Carbonation sensation imparting or enhancing agent

Abstract

The present invention provides a carbonation sensation imparting or enhancing agent or the like containing, as an active ingredient, a diester compound represented by general formula (I). [In the formula, R is methyl, ethyl or isopropyl, n is an integer from 1 to 8, and m is an integer from 0 to 6. ] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to an agent for imparting or enhancing a carbonation sensation, a flavor composition for imparting or enhancing a carbonation sensation, a food or oral care product imparted with a carbonation sensation or having its carbonation sensation enhanced, a method for producing a food or oral care product imparted with a carbonation sensation or having its carbonation sensation enhanced, a method for imparting or enhancing a carbonation sensation, a mouthfeel improver, and a mouthfeel improving method. Background Art

[0002] Carbonated beverages are often consumed because of the unique stimulation felt in the oral cavity by the carbon dioxide gas in the beverage, and can give an exhilarating feeling or a refreshing feeling. Therefore, carbonated beverages are popular beverages on the market. In addition, with the diversification of consumer preferences in recent years, the popularity of so-called strongly carbonated beverages has also increased.

[0003] Consumers who expect stronger stimulation not only have demand for carbonated beverages, but also have demand for foods such as confectionery that give carbonic acid stimulation. In addition, there is a demand for technology that imparts a carbonic acid sensation to food and beverage products without carbonic acid stimulation that have carbonated beverage flavor or fruit flavor given by spices.

[0004] In order to enhance the carbonation stimulation of carbonated beverages, a method of increasing the carbon dioxide gas pressure by increasing the amount of carbon dioxide gas added is generally used. However, when the carbon dioxide gas pressure increases, there is a risk of the beverage spraying out during filling into the container or opening when drinking, and from the perspective of production equipment, the carbon dioxide gas pressure that can be increased is also limited. Therefore, a method of enhancing the carbonation sensation without increasing the carbon dioxide gas pressure has been proposed in the related art.

[0005] For example, Patent Document 1 proposes a carbonic acid enhancer, which contains chili extract, pepper extract, ginger extract and the pungent components contained therein as active ingredients. Patent Document 2 proposes a method for enhancing carbonic acid, in which caffeine, quasin and naringin as bitter components are used as active ingredients. Patent Document 3 proposes a carbonic acid enhancer, which contains 3-heptene-2-one, 3-octen-2-one, 3-nonene-2-one and 3-decene-2-one with characteristic aroma as active ingredients. Patent Document 4 proposes a carbonic acid enhancer, which contains rotundone (rotundone) and the like with unique spicy and peppery aroma as active ingredients. Patent Document 5 proposes a method for enhancing carbonic acid stimulation, in which (3-oxo-2-pentylcyclopentyl) methyl acetate, a compound usually added to food and drink as a spice, is used as a raw material.

[0006] However, in the above-mentioned technology, the carbonation feeling imparting effect is hardly obtained, and the reinforcing effect may not be exhibited in a wide range of addition concentration.

[0007] In view of such background, there is a need for new technologies for imparting a carbonation sensation to products such as food and beverage products and oral care products or enhancing the carbonation sensation of the products.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: JP2010-68749A

[0011] Patent Document 2: JP2017-104046A

[0012] Patent Document 3: JP2019-62867A

[0013] Patent Document 4: JP2021-94024A

[0014] Patent Document 5: WO2014 / 147886 Summary of the invention

[0015] Problem that the invention aims to solve

[0016] An object of the present invention is to provide an agent for imparting a carbonic acid sensation to a food or drink or an oral care product or for enhancing the carbonic acid sensation of a food or drink or an oral care product.

[0017] Solutions for solving problems

[0018] The present invention has been made in view of the above circumstances, and includes the following aspects.

[0019] [1] A carbonation feeling imparting or enhancing agent comprising a diester compound represented by the following general formula (I) as an active ingredient.

[0020] [Chemical formula 1]

[0021]

[0022] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0023] [2] The carbonation feeling imparting or enhancing agent according to the above [1], wherein in the diester compound, R represents an ethyl group or an isopropyl group, n represents an integer of 2 to 8, and m represents an integer of 0 to 4.

[0024] [3] The carbonation feeling imparting or enhancing agent according to the above [1], wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

[0025] [4] A flavor composition for imparting or enhancing a carbonation sensation, comprising the agent for imparting or enhancing a carbonation sensation according to any one of [1] to [3] above.

[0026] [5] A food or oral care product imparted with a carbonation sensation or having its carbonation sensation enhanced, comprising the carbonation sensation imparting or enhancing agent according to any one of [1] to [3] above or the flavor composition for imparting or enhancing a carbonation sensation according to [4] above.

[0027] [6] The food or oral care product according to [5] above, wherein the content of the diester compound is 0.01 ppm to 10000 ppm.

[0028] [7] A method for producing a food or oral care product to which a carbonation sensation is imparted or to which the carbonation sensation is enhanced, the method comprising the step of blending a diester compound in an amount of 0.01 ppm to 10000 ppm into the food or oral care product, wherein the diester compound is represented by the following general formula (I):

[0029] [Chemical formula 2]

[0030]

[0031] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0032] [8] The method for producing a food or oral care product imparted with a carbonation feeling or an enhanced carbonation feeling according to the above [7], wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

[0033] [9] A method for imparting or enhancing a carbonic acid sensation, the method comprising blending a diester compound as an effective ingredient into a food or oral care product, wherein the diester compound is represented by the following general formula (I):

[0034] [Chemical formula 3]

[0035]

[0036] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0037]

[10] The method for imparting or enhancing a carbonation feeling according to [9] above, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

[0038]

[11] A mouthfeel improving agent comprising a diester compound represented by the following general formula (I) as an active ingredient.

[0039] [Chemical formula 4]

[0040]

[0041] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0042]

[12] The mouthfeel improving agent according to the above

[11] , wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

[0043]

[13] A method for improving taste, comprising blending a diester compound as an effective ingredient into a food or oral care product, wherein the diester compound is represented by the following general formula (I):

[0044] [Chemical formula 5]

[0045]

[0046] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0047]

[14] The method for improving taste according to

[13] above, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

[0048] Effects of the Invention

[0049] According to an aspect of the present invention, the carbonation feeling imparting or enhancing agent or the carbonation feeling imparting or enhancing flavor composition can impart carbonation feeling to food, drink or oral care products, or can enhance the carbonation feeling of food, drink or oral care products. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 is a schematic diagram showing the response of TRPV1 and TRPA1 to diethyl sebacate. DETAILED DESCRIPTION

[0051] The present invention will be described below. In this specification, the unit "ppm" means "ppm by mass". That is, in this specification, "ppm" means 0.001 mg / g. In addition, the expression "to" indicating a numerical range is used to include the numerical values ​​described before and after as the lower limit value and the upper limit value.

[0052] In the present specification, "providing or enhancing a carbonation feeling" means providing a carbonation feeling or enhancing a carbonation feeling.

[0053] <Carbonation Imparting or Enhancing Agent>

[0054] The carbonation feeling imparting or enhancing agent according to one aspect of the present invention can impart or enhance the carbonation feeling.

[0055] The carbonation sensation imparting or enhancing agent according to one aspect of the present invention can enhance, for example, the carbonation sensation caused by carbon dioxide gas contained in a food or drink, or the carbonation sensation caused by carbon dioxide gas generated when a food or drink exhibiting a stimulation specific to carbonic acid is placed in the oral cavity. In addition, for example, the carbonation sensation can be imparted to a food or drink or an oral care product without the original carbonation stimulation, which does not contain a component causing the carbonation sensation (carbonic acid, sodium bicarbonate, etc.) and is flavored with a carbonated beverage flavor or a fruit flavor, etc., by spices.

[0056] The carbonation feeling imparting or enhancing agent according to one aspect of the present invention contains a diester compound represented by the following general formula (I) as an effective ingredient.

[0057] [Chemical formula 6]

[0058]

[0059] [In the formula, R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer from 1 to 8, and m represents an integer from 0 to 6.]

[0060] The above-mentioned R is preferably an ethyl group or an isopropyl group, and more preferably an ethyl group.

[0061] The above-mentioned n is preferably an integer of 2-8, and more preferably an integer of 4-8.

[0062] The above-mentioned m is preferably an integer of 0-4, and more preferably an integer of 0-1.

[0063] In the present specification, the diester compound represented by formula (I) is preferably diethyl sebacate (n=8, m=0, R=ethyl), diethyl succinate (n=2, m=0, R=ethyl), diisobutyl adipate (n=4, m=1, R=isopropyl), diethyl malonate (n=1, m=0, R=ethyl), dibutyl sebacate (n=8, m=2, R=ethyl), dimethyl sebacate (n=8, m=0, R=methyl) or dipropyl adipate (n=4, m=1, R=ethyl), more preferably diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate or dibutyl sebacate, and particularly preferably diethyl sebacate.

[0064] As the diester compound represented by the above formula (I), a diester compound obtained by chemical synthesis may be used, a diester compound obtained by extraction from a natural product may be used, or a combination thereof may be used. The above diester compounds may be used alone or in combination of two or more thereof.

[0065] The preferred content of the above-mentioned diester compound in the carbonation feeling imparting or enhancing agent according to one aspect of the present invention is appropriately determined depending on the purpose and application, and is not particularly limited. The preferred content of the diester compound is preferably 0.01% by mass to 100% by mass, more preferably 0.02% by mass to 100% by mass, and still more preferably 0.05% by mass to 100% by mass.

[0066] The carbonic acid sense imparting or enhancing agent according to one aspect of the present invention may contain various spices in addition to the diester compound represented by the above formula (I). In this specification, examples of various spices include essential oils, natural spices and synthetic spices described in, for example, "Official Gazette Known / Common Technical Book (Flavor or Fragrances) part II Food Flavors" (January 14, 2000, published by the Japan Patent Office). These spices can be used alone or in combination of two or more thereof.

[0067] <Method for imparting or enhancing carbonation>

[0068] The present invention also provides a method for imparting a carbonic acid sensation to a food or oral care product or enhancing the carbonic acid sensation of a food or oral care product. The method for imparting or enhancing a carbonic acid sensation comprises blending a diester compound as an effective ingredient into a food or oral care product.

[0069] The method for imparting or enhancing a carbonation sensation means a method of imparting a carbonation sensation by blending the diester compound without causing carbonation stimulation in the absence of the diester compound, or a method of enhancing a carbonation sensation by containing the diester compound when a carbonation sensation is produced even in the absence of the diester compound.

[0070] In this specification, the expression "carbonation feeling" means a unique stimulating feeling felt in the mouth or throat, as felt when drinking a carbonated beverage containing carbon dioxide gas. This stimulation usually brings a refreshing feeling or a cool feeling. In addition, the expression "imparting carbonation feeling" means newly adding carbonation feeling, and the expression "enhancing carbonation feeling" means increasing carbonation feeling.

[0071] <Fragrance composition for imparting or enhancing carbonation>

[0072] The carbonic acid sense imparting or enhancing perfume composition according to one aspect of the present invention contains a carbonic acid sense imparting or enhancing agent, and can be used in combination with various spices. The content of the diester compound represented by formula (I) in the carbonic acid sense imparting or enhancing perfume composition depends on the purpose and application and is appropriately determined, and is not particularly limited. The content of the diester compound is preferably 0.001% by mass to 99.5% by mass, more preferably 0.002% by mass to 99.5% by mass, and still more preferably 0.005% by mass to 99.5% by mass.

[0073] Carbonation sense imparting or enhancing flavor composition according to one aspect of the present invention may further contain solvent or retainer (fixative).Solvent and retainer are not particularly limited, and examples thereof include water, ethanol, isopropanol, ethylene glycol, propylene glycol, dipropylene glycol, glycerine, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, methyl hydrogenated rosin (Hercolyn), medium chain triglyceride and medium chain diglyceride.These solvents and retainer can be used alone or in combination with two or more thereof.

[0074] The carbonation sense imparting or enhancing flavor composition according to one aspect of the present invention may contain various additives. The additive is not particularly limited, and examples thereof include antioxidants, higher alcohols, emulsifiers, surfactants, ultraviolet absorbers, chelating agents, solubilizers, stabilizers, coolants, preservatives, antibacterial agents, bactericides, dyes, and pH regulators. These additives may be used alone or in combination of two or more thereof.

[0075] <Food, drink or oral care products>

[0076] One aspect of the present invention also relates to a food or oral care product to which a carbonation sensation is imparted or to which a carbonation sensation is enhanced, and a method for producing the food or oral care product. The expression "food or oral care product to which a carbonation sensation is imparted or to which a carbonation sensation is enhanced" means a food or oral care product to which a carbonation sensation is imparted without the above-mentioned diester compound but without carbonation stimulation, or a food or oral care product to which a carbonation sensation is enhanced by containing the above-mentioned diester compound when a carbonation sensation is generated even without the above-mentioned diester compound.

[0077] Those skilled in the art can appropriately determine the concentration of the carbonic acid sense imparting or reinforcing agent in the food or oral care product or the concentration of the flavor composition for reinforcing the carbonic acid sense imparting or reinforcing according to the properties of the target food or target oral care product or the desired effect. For example, the content of the diester compound represented by formula (I) as the active ingredient of the carbonic acid sense imparting or reinforcing agent according to one aspect of the present invention in the food or oral care product is not particularly limited, and is preferably 0.01ppm to 10000ppm, more preferably 0.02ppm to 5000ppm, and still more preferably 0.05ppm to 1000ppm. The above-mentioned content of the diester compound is not intended to be particularly limited, and more specifically, for example, the content of the above-mentioned diester compound in the beverage is preferably 0.01ppm to 100ppm, more preferably 0.01ppm to 50ppm, still more preferably 0.02ppm to 40ppm, and particularly preferably 0.05ppm to 20ppm. The content of the above diester compound in fruits is preferably 0.05 ppm to 10000 ppm, more preferably 0.1 ppm to 5000 ppm, and still more preferably 0.25 ppm to 1000 ppm. The content of the above diester compound in oral care products is preferably 0.05 ppm to 2000 ppm, more preferably 0.1 ppm to 1000 ppm, and still more preferably 0.25 ppm to 500 ppm.

[0078] <Method for producing food, drink or oral care product>

[0079] The method for producing a food or oral care product to which a carbonation sensation is imparted or to which a carbonation sensation is enhanced comprises the step of blending a diester compound into the food or oral care product. Note that "blending a diester compound into the food or oral care product" means adding a diester compound from the outside of the food or oral care product.

[0080] Food and drink products are not intended to be limited, and examples of food and drink products include beverages such as carbonated drinks, soft drinks, fruit juice drinks, milk drinks, lactic acid bacteria drinks, energy drinks, soy milk and tea drinks; alcoholic beverages such as Chu-Hi, cocktails, sparkling wine, fruit wine and medicinal wine; desserts such as ice cream, ice milk, lactose ice cream, frozen desserts, yogurt, pudding, jelly and daily desserts; fruits such as caramel, candy, soft candy, pressed candy, crackers, biscuits, cookies, pies, chocolates, snacks and chewing gum; and jam. Examples of oral care products include toothbrushing powder, toothpaste, liquid toothpaste, mouthwash and oral spray.

[0081] In addition, the food and drink may be a food and drink that exhibits stimulation peculiar to carbonic acid (hereinafter also referred to as "food and drink with carbonic acid stimulation"). Examples of food and drink with carbonic acid stimulation include carbonated beverages, frozen desserts, chewing gum, candy, soft candy, pressed candy and jelly imparted with carbonic acid stimulation. In non-beverage foods, sodium bicarbonate and acidulants (citric acid, etc.) may coexist, and there is a case where carbonic acid stimulation may be imparted by generating carbon dioxide gas when the two ingredients are dissolved in the oral cavity, or there is a case where high-pressure carbon dioxide gas sealed sugar may be used in which high-pressure carbon dioxide gas is sealed in hard candy.

[0082] <Taste Improver>

[0083] The agent containing the diester compound represented by formula (I) as an effective ingredient of the carbonation feeling imparting or enhancing agent according to one aspect of the present invention can also be used as a mouthfeel improver. In this specification, the expression "mouthfeel" refers to a feeling different from taste, aroma, and appearance (visual feeling), and refers to the feeling, mucosal feeling or skin feeling felt in the oral cavity (including teeth and tongue) when taking food or oral care products. In this specification, the expression "mouthfeel" more specifically means feelings such as "carbonic acid stimulation" or "foaming feeling". Here, the expression "carbonic acid stimulation" means, for example, a stimulating feeling including stinging pain caused by carbonic acid and a burning feeling caused by an acid such as carbonic acid, and the expression "foaming feeling" more specifically means feelings such as "carbonic acid stimulation". In addition, the expression "improving mouthfeel" means improving the above-mentioned "mouthfeel", and specifically, means enhancing or imparting feelings such as "heavy mouthfeel" or "mineral feeling (minerality)" to food or oral care products. Here, the expressions "heavy mouthfeel" and "mineral taste" mean, for example, salty taste and slight bitter taste felt from carbonic acid.

[0084] <Methods to improve taste>

[0085] The present invention also provides a method for improving taste, which comprises blending a diester compound as an effective ingredient into a food or oral care product.

[0086] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

[0087] Example

[0088] In the following examples, the action and effect were verified using the value obtained by calculating the average score of the score for imparting or enhancing the carbonation feeling through sensory evaluation performed by a panelist. The sensory evaluation was performed according to the criteria shown in Table 1 below. The expression "1 point" in the evaluation is an evaluation in the case where no ingredient was added at all (no addition).

[0089] [Table 1]

[0090] Table 1

[0091] (Evaluation criteria for carbonation enhancement) 5 points: Greatly enhances the carbonation 4 points: Fully enhance the carbonation 3 points: Enhanced carbonation 2 points: Slightly enhanced carbonation 1 point: No enhancement of carbonation (Evaluation criteria for carbonation) 5 points: Greatly gives a sense of carbonation 4 points: Fully imparts a sense of carbonation 3 points: Gives a sense of carbonation 2 points: Slightly gives a sense of carbonation 1 point: Almost no carbonation

[0092] [Example 1] Carbonated water (raw materials: water, carbon dioxide)

[0093] Diethyl sebacate (manufactured by Inoue Perfumery Mfg. Co., Ltd., the same applies to the following examples) was added alone to "WILKINSON (registered trademark) TANSAN (manufactured by Asahi Soft Drinks Co., Ltd.)" so as to reach the concentrations shown in Table 2 below, and sensory evaluation was performed by 7 panelists to determine the degree to which the carbonation feeling was enhanced compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 2.

[0094] [Table 2]

[0095] Table 2

[0096]

[0097] This experiment shows that the carbonation sensation of carbonated water can be enhanced by adding diethyl sebacate. In addition, "carbonation stimulation" is exemplified as a specific example of the sensation of "mouthfeel", and therefore, the effect of improving the mouthfeel is also confirmed from the above-mentioned carbonation sensation enhancement evaluation results.

[0098] [Example 2] Carbonated water (raw materials: water, carbon dioxide)

[0099] Diisobutyl adipate (manufactured by Inoue Perfumery Mfg. Co., Ltd., the same applies to the following examples) was added alone to "WILKINSON (registered trademark) TANSAN (manufactured by Asahi Soft Drinks Co., Ltd.)" so as to achieve the concentrations shown in Table 3 below, and sensory evaluation was performed by 7 panelists to determine the degree to which the carbonation feeling was enhanced compared to a control to which diisobutyl adipate was not added. The average score of the scores is shown in Table 3.

[0100] [Table 3]

[0101] Table 3

[0102]

[0103] This experiment showed that the carbonation sensation of carbonated water can be enhanced by adding diisobutyl adipate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation sensation enhancement evaluation results.

[0104] [Example 3] Carbonated water (raw materials: water, carbon dioxide)

[0105] Dimethyl sebacate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added alone to "WILKINSON (registered trademark) TANSAN (manufactured by Asahi Soft Drinks Co., Ltd.)" so as to achieve the concentrations shown in Table 4 below, and sensory evaluation was performed by 7 panelists to determine the degree to which the carbonation feeling was enhanced compared to a control to which dimethyl sebacate was not added. The average score of the scores is shown in Table 4.

[0106] [Table 4]

[0107] Table 4

[0108]

[0109] This experiment showed that the carbonation sensation of carbonated water can be enhanced by adding dimethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation sensation enhancement evaluation results.

[0110] [Example 4] Carbonated water (raw materials: water, carbon dioxide)

[0111] Dipropyl adipate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added alone to "WILKINSON (registered trademark) TANSAN (manufactured by Asahi Soft Drinks Co., Ltd.)" so as to achieve the concentrations shown in Table 5 below, and sensory evaluation was performed by 7 panelists to determine the degree to which the carbonation feeling was enhanced compared to a control to which dipropyl adipate was not added. The average score of the scores is shown in Table 5.

[0112] [Table 5]

[0113] Table 5

[0114]

[0115] This experiment showed that the carbonation sensation of carbonated water can be enhanced by adding dipropyl adipate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation sensation enhancement evaluation results.

[0116] [Example 5] (Apple cider flavored carbonated beverage)

[0117] Diethyl sebacate was added alone to "Mitsuya Cider (registered trademark) Zero Strong (manufactured by AsahiSoft Drinks Co., Ltd.)" so as to achieve the concentrations shown in Table 6 below, and sensory evaluation was performed by 7 panelists to determine the extent to which the carbonation sensation was enhanced compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 6.

[0118] [Table 6]

[0119] Table 6

[0120]

[0121] As a result, it was shown that the carbonation feeling of cider-flavored carbonated beverages can be enhanced by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation feeling enhancement evaluation results.

[0122] [Example 6] (Carbonated grapefruit flavor Chu-Hi)

[0123] Diethyl sebacate was added alone to "Hyoketsu (registered trademark) Sicilian lemon (manufactured by Kirin Brewery Co., Ltd.)" so as to achieve the concentrations shown in Table 7 below, and sensory evaluation was performed by 7 panelists to determine the extent to which the carbonation sensation was enhanced compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 7.

[0124] [Table 7]

[0125] Table 7

[0126]

[0127] As a result, it was shown that the carbonation feeling of carbonated grapefruit-flavored Chu-Hi can be enhanced by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation feeling enhancement evaluation results.

[0128] [Example 7] (Beer flavored beverage)

[0129] Diethyl sebacate was added alone to "Asahi Dry Zero (registered trademark) (manufactured by Asahi Breweries, Ltd.)" so as to achieve the concentrations shown in Table 8 below, and sensory evaluation was performed by 7 panelists to determine the degree to which the carbonation feeling was enhanced compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 8.

[0130] [Table 8]

[0131] Table 8

[0132]

[0133] As a result, it was shown that the carbonation feeling of carbonated beer-flavored beverages can be enhanced by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation feeling enhancement evaluation results.

[0134] [Example 8] (Black tea beverage containing fruit juice)

[0135] Diethyl sebacate was added alone to "Afternoon Tea Apple Tea Plus (registered trademark) (manufactured by Kirin Beverage Co., Ltd.)" so as to achieve the concentrations shown in Table 9 below, and sensory evaluation was performed by 7 panelists to determine the degree to which a carbonic acid sensation was imparted compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 9.

[0136] [Table 9]

[0137] Table 9

[0138]

[0139] As a result, it was shown that a carbonation feeling can be imparted to a black tea beverage containing fruit juice and not containing carbon dioxide by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned evaluation results of imparting a carbonation feeling.

[0140] [Example 9] (Fragrance composition for enhancing carbonation sensation; citrus-flavored carbonated water)

[0141] The citrus flavor was prepared according to the recipe shown in Table 10.

[0142] [Table 10]

[0143] Table 10 Citrus flavor formula

[0144]

[0145] *Registered trademark, manufactured by Takasago International Corporation; 3,7-dimethyl-2-methylene-6-octen-1-ol.

[0146] Each of the above citrus flavors was added in an amount of 0.05% by mass to "WILKINSON (registered trademark) TANSAN (manufactured by Asahi Soft Drinks Co., Ltd.)", and sensory evaluation was performed by 7 panelists to evaluate whether a carbonation enhancement effect was observed in Examples 9-1 to 9-9 compared with Comparative Example 1. The average score of the scores is shown in Table 11.

[0147] [Table 11]

[0148] Table 11

[0149]

[0150] As a result, it was shown that the flavor composition containing diethyl sebacate can enhance the carbonation feeling of carbonated water. In addition, the effect of improving the taste was also confirmed from the above-mentioned carbonation feeling enhancement evaluation results.

[0151] [Example 10] (Carbonation-imparting flavor composition; mineral water)

[0152] Lemonade flavor was prepared according to the recipe shown in Table 12.

[0153] [Table 12]

[0154] Table 12

[0155]

[0156] *Registered trademark, manufactured by Takasago International Corporation; 3,7-dimethyl-2-methylene-6-octen-1-ol.

[0157] Each of the above lemonade flavors was added to "Suntory Natural Mineral Water (manufactured by Suntory Beverage & Food Limited.)" in an amount of 0.02%, and a sensory evaluation was performed by 7 panelists to evaluate whether a carbonation feeling imparting effect was observed in Examples 10-1 to 10-8 compared with Comparative Example 2. The average score of the scores is shown in Table 13.

[0158] [Table 13]

[0159] Table 13

[0160]

[0161] As a result, it was shown that the flavor composition containing diethyl sebacate can impart a carbonic acid feeling to mineral water. In addition, the effect of improving the taste was also confirmed from the above-mentioned evaluation results of imparting a carbonic acid feeling.

[0162] [Example 11] (Fruit)

[0163] Diethyl sebacate was added alone to cola-flavored compressed candies prepared according to the recipe shown in Table 14 using a pestle having a diameter of 7 mm so as to achieve the concentrations shown in Table 15 below, and sensory evaluation was performed by 6 panelists to determine the extent to which a carbonic acid sensation was imparted compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 15.

[0164] [Table 14]

[0165] Table 14

[0166] Recipe for cola flavored pressed candy

[0167]

[0168] *"Cola Flavor M-24190" manufactured by Takasago International Corporation

[0169] [Table 15]

[0170] Table 15

[0171]

[0172] As a result, it was shown that a carbonation feeling can be imparted to a compressed candy not containing diethyl sebacate by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned evaluation results of imparting a carbonation feeling.

[0173] [Example 12] (Apple cider flavored frozen dessert)

[0174] Diethyl sebacate was added alone to the cider-flavored frozen dessert prepared according to the recipe shown in Table 16 so as to achieve the concentration shown in Table 17 below, and sensory evaluation was performed by 7 panelists to determine the extent to which a carbonic acid sensation was imparted compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 17.

[0175] [Table 16]

[0176] Table 16

[0177] Apple Cider Flavored Frozen Dessert Recipe

[0178] Weight Fructose Glucose Liquid Sugar 10.00 fructose 2.00 Granulated sugar 2.00 Pectin 0.30 Citric acid 0.25 Salt 0.05 water 85.30 Apple cider spice(*) 0.10 Diethyl Sebacate (Concentrations shown in Table 17)

[0179] *Apple cider flavoring manufactured by Takasago International Corporation

[0180] [Table 17]

[0181] Table 17

[0182]

[0183] As a result, it was shown that a carbonation feeling can be imparted to a cider-flavored frozen dessert by adding diethyl sebacate. In addition, the effect of improving the taste was also confirmed from the above-mentioned evaluation results of imparting a carbonation feeling.

[0184] [Example 13] (Mouthwash)

[0185] Diethyl sebacate was added alone to the grape-flavored mouthwash prepared according to the formula shown in Table 18 so as to achieve the concentration shown in Table 19 below, and sensory evaluation was performed by 5 panelists to determine the extent to which a carbonic acid sensation was imparted compared to a control to which diethyl sebacate was not added. The average score of the scores is shown in Table 19.

[0186] [Table 18]

[0187] Table 18 Formula of grape flavored mouthwash

[0188] Element Weight water 84.47 glycerin 10.00 Ethanol 5.00 Hydrogenated castor oil 0.40 Sodium Benzoate 0.05 Saccharin Sodium 0.01 Grape flavor(*) 0.07 Diethyl Sebacate (Concentrations shown in Table 19)

[0189] *"Grape Flavor G-83947" manufactured by Takasago International Corporation

[0190] [Table 19]

[0191] Table 19

[0192]

[0193] As a result, it was shown that a carbonic acid feeling can be imparted to a mouthwash by adding diethyl sebacate. In addition, the effect of improving the mouthfeel was also confirmed from the above-mentioned evaluation results of imparting a carbonic acid feeling.

[0194] [Reference example]

[0195] The researchers analyzed whether transient receptor potential ankyrin 1 (TRPA1), a receptor known as carbonic acid, and transient receptor potential vanilloid 1 (TRPV1), which responds to acids such as carbonic acid, responded to diethyl sebacate, which has been shown to enhance fizziness.

[0196] <Preparation of human TRPA1 stable expression cell line and human TRPV1 stable expression cell line>

[0197] The full-length human TRPA1 gene (GenBank accession number: NM_007332) was amplified from plasmid pFN21AB7348 (manufactured by Kazusa DNA Research Institute) using PCR, and the full-length human TRPV1 gene (GenBank accession number: NM_018727) was amplified from pFN21AE2418 (manufactured by Kazusa DNA Research Institute). The obtained PCR products were subcloned into pcDNA5 / FRT / TO (manufactured by ThermoFisher Scientific), and then introduced into Flp-In 293 cells (manufactured by ThermoFisherScientific) using the Flp-In T-REx system (manufactured by Thermo Fisher Scientific) to prepare a human TRPA1 stable expression cell line and a human TRPV1 stable expression cell line.

[0198] <Evaluation of human TRPA1 activity and human TRPV1 activity>

[0199] The cultured human TRPA1 stably expressing cells and human TRPV1 stably expressing cells were seeded at a ratio of 50,000 cells / well into a collagen-coated 96-well microplate, 1 μg / mL of doxycycline (manufactured by Takara Bio Inc.) was added and cultured overnight at 37°C to induce the expression of human TRPA1 and human TRPV1.

[0200] After replacing the culture medium with a buffer solution, a fluorescent calcium indicator Fluo 4-AM (manufactured by Dojindo Laboratories) was added and incubated at 37°C for 1 hour. After replacing the culture solution with a buffer solution again, the microplate was set in a fluorescence microplate reader FlexStation 3 (manufactured by Molecular Devices, LLC.). Diethyl sebacate was added at various concentrations at an internal temperature of 27°C, and the fluorescence intensity at a wavelength of 525nm was measured when excited at a wavelength of 485nm. The change in fluorescence intensity before and after the addition of the test substance was calculated, and the EC50 value was calculated to evaluate the activity of TRPA1 and TRPV1. The results are shown in Figure 1 These results show that diethyl sebacate exhibits excellent TRPA1 activity and TRPV1 activity.

[0201] Although the present invention has been described in detail with reference to specific aspects, it will be apparent to those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the present invention. Note that this application is based on Japanese patent application (Japanese patent application No. 2022-105336) filed on June 30, 2022, which is incorporated by reference in its entirety. In addition, all references cited herein are incorporated in their entirety.

Claims

1. A carbonation sensation imparting or enhancing agent, comprising a diester compound represented by the following general formula (I) as an active ingredient: [Chemical formula 1] wherein R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer of 1 to 8, and m represents an integer of 0 to 6. 2 . The carbonation feeling imparting or enhancing agent according to claim 1 , wherein in the diester compound, R represents an ethyl group or an isopropyl group, n represents an integer of 2 to 8, and m represents an integer of 0 to 4.

3. The carbonation feeling imparting or enhancing agent according to claim 1, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate. 4 . A flavor composition for imparting or enhancing a carbonation sensation, comprising the agent for imparting or enhancing a carbonation sensation according to claim 1 .

5. A food or oral care product imparted with a carbonation sensation or having its carbonation sensation enhanced, comprising the carbonation sensation imparting or enhancing agent according to any one of claims 1 to 3 or the flavor composition for imparting or enhancing a carbonation sensation according to claim 4. 6 . The food or oral care product according to claim 5 , wherein the content of the diester compound is 0.01 ppm to 10000 ppm.

7. A method for producing a food or oral care product to which a carbonation sensation is imparted or to which a carbonation sensation is enhanced, the method comprising the step of blending a diester compound having a content of 0.01 ppm to 10000 ppm in the food or oral care product, wherein the diester compound is represented by the following general formula (I): [Chemical formula 2] wherein R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer of 1 to 8, and m represents an integer of 0 to 6.

8. The method for producing a food or oral care product to which a carbonation feeling is imparted or to which a carbonation feeling is enhanced according to claim 7, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

9. A method for imparting or enhancing a carbonation sensation, the method comprising blending a diester compound as an effective ingredient into a food or oral care product, wherein the diester compound is represented by the following general formula (I): [Chemical formula 3] wherein R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer of 1 to 8, and m represents an integer of 0 to 6.

10. The method for imparting or enhancing a carbonation feeling according to claim 9, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

11. A mouthfeel improving agent comprising a diester compound represented by the following general formula (I) as an effective ingredient: [Chemical formula 4] wherein R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer of 1 to 8, and m represents an integer of 0 to 6. 12 . The mouthfeel improving agent according to claim 11 , wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

13. A method for improving taste, comprising blending a diester compound as an effective ingredient into a food or oral care product, wherein the diester compound is represented by the following general formula (I): [Chemical formula 5] wherein R represents a methyl group, an ethyl group or an isopropyl group, n represents an integer of 1 to 8, and m represents an integer of 0 to 6.

14. The method for improving taste according to claim 13, wherein the diester compound is one or more diester compounds selected from the group consisting of diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, dibutyl sebacate, dimethyl sebacate and dipropyl adipate.

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