Carbonation sensation imparting or enhancing agent

Abstract

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

Description

Carbonation enhancer or enhancer

[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, drink, or oral care product to which a carbonation sensation has been imparted or enhanced, a method for producing a food, drink, or oral care product to which a carbonation sensation has been imparted or enhanced, a method for imparting or enhancing a carbonation sensation, an agent for improving mouthfeel, and a method for improving mouthfeel.

[0002] Carbonated beverages are popular on the market because they are often consumed for the unique sensation felt in the mouth by the carbon dioxide gas in the beverage, and because they provide a refreshing and cool sensation. Furthermore, with the recent diversification of consumer preferences, so-called highly carbonated beverages are also becoming increasingly popular. Consumers are demanding a stronger sensation not only from carbonated beverages but also from foods such as confectioneries that provide a carbonation-like sensation. Furthermore, there is a need for a technology that can impart a carbonation sensation to systems that do not have a carbonation sensation but that have been given a carbonated beverage flavor or fruit flavor with flavorings.

[0003] In order to enhance the carbonation sensation of carbonated beverages, a common method is to increase the amount of carbon dioxide gas added and thereby the carbon dioxide pressure. However, increasing the carbon dioxide pressure poses a risk of the beverage spraying out when filling the container or opening the container for drinking, and there is also a limit to the carbon dioxide pressure that can be increased from the viewpoint of manufacturing equipment. Therefore, methods for enhancing the carbonation sensation without increasing the carbon dioxide pressure have been proposed.

[0004] For example, Patent Document 1 proposes a carbonation sensation enhancer containing capsicum extract, pepper extract, ginger extract, and the pungent components contained therein as active ingredients. Patent Document 2 proposes a method for enhancing carbonation sensation using bitter components such as caffeine, quasin, and naringin as active ingredients. Patent Document 3 proposes a carbonation sensation enhancer containing 3-hepten-2-one, 3-octen-2-one, 3-nonen-2-one, and 3-decen-2-one, which have characteristic aromas, as active ingredients. Patent Document 4 proposes a carbonation sensation enhancer containing rotundone, etc., which has a unique spicy, pepper-like aroma, as an active ingredient. Furthermore, Patent Document 5 proposes a method for enhancing carbonation sensation using methyl(3-oxo-2-pentylcyclopentyl)acetate, a compound commonly added to foods and beverages as a flavoring, as a raw material.

[0005] However, the above techniques have hardly provided any effect of imparting a carbonation sensation, and the enhancing effect has not been exhibited in a wide range of addition concentrations. In light of this background, there is a demand for new techniques for imparting or enhancing a carbonation sensation to products such as foods and beverages and oral care products.

[0006] Japanese Patent Publication No. 2010-68749 Japanese Patent Publication No. 2017-104046 Japanese Patent Publication No. 2019-62867 Japanese Patent Publication No. 2021-94024 International Publication No. 2014 / 147886

[0007] An object of the present invention is to provide an agent that imparts or enhances a carbonation sensation to foods, beverages, and oral care products.

[0008] The present invention has been made in consideration of the above circumstances and includes the following aspects: [1] An agent for imparting or enhancing a carbonic acid feeling, comprising a diester compound represented by the following general formula (I) as an active ingredient:

[0009]

[0010] [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer of 1 to 8, and m is an integer of 0 to 6.]

[0011] [2] The carbonation feeling imparting or enhancing agent according to [1] above, wherein in the diester compound, R is an ethyl group or an isopropyl group, n is an integer of 2 to 8, and m is an integer of 0 to 4.

[0012] [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.

[0013] [4] A fragrance 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.

[0014] [5] A food or drink or oral care product to which a carbonation sensation is imparted or enhanced, comprising the agent for imparting or enhancing a carbonation sensation described in any one of [1] to [3] above, or the flavor composition for imparting or enhancing a carbonation sensation described in [4] above.

[0015] [6] The food, drink, or oral care product according to [5] above, wherein the content of the diester compound is 0.01 ppm to 10,000 ppm.

[0016] [7] A method for producing a food, drink, or oral care product having an imparted or enhanced carbonation sensation, the method comprising a step of blending a diester compound represented by the following general formula (I) in the food, drink, or oral care product so that the content of the diester compound in the food, drink, or oral care product is 0.01 ppm to 10,000 ppm:

[0017]

[0018] [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer of 1 to 8, and m is an integer of 0 to 6.]

[0019] [8] The method for producing a food or beverage product or oral care product having an imparted or enhanced carbonation feeling according to [7] 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.

[0020] [9] A method for imparting or enhancing a carbonation sensation, comprising blending a diester compound represented by the following general formula (I) as an active ingredient in a food, drink, or oral care product:

[0021]

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

[0023]

[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.

[0024]

[11] A mouthfeel improver containing a diester compound represented by the following general formula (I) as an active ingredient:

[0025]

[0026] [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer of 1 to 8, and m is an integer of 0 to 6.]

[0027]

[12] The mouthfeel improver according to

[11] 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.

[0028]

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

[0029]

[0030] [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer of 1 to 8, and m is an integer of 0 to 6.]

[0031]

[14] The method for improving the mouthfeel 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.

[0032] According to one embodiment of the present invention, the carbonation sensation imparting or enhancing agent or the flavor composition for imparting or enhancing a carbonation sensation can impart or enhance a carbonation sensation to foods, beverages, and oral care products.

[0033] FIG. 1 shows the response of TRPV1 and TRPA1 to diethyl sebacate.

[0034] The present invention will be described below. In this specification, the unit "ppm" refers to "ppm by mass." That is, in this specification, ppm means 0.001 mg / g. Furthermore, the use of "to" to indicate a numerical range means that the numerical values ​​before and after it are included as the lower and upper limits. In this specification, the term "imparting or enhancing a carbonation feeling" means imparting or enhancing a carbonation feeling.

[0035] <Agent for imparting or enhancing a carbonation sensation> The agent for imparting or enhancing a carbonation sensation of one embodiment of the present invention can impart or enhance a carbonation sensation. The agent for imparting or enhancing a carbonation sensation of one embodiment of the present invention can enhance, for example, the carbonation sensation provided by carbon dioxide gas contained in food or beverage, or the carbonation sensation caused by carbon dioxide gas generated when a food or beverage that exhibits a stimulation unique to carbon dioxide is placed in the oral cavity. Furthermore, the agent can impart a carbonation sensation to a food or beverage or oral care product that has been imparted with a carbonated drink flavor or fruit flavor by a flavoring, but that does not originally contain any carbonation stimulation, such as a component that leads to a carbonation sensation (carbon dioxide, baking soda, etc.).

[0036] The carbonation sensation imparting or enhancing agent according to one embodiment of the present invention is represented by the following general formula (I):

[0037] [wherein R is a methyl group, an ethyl group, or an isopropyl group, n is an integer of 1 to 8, and m is an integer of 0 to 6].

[0038] The R is preferably an ethyl group or an isopropyl group, more preferably an ethyl group. The n is preferably an integer of 2 to 8, more preferably an integer of 4 to 8. The m is preferably an integer of 0 to 4, more preferably an integer of 0 to 1. In this specification, the diester compound represented by formula (I) is preferably diethyl sebacate (n=8, m=0, R=ethyl group), diethyl succinate (n=2, m=0, R=ethyl group), diisobutyl adipate (n=4, m=1, R=isopropyl group), diethyl malonate (n=1, m=0, R=ethyl group), dibutyl sebacate (n=8, m=2, R=ethyl group), dimethyl sebacate (n=8, m=0, R=methyl group), or dipropyl adipate (n=4, m=1, R=ethyl group), more preferably diethyl sebacate, diethyl succinate, diisobutyl adipate, diethyl malonate, or dibutyl sebacate, and particularly preferably diethyl sebacate.

[0039] The diester compound represented by formula (I) may be one obtained by chemical synthesis, one obtained by extraction from a natural product, or a combination of these. The diester compound may be used alone or in combination of two or more.

[0040] The preferred content of the diester compound in the carbonation sensation imparting or enhancing agent of one embodiment of the present invention is determined appropriately depending on the purpose and application and is not particularly limited. However, it is usually preferably 0.01 to 100 mass%, more preferably 0.02 to 100 mass%, and even more preferably 0.05 to 100 mass%.

[0041] The carbonation sensation imparting or enhancing agent of one embodiment of the present invention may contain various flavorings in addition to the diester compound represented by formula (I). In this specification, examples of the various flavorings include essential oils, natural flavorings, and synthetic flavorings described in "Patent Office Gazette: Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II: Food Flavorings" (published January 14, 2000, Japan Patent Office). These various flavorings may be used alone or in combination of two or more types.

[0042] <Method for imparting or enhancing a carbonation sensation> The present invention also provides a method for imparting or enhancing a carbonation sensation to a food or beverage or an oral care product. The method for imparting or enhancing a carbonation sensation comprises incorporating the diester compound as an active ingredient into the food or beverage or oral care product. The method for imparting or enhancing a carbonation sensation refers to a method in which there is no carbonation sensation in the absence of the diester compound, but the carbonation sensation is imparted by incorporating the diester compound, or a method in which there is a carbonation sensation even in the absence of the diester compound, and the carbonation sensation is enhanced by incorporating the diester compound.

[0043] As used herein, "carbonation" refers to the unique stimulating sensation felt in the mouth and throat, such as that felt when drinking a carbonated beverage containing carbon dioxide. This stimulation generally brings about a refreshing or cool feeling. Furthermore, "imparting a carbonation" refers to adding a new carbonation feeling, and "enhancing the carbonation" refers to strengthening the carbonation feeling.

[0044] <Fragrance Composition for Imparting or Enhancing a Carbonated Feeling> A fragrance composition for imparting or enhancing a carbonated feel according to one embodiment of the present invention comprises the agent for imparting or enhancing a carbonated feel described above, and can be used in combination with the various fragrances described above. The content of the diester compound represented by formula (I) in the fragrance composition for imparting or enhancing a carbonated feel is determined appropriately depending on the purpose and application, and is not particularly limited, but is usually preferably 0.001 to 99.5 mass%, more preferably 0.002 to 99.5 mass%, and even more preferably 0.005 to 99.5 mass%.

[0045] The flavor composition for imparting or enhancing a carbonation sensation according to one embodiment of the present invention may further contain a solvent or a retaining agent. The solvent or retaining agent is not particularly limited, but examples thereof include water, ethanol, isopropyl alcohol, ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Hercolin, medium-chain fatty acid triglycerides, and medium-chain fatty acid diglycerides. These solvents and retaining agents may be used alone or in combination of two or more.

[0046] The flavor and fragrance composition for imparting or enhancing a carbonation sensation according to one embodiment of the present invention may also contain various additives. Examples of additives include, but are not limited to, antioxidants, higher alcohols, emulsifiers, surfactants, ultraviolet absorbers, chelating agents, solubilizers, stabilizers, cooling agents, preservatives, antibacterial agents, disinfectants, colorants, and pH adjusters. These additives may be used alone or in combination of two or more.

[0047] <Food, drink, or oral care product> Another aspect of the present invention relates to a food, drink, or oral care product to which a carbonated sensation has been imparted or enhanced, and a method for producing the food, drink, or oral care product. The food, drink, or oral care product to which a carbonated sensation has been imparted or enhanced refers to a food, drink, or oral care product that does not have a carbonation sensation when not containing the diester compound but to which a carbonated sensation has been imparted by containing the diester compound, or a food, drink, or oral care product that has a carbonated sensation even when not containing the diester compound and to which the carbonated sensation has been enhanced by containing the diester compound.

[0048] The concentration of the carbonation sensation imparting or enhancing agent, or the concentration of the flavor composition for imparting or enhancing a carbonation sensation in a food, beverage, or oral care product, can be appropriately determined by one skilled in the art depending on the properties of the food, beverage, or oral care product and the desired effect. For example, the content of the diester compound represented by formula (I), which is the active ingredient of the carbonation sensation imparting or enhancing agent of one embodiment of the present invention, in a food, beverage, or oral care product is not particularly limited, but is typically preferably 0.01 ppm to 10,000 ppm, more preferably 0.02 to 5,000 ppm, and even more preferably 0.05 to 1,000 ppm. More specifically, for example, in a beverage, the content of the diester compound is preferably 0.01 ppm to 100 ppm, more preferably 0.01 ppm to 50 ppm, even more preferably 0.02 to 40 ppm, and particularly preferably 0.05 to 20 ppm, although this is not intended to be particularly limiting. In confectionery, the content of the diester compound is preferably 0.05 ppm to 10,000 ppm, more preferably 0.1 to 5,000 ppm, and even more preferably 0.25 to 1,000 ppm, while in oral care products, the content of the diester compound is preferably 0.05 ppm to 2,000 ppm, more preferably 0.1 to 1,000 ppm, and even more preferably 0.25 to 500 ppm.

[0049] <Method for producing a food, drink, or oral care product> A method for producing a food, drink, or oral care product to which a carbonation sensation has been imparted or enhanced includes a step of blending the diester compound into the food, drink, or oral care product. Note that "blending" the diester compound into the food, drink, or oral care product refers to adding the diester compound from outside the food, drink, or oral care product.

[0050] Examples of foods and beverages include, but are not limited to, beverages such as carbonated drinks, soft drinks, fruit juice drinks, dairy drinks, lactic acid bacteria drinks, health supplements, soy milk, and tea drinks; alcoholic beverages such as chuhai, cocktail drinks, happoshu (low-malt beer), fruit wine, and condiment-flavored wine; desserts such as ice cream, ice milk, lacto ice cream, frozen desserts, yogurt, pudding, jelly, and daily desserts; confectioneries such as caramel, candy, gummies, candy tablets, crackers, biscuits, cookies, pies, chocolates, snacks, and chewing gum; jams, etc. Furthermore, examples of oral care products include toothpaste, toothpaste, liquid toothpaste, mouthwash, and mouth spray.

[0051] The food and drink may also be a food and drink that provides a stimulation unique to carbonation (hereinafter also referred to as a "carbonated food and drink"). Examples of carbonated food and drink include carbonated drinks, as well as frozen desserts, chewing gum, candy, gummy candy, tablet candy, jelly, and the like that have been given a carbonation stimulation. In non-beverage foods, baking soda and an acidulant (such as citric acid) may be present together, and the carbon dioxide gas generated when both components dissolve in the mouth may give the carbonation stimulation, or a pressurized gas-filled candy may be a hard candy that has pressurized carbon dioxide gas sealed inside.

[0052] <Mouthfeel Improver> An agent containing the diester compound represented by formula (I), which is an active ingredient of an agent for imparting or enhancing carbonation in one embodiment of the present invention, can also be used as a mouthfeel improver. In this specification, "mouthfeel" refers to a sensation distinct from taste, aroma, and appearance (visual appearance), and refers to the sensation felt in the oral cavity, including the teeth and tongue, when ingesting a food, beverage, or oral care product, as well as the sensation felt by the mucous membranes or skin. In this specification, "mouthfeel" more specifically refers to the sensations of "carbonation irritation" and "foaminess." Here, "carbonation irritation" refers to a stimulating sensation consisting of, for example, the stinging pain caused by carbonation and the burning sensation caused by acids such as carbonic acid, and "foaminess" more specifically refers to the sensation of "carbonation irritation." Furthermore, "improving the mouthfeel" refers to improving the "mouthfeel," specifically, enhancing or imparting the sensation of a "heavy mouthfeel" or "minerality" of a food, beverage, or oral care product. Here, "heavy mouthfeel" and "minerality" refer to, for example, the salty taste or subtle bitterness felt from carbonation.

[0053] <Method for Improving Mouthfeel> The present invention also provides a method for improving mouthfeel, which comprises blending the diester compound as an active ingredient in a food or beverage product or an oral care product.

[0054] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0055] In the following examples, the effects were verified by calculating the average score of the scores for imparting or enhancing the carbonation sensation through sensory evaluation by expert panelists. The sensory evaluation was conducted according to the criteria shown in Table 1 below. A score of "1" in the evaluation is the score for when no additive was added at all (no addition).

[0056]

[0057] Example 1 (Carbonated Water (Ingredients: Water, Carbonated Water)) Diethyl sebacate (manufactured by Inoue Aromatics Co., Ltd.; the same applies to the following Examples) was added to Wilkinson (registered trademark) Tansan (manufactured by Asahi Soft Drinks Co., Ltd.) to the concentrations shown in Table 2 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without diethyl sebacate. The average scores are shown in Table 2.

[0058]

[0059] This experiment demonstrated that adding diethyl sebacate can enhance the carbonation sensation of carbonated water. Furthermore, since "carbonation stimulation" is a specific example of the sensation of "mouthfeel," the results of the evaluation of enhanced carbonation sensation above confirmed the effect of improving mouthfeel.

[0060] Example 2 (Carbonated Water (Ingredients: Water, Carbonated Water)) Diisobutyl adipate (manufactured by Inoue Perfume & Fragrance Co., Ltd.) was added to Wilkinson (registered trademark) Tansan (manufactured by Asahi Soft Drinks Co., Ltd.) to the concentrations shown in Table 3 below, and a sensory evaluation was conducted by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without diisobutyl adipate. The average scores are shown in Table 3.

[0061]

[0062] This experiment demonstrated that adding diisobutyl adipate can enhance the carbonation sensation of carbonated water. Furthermore, the results of the carbonation sensation enhancement evaluation confirmed that it also has an effect of improving the mouthfeel.

[0063] Example 3 (Carbonated Water (Ingredients: Water, Carbonated Water)) Dimethyl sebacate (Tokyo Chemical Industry Co., Ltd.) was added to Wilkinson (registered trademark) Tansan (Asahi Soft Drinks Co., Ltd.) at the concentrations shown in Table 4 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without dimethyl sebacate. The average scores are shown in Table 4.

[0064]

[0065] This experiment demonstrated that adding dimethyl sebacate can enhance the carbonation sensation of carbonated water. Furthermore, the results of the carbonation sensation enhancement evaluation confirmed that it also has an effect of improving the mouthfeel.

[0066] Example 4 (Carbonated Water (Ingredients: Water, Carbonated Water)) Dipropyl adipate (Tokyo Chemical Industry Co., Ltd.) was added to Wilkinson (registered trademark) Tansan (Asahi Soft Drinks Co., Ltd.) at the concentrations shown in Table 5 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without dipropyl adipate. The average scores are shown in Table 5.

[0067]

[0068] This experiment demonstrated that adding dipropyl adipate can enhance the carbonation sensation of carbonated water. Furthermore, the results of the carbonation sensation enhancement evaluation confirmed that it also has an effect of improving the mouthfeel.

[0069] [Example 5] (Cider-flavored carbonated beverage) Diethyl sebacate was added to Mitsuya Cider (registered trademark) Zero Strong (manufactured by Asahi Soft Drinks Co., Ltd.) to the concentrations shown in Table 6 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without diethyl sebacate. The average scores are shown in Table 6.

[0070]

[0071] The results showed that the addition of diethyl sebacate could enhance the carbonation of cider-flavored carbonated beverages. Furthermore, the results of the carbonation enhancement evaluation confirmed the effect of improving the mouthfeel.

[0072] [Example 6] (Carbonated grapefruit-flavored chuhai) Diethyl sebacate was added to "Hyoketsu (registered trademark) Sicilian Lemon (Kirin Brewery Co., Ltd.)" at the concentrations shown in Table 7 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without diethyl sebacate. The average scores are shown in Table 7.

[0073]

[0074] The results showed that the addition of diethyl sebacate could enhance the carbonation sensation of carbonated grapefruit-flavored chuhai. Furthermore, the results of the evaluation of the enhanced carbonation sensation confirmed the effect of improving the mouthfeel.

[0075] [Example 7] (Beer-flavored beverage) Diethyl sebacate was added to Asahi Dry Zero (registered trademark) (manufactured by Asahi Breweries, Ltd.) at the concentrations shown in Table 8 below, and a sensory evaluation was performed by seven expert panelists to determine the extent to which the carbonation sensation was enhanced compared to a control without diethyl sebacate. The average scores are shown in Table 8.

[0076]

[0077] The results showed that the addition of diethyl sebacate could enhance the carbonation of carbonated beer-flavored beverages. Furthermore, the results of the carbonation enhancement evaluation confirmed the effect of improving the mouthfeel.

[0078] [Example 8] (Black tea beverage containing fruit juice) Diethyl sebacate was added to "Gogo no Kocha Apple Tea Plus (registered trademark) (manufactured by Kirin Beverage Co., Ltd.)" at the concentrations shown in Table 9 below, and a sensory evaluation was performed by seven expert panelists to determine the degree of carbonated sensation imparted compared to a control without diethyl sebacate. The average scores are shown in Table 9.

[0079]

[0080] The results showed that adding diethyl sebacate could impart a carbonated sensation to non-carbonated fruit juice-containing black tea beverages. Furthermore, the results of the evaluation of the carbonation sensation also confirmed the effect of improving the mouthfeel.

[0081] Example 9 (Flavor composition for enhancing carbonation sensation; citrus-flavored carbonated water) A citrus flavor was prepared according to the formulation shown in Table 10.

[0082]

[0083] The above citrus flavors were each added in an amount of 0.05% by mass to "Wilkinson (registered trademark) Tansan (manufactured by Asahi Soft Drinks Co., Ltd.)," and a sensory evaluation was conducted by seven expert panelists to evaluate whether Examples 9-1 to 9-9 had a carbonation sensation enhancement effect compared to Comparative Example 1. The average scores are shown in Table 11.

[0084]

[0085] The results showed that the flavor composition containing diethyl sebacate can enhance the carbonation sensation of carbonated water. Furthermore, the results of the evaluation of the enhancement of carbonation sensation confirmed the effect of improving the mouthfeel.

[0086] Example 10 (Flavor composition for imparting a carbonation sensation; mineral water) A lemonade flavor was prepared according to the formulation shown in Table 12.

[0087]

[0088] The lemonade flavor was added to "Suntory Tennensui (manufactured by Suntory Beverage & Food Limited)" at 0.02%, and a sensory evaluation was carried out by seven expert panelists to evaluate whether Examples 10-1 to 10-8 had a carbonation effect different from that of Comparative Example 2. The average scores are shown in Table 13.

[0089]

[0090] The results showed that the flavor composition containing diethyl sebacate can impart a carbonated sensation to mineral water. Furthermore, the results of the evaluation of the carbonation sensation imparted above confirmed its effect of improving the mouthfeel.

[0091] [Example 11] (Confectionery) Cola-flavored tablets were prepared according to the recipe in Table 14 using a 7 mm diameter mortar and pestle, and diethyl sebacate was added to each tablet at the concentration shown in Table 15 below. Six panelists performed a sensory evaluation to determine the degree of carbonated sensation imparted compared to a control without diethyl sebacate. The average scores are shown in Table 15.

[0092]

[0093]

[0094] The results showed that adding diethyl sebacate could impart a carbonated feel to tablets that do not contain sodium bicarbonate. Furthermore, the results of the evaluation of the carbonated feel imparted above confirmed the effect of improving the mouthfeel.

[0095] [Example 12] (Cider-flavored frozen dessert) Diethyl sebacate was added to each of the cider-flavored frozen desserts prepared according to the recipes in Table 16 to the concentrations shown in Table 17 below, and a sensory evaluation was performed by seven panelists to determine the degree of carbonated sensation imparted compared to a control without diethyl sebacate. The average scores are shown in Table 17.

[0096]

[0097]

[0098] The results showed that the addition of diethyl sebacate could impart a carbonated feel to the cider-flavored frozen dessert. Furthermore, the results of the evaluation of the carbonated feel imparted above confirmed the effect of improving the mouthfeel.

[0099] [Example 13] (Mouthwash) Diethyl sebacate was added to each of the grape-flavored mouthwashes prepared according to the formulation in Table 18 to the concentrations shown in Table 19 below, and a sensory evaluation was conducted by five panelists to determine the degree of carbonated sensation imparted compared to a control to which no diethyl sebacate was added. The average scores are shown in Table 19.

[0100]

[0101]

[0102] The results showed that adding diethyl sebacate could impart a carbonated sensation to the mouthwash. Furthermore, the results of the evaluation of the carbonated sensation also confirmed the effect of improving the mouthfeel.

[0103] [Reference Example] Diethyl sebacate, which has been shown to have an enhancing effect on the sensation of carbonic acid stimulation, was analyzed to determine whether TRPA1 (Transient receptor potential ankyrin 1), which is known as a receptor for carbonic acid, and TRPV1 (Transient receptor potential vanilloid 1), which responds to acids such as carbonic acid, respond to it.

[0104] <Preparation of human TRPA1 stably expressing cell lines and human TRPV1 stably expressing cell lines> The full-length human TRPA1 gene (GenBank accession number: NM_007332) was amplified from the plasmid pFN21AB7348 (Kazusa DNA Research Institute), and the full-length human TRPV1 gene (GenBank accession number: NM_018727) was amplified from the plasmid pFN21AE2418 (Kazusa DNA Research Institute) using PCR. The resulting PCR products were subcloned into pcDNA5 / FRT / TO (Thermo Fisher Scientific) and then transfected into Flp-In293 cells (Thermo Fisher Scientific) using the Flp-In T-REx system (Thermo Fisher Scientific) to prepare human TRPA1 stably expressing cell lines and human TRPV1 stably expressing cell lines.

[0105] <Evaluation of Human TRPA1 and Human TRPV1 Activity> Cultured human TRPA1 stably expressing cells and human TRPV1 stably expressing cells were seeded at 50,000 cells / well on a collagen-coated 96-well microplate. 1 μg / mL doxycycline (Takara Bio) was added and the cells were cultured overnight at 37°C to induce expression of human TRPA1 and human TRPV1. After replacing the culture medium with buffer, the fluorescent calcium indicator Fluo 4-AM (Dojin Chemical Laboratory) was added and the cells were incubated at 37°C for 1 hour. After replacing the culture medium with buffer again, the cells were transferred to a fluorescence microplate reader FlexStation 3 (Molecular Devices). Diethyl sebacate was added at various concentrations at 27°C, and the fluorescence intensity at a wavelength of 525 nm when excited at a wavelength of 485 nm was measured. 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 against TRPA1 and TRPV1. The results are shown in Figure 1. These results demonstrate that diethyl sebacate has excellent TRPA1 activity and TRPV1 activity.

[0106] Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention. This application is based on a Japanese patent application (Patent Application No. 2022-105336) filed on June 30, 2022, the entirety of which is incorporated by reference. All references cited herein are incorporated in their entirety.

Claims

1. An agent for imparting or enhancing a carbonation sensation, comprising as an active ingredient a diester compound represented by the following general formula (I): 【Chemistry 1】 [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer from 1 to 8, m is an integer from 0 to 6.

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

3. The carbonation sensation 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 any one of claims 1 to 3.

5. A food, drink or oral care product having a carbonation sensation imparted or enhanced, comprising the carbonation sensation imparting or enhancing agent according to any one of claims 1 to 3.

6. The food, beverage or oral care product according to claim 5, wherein the content of the diester compound is 0.01 ppm to 10,000 ppm.

7. A method for producing a food, drink, or oral care product having a carbonation sensation imparted or enhanced, the method comprising the step of blending a diester compound represented by the following general formula (I) in the food, drink, or oral care product so that the content of the diester compound in the food, drink, or oral care product is 0.01 ppm to 10,000 ppm: 【Chemistry 2】 [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer from 1 to 8, m is an integer from 0 to 6.

8. The method for producing a food or beverage or oral care product having a carbonation feeling imparted or enhanced, as described in 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, comprising blending a diester compound represented by the following general formula (I) as an active ingredient in a food, drink, or oral care product: 【Chemistry 3】 [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer from 1 to 8, m is an integer from 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 improver comprising, as an active ingredient, a diester compound represented by the following general formula (I): 【Chemistry 4】 [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer from 1 to 8, m is an integer from 0 to 6.

12. The mouthfeel improver 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 mouthfeel, comprising blending a diester compound represented by the following general formula (I) as an active ingredient into a food, beverage, or oral care product: 【Chemistry 5】 [In the formula, R is a methyl group, an ethyl group, or an isopropyl group, n is an integer from 1 to 8, m is an integer from 0 to 6.

14. 14. The method for improving the mouthfeel 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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