or odor originating from beans such as soybeans, seafood, meat, proteins and their hydrolysates, grains such as milk, rice and wheat, fermented foods, alcohol, vitamins, eggs, melons, cucumbers and other squash, potatoes, vegetables, insects, herbs, gelatin, agar, starch, modified starch, emulsifiers, pigments, organic acids such as sodium acetate and sodium lactate, sweeteners, sugars, polyphenol-containing substances such as cocoa, etc., as well as unpleasant tastes or odors caused by processing such as retort, and unpleasant tastes or odors caused by the deterioration of rice or oil. The unpleasant taste or odor referred to here can be more specifically expressed as, for example, an unpleasant bean odor such as soybean odor, fish odor, meat odor, protein odor, milk odor, grain odor, gluten odor, fermentation odor, alcohol odor, vitamin odor, egg odor, melon odor, potato odor, vegetable odor, insect odor, green odor, gelatin odor, agar odor, modified starch odor, emulsifier odor, pigment odor, oil odor, sourness, acridness, sweetness, bitterness, astringency, retort odor, deteriorated rice or oil odor, etc., and the masking composition of the present invention can mask these.

[0014] The specific form of the oral composition to be masked in the present invention is not particularly limited as long as it is an oral composition having an unpleasant taste or odor, and examples thereof include protein supplements, protein bars, protein jellies, and other protein supplement foods; soy products such as soy flour, soy milk, tofu, okara, fried tofu, natto, yuba, and soy snacks; plant-based foods that use plant ingredients such as beans, grains, and nuts instead of animal ingredients; retort foods, seafood products, meat products, egg products, dairy products, and milk-containing products such as cream sauces; grain products such as cooked rice, bread, noodles, granola, cookies, snacks, and dumplings; fermented foods, fried foods, pickles, green juice, vitamin supplements, gummies, and gelatin- or agar-containing products such as jellies; foods and beverages using melons, starch, modified starch, emulsifiers, colorings, fats and oils, or organic acids; alcoholic beverages and alcohol-containing seasonings; and foods and beverages with a high polyphenol content. When the oral composition having the unpleasant taste or odor is a food or beverage containing soy protein, the unpleasant bean odor is mainly n-hexanal and n-hexanol, and the unpleasant taste of soy means a harsh taste, astringency, etc., the main components of which are saponin, isoflavone, phenolic acid, etc.

[0015] Another aspect of the present invention is a method for masking an unpleasant taste or odor in an oral composition, which comprises adding the masking composition to the oral composition. The oral composition having an unpleasant taste or odor to be masked is similar to the above-mentioned examples. The timing for adding the masking composition of the present invention to the oral composition having an unpleasant taste or odor may be any stage during the preparation of the oral composition or any stage after preparation and before ingestion. The concentration of the active ingredient of the present invention in the target oral composition is preferably 0.1 to 400 ppm, more preferably 0.5 to 300 ppm, even more preferably 1 to 250 ppm, and most preferably 10 to 200 ppm. The concentration can be confirmed using a calibration curve of a component standard obtained by HPLC. For example, the concentration can be measured using a reverse-phase column such as a C18 or C30 column, preferably a C30 column, and a UV detector under typical HPLC conditions, using a typical mobile phase such as a 5 to 60% (v / v) aqueous acetonitrile solution, preferably a 10 to 50% (v / v) aqueous acetonitrile solution, based on a calibration curve prepared using each isoliquiritigenin glycoside standard.

[0016] Another aspect of the present invention is an oral composition containing the masking composition, wherein an unpleasant taste or odor is masked by the inclusion of the masking composition. Furthermore, yet another aspect of the present invention is a method for producing an oral composition having an unpleasant taste or odor, characterized by including the masking composition of the present invention in an oral composition having an unpleasant taste or odor. Here, the oral composition having an unpleasant taste or odor and the masking composition are both the oral composition and masking composition described above. The oral composition of the present invention, which masks unpleasant tastes or odors, contains isoliquiritigenin glycoside as an active ingredient, more preferably isoliquiritin, neoisoliquiritin, isoliquiritin apioside, or liclaside. By containing the active ingredient, for example, beans such as soybeans, seafood, meat, protein products and their decomposition products, milk, rice, grains such as wheat, fermented foods, alcohol, vitamins, eggs, gelatin, watermelon, melon, cucumber, potatoes, vegetables, insects, herbs, gelatin, agar, starch, modified starch, emulsifiers, pigments, organic acids such as sodium acetate and sodium lactate, sweeteners, sugars, polyphenol-containing substances such as cocoa, unpleasant tastes or odors caused by processing such as retort, and unpleasant tastes or odors caused by the deterioration of rice or oil are masked. Examples of such foods and beverages include: More specifically, the unpleasant taste or odor referred to here is one or more selected from bean odors such as soybean odor, fish odor, meat odor, protein odor, milk odor, grain odor, gluten odor, fermentation odor, alcohol odor, vitamin odor, egg odor, melon odor, potato odor, vegetable odor, insect odor, green odor, gelatin odor, agar odor, modified starch odor, emulsifier odor, pigment odor, oil odor, sourness, harshness, sweetness, bitterness, astringency, retort odor, and the odor of deteriorated rice or oil. When the oral composition having the unpleasant taste or odor is a food or beverage containing soy protein, the food or beverage can be one in which the unpleasant taste or odor derived from the beans is masked.

[0017] The amount of the masking composition added to an oral composition having an unpleasant taste or odor is preferably 0.1 to 400 ppm, more preferably 0.5 to 300 ppm, even more preferably 1 to 250 ppm, and most preferably 10 to 200 ppm, of the active ingredient in the oral composition. Furthermore, the oral composition preferably contains 0.0002 to 2 parts by weight of isoliquiritigenin glycoside per 100 parts by weight of bean protein, more preferably 0.0005 to 1.5 parts by weight, and even more preferably 0.001 to 1 part by weight. By adding the active ingredient isoliquiritigenin glycoside to achieve this content, a bean protein-containing oral composition with reduced unpleasant taste or odor can be obtained. [Example]

[0018] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. In the present invention, all % means % by weight unless otherwise specified.

[0019] Example 1: Effect of treating licorice root extract with glycoside-degrading enzyme on masking effect "Lycospice B" (glycyrrhizinic acid: less than 5%, manufactured by Ikeda Tohka Kogyo Co., Ltd.), a powdered product of licorice root extract, was used as Example 1 in the following evaluation.

[0020] (Preparation of licorice root extract (comparison product) treated with glycoside-degrading enzyme) The β-glucosidase preparations "Aromase®" (Amano Enzyme Inc.) and "Sumiteam® BGA" (Shin-Nihon Chemical Industry Co., Ltd.) were used as glycoside-degrading enzymes with the activity of cleaving glycosidic bonds in glycosides. 0.1% of each enzyme preparation was added to a 10% aqueous solution of licorice spice B, and the mixture was treated with the enzyme at 50°C for 15 hours. The enzyme was then inactivated by heat treatment, and the mixture was spray-dried to obtain a licorice root extract treated with glycoside-degrading enzymes (Comparative Product 1).

[0021] (Sensory evaluation test: Masking effect of unpleasant soybean odor or taste) The effectiveness of Example Product 1 and Comparative Product 1 in masking the unpleasant smell or taste of soybeans in soy cookies was evaluated. After adding salad oil to a mixture of white sugar and water, soy flour (protein: 35%), soft flour, and a mixture of Example Product 1 or Comparative Product 1 that had been sifted were added and mixed, and the resulting dough was formed into a mass and left to rest in the refrigerator for more than an hour.Then, it was stretched evenly, cut into shapes, and baked in a preheated oven at 150°C for 15 minutes to obtain soy cookies. The formulation of the soy cookies is shown in Table 1 below, and the amount of Example Product 1 or Comparative Product 1 added was 0.02% relative to the total formulation below (100%). As a control, soy cookies without the addition of Product 1 or Comparative Product 1 were used, and a sensory evaluation of soy cookies with the addition of Product 1 or Comparative Product 1 was conducted to evaluate the masking effect of the unpleasant odor or taste of soybeans.

[0022]

Table 1

[0023] A sensory evaluation was conducted by four trained panelists, and the results are shown in Table 2 below. The sensory evaluation was performed on a three-point scale: "2" for samples with a strong masking effect of the unpleasant odor or taste of soybeans compared to the control group (no addition), "1" for samples with a masking effect, and "0" for samples without a masking effect. The average value of the four panelists was rated as "◎" if it was 1.5 or more and 2.0 or less, "○" if it was 0.5 or more and less than 1.5, and "×" if it was less than 0.5.

[0024] (Component Analysis of Product 1 and Comparative Product 1) The contents of liquiritin, liquiritigenin, isoliquiritin, and isoliquiritigenin in Product 1 and Comparative Product 1 were measured according to the following "HPLC Conditions 1". The resulting numerical values are also shown in Table 2.

[0025] <HPLC Conditions 1> Detector: UV detector (ultraviolet wavelengths 280 nm, 360 nm) Column: Inertsil ODS-EP (inner diameter 4.6 mm, length 250 mm, manufactured by GL Sciences Inc.) Mobile Phase A: 0.1% by volume aqueous phosphoric acid solution Mobile Phase B: 80% by volume aqueous acetonitrile solution (containing 0.1% by volume phosphoric acid) Gradient: Gradient from Mobile Phase A to Mobile Phase B (for 50 minutes) Flow rate: 0.8 ml / min Column temperature: 40°C Standards: Liquiritin (Pharmacopoeia for testing crude drugs, 98.0+%, Fujifilm Wako Pure Chemical Industries, Ltd.), Liquiritigenin (Pharmful drug testing, 98.0+%, Fujifilm Wako Pure Chemical Industries, Ltd.), Isoliquiritin (>98.0%, Tokyo Chemical Industry Co., Ltd.), and Isoliquiritigenin (>97.0%, Tokyo Chemical Industry Co., Ltd.) were each diluted appropriately with 50% by volume acetonitrile aqueous solution, and calibration curves for each were prepared.

[0026] [Table 2]

[0027] As can be seen from Table 2, Comparative Product 1 contains almost no liquiritin and isoliquiritin, which are glycosides found in large amounts in Example Product 1, and contains more of the aglycones liquiritigenin and isoliquiritigenin than Example Product 1. This indicates that by treating Example Product 1 with a glycoside-degrading enzyme, the glycosidic bond of the glycoside was cleaved to produce the aglycone. While Example Product 1 showed a strong masking effect against the unpleasant odor or taste of soybeans, Comparative Product 1 showed no masking effect. This indicates that, among the components in licorice root extract, either or both of the glycosides liquiritin and isoliquiritin have a strong masking effect, while the aglycones liquiritigenin and isoliquiritigenin do not have a masking effect.

[0028] [Example 2: Effect of each fraction of licorice root extract on masking effect] (ODS column fractionation) 10 g of lycospice B was dissolved in 90 mL of 20% (v / v) aqueous ethanol and applied to an ODS column (Biotage Sfar Flash Column C18-D, 30 μm, 120 g) equilibrated with 20% (v / v) aqueous ethanol. Next, the column was eluted with 600 mL of 20% (v / v) aqueous ethanol, followed by 600 mL of 30% (v / v) aqueous ethanol. The fraction was separated into 24 fractions, each lasting 5 minutes. The flow rate was 10 mL / min. The concentrations of liquiritin and isoliquiritin in each fraction were measured under the above-mentioned HPLC condition 1. As a result, a "liquiritin-containing fraction" was collected by combining fractions 8 to 13, and an "isoliquiritin-containing fraction" was collected by combining fractions 16 to 23. These were then dried under reduced pressure to give "liquiritin-containing fraction powder" (purified product A) and "isoliquiritin-containing fraction powder" (purified product B), respectively. The contents of liquiritin, liquiritigenin, isoliquiritin, and isoliquiritigenin in each fraction were measured under the above-mentioned HPLC condition 1, and the results are shown in Table 3.

[0029] [Table 3]

[0030] (Sensory evaluation test: Masking effect of unpleasant odor or taste of soybeans ) A mixture (test sample 2-1) was prepared by mixing comparison product 1, which did not show any masking effect on the unpleasant odor or taste of soybeans in Example 1, with the "liquiritin-containing fraction powder" (purified product A) in a ratio of 6:1, and a mixture (test sample 2-2) was prepared by mixing comparison product 1 with the "isoliquiritin-containing fraction powder" (purified product B) in a ratio of 5:1. This test product 2-1 or 2-2 was added instead of the test product 1 in the sensory evaluation test of the masking effect of the unpleasant odor or taste of soybeans in Example 1, and the sensory evaluation was similarly carried out. The results are shown in Table 4 below.

[0031] (Component analysis of test sample 2-1 or 2-2) The contents of liquiritin, liquiritigenin, isoliquiritin and isoliquiritigenin in test sample 2-1 or 2-2 were measured according to the above "HPLC condition 1", and the results are shown in Table 4.

[0032] [Table 4]

[0033] Test product 2-2 was found to have a strong masking effect on the unpleasant odor or taste of soybeans, whereas test product 2-1 showed no masking effect. From Table 4, it can be seen that test product 2-1, which has a high content of liquiritigenin glycoside liquiritin, did not have any effect in masking the unpleasant odor or taste of soybeans, while test product 2-2, which has a high content of isoliquiritin, did have a masking effect on the unpleasant odor or taste of soybeans. This indicates that isoliquiritin, an isoliquiritigenin glycoside, is effective in masking the unpleasant odor or taste of soybeans.

[0034] [Example 3: Influence of various glycosides on masking effect] (Fractionation and purification using an ODS column) Purified Product B was dissolved in 20% (v / v) aqueous ethanol and applied to an ODS column (Biotage Sfar Flash Column C18-D, 30 μm, 120 g) equilibrated with 20% (v / v) aqueous ethanol. Next, elution was performed with 20% (v / v) aqueous ethanol. Starting at 145 minutes, the column was fractionated into 41 fractions, each lasting 10 minutes. The contents of liquiritin, liquiritin apioside, isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside in each fraction were measured using the HPLC analysis conditions described below. Fractions 15 to 24 were then combined and dried under reduced pressure to prepare Purified Product C. Fractions 29 to 41 were combined and dried under reduced pressure to prepare Purified Product D. Purified Product C was fractionated and purified in the same manner using the same column. After analyzing each fraction in the same manner as above, fractions 14 to 18 were combined and dried under reduced pressure to prepare Purified Product E. Fractions 19 to 29 were combined and dried under reduced pressure to prepare Purified Product F. The flow rate was 10 mL / min. The contents of the liquiritigenin glycosides liquiritin and liquiritin apioside, and the isoliquiritigenin glycosides isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liculaside were measured for each purified product under the HPLC analysis conditions below. The results are shown in Table 5. In addition, the sum of liquiritin and liquiritin apioside is referred to as the "liquiritigenin glycoside content," and the sum of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside is referred to as the "isoliquiritigenin glycoside content," both of which are shown in Table 5.

[0035] (Component analysis of refined products A to F) <Analysis conditions for liquiritigenin glycoside> Detector: UV detector (ultraviolet wavelength 280 nm) Column: InertSustain C30 (inner diameter φ4.6 mm, length 250 mm) Mobile phase: 12% (v / v) acetonitrile in water Flow rate: 0.8mL / min Column temperature: 40℃ Standards: Liquiritin (for herbal medicine testing, 98.0+%, Fujifilm Wako Pure Chemical Industries, Ltd.) and Liquiritin apioside (98%, ChemFaces) were dissolved in 50% DMSO and then diluted appropriately to prepare a calibration curve.

[0036] <Analysis conditions for isoliquiritigenin glycoside> Detector: UV detector (ultraviolet wavelength 360 nm) Column: InertSustain C30 (inner diameter φ4.6 mm, length 250 mm) Mobile phase: 20% (v / v) acetonitrile in water Flow rate: 0.8mL / min Column temperature: 40℃ Standards: Isoliquiritin (>98.0%, Tokyo Chemical Industry Co., Ltd.), neoisoliquiritin (98%, ChemFaces), isoliquiritin apioside (98%, ChemFaces), and liclaside (98%, ChemFaces) were dissolved in 50% DMSO and then diluted appropriately to prepare a calibration curve.

[0037] (Sensory evaluation test: Masking effect of unpleasant soybean odor or taste) Refined Products A to F were added instead of Example 1 in the sensory evaluation test for the masking effect of the unpleasant soybean odor or unpleasant taste in Example 1, and the intensity of the unpleasant soybean odor or unpleasant taste was evaluated in the same manner as in Example 1. The unpleasant soybean odor or unpleasant taste was evaluated in the sensory evaluation, with the flavor felt the moment the food was placed in the mouth being the "initial taste," the flavor felt while chewing the food being the "middle taste," and the flavor felt after swallowing the food being the "aftertaste." The presence or absence of a licorice odor derived from the raw materials was also evaluated. The results are shown in Table 5. The content of each component in the soy cookies and the "isoliquiritigenin glycoside content," which is the sum of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside, are shown in Table 6. In addition, since soy flour, the raw material for the soy cookies, contains 35% soy protein, the total amount of isoliquiritigenin glycoside was calculated when soy protein was set at 100, and is shown in Table 6.

[0038] Furthermore, to confirm the effect on soy milk, soy milk was prepared by adding 0.05% of refined product A or B to soy milk (unadjusted, protein: 4.15%), and the masking effect on the unpleasant odor or taste of soy was evaluated using soy milk (unadjusted) without the addition of refined product A or B as a control. The intensity of the unpleasant odor or taste of soy was evaluated in the same manner as in Example 1, and the results are shown in Table 5. The content of each component in soy milk and the "isoliquiritigenin glycoside content," which is the sum of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liculaside, are shown in Table 6. In addition, since soy milk contains 4.15% soy protein, the total amount of isoliquiritigenin glycoside was calculated when soy protein was set at 100, and is shown in Table 6.

[0039] [Table 5]

[0040] Refined product A, whose main ingredients are liquiritigenin glycosides such as liquiritin and liquiritin apioside, did not exhibit any masking effect on the unpleasant odor or taste of soy in soy cookies or soy milk. However, refined products B to F, whose main ingredients are isoliquiritigenin glycosides such as isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside, were found to have a masking effect on the unpleasant odor or taste of soy in soy cookies, and refined product B exhibited a similar effect in soy milk. Furthermore, while refined product F, which contains licorice root extract before refinement, licorice spice B, and licoracide as its main ingredients, was unable to mask the unpleasant soybean-derived initial taste, refined products B, C, D, and E, which contain a certain amount (approximately 35% or more) of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, or a total amount of these, added at 0.02% to soy cookies increased the active ingredient concentration in the soy cookies to approximately 70 ppm or more, and a masking effect on the unpleasant soybean-derived initial and inner taste was observed. However, isoliquiritin apioside did not have a masking effect on the unpleasant soybean-derived aftertaste. From the above, it was suggested that one or more of isoliquiritin, neoisoliquiritin, and isoliquiritin apioside have a masking effect on the unpleasant initial taste derived from soybeans, one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside have a masking effect on the unpleasant middle taste derived from soybeans, and one or more of isoliquiritin, neoisoliquiritin, and liclaside have a masking effect on the unpleasant aftertaste derived from soybeans.

[0041] [Table 6]

[0042] From Table 6, it was found that the unpleasant taste or odor derived from soybeans can be masked by having 15 to 200 ppm of isoliquiritigenin glycoside in foods and drinks. It was also found that the unpleasant taste or odor derived from soybeans can be masked by having 0.0045 to 0.437 of isoliquiritigenin glycoside relative to 100 of soybean protein.

Claims

1. A composition for masking unpleasant tastes or odors in oral compositions, comprising isoliquiritigenin glycoside as an active ingredient.

2. 2. The masking composition according to claim 1, wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liculaside.

3. The masking composition according to claim 1 or 2, wherein the unpleasant taste or odor is derived from beans.

4. A method for masking an unpleasant taste or odor of an oral composition, comprising adding isoliquiritigenin glycoside to the oral composition.

5. 5. The masking method according to claim 4, wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside.

6. The masking method according to claim 4 or 5, wherein the unpleasant taste or odor is derived from beans.

7. A soy protein-containing oral composition comprising 0.0002 to 2 parts by weight of isoliquiritigenin glycoside per 100 parts by weight of soy protein.

8. 8. The soy protein-containing oral composition according to claim 7, wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside.

9. A method for producing a soy protein-containing oral composition, characterized in that isoliquiritigenin glycoside is contained in an amount of 0.0002 to 2 parts by weight per 100 parts by weight of soy protein.

10. 10. The method for producing a soy protein-containing oral composition according to claim 9, wherein the isoliquiritigenin glycoside is one or more of isoliquiritin, neoisoliquiritin, isoliquiritin apioside, and liclaside.

Citation Information

Patent Citations

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