Flavor improver for beer-flavored beverages

Abstract

To provide a flavor improver for beer-taste beverages that imparts and / or enhances beer-like sharpness, richness, and stimulation, thereby improving the flavor of the beer-taste beverages, a flavor improving composition for beer-taste beverages and a flavor improving method for beer-taste beverages.SOLUTION: The present invention provides a flavor improver for beer-taste beverages composed of 3-p-menthen-7-al, a flavor improving composition for beer-taste beverages containing 3-p-menthen-7-al as an active ingredient, and a flavor improving method for beer-taste beverages that includes a step for adding the flavor improver for beer-taste beverages or the flavor improving composition for beer-taste beverages to beer-taste beverages.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a flavor improving agent for a beer-taste beverage, a flavor improving composition for a beer-taste beverage, and a method for improving the flavor of a beer-taste beverage. [Background technology]

[0002] With the recent health boom and other factors, many beer-flavored beverages that claim to be functional, such as low-sugar, low-calorie, low-alcohol, zero-sugar, or non-alcoholic, are now on the market.

[0003] These beer-flavored beverages use less malt than beer, use other carbohydrate ingredients (barley, corn, koryan, potato, starch, sugars, etc.), add a process to remove carbohydrates, or use a different fermentation method.In some cases, non-alcoholic beer with an alcohol content of less than 1% by volume is produced without going through the fermentation process.As a result, they lack the characteristic beer flavor, and there is a strong demand for the development of technology that can make the flavor of beer-flavored beverages closer to that of beer.

[0004] To solve these problems, for example, methods have been proposed to add undecatrienes or undecatetraenes (Patent Document 1) and davana extract and / or tolu balsam extract (Patent Document 2) to impart an alcoholic flavor to beer-flavored beverages. Also proposed are methods to add malt extract (Patent Document 3) to impart a malty flavor to beer-flavored beverages, and methods to add vanillyl ethyl ether (Patent Document 4) or myrcenyl methyl ether (Patent Document 5) to impart a hop flavor. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2015-50955 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-45712 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-13166 [Patent Document 4] Japanese Patent Application Laid-Open No. 2004-229562 [Patent Document 5] Japanese Patent Application Laid-Open No. 2004-187536 Summary of the Invention [Problem to be solved by the invention]

[0006] The above-mentioned methods proposed so far have been fairly effective in imparting an alcoholic feel, a malty feel, and a hop flavor to beer-flavored beverages such as happoshu, new genre beers, and non-alcoholic beers, but have not produced satisfactory results in terms of imparting, enhancing, or improving the crispness, satisfying taste, and stimulating flavor that are inherently beer-like.

[0007] An object of the present invention is to provide a flavor improver for beer-taste beverages, a flavor improving composition for beer-taste beverages, and a method for improving the flavor of beer-taste beverages, which can impart and / or enhance the crispness, satisfying taste, and stimulating sensation that are characteristic of beer to beer, happoshu, new genre beer, non-alcoholic beer, and other beer-taste beverages, thereby improving the flavor of the beer-taste beverages. [Means for solving the problem]

[0008] As a result of intensive research conducted by the present inventors to solve the above-mentioned problems, they discovered that adding 3-p-menthen-7-al to a beer-taste beverage can impart and / or enhance the crispness, satisfying taste, and stimulating sensation characteristic of beer, thereby improving the flavor and aroma of the beer-taste beverage, and thus completed this research.

[0009] Thus, the present invention provides the following:

[0010] [1] A flavor improver for beer-flavored beverages consisting of 3-p-menthen-7-al. [2] A flavor-improving composition for beer-flavored beverages, comprising 3-p-menthen-7-al as an active ingredient. [3] A method for improving the flavor of a beer-taste beverage, comprising the step of adding the flavor improving agent for a beer-taste beverage described in [1] or the flavor improving composition for a beer-taste beverage described in [2] to the beer-taste beverage. [4] A method for improving the flavor of a beer-taste beverage as described in [3], wherein in the step, the flavor improving agent for a beer-taste beverage or the flavor improving composition for a beer-taste beverage is added so that the concentration of 3-p-menthen-7-al is in the range of 0.1 ppt to 1 ppb, based on the total mass of the beer-taste beverage. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a flavor improver for beer-taste beverages, a flavor improving composition for beer-taste beverages, and a method for improving the flavor of beer-taste beverages, which can impart and / or enhance the crispness, satisfying taste, and stimulating sensation that are characteristic of beer to beer, happoshu, new genre beer, or non-alcoholic beer, thereby improving the flavor of the beer-taste beverage. DETAILED DESCRIPTION OF THE INVENTION

[0012] An embodiment of the present invention will be described in detail below. In this specification, the symbols "to" indicate a range including a lower limit and an upper limit, and "concentration (ppm, ppb, ppt)" and "%" represent "mass concentration" and "mass percent concentration," respectively, unless otherwise specified. Furthermore, in this specification, "flavor" refers to one or more senses that can be changed by aroma (fragrance), typically including smell and / or taste. In this specification, the term "flavoring" includes adding a new flavor and / or enhancing a flavor, and also includes flavors that are improved as a result of flavoring or enhancement. Furthermore, the term "flavoring" also includes enhancing, suppressing, or improving sensations other than smell and / or taste, such as coolness, warmth, texture (e.g., smoothness, hardness, viscosity, etc., also known as texture), and stimulating sensations such as carbonation and spiciness, as a result of flavoring. In this specification, the flavor of a food or beverage is sometimes referred to as flavor. In addition, in this specification, the term "adding" includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object.

[0013] (flavor improver) A flavor improver for beer-taste beverages according to one embodiment of the present invention (hereinafter sometimes referred to as "the flavor improver") comprises 3-p-menthen-7-al (3-p-menthen-7-al, also known as 4-(propan-2-yl)cyclohex-3-ene-1-carbaldehyde, CAS number: 27841-22-1) represented by the following formula (1):

[0014] [ka]

[0015] 3-p-Menthen-7-al can be obtained by any method known to those skilled in the art, for example, by purchasing it as a food flavoring compound or reagent, extracting it from natural products, or synthesizing it according to a standard method (e.g., the method described in Japanese Patent Publication No. 4-76660). 3-p-Menthen-7-al has been identified as a compound contained in cumin seeds and kiwi fruit, and is known to be usable as an active ingredient in citrus-like flavor enhancers (Japanese Patent Publication No. 6348555). However, there have been no reports of its discovery as a volatile component of beer, malt, hops, or the like, much less its ability to improve the flavor of beer-flavored beverages such as beer, happoshu, new genre beer, and non-alcoholic beer by adding it to such beverages. This discovery was the first by the present inventors.

[0016] As will be shown in the Examples below, the present flavor improving agent can impart and / or enhance the crispness, satisfying taste, and stimulating sensation that are characteristic of beer by adding it to beer-taste beverages such as beer, happoshu, new genre beer, and non-alcoholic beer, thereby improving the flavor of the beer-taste beverage. Here, "beer-like stimulating sensation" refers to a flavor that, among beer flavors, evokes the pleasant stimulating sensation felt in the mouth or throat when drinking beer.

[0017] The flavor improver of the present invention consists solely of the compound of the present invention, and based on the common knowledge of a person skilled in the art, it is sufficient if the flavor improver consists essentially of the compound of the present invention. For example, the inclusion of impurities remaining when the compound of the present invention is purchased as a reagent is not a problem as long as it does not affect flavor improvement.

[0018] The concentration of the flavor improving agent in the beer-taste beverage to which it is added can be determined arbitrarily depending on the flavor characteristics of the beer-taste beverage, but is preferably within the range of 0.1 ppt to 1 ppb relative to the total mass of the beer-taste beverage. More specifically, the lower limit can be set to any of 0.1 ppt, 1 ppt, 10 ppt, or 100 ppt, and the upper limit can be set to any of 1 ppb, 100 ppt, 10 ppt, or 1 ppt, and the range can be determined by any combination of these lower and upper limits, but is not limited to these.

[0019] As mentioned above, examples of beverages to which the flavor improving agent of the present invention can be added include beer, happoshu, new genre beer, non-alcoholic beer and other beer-flavored beverages.

[0020] (Flavor improving composition) A flavor improving composition according to one embodiment of the present invention (hereinafter may be referred to as "the flavor improving composition") contains 3-p-menthen-7-al (hereinafter may be referred to as "the compound") represented by the following formula (1) as an active ingredient.

[0021] [ka]

[0022] As will be shown in the Examples below, the present flavor improving composition can impart and / or enhance the crispness, fullness, and stimulating sensation that are characteristic of beer by adding it to beer, happoshu, new genre beer, non-alcoholic beer, and other beer-taste beverages, thereby improving the flavor and aroma of the beer-taste beverage. Here, "(beer-like) crispness" refers to a sensation of being refreshed and cool without any aftertaste such as an unpleasant taste lingering in the mouth, "(beer-like) fullness" refers to a sensation of being satisfied when drinking and feeling resistance in the throat when swallowing, and "(beer-like) stimulating sensation" refers to a beer flavor that evokes the pleasant stimulating sensation felt in the mouth or throat when drinking beer.

[0023] The present flavor improving composition may consist solely of the present compound, or may contain other ingredients as long as it contains a predetermined amount of the present compound as an active ingredient. That is, the present compound (which may contain other ingredients) obtained by any method known to those skilled in the art, such as by purchasing it as a food flavor compound or reagent, extracting it from a natural product, or synthesizing it according to a standard method, may be used as the present flavor improving composition as is, or may be added to a solvent or other flavor-imparting composition to form the present flavor improving composition. Furthermore, when the present flavor improving composition contains a solvent and / or other flavor components as ingredients other than the present compound, the present flavor improving composition itself may also be used as a flavor composition.

[0024] The present flavor improving composition may contain the following compounds or ingredients, examples of which include various flavor compounds or flavor compositions, oil-soluble colorants, vitamins, functional substances, fish meat extracts, meat extracts, plant extracts, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, etc.

[0025] Examples of fragrance compounds and the like include those described in "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II Food Flavors, published January 14, 2000," "Survey on the Actual Use of Food Flavoring Compounds in Japan" (2000 Ministry of Health, Labour and Welfare Science Research Report, Japan Flavor and Flavor Manufacturers Association, published March 2001), and "Synthetic Flavors: Chemistry and Product Knowledge" (revised and expanded edition published December 20, 2016, edited by the Synthetic Flavors Editorial Committee, Chemical Daily Co., Ltd.).

[0026] Specific examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, γ-terpinene, myrcene, camphene, and limonene, sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene, and 1,3,5-undecatriene.

[0027] Examples of alcohol compounds include saturated alcohols such as butanol, pentanol, 3-octanol, and hexanol; unsaturated alcohols such as (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol; terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol, and borneol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0028] Examples of aldehyde compounds include saturated aldehydes such as acetaldehyde, hexanal, octanal, and decanal; unsaturated aldehydes such as (E)-2-hexenal and 2,4-octadienal; terpene aldehydes such as citronellal, hydroxycitronellal, citral, myrtenal, and perillaldehyde; and aromatic aldehydes such as benzaldehyde, cinnamyl aldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolyl aldehyde.

[0029] Examples of ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, and 6-methyl-5-hepten-2-one (methylheptenone); diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone; terpene ketones such as carvone, menthone, and nootkatone; ketones derived from terpene degradation products such as α-ionone, β-ionone, and β-damascenone; and aromatic ketones such as raspberry ketone.

[0030] Examples of furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, and 1,8-cineole.

[0031] Examples of the ester compound include aliphatic esters such as ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, ethyl octanoate, isoamyl isovalerate, and ethyl nonanoate; terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terpinyl acetate, and neryl acetate; and aromatic esters such as benzyl acetate, methyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

[0032] Examples of the lactone compound include saturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, and δ-dodecalactone, and unsaturated lactones such as 7-decen-4-olide and 2-decen-5-olide.

[0033] Acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, hexanoic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0034] Examples of the nitrogen-containing compound include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

[0035] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one, and furfuryl mercaptan.

[0036] Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, and labdanum.

[0037] Examples of various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or dairy products, and various enzymatic decomposition products thereof using lipase or protease, etc.

[0038] As will be shown in the Examples below, the present flavor improving composition preferably contains, in addition to the present compound, natural materials such as malt extract and hop extract, or flavor compounds found in beer, malt, hops, etc. Examples of malt extracts include the enzyme-treated malt extract and water and / or ethanol extract of malt described in JP 2011-97855 A, and examples of hop extracts include the yeast-treated hop extract and water and / or ethanol extract of hop described in JP 2014-82976 A.

[0039] The present flavor improving composition is preferably in the form of a solution in which the present compound and other ingredients are dissolved in a water-soluble or oil-soluble solvent, an emulsion preparation, a powder preparation, or other solid preparations (such as solid fat).

[0040] Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, and dipropylene glycol. Among these, propylene glycol, ethanol, and glycerin are particularly preferred from the viewpoint of use in foods and beverages. Examples of oil-soluble solvents include vegetable oils and fats, animal oils and fats, refined oils and fats (e.g., processed oils and fats such as medium-chain fatty acid triglycerides (MCT), and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethyl citrate.

[0041] Furthermore, to prepare an emulsified preparation, the flavor improving composition can be emulsified with a water-soluble solvent and an emulsifier. The method for emulsifying the flavor improving composition is not particularly limited, and an emulsion with excellent stability can be obtained by emulsifying using various types of emulsifiers conventionally used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerol fatty acid esters, lecithin, modified starch, sorbitan fatty acid esters, Quillaja extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein Quillaja saponin, or sodium caseinate, using a homomixer, colloid mill, rotating disk homogenizer, high-pressure homogenizer, etc. The amount of these emulsifiers used is not strictly limited, and can be varied over a wide range depending on the type of emulsifier used, etc. In addition, in order to stabilize the emulsified state, in addition to water, the emulsion may contain one or a mixture of two or more polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup.

[0042] The emulsion thus obtained can be dried as needed to produce a powder formulation. During powdering, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as needed. The amounts of these can be selected as appropriate depending on the desired properties of the powder formulation.

[0043] In addition to the above, the flavor improving composition may contain, if necessary, ingredients that are commonly used in flavor compositions, such as solvents such as water and ethanol, and flavor retainers such as 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.

[0044] The flavor improving composition of this invention may be added to beer-taste beverages by itself, or may be added to various foods and beverages in combination with one or more of the water-soluble or oil-soluble flavors, emulsified flavor compositions, natural essential oils, natural flavors, and synthetic flavors (flavor compounds) listed in the aforementioned "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Techniques (Flavors) Part II Food Flavors, published January 14, 2000," "Survey on the Actual Use of Food Flavor Compounds in Japan" (2000 Ministry of Health, Labour and Welfare Science Research Report, Japan Flavor and Flavor Manufacturers Association, published March 2001), and "Synthetic Flavors: Chemistry and Product Knowledge" (revised and expanded edition published December 20, 2016, edited by the Synthetic Flavor Editorial Committee, Chemical Daily Co., Ltd.).

[0045] The concentration of the present compound in the present flavor improving composition can be determined arbitrarily depending on the flavor characteristics of the present flavor improving composition and / or the flavor characteristics of the beer-taste beverage to which the present flavor improving composition is to be added, but is preferably within the range of 0.1 ppb to 1 ppm, based on the total mass of the present flavor improving composition. More specifically, the concentration can be within a range determined by any combination of the lower limit of 0.1 ppb, 1 ppb, 10 ppb, or 100 ppb and the upper limit of 1 ppm, 100 ppb, 10 ppb, or 1 ppb, but is not limited to these.

[0046] As mentioned above, examples of beverages to which the flavor improving composition of the present invention can be added include beer-flavored beverages such as beer, happoshu, new genre beer, and non-alcoholic beer.

[0047] (Beer-flavored beverage) A beer-taste beverage according to one embodiment of the present invention (hereinafter sometimes referred to as "the present beer-taste beverage") is a beer-taste beverage containing a predetermined amount of the present flavor improving agent or the present flavor improving composition. As will be shown, for example, in the Examples below, the present beer-taste beverage has an improved flavor due to the addition of an effective amount of the present flavor improving agent consisting of the present compound or the present flavor improving composition containing the present compound as an active ingredient. More specifically, the addition of the present flavor improving agent or the present flavor improving composition imparts and / or enhances the crispness, satisfying taste, and stimulating sensation that are characteristic of beer, thereby improving the flavor of the beer-taste beverage.

[0048] The amount of the present flavor improving agent or the present flavor improving composition added to the present beer-taste beverage can be determined as desired depending on the degree of flavor improving effect of the present compound and / or the flavor of the beer-taste beverage itself. However, it is preferable that the concentration of the present compound contained in the present beer-taste beverage be within the range of 0.1 ppt to 1 ppb based on the total mass of the beer-taste beverage. More specifically, the lower limit can be set to 0.1 ppt, 1 ppt, 10 ppt, or 100 ppt, and the upper limit can be set to 1 ppb, 100 ppt, 10 ppt, or 1 ppt, and the range can be any combination of these lower and upper limits, but is not limited to these.

[0049] (Method for improving the flavor of beer-flavored beverages) A method for improving the flavor of a food or beverage according to one embodiment of the present invention includes the step of adding a flavor improving agent comprising the present compound or a flavor improving composition containing the present compound as an active ingredient to a beer-taste beverage.

[0050] As will be shown in the examples below, the flavor of a beer-taste beverage can be improved by adding the present flavor improving agent or the present flavor improving composition to the beer-taste beverage.

[0051] When the present flavor improving agent or present flavor improving composition is added to a beer-taste beverage, the concentration of the present flavor improving agent or present flavor improving composition can be determined as desired depending on the flavor characteristics of the beer-taste beverage. However, it is preferable to add the present flavor improving agent or present flavor improving composition so that the concentration of the present compound is within the range of 0.01 ppt to 1 ppm relative to the total mass of the beer-taste beverage. More specifically, the lower limit can be any of 0.1 ppt, 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, or 100 ppb, and the upper limit can be any of 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, or 1 ppt, and the range can be any combination of these lower and upper limits, but is not limited to these.

[0052] In the method for improving the flavor of a beer-taste beverage according to this embodiment, the method for adding the present flavor improving agent or the present flavor improving composition to a beer-taste beverage is not particularly limited, and the timing for adding the present flavor improving agent or the present flavor improving composition to a beer-taste beverage is also not particularly limited. [Example]

[0053] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to these examples.

[0054] [Example 1] Effect of adding to non-alcoholic beer (flavor improver) A commercially available non-alcoholic beer (alcohol content: 0.00%) and 3-p-menthen-7-al synthesized by the method described in Japanese Patent Publication No. 4-76660 (hereinafter referred to as "the synthesized 3-p-menthen-7-al") were prepared. The synthesized 3-p-menthen-7-al, or the synthesized 3-p-menthen-7-al diluted with propylene glycol as necessary, was added to the commercially available non-alcoholic beer so that the concentrations of 3-p-menthen-7-al corresponded to the present invention products 1-1 to 1-5 in Table 1 below, to prepare the beer-taste beverages of the present invention products 1-1 to 1-5. Similarly, the above-synthesized 3-p-menthen-7-al, or the above-synthesized 3-p-menthen-7-al diluted with propylene glycol as necessary, was added to the above-mentioned commercially available non-alcoholic beer so that the 3-p-menthen-7-al concentrations corresponded to Comparative Products 1-1 to 1-2 in Table 1 below, to prepare beer-taste beverages, Comparative Products 1-1 to 1-2. Meanwhile, the above-mentioned commercially available beer-taste beverage without added 3-p-menthen-7-al was designated Control Product 1.

[0055] The resulting beer-taste beverages, Invention Products 1-1 to 1-5 and Comparative Products 1-1 to 1-2, were then subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation involved asking the panelists to comment on the differences in flavor between Invention Products 1-1 to 1-5 and Comparative Products 1-1 to 1-2 and Control Product 1, and averaging the scores given by the panelists for crispness, mouthfeel, and spiciness (as defined above) compared to Control Product 1 according to the following evaluation criteria.

[0056] <Evaluation criteria for sharpness, drinkability and stimulating sensation> Significantly increased compared to control product 1: 5 points Significant increase compared to control product 1: 4 points Somewhat increased compared to control product 1: 3 points Slight increase compared to control 1: 2 points Equivalent to control product 1: 1 point

[0057] The results of the sensory evaluation of the beer-taste beverages of Invention Products 1-1 to 1-5 and Comparative Products 1-1 and 1-2 are shown in Table 1 below.

[0058] [Table 1]

[0059] As shown in Table 1, it was confirmed that non-alcoholic beer containing 3-p-menthen-7-al had an improved flavor compared to non-alcoholic beer containing no 3-p-menthen-7-al.

[0060] [Example 2] Effect of adding to happoshu (flavor improver) Commercially available happoshu (5% alcohol content) and the synthesized 3-p-menthen-7-al were prepared. The synthesized 3-p-menthen-7-al, or the synthesized 3-p-menthen-7-al diluted with propylene glycol as needed, was added to the commercially available happoshu so that the 3-p-menthen-7-al concentration corresponded to Invention Products 2-1 to 2-5 in Table 2 below, to prepare beer-taste beverages of Invention Products 2-1 to 2-5. Similarly, the synthesized 3-p-menthen-7-al, or the synthesized 3-p-menthen-7-al diluted with propylene glycol as needed, was added to the commercially available happoshu so that the 3-p-menthen-7-al concentration corresponded to Comparative Products 2-1 to 2-2 in Table 2 below, to prepare beer-taste beverages of Comparative Products 2-1 to 2-2. The commercially available beer-taste beverage without added 3-p-menthen-7-al was designated Control Product 2.

[0061] The resulting beer-taste beverages, Invention Products 2-1 to 2-5 and Comparative Products 2-1 to 2-2, were then subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation involved asking the panelists to comment on the differences in flavor between Invention Products 2-1 to 2-5 and Comparative Products 2-1 to 2-2 and Control Product 1, and averaging the scores given by the panelists for crispness, mouthfeel, and spiciness (as defined above) compared to Control Product 2 according to the following evaluation criteria.

[0062] <Evaluation criteria for sharpness, drinkability and stimulating sensation> Significantly increased compared to control product 2: 5 points Significant increase compared to control product 2: 4 points Somewhat increased compared to control product 2: 3 points Slight increase compared to control 2: 2 points Equivalent to control product 2: 1 point

[0063] The results of the sensory evaluation of the beer-taste beverages of the present invention products 2-1 to 2-5 and the comparative products 2-1 and 2-2 are shown in Table 2 below.

[0064] [Table 2]

[0065] As shown in Table 2, it was confirmed that the flavor of happoshu to which 3-p-menthen-7-al was added was improved compared to happoshu to which 3-p-menthen-7-al was not added.

[0066] [Example 3] Effect of Addition to Happoshu (Flavor-improving Composition) <Example 3-1> According to the formulations shown in Table 3, flavor-improving compositions of the present invention products 3-1 to 3-5 and comparative product 3-1 were prepared.

[0067] [Table 3]

[0068] <Example 3-2> The flavor-improving compositions of Invention Products 3-1 to 3-5 and Comparative Product 3-1 prepared in Example 3-1 were added at a concentration of 0.1% to the same commercially available happoshu (alcohol content 5%) used in Example 2 to prepare beer-flavored beverages of Invention Products 3-6 to 3-10 and Comparative Product 3.

[0069] The resulting beer-taste beverages, Invention Products 3-6 to 3-10, were then subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation involved asking the panelists to comment on the differences in flavor between Invention Products 3-6 to 3-10 and Control Product 3, and averaging the scores given by the panelists for crispness, mouthfeel, and spiciness (as defined above) compared to Control Product 3 according to the following evaluation criteria.

[0070] <Evaluation criteria for sharpness, drinkability and stimulating sensation> Significantly increased compared to control product 3: 5 points Significant increase compared to control product 3: 4 points Somewhat increased compared to control 3: 3 points Slight increase compared to control 3: 2 points Equivalent to control product 3: 1 point

[0071] The results of the sensory evaluation of the beer-taste beverages of invention products 3-6 to 3-10 are shown in Table 4 below.

[0072] [Table 4]

[0073] As shown in Table 4, it was confirmed that the flavor of happoshu to which a flavor-improving composition containing 3-p-menthen-7-al was added was improved compared to happoshu to which 3-p-menthen-7-al was not added.

Claims

1. A flavor improver for beer-flavored beverages, comprising 3-p-menthen-7-al.

2. A flavor-improving composition for beer-taste beverages, comprising 3-p-menthen-7-al as an active ingredient.

3. A method for improving the flavor of a beer-taste beverage, comprising the step of adding the flavor improving agent for a beer-taste beverage according to claim 1 or the flavor improving composition for a beer-taste beverage according to claim 2 to a beer-taste beverage, a method for improving the flavor of a beer-taste beverage, wherein in the step, the flavor improving agent for a beer-taste beverage or the flavor improving composition for a beer-taste beverage is added so that the concentration of 3-p-menthen-7-al falls within the range of 0.1 ppt to 1 ppb, based on the total mass of the beer-taste beverage.

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