Beverage, acidity suppressant, and acidity suppression method

Chlorogenic acids in beverages at specific concentrations mitigate the sour taste of compounds (1) and (2), addressing the sourness challenge and improving beverage palatability.

JP7807050B2Active Publication Date: 2026-01-27MARUZEN PHARMA
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Patent Information

Application Number
JP2022022335
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2022-02-16
Publication Date
2026-01-27
Estimated Expiration
2042-02-16

AI Technical Summary

Technical Problem

Compounds represented by structural formulas (1) and (2) possess a distinctive sour taste when used in beverages, making their incorporation challenging due to the sourness they impart.

Method used

Incorporating chlorogenic acids in beverages at a concentration of 5 to 350 mg/100 mL to suppress the sourness of compounds represented by structural formulas (1) and (2), which are present at 1 to 50 mg/100 mL, effectively reduces the sour taste.

Benefits of technology

The method effectively suppresses the sourness of compounds (1) and (2) in beverages, making them easier to ingest and enhancing the beverage's palatability.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a beverage that contains one or more compounds selected from the group consisting of a compound represented by the structural formula (1) and a compound represented by the structural formula (2) but yet can inhibit sourness in these compounds; an agent for inhibiting sourness of one or more compounds selected from the group consisting of a compound represented by the structural formula (1) and a compound represented by the structural formula (2) in a beverage; and a method for inhibiting sourness of one or more compounds selected from the group consisting of a compound represented by the structural formula (1) and a compound represented by the structural formula (2) in a beverage.SOLUTION: A beverage contains (A) chlorogenic acids of 5-350 mg / 100 mL in total and (B) one or more compounds selected from the group consisting of a compound represented by the structural formula (1) and a compound represented by the structural formula (2) of 1-50 mg / 100 mL in total.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present invention relates to a beverage containing one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2), an acidity suppressant in a beverage, which comprises one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2), and a method for suppressing the acidity of a beverage, which comprises one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2). [Background technology]

[0002] The name of the compound represented by the following structural formula (1) is 3-(4-hydroxy-3-methoxyphenyl)propionic acid. It is known that the compound represented by the following structural formula (1) can be detected when a certain type of lactic acid bacteria is cultured in a medium containing specific components (see, for example, Patent Document 1). [ka]

[0003] The compound represented by the structural formula (1) is an active ingredient of a dipeptidyl peptidase IV activity inhibitor, etc., and is a very useful ingredient known to be able to be incorporated into foods and beverages for inhibiting dipeptidyl peptidase IV activity (see, for example, Patent Document 2).

[0004] The name of the compound represented by the following structural formula (2) is 3,4-dihydroxyhydrocinnamic acid. [ka]

[0005] The compound represented by the structural formula (2) is a compound contained in plants such as grapes, and is known to reduce IL-6 production in mice by downregulating DNMT1 expression and inhibiting DNA methylation of the IL-6 gene.

[0006] Chlorogenic acids are polyphenols found in green coffee beans. Chlorogenic acids are known to have various physiological effects, and their use as active ingredients in hot flash relief agents has been proposed (see, for example, Patent Document 3). [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-003929 [Patent Document 2] Japanese Patent Publication No. 2020-055887 [Patent Document 3] Japanese Patent Publication No. 2020-169124 Summary of the Invention [Problem to be solved by the invention]

[0008] As described above, the compound represented by the structural formula (1) and the compound represented by the structural formula (2) are useful materials. However, when the present inventors investigated the use of the compound represented by the structural formula (1) and the compound represented by the structural formula (2) in beverages, they found that the compound represented by the structural formula (1) and the compound represented by the structural formula (2) have a distinctive sour taste.

[0009] The present invention aims to solve the above-mentioned conventional problems and achieve the following objects: That is, the present invention aims to provide a beverage that contains one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2) but can suppress the sourness of these compounds, an acidity suppressant for a beverage that contains one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2), and a method for suppressing the sourness of one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2) in a beverage. [Means for solving the problem]

[0010] As a result of extensive research conducted by the present inventors to solve the above problems, it was discovered that chlorogenic acids have an excellent effect in suppressing the sourness of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2) in beverages. [ka] [ka]

[0011] The present invention is based on the above findings of the present inventors, and the means for solving the above problems are as follows: <1> (A) Chlorogenic acids total 5 to 350 mg / 100 mL, (B) A beverage characterized by containing 1 to 50 mg / 100 mL of a total of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2). [ka] [ka] <2> The above-mentioned coffee drink <1> The beverage is as described in the above. <3> The present invention is used in a beverage containing 1 to 50 mg / 100 mL of a total of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2), (A) Contains chlorogenic acids, The component (A) is an acidity suppressant comprising one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2) in a beverage, wherein the component (A) is blended into the beverage at a total concentration of 5 to 350 mg / 100 mL. [ka] [ka] <4> A method for suppressing the sourness of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2) in a beverage, characterized by blending chlorogenic acids at a total concentration of 5 to 350 mg / 100 mL into a beverage containing a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2): [ka] [ka] [Effects of the Invention]

[0012] The present invention can solve the above-mentioned problems in the prior art and achieve the above-mentioned object, and can provide a beverage that contains one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2) but can suppress the sourness of these compounds; an acidity suppressor for a beverage, which is one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2); and a method for suppressing the sourness of one or more compounds selected from the group consisting of the compound represented by structural formula (1) and the compound represented by structural formula (2) in a beverage. DETAILED DESCRIPTION OF THE INVENTION

[0013] (beverage) The beverage of the present invention contains at least (A) chlorogenic acids (hereinafter, sometimes referred to as "component (A)") and (B) one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2) (hereinafter, sometimes referred to as "component (B)"), and may further contain other components as necessary.

[0014] <Component (A)> The component (A) is a chlorogenic acid. The component (A) may be used singly or in combination of two or more kinds.

[0015] -Chlorogenic acids- In this specification, chlorogenic acids refer to 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid, 5-feruloylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid.

[0016] The chlorogenic acids are known compounds, and commercially available products may be used, or products produced by known methods may be used. For example, natural products containing chlorogenic acids, particularly those extracted from plants or their purified products, may be used, or those industrially produced by chemical synthesis may be used. The chlorogenic acids are preferably derived from plant extracts. Plants containing chlorogenic acids are not particularly limited and can be appropriately selected depending on the purpose, and examples include coffee beans, nandina leaves, and apples. The method for preparing the plant extract is not particularly limited, and known methods can be appropriately selected.

[0017] The total content of the component (A) in the beverage is not particularly limited as long as it is 5 to 350 mg / 100 mL, and can be appropriately selected depending on the purpose. When two or more types of chlorogenic acids are used as the component (A), the ratio (mass ratio) of the amounts of the chlorogenic acids used is not particularly limited and can be appropriately selected depending on the purpose.

[0018] The method for measuring the content of component (A) in a beverage is not particularly limited, and any known method can be appropriately selected. For example, it can be measured by high performance liquid chromatography (HPLC). More specifically, it can be measured by the [Measurement Method] described in (Test Example 2) in the [Examples] section below.

[0019] <(B) component> The component (B) is one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2). As the component (B), the compound represented by structural formula (1) may be used alone, or the compound represented by structural formula (2) may be used alone, or these may be used in combination.

[0020] -Compound represented by structural formula (1)- The name of the compound represented by the following structural formula (1) is 3-(4-hydroxy-3-methoxyphenyl)propionic acid (hereinafter sometimes referred to as "HMPA"). [ka]

[0021] The compound represented by the structural formula (1) is a known compound, and a commercially available product may be used, or one produced by a known method may be used.

[0022] -Compound represented by structural formula (2)- The name of the compound represented by the following structural formula (2) is 3,4-dihydroxyhydrocinnamic acid. [ka]

[0023] The compound represented by the structural formula (2) is a known compound, and a commercially available product may be used, or one produced by a known method may be used.

[0024] The total content of the component (B) in the beverage is not particularly limited as long as it is 1 to 50 mg / 100 mL, and can be appropriately selected depending on the purpose. When two types of compounds are used as the component (B), the ratio of the amounts used (mass ratio) of the two compounds is not particularly limited and can be appropriately selected depending on the purpose.

[0025] The method for measuring the content of the compound represented by the structural formula (1) in a beverage is not particularly limited, and any known method can be appropriately selected. For example, the content can be measured by HPLC under the following conditions. -HPLC conditions- Column: COSMOSIL 3PBr Packed Column (Nacalai Tesque, Inc.) Guard column: COSMOSIL 3PBr Guard Cartridge (Nacalai Tesque, Inc.) COSMOSIL Guard Cartridge Holder (manufactured by Nacalai Tesque, Inc.) COSMOSIL Column Connecting Tube (manufactured by Nacalai Tesques, Inc.) Mobile phase: A) Methanol:water:formic acid = 500:500:1 B) Methanol Standard solution analysis) 0-10min (100%A) When analyzing sample solution: 0-10 min (100% A), 10.01-24min (100%B), 24.01-38min(100%A) Column temperature: 40℃ · Injection volume: 10μL · Flow rate: 1.0mL / min Detection conditions: UV280nm

[0026] Furthermore, the method for measuring the content of the compound represented by the structural formula (2) in a beverage is not particularly limited, and any known method can be appropriately selected. For example, the content can be measured by HPLC under the following conditions. -HPLC conditions- Column: Wakosil II 5C18HG (Fujifilm Wako Pure Chemical Industries, Ltd.) Mobile phase: A) Water: Trifluoroacetic acid = 1000:1 B) Acetonitrile 0-12min (82%A), 12-20min (82%A → 75%A), 20-35min (75%A → 70%A), 35-40min (70%A), 40-50min (10%A), 50-65min(82%A) Column temperature: 40℃ · Injection volume: 10μL · Flow rate: 0-40min(1.0mL / min), 40-55 min (1.4 mL / min), 55-65 min (1.0 mL / min) Detection conditions: UV280nm

[0027] <Other ingredients> The other ingredients in the beverage are not particularly limited as long as they do not impair the effects of the present invention, and can be appropriately selected from ingredients that can be used in beverages depending on the purpose, and examples include amino acids, sweeteners, acidulants, flavorings, vitamins, minerals, colorants, antioxidants, emulsifiers, preservatives, extracts, quality stabilizers, dietary fiber, etc. These may be used alone or in combination of two or more. The content of other ingredients in the beverage is not particularly limited and can be selected appropriately depending on the purpose.

[0028] <Beverage> The type of beverage is not particularly limited and can be appropriately selected depending on the purpose. Examples include soft drinks, nutritional drinks, functional drinks, and flavored water (near water) drinks. The beverage may contain carbon dioxide or may not contain carbon dioxide. The beverage also includes jelly drinks. The beverage may be colorless or colored, and may be transparent or not transparent. Examples of the non-carbonated beverages include fruit juice drinks, coffee drinks, milk drinks, sports drinks, and tea drinks. Examples of the carbonated beverage include cola, diet cola, ginger ale, cider, and carbonated water with fruit juice flavor. Among these, coffee drinks are preferred.

[0029] The term "coffee beverage" refers to a beverage produced using coffee as an ingredient. The coffee component refers to a liquid containing components derived from coffee beans, and examples thereof include coffee extracts, i.e., liquids obtained by extracting roasted and ground coffee beans with water, hot water, etc. Other examples of coffee components include coffee extracts obtained by concentrating coffee extracts, and liquids obtained by adjusting the amount of instant coffee obtained by drying coffee extracts to an appropriate amount with water, hot water, etc. The coffee component contains chlorogenic acids. Therefore, a coffee beverage containing chlorogenic acids as part of the ingredients is a preferred embodiment of the beverage of the present invention from the standpoints of ease of production and flavor. In particular, black coffee, which does not contain any components other than the coffee component, such as milk or sweeteners, is a preferred embodiment of the present invention.

[0030] The beverage is easy to drink because the acidity of component (B) has been reduced. Therefore, from the standpoint of convenience for users, it is advantageous to make the beverage in a ready-to-drink (RTD) form that can be stored at room temperature for a long period of time and is suitable for continuous consumption in anticipation of the physiological effects of component (B).

[0031] The beverage may be a bottled beverage obtained through heat sterilization. The type of container is not particularly limited and can be appropriately selected depending on the purpose. Examples include plastic containers such as polyethylene terephthalate (PET) containers, polyethylene containers, and polypropylene containers; glass containers; metal containers; and paper containers. The capacity of the container is not particularly limited and can be appropriately selected depending on the purpose, and examples include 100 mL to 2 L.

[0032] According to the inventors' investigations, the sourness of component (B) tends to be more pronounced in low-sweetness beverages, where the sweetness level is kept below a certain level, compared to beverages with higher sweetness levels. Therefore, from the viewpoint of being able to significantly exert the effects of the present invention, low-sweetness beverages are a preferred embodiment of the beverage of the present invention. Here, the sweetness of a "low sweetness" beverage is not particularly limited and can be selected appropriately depending on the purpose, but is preferably 2 or less, more preferably 1.5 or less, even more preferably 1 or less, and particularly preferably 0.5 or less. The lower limit of the sweetness of the beverage is preferably 0 or more. The sweetness intensity is a measure of sweetness, and is a relative ratio where the sweetness of 1% by weight of sucrose (at 20°C) is set to 1. The sweetness intensity of a beverage can be determined by converting the amount (weight concentration) of each sweet component contained in the beverage into an equivalent amount of sucrose based on the relative ratio of the sweetness of that sweet component to the sweetness of sucrose of 1, and then totaling the sucrose-equivalent amounts of all sweet components contained in the beverage. The relative ratio of the sweetness of each sweet component to the sweetness of sucrose of 1 can be determined from the known sugar sweetness conversion table (McMurry Organic Chemistry (7th Edition), p. 988).

[0033] The method for producing the beverage of the present invention is not particularly limited, and any known method for producing beverages can be appropriately selected, including, for example, a method in which component (A), component (B), and, if necessary, other components are blended during the beverage production process. The beverage of the present invention can also be produced by adding component (A), component (B), and, if necessary, other components to a beverage produced by a known method. The order in which the various components are blended is not particularly limited and can be appropriately selected depending on the purpose. Furthermore, the production of the beverage of the present invention may include a step of adjusting the contents of the various components. Furthermore, the beverage of the present invention can be made into a bottled beverage by undergoing a process such as sterilization, if necessary. For example, a sterilized bottled beverage can be produced by a method in which the beverage is filled into a container and then subjected to heat sterilization, or by a method in which the beverage is sterilized and then filled into a container in a sterile environment. The heat sterilization treatment can be carried out under sterilization conditions specified in the Food Sanitation Act. There are no particular limitations on the sterilizer and it can be selected appropriately depending on the purpose. For example, a tube-type sterilizer, a plate-type sterilizer, an FP (Flash Pastrization) plate-type sterilizer, a UHT (Ultra High Temperature) sterilizer, etc. can be used. There are no particular limitations on the heating temperature or treatment time and they can be selected appropriately depending on the type of beverage. Typically, heating is carried out at 60 to 150°C for 1 second to 30 minutes.

[0034] The beverage of the present invention contains one or more compounds selected from the group consisting of compounds represented by the structural formula (1) and compounds represented by the structural formula (2), but the sourness that is a taste unique to these compounds is suppressed (sometimes referred to as mitigated), making it easy to ingest.

[0035] (acidity reducer) The acidity suppressant of the present invention is used in a beverage containing a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2), and contains at least (A) chlorogenic acids, and optionally further contains other ingredients. The sourness reducer of the present invention reduces the sourness of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2) in a beverage. In this specification, "reducing sourness" refers to alleviating the sourness, which is a unique taste possessed by compounds represented by structural formula (1) and compounds represented by structural formula (2). For example, it can be said that sourness is reduced when the sourness is reduced compared to a beverage that does not contain component (A).

[0036] <Component (A)> The component (A) is a chlorogenic acid. The component (A) may be used singly or in combination of two or more kinds.

[0037] -Chlorogenic acids- The chlorogenic acids are the same as those described in the above section (Drinks).

[0038] The content of the chlorogenic acids in the acidity suppressant is not particularly limited and can be appropriately selected depending on the amount to be used, etc.

[0039] <Other ingredients> The other components in the acidity suppressant are not particularly limited as long as they do not impair the effects of the present invention and can be appropriately selected depending on the purpose, and examples thereof include excipients, moisture-proofing agents, preservatives, strengthening agents, thickeners, emulsifiers, antioxidants, sweeteners, acidulants, seasonings, water, components used in foods and beverages, etc. These may be used alone or in combination of two or more. The content of other components in the acidity suppressing agent is not particularly limited and can be appropriately selected depending on the purpose.

[0040] <Aspect> The acidity reducer may be in a form in which the component (A) and, if necessary, the other components are contained in the same packaging material, or in a form in which the components are contained in separate packaging materials and used together at the time of use. The form of the acidity suppressing agent is not particularly limited and can be appropriately selected. Examples thereof include solids such as powder and granules, and liquids obtained by dissolving the agent in a solvent such as water.

[0041] <Use> The method of using the acidity reducer is not particularly limited and can be appropriately selected depending on the purpose, and examples thereof include a method of adding the acidity reducer to a produced beverage, a method of adding the acidity reducer during the production process of a beverage, etc. These methods may be used alone or in combination.

[0042] The order in which the components of the acidity suppressant are added to the beverage is not particularly limited and can be appropriately selected depending on the purpose. The components of the acidity suppressant may be added all at once or in multiple portions.

[0043] The amount of the acidity suppressant used is not particularly limited, and can be appropriately selected taking into consideration the amounts of the component (A) and the other components used as needed.

[0044] The amount of component (A) used is not particularly limited as long as it is blended into the beverage at a total concentration of 5 to 350 mg / 100 mL, and can be appropriately selected depending on the type of beverage to be consumed. When two or more types of chlorogenic acids are used as the component (A), the ratio (mass ratio) of the amounts of the chlorogenic acids used is not particularly limited and can be appropriately selected depending on the purpose.

[0045] The acidity reducing agent may be used alone or in combination with other acidity reducing agents.

[0046] <Beverage> The beverage is not particularly limited as long as it contains a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2), and can be appropriately selected depending on the purpose. For example, the beverage may be the same as those described in the above section (Beverage).

[0047] (How to suppress acidity) The method for suppressing sourness of the present invention includes at least a blending step, and may further include other steps as necessary. The method for suppressing sourness of the present invention is a method for suppressing the sourness of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2).

[0048] <Blending process> The blending step is a step of blending chlorogenic acids at a total concentration of 5 to 350 mg / 100 mL into a beverage containing a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2).

[0049] -Chlorogenic acids- The chlorogenic acids may be used alone or in combination of two or more.

[0050] The chlorogenic acids are the same as those described in the above section (Drinks).

[0051] The method for incorporating the chlorogenic acids into the beverage is not particularly limited and can be selected as appropriate. For example, it can be carried out in the same manner as described in the above-mentioned section on "Use" of the acidity suppressant of the present invention, and the amount used can also be the same.

[0052] <Beverage> The beverage is not particularly limited as long as it contains a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2), and can be appropriately selected depending on the purpose. For example, the beverage may be the same as those described in the above section (Beverage).

[0053] The sourness suppressant and sourness suppression method of the present invention can suppress the sourness of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2) in a beverage containing a total of 1 to 50 mg / 100 mL of one or more compounds selected from the group consisting of compounds represented by structural formula (1) and compounds represented by structural formula (2). [Example]

[0054] Test examples will be described below, but the present invention is not limited to these test examples.

[0055] (Test Example 1: Suppression of sourness of compound represented by structural formula (1) by chlorogenic acids) The compound represented by the structural formula (1) (manufactured by Tokyo Chemical Industry Co., Ltd.) and chlorogenic acid 0.5 hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were dissolved in water in the amounts shown in Tables 1-1 to 1-5 below to prepare a beverage (sweetness level: 0). Note that the "chlorogenic acids" column in Tables 1-1 to 1-5 below indicates the amount of chlorogenic acid, not the amount of chlorogenic acid 0.5 hydrate.

[0056] <Evaluation> The prepared beverages were subjected to a sensory evaluation of their flavor. The flavor was evaluated primarily from the perspective of the sourness characteristic of the compound represented by structural formula (1). Specifically, six well-trained expert panelists evaluated the beverages according to the following criteria. The evaluation temperature was room temperature. -Evaluation criteria- 5 points: The sourness characteristic of the compound represented by structural formula (1) is greatly reduced. 4 points: The sourness characteristic of the compound represented by structural formula (1) is reduced. 3 points: The sourness characteristic of the compound represented by structural formula (1) is slightly reduced. 2 points: The compound represented by structural formula (1) has a sour taste that lingers in the aftertaste. 1 point: The compound represented by structural formula (1) has a strong sour taste that lingers in the aftertaste.

[0057] The results are shown in the following Tables 1-1 to 1-5. The evaluation scores are the average scores of the six expert panelists.

[0058] [Table 1-1]

[0059] [Table 1-2]

[0060] [Table 1-3]

[0061] [Table 1-4]

[0062] [Table 1-5]

[0063] As shown in Tables 1-1 to 1-5, it was found that the sourness characteristic of the compound represented by structural formula (1) can be suppressed by adding 5 to 350 mg / 100 mL of chlorogenic acids to a beverage containing a compound represented by structural formula (1) at a concentration of 1 to 50 mg / 100 mL.

[0064] Test Example 2: Evaluation of coffee drinks containing the compound represented by structural formula (1) <Coffee> Commercially available instant coffee was used as the coffee, and its powder was dissolved in water in a predetermined ratio to prepare a coffee solution. The content of chlorogenic acids in the coffee solution was measured using the following measurement method, and was found to be 20 mg / 100 mL. [Measurement method] The coffee solution was diluted 10-fold with mobile phase A, filtered through a membrane filter, and injected into HPLC. Chlorogenic acid 0.5 hydrate was used as a standard substance, and the chlorogenic acid content was determined from the peak area values ​​of nine chlorogenic acids: 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid, 5-feruloylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid. -HPLC conditions- Column Cadenza CD-C18: φ4.6mm x 150mm, particle size 3μm (Intact Co., Ltd.) · Mobile phase Solution A: 0.05 mol / L acetic acid, 0.01 mol / L sodium acetate, 0.1 mmol / L HEDPO containing 5% acetonitrile Solution B: Acetonitrile Gradient conditions: See Table 2-1 below · Flow rate: 1.0mL / min Column temperature: 35℃ Sample injection volume: 10 μL Detection wavelength: 325nm Standard substance: Chlorogenic acid 0.5 hydrate (99% content) (Wako Grade 1) (Fujifilm Wako Pure Chemical Industries, Ltd.)

[0065] [Table 2-1]

[0066] <Sample preparation> Chlorogenic acids (chlorogenic acid 0.5 hydrate (Fujifilm Wako Pure Chemical Industries, Ltd.)) were added to the above coffee solution to prepare samples (sweetness level: 0) with chlorogenic acid concentrations of 50 mg / 100 mL and 150 mg / 100 mL. The compound represented by structural formula (1) was also added to give a concentration of 1 to 50 mg / 100 mL. The column "Added chlorogenic acids" in Tables 2-2 and 2-3 below indicates the amount of chlorogenic acid, not the amount of chlorogenic acid 0.5 hydrate.

[0067] <Evaluation> The prepared samples were evaluated for the intensity of the sourness derived from the compound represented by structural formula (1) by six expert panelists in the same manner as in Test Example 1. The results are shown in Tables 2-2 to 2-3 below. The evaluation scores are the average scores of the six expert panelists.

[0068] [Table 2-2]

[0069] [Table 2-3]

[0070] As shown in Tables 2-2 to 2-3, it was found that the acidity characteristic of the compound represented by structural formula (1) was suppressed even in commercially available coffee beverages containing the compound represented by structural formula (1) at concentrations of 1 to 50 mg / 100 mL.

[0071] (Test Example 3: Suppression of sourness of compound represented by structural formula (2) by chlorogenic acids) The compound represented by the structural formula (2) (manufactured by Tokyo Chemical Industry Co., Ltd.) and chlorogenic acid 0.5 hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were dissolved in water in the amounts shown in Tables 3-1 to 3-5 below to prepare a beverage (sweetness level: 0). Note that the "chlorogenic acids" column in Tables 3-1 to 3-5 below indicates the amount of chlorogenic acid, not the amount of chlorogenic acid 0.5 hydrate.

[0072] <Evaluation> The prepared beverages were subjected to a sensory evaluation of their flavor. The flavor was evaluated primarily from the perspective of the sourness characteristic of the compound represented by structural formula (2). Specifically, six well-trained expert panelists evaluated the beverages according to the following criteria. The evaluation temperature was room temperature. -Evaluation criteria- 5 points: The sourness characteristic of the compound represented by structural formula (2) is greatly reduced. 4 points: The sourness characteristic of the compound represented by structural formula (2) is reduced. 3 points: The sourness characteristic of the compound represented by structural formula (2) is slightly reduced. 2 points: The compound represented by structural formula (2) has a sour taste that lingers in the aftertaste. 1 point: The compound represented by structural formula (2) has a strong sour taste that lingers in the aftertaste.

[0073] The results are shown in Tables 3-1 to 3-5 below. The evaluation scores are the average scores of the six expert panelists.

[0074] [Table 3-1]

[0075] [Table 3-2]

[0076] [Table 3-3]

[0077] [Table 3-4]

[0078] [Table 3-5]

[0079] As shown in Tables 3-1 to 3-5, it was found that the sourness characteristic of the compound represented by structural formula (2) can be suppressed by adding 5 to 350 mg / 100 mL of chlorogenic acids to a beverage containing a compound represented by structural formula (2) at a concentration of 1 to 50 mg / 100 mL.

[0080] Test Example 4: Evaluation of coffee drinks containing the compound represented by structural formula (2) <Coffee> Commercially available instant coffee was used as the coffee, and its powder was dissolved in water in a predetermined ratio to prepare a coffee solution. The content of chlorogenic acids in the coffee solution was measured in the same manner as in Test Example 2, and was found to be 20 mg / 100 mL.

[0081] <Sample preparation> Chlorogenic acids (chlorogenic acid 0.5 hydrate (Fujifilm Wako Pure Chemical Industries, Ltd.)) were added to the above coffee solution to prepare samples (sweetness level: 0) with chlorogenic acid concentrations of 50 mg / 100 mL and 150 mg / 100 mL. The compound represented by structural formula (2) was also added to the coffee solution to a concentration of 1 to 50 mg / 100 mL. The column "Added chlorogenic acids" in Tables 4-1 and 4-2 below indicates the amount of chlorogenic acid, not the amount of chlorogenic acid 0.5 hydrate.

[0082] <Evaluation> The prepared samples were evaluated for the intensity of the sourness derived from the compound represented by structural formula (2) by six expert panelists in the same manner as in Test Example 3. The results are shown in Tables 4-1 to 4-2 below. The evaluation scores are the average scores of the six expert panelists.

[0083] [Table 4-1]

[0084] [Table 4-2]

[0085] As shown in Tables 4-1 to 4-2, it was found that the acidity characteristic of the compound represented by structural formula (2) was suppressed even in commercially available coffee beverages containing the compound represented by structural formula (2) at concentrations of 1 to 50 mg / 100 mL.

Claims

1. (A) a total of 5 to 350 mg / 100 mL of chlorogenic acids; (B) A beverage characterized by comprising one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2), in a total amount of 1 to 50 mg / 100 mL: 【Chemistry 1】 【Chemistry 2】

2. 10. The beverage of claim 1 which is a coffee beverage.

3. The present invention is used in a beverage containing 1 to 50 mg / 100 mL in total of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2), (A) Contains chlorogenic acids, The acidity suppressant for a beverage, wherein the component (A) is blended in the beverage at a total concentration of 5 to 350 mg / 100 mL, is one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2). 【Transformation 3】 【Chemistry 4】

4. A method for suppressing the sourness of a beverage by blending chlorogenic acids at a concentration of 5 to 350 mg / 100 mL in total with a beverage containing 1 to 50 mg / 100 mL in total of one or more compounds selected from the group consisting of compounds represented by the following structural formula (1) and compounds represented by the following structural formula (2): 【Transformation 5】 【Transformation 6】

Citation Information

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