Flavor improver for beer-flavored beverages and beer-flavored beverages

Abstract

To provide an additive that can improve the beer-like flavor of a beer-taste beverage, especially an additive that can improve the beer-like flavor by enhancing the malt feeling of beer-taste beverage or the after-drinking nasal passage feeling.SOLUTION: Provided is a flavor improving agent for a beer-taste beverage that contains 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a flavor improver for beer-taste beverages that is used to improve the flavor of beer-taste beverages, and to the beer-taste beverages for which it is to be used. [Background technology]

[0002] The beer-flavored beverage is a beverage that provides a beer-like flavor and taste, including floral notes, bitterness, a malty flavor, a full-bodied flavor, a refreshing aftertaste, and a fermented flavor. Known beer-flavored beverages include beer, happoshu, new genre beverages, and non-alcoholic beer-flavored beverages.

[0003] Among beer-flavored beverages, particularly happoshu or new genre beverages with a malt ratio (ratio of the weight of malt in the ingredients to the total weight of ingredients other than hops and water) of less than 50%, and beer-flavored beverages produced without fermenting the ingredients, tend to lack a beer-like flavor.

[0004] Patent Document 1 describes 4-(4-methyl-3-pentenyl)-2(3H)-furanone, which is a flavor compound that exhibits a sharp citrus-like odor including bitter, green, metallic, and oily notes, and which can be added to beer-flavored beverages to improve their flavor. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2020-29424 Summary of the Invention [Problem to be solved by the invention]

[0006] No additives have yet been identified that can enhance the malt flavor or the refreshing after-nasal sensation of a beer-taste beverage. An object of the present invention is to provide an additive that can improve the beer-like flavor by enhancing the malt flavor or refreshing after-nasal sensation of a beer-taste beverage.

[0007] "Floral" refers to the image of floral aroma, the gorgeous aroma of hops, linalool, etc. "Bitterness" is the bitterness of beer. "Maltiness" is a grain or nutty aroma. "Body" is the depth of flavor that comes from the aroma and taste of beer. "Aftertaste" is the volume of the aroma that returns after swallowing. "Aftertaste" is the persistence of the aroma and flavor felt after swallowing. "Fermentation" is the complex flavor produced by yeast during the fermentation process, and specific aroma components include esters, lower alcohols, and 2-phenylethyl alcohol. "Beer-like flavor" is an overall evaluation of beer-likeness. [Means for solving the problem]

[0008] The present invention provides a flavor improver for beer-taste beverages, comprising 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one.

[0009] In one embodiment, the beer-taste beverage whose flavor is to be improved by the flavor improving agent for beer-taste beverages is at least one selected from the group consisting of beer, happoshu, new genre beer, and non-alcoholic beer-taste beverages.

[0010] In one embodiment, the beer-taste beverage for which the flavor is to be improved does not use malt or has a malt content of 25% or less.

[0011] In one embodiment, the beer-taste beverage whose flavor is to be improved is a non-fermented beer-taste beverage.

[0012] The present invention also provides a method for producing a beer-taste beverage, which comprises the step of adding the flavor improver for beer-taste beverages to a beer-taste beverage whose flavor is to be improved.

[0013] In one embodiment, the flavor improving agent for beer-taste beverages is added in an amount such that the amount of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one added is 0.1 to 1000 ng / g relative to the amount of the beer-taste beverage whose flavor is to be improved.

[0014] The present invention also provides a method for enhancing the malt flavor or the after-nasal finish of a beer-taste beverage, which method comprises the step of adding the flavor improving agent for beer-taste beverages to a beer-taste beverage whose flavor is to be improved.

[0015] The present invention also provides use of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one for producing a flavor improving agent for beer-taste beverages.

[0016] The present invention also provides a beer-taste beverage containing 0.1 to 1000 ng / g of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one.

[0017] In one embodiment, the content of the 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one is 4 to 20 ng / g.

[0018] In one embodiment, the beer-taste beverage is at least one selected from the group consisting of beer, happoshu, new genre beverages, and non-alcoholic beer-taste beverages.

[0019] In one embodiment, the beer-taste beverage does not use malt or has a malt content of 25% or less.

[0020] In one embodiment, the beer-taste beverage is a non-fermented beer-taste beverage. [Effects of the Invention]

[0021] According to the present invention, an additive is provided that can improve the beer-like flavor by enhancing the malt flavor or the refreshing after-nasal sensation of a beer-taste beverage. DETAILED DESCRIPTION OF THE INVENTION

[0022] <Flavor improver for beer-flavored beverages> The flavor improver for beer-taste beverages of the present invention contains 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one (hereinafter sometimes referred to as "DHMPO"). DHMPO has floral characteristics and a cereal-like aroma and can be chemically synthesized.

[0023] The flavor improver for beer-taste beverages of the present invention is a flavor composition, which may contain flavor compounds other than DHMPO. Furthermore, the form of the flavor improver is not important, but it is preferably a water-soluble flavor composition that can be extracted and dissolved in a water-soluble solvent such as aqueous alcohol or propylene glycol.

[0024] DHMPO is the active ingredient of the flavor improver for beer-taste beverages of the present invention. The content of DHMPO in the flavor improver for beer-taste beverages is not particularly limited as long as the object of the present invention can be achieved, but it may be, for example, 50 to 100% by weight, preferably 80 to 100% by weight, and more preferably substantially 100% by weight. By adjusting the DHMPO content in this manner, the malt flavor or the refreshing after-nasal feeling of the beer-taste beverage can be effectively enhanced.

[0025] The flavor improver for beer-taste beverages of the present invention is added in an amount of DHMPO to the beer-taste beverage whose flavor is to be improved so that the amount of DHMPO added is at least 0.01 ng / g, preferably 0.1 ng / g or more, more preferably 1 ng / g or more, and even more preferably 4 ng / g or more. If the amount of DHMPO added is less than 0.01 ng / g, the enhancement of the malt flavor or the post-nasal finish of the beer-taste beverage will be insufficient.

[0026] Furthermore, the flavor improver for beer-taste beverages of the present invention is added to the beer-taste beverage whose flavor is to be improved in an amount such that the amount of DHMPO added is 1000 ng / g or less, preferably 100 ng / g or less, more preferably 50 ng / g or less, and even more preferably 20 ng / g or less. If the amount of DHMPO added exceeds 1000 ng / g, the floral notes and bitterness of the beer-taste beverage will be too strong, and the beer-like flavor will be lost.

[0027] The lower and upper limits of the amount of DHMPO added to a beer-taste beverage in which the flavor or aroma of the DHMPO is to be improved may be arbitrarily combined to form a numerical range.

[0028] The concentration of DHMPO in the resulting beer-taste beverage is, for example, 0.1 to 100 ng / g, preferably 1 to 50 ng / g, and more preferably 4 to 20 ng / g.

[0029] <Beer-flavored beverages with improved flavor> The flavor improver of the present invention is used to improve the flavor of beer-taste beverages. "Flavor" refers to the aroma and taste. "Improving" refers to modifying the flavor to suit consumer preferences. Beer-taste beverages whose flavor can be improved include beer, happoshu (low-malt beer), new genre beverages, and non-alcoholic beer-taste beverages.

[0030] "Beer" refers to the following alcoholic beverages (1) to (3) with an alcohol content of less than 20%. (1) Fermented products made from malt, hops, and water (2) Fermented products made from malt, hops, water, barley, and other items specified by government ordinance (limited to those in which the weight of malt among the ingredients is 50 percent or more of the total weight of ingredients other than hops and water, and the total weight of the items specified by government ordinance among the ingredients does not exceed 5 percent of the weight of malt). (3) Alcoholic beverages listed in (1) or (2) that have been fermented with hops or other substances specified by government ordinance (limited to those in which the weight of malt among the raw materials is 50% or more of the total weight of the raw materials other than hops and water, and the total weight of the substances specified by government ordinance among the raw materials does not exceed 5% of the weight of the malt).

[0031] Furthermore, "happoshu" refers to alcoholic beverages that use malt or barley as part of their ingredients (excluding sake, synthetic sake, continuously distilled shochu, single distilled shochu, mirin, beer, fruit liquor, sweet fruit liquor, whiskey, brandy, raw alcohol, and beverages that use as part of their ingredients distilled from alcohol-containing substances that use malt or barley as part of their ingredients), and that have a sparkling quality (limited to those with an alcohol content of less than 20%.)

[0032] The so-called "new genre" includes "other brewed alcoholic beverages" that have a beer-like flavor without using malt or barley as part of the ingredients, and "liqueurs" that use malt or barley as part of the ingredients and also use distilled alcoholic substances that also use malt or barley as part of the ingredients.

[0033] "Non-alcoholic beer-flavored beverages" are soft drinks (with an alcohol content of less than 1% by volume) that have a beer-flavored flavor. Examples include fermented non-alcoholic beer-flavored beverages, which are produced by removing the alcohol from alcohol-containing beer-flavored beverages, and non-fermented non-alcoholic beer-flavored beverages that have a beer-flavored flavor by suppressing the production of alcohol during the fermentation process or by blending flavorings, etc., without fermenting the ingredients.

[0034] The proportion of malt used in the starch raw material when brewing a beer-taste beverage may be, for example, 10% by weight or less, 10 to 25% by weight, or 25 to 50% by weight. If a strong grain flavor is required, the proportion of malt used may be 50% by weight or more. However, from the perspective of suppressing amino acids and amino acid metabolites, the proportion of malt used is preferably 80% by weight or less.

[0035] In one embodiment, the proportion of malt used in the starch raw material when brewing a beer-taste beverage is less than 50% by weight, preferably 40% by weight or less, more preferably 30% by weight or less, and even more preferably 25% by weight or less. Malt does not necessarily have to be used as a starch raw material.

[0036] Furthermore, some beer-flavored alcoholic beverages are made by adding wort, malt extract, sugars, flavorings, ethanol, etc. to drinking water to create a beer-like aroma and taste. Beer-flavored alcoholic beverages that do not undergo a fermentation process, or that, if they do, limit the fermentation process to a level that does not produce a substantial amount of alcohol, are hereinafter referred to as "non-fermented beer-flavored alcoholic beverages."

[0037] In the present invention, the targets for flavor improvement are preferably beer-taste beverages with a low malt content, beer-taste beverages that do not use malt, and non-fermented beer-taste beverages produced without fermenting raw materials. These beer-taste beverages tend to lack a malt flavor or a clear aftertaste, and the flavor can be improved particularly by adding / blending DHMPO.

[0038] In one embodiment, a beer-flavored beverage that is preferred for flavor improvement is a low-sugar beer-flavored beverage. A low-sugar beer-flavored beverage refers to a beer-flavored beverage with a sugar content of 1.0 g / 100 ml or less. This is because low-sugar beer-flavored beverages have a low sugar or aroma component content, and therefore lack a malty flavor or a refreshing aftertaste. The low-sugar beer-flavored beverage may be a low-sugar beer-flavored alcoholic beverage.

[0039] In one embodiment, a beer-flavored beverage that is preferred for flavor improvement is a low-purine beer-flavored beverage. A low-purine beer-flavored beverage refers to a beer-flavored beverage with a purine content of 0.5 mg / 100 ml or less. This is because low-purine beer-flavored beverages have a low content of purines or aromatic components, and therefore lack a malty flavor or a refreshing aftertaste. The low-purine beer-flavored beverage may be a low-purine beer-flavored alcoholic beverage.

[0040] In one embodiment, a beer-taste beverage that is preferred for flavor improvement is a non-alcoholic beer-taste beverage. This is because non-alcoholic beer-taste beverages have a low alcohol content and therefore lack a malty flavor or a refreshing aftertaste. The non-alcoholic beer-taste beverage may be a non-fermented non-alcoholic beer-taste beverage or a fermented non-alcoholic beer-taste beverage. A fermented non-alcoholic beer-taste beverage can be produced, for example, by removing alcohol from a fermented beer-taste alcoholic beverage using membrane distillation.

[0041] Because DHMPO enhances bitterness, a beer-taste beverage intended to have an improved flavor may be one in which the bitterness caused by hops (iso-α acids) has been suppressed. Such a beer-taste beverage has a bitterness value of, for example, 25 or less, preferably 10 or less, and more preferably 5 or less. The bitterness value of a beer-taste beverage is measured, for example, according to the method described in "Revised BCOJ Beer Analysis Methods, 3rd Edition," edited by the International Technical Committee of the Brewers Association of Japan, published in November 2004.

[0042] <Beer-flavored beverage manufacturing method> The beer-taste beverage of the present invention can be produced in the same manner as a typical fermented or non-fermented beer-taste beverage, except for the inclusion of DHMPO. The methods for producing a typical fermented or non-fermented beer-taste beverage are now described.

[0043] Fermented beer-taste beverages produced through a fermentation process can generally be produced through the steps of brewing, fermentation, storage, and filtration.

[0044] In the mashing process, a fermentation raw material liquid such as wort is prepared from one or more raw materials selected from the group consisting of grain raw materials and carbohydrate raw materials. Specifically, a mixture containing the grain raw material and raw material water is heated to saccharify the starch to prepare a sugar liquid, and the resulting sugar liquid is then boiled and at least a portion of the solids are removed to obtain the fermentation raw material liquid.

[0045] First, a mixture containing at least one of a grain raw material and a carbohydrate raw material and raw material water is prepared and heated to saccharify the starch in the grain raw material, etc., to prepare a sugar solution. As the raw material for the sugar solution, only the grain raw material may be used, only the carbohydrate raw material may be used, or both may be mixed and used.

[0046] Examples of grain raw materials include barley, wheat, rye, oats, and malts thereof, as well as rice, corn, soybeans, and other legumes, and potatoes. While grain raw materials can be used as grain syrup, grain extract, and the like, they are preferably used as ground grains obtained by grinding. The grinding of grains can be carried out by conventional methods. Ground grains may be prepared by conventional treatments before or after grinding, such as ground malt, corn starch, and corn grits. In the present invention, the ground grain used is preferably ground malt. The use of ground malt allows for the production of a fermented beer-flavored beverage with a more pronounced beer-like flavor. Ground malt may be prepared by germinating barley, such as two-row barley, by conventional methods, drying the resulting product, and then grinding it to a predetermined particle size. Furthermore, the grain raw material used in the present invention may be a single type of grain raw material or a mixture of multiple types of grain raw materials. For example, ground malt may be used as the primary raw material, and ground rice or corn may be used as the secondary raw material.

[0047] The carbohydrate raw material is a sugar, i.e., a carbohydrate that is relatively low molecular weight, soluble in water, and generally sweet. The sugar raw material is preferably a sugar as defined in Article 3 of the Interpretation Notice of the Liquor Tax Act and Liquor Administration Laws and Regulations, etc., dated June 25, 1999, i.e., "a carbohydrate of trisaccharides or less that is soluble in water and generally sweet, or a mixture of these." The sugar used as the carbohydrate raw material may be at least one selected from the group consisting of monosaccharides, disaccharides, and trisaccharides, and may further contain sugars of tetrasaccharides or more. Examples of monosaccharides include glucose, fructose, galactose, xylose, arabinose, tagatose, etc. Examples of disaccharides include sucrose, lactose, maltose, isomaltose, trehalose, cellobiose, etc. Examples of trisaccharides include maltotriose, isomaltotriose, raffinose, etc. Examples of sugars having tetrasaccharides or more include stachyose and maltotetraose. The sugars may be in the form of, for example, powder, granules, paste, liquid, etc. Liquid sugars may be, for example, liquid sugars such as glucose-fructose liquid sugar, fructose-glucose liquid sugar, high-fructose liquid sugar, and mixed isomerized liquid sugar. The sugars may be granulated sugar or white sugar.

[0048] To the mixture, auxiliary ingredients other than the grain ingredients and water typically used in beverages may be added, provided that the desired effects of the present invention are not impaired. Examples of such auxiliary ingredients include hops, dietary fiber, yeast extract, fruit juice, bittering agents, coloring agents, herbs, flavorings, sweeteners, high-intensity sweeteners, antioxidants, acidulants, salts, etc. Furthermore, saccharifying enzymes such as α-amylase, glucoamylase, and pullulanase, and enzymes such as proteases, can be added as needed. These ingredients can be commercially available.

[0049] Examples of sweeteners that can be used include high-fructose corn syrup, glucose, galactose, mannose, fructose, lactose, sucrose, maltose, glycogen, and starch. Examples of high-intensity sweeteners that can be used include neotame, acesulfame potassium, sucralose, saccharin, saccharin sodium, disodium glycyrrhizinate, cyclamate, dulcin, stevia, glycyrrhizin, thaumatin, monellin, aspartame, and alitame. Examples of antioxidants that can be used include vitamin C, vitamin E, and polyphenols. Examples of acidulants that can be used include adipic acid, citric acid, trisodium citrate, glucono-delta-lactone, gluconic acid, potassium gluconate, sodium gluconate, succinic acid, monosodium succinate, disodium succinate, sodium acetate, DL-tartaric acid, L-tartaric acid, sodium DL-tartrate, sodium L-tartrate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, fumaric acid, monosodium fumarate, DL-malic acid, sodium DL-malate, acetic acid, and phosphoric acid. Examples of salts that can be used include table salt, potassium acid phosphate, calcium acid phosphate, ammonium phosphate, magnesium sulfate, calcium sulfate, potassium metabisulfite, calcium chloride, magnesium chloride, potassium nitrate, and ammonium sulfate. Examples of dietary fibers that can be used include indigestible dextrin, pectin, polydextrose, and guar gum hydrolyzate.

[0050] Saccharification is carried out using enzymes derived from the grain raw materials or enzymes added separately. The temperature and time during saccharification are adjusted appropriately taking into consideration the type of grain raw materials used, the proportion of the grain raw materials in the total fermentation raw materials, the type and amount of enzymes added, and the desired quality of the fermented beer-flavored beverage. For example, saccharification can be carried out by conventional methods, such as by maintaining a mixture containing the grain raw materials at 35 to 70°C for 20 to 90 minutes.

[0051] The sugar solution obtained after saccharification can be boiled to prepare a broth (a boiled product of the sugar solution). It is preferable to filter the sugar solution before boiling, and then boil the obtained filtrate. Alternatively, instead of the filtrate of the sugar solution, a mixture of malt extract and warm water may be used and boiled. The boiling method and conditions can be determined as appropriate.

[0052] By adding herbs and other ingredients as appropriate before or during the boiling process, a fermented beer-flavored beverage with the desired flavor can be produced. For example, by adding hops before or during the boiling process and then performing the boiling process in the presence of hops, the flavor and aroma components of the hops, particularly the bitter components, can be efficiently extracted. The amount of hops added, the manner of addition (e.g., adding hops in several batches), and the boiling conditions can be determined as appropriate.

[0053] The broth obtained after the boiling treatment contains residues such as proteins that have been produced by precipitation. Therefore, at least a portion of the solid components such as residues are removed from the broth. The removal of the residues can be carried out by any solid-liquid separation process, but typically a tank called a whirlpool is used to remove the sediment. The temperature of the broth at this time should be 15°C or higher, and is generally around 50 to 100°C. The broth (filtrate) after the residue removal is cooled to an appropriate fermentation temperature using a plate cooler or the like. This broth after the residue removal becomes the fermentation raw material liquid.

[0054] Next, in the fermentation step, yeast is inoculated into the cooled fermentation raw material liquid and fermentation is carried out. The cooled fermentation raw material liquid may be subjected to the fermentation step as is, or may be subjected to the fermentation step after being adjusted to a desired extract concentration. The yeast used for fermentation is not particularly limited, and can be appropriately selected from yeasts normally used in the production of alcoholic beverages. Either top-fermenting yeast or bottom-fermenting yeast may be used, but bottom-fermenting yeast is preferred because it is easily applicable to large-scale brewing equipment.

[0055] Furthermore, in the storage step, the obtained fermented liquid is aged in a storage tank and stored under low-temperature conditions at about 0°C for stabilization, and then in the filtration step, the aged fermented liquid is filtered to remove yeast and proteins that are insoluble in that temperature range, thereby obtaining the desired fermented beer-flavored beverage. Any method can be used for this filtration as long as it is capable of filtering out the yeast, and examples of such filtration include diatomaceous earth filtration and filter filtration using a filter with an average pore size of about 0.4 to 1.0 μm.

[0056] In the fermentation process, the fermentation conditions can be appropriately adjusted to reduce the degree of fermentation, the alcohol content can be removed from the resulting fermented liquid, or the resulting fermented liquid can be diluted, thereby producing a non-alcohol beer-flavored beverage or a low-alcohol beer-flavored beverage.

[0057] The beer-taste beverage may be a so-called new genre, using as an ingredient a distilled alcohol-containing material that uses malt or barley as a part of the ingredients. The distilled alcohol-containing material that uses malt or barley as a part of the ingredients can be added as an ingredient at any step in the production process of the fermented beer-taste beverage.

[0058] The produced fermented beer-taste beverage is filled into a container. The container into which the beer-taste sparkling beverage is filled is not particularly limited. Specific examples include glass bottles, cans, and flexible containers. Flexible containers include containers made by molding flexible resins such as PE (polyethylene), PP (polypropylene), EVOH (ethylene-vinyl alcohol copolymer), and PET (polyethylene terephthalate). Flexible containers may be made of a single-layer resin or a multi-layer resin.

[0059] The bottled fermented beer-taste beverage may be heat sterilized, if necessary. The heat sterilization strength is sufficient to prevent microbial growth during storage, and is determined appropriately taking into account the alcohol concentration of the beer-taste beverage, etc. For example, heat sterilization can be performed at 60 to 85°C for about 0.5 to 60 minutes, preferably at 60 to 80°C for about 1 to 30 minutes, and more preferably at 60 to 70°C for about 5 to 15 minutes.

[0060] Non-fermented beer-taste beverages, which are produced without a fermentation process, can generally be produced by mixing ingredients (blending method). For example, specifically, they can be produced by a blending step in which ingredients are mixed to prepare a blend, and a gas introduction step in which carbon dioxide gas is added to the resulting blend.

[0061] First, in the blending step, the raw materials are mixed to prepare a blended liquid. In the blending step, it is preferable to prepare a blended liquid in which all raw materials except carbon dioxide gas are mixed. The order in which the raw materials are mixed is not particularly limited. All raw materials may be added to raw material water at the same time, or the raw materials may be added sequentially, such as by dissolving previously added raw materials and then adding the remaining raw materials. Furthermore, for example, raw material water may be mixed with solid raw materials (e.g., powder or granules) and, if necessary, alcohol, or the solid raw materials may be prepared as aqueous solutions in advance, and raw material water and, if necessary, alcohol may be mixed with these aqueous solutions.

[0062] Examples of ingredients include bittering agents, acidulants, sweetening agents, coloring agents, flavoring agents, ethanol (raw alcohol), emulsifiers, polysaccharides, water-soluble dietary fiber, proteins or their decomposition products, etc.

[0063] As the acidulant, it is more preferable to use an organic acid than an inorganic acid in terms of safety and flavor. The organic acid is not particularly limited as long as it is one that is generally used in the production of foods and beverages, and examples thereof include lactic acid, citric acid, gluconic acid, malic acid, tartaric acid, fumaric acid, succinic acid, adipic acid, fumaric acid, and salts thereof. These organic acids may be used alone or in combination of two or more.

[0064] The bittering agents may be any of those listed above. Also, isohumulones such as oxides of hops, iso-α acids, tetraiso-α acids, and β acids may be used as bittering agents. Only one type of bittering agent may be used, or two or more types may be used in combination.

[0065] Examples of sweeteners include sucrose, glucose, fructose, isomerized liquid sugar, and high-intensity sweeteners. Examples of high-intensity sweeteners include aspartame, sucralose, acesulfame potassium, neotame, stevia, and enzyme-treated stevia. These sweeteners may be used alone or in combination.

[0066] Examples of coloring agents include caramel color, etc. Only one type of coloring agent may be used, or two or more types may be used in combination.

[0067] Flavoring agents include beer extract, beer flavoring, hop flavoring, etc. These flavoring agents may be used alone or in combination of two or more.

[0068] Examples of emulsifiers include polyglycerin fatty acid esters, glycerin fatty acid esters, sucrose fatty acid esters, polypropylene glycol fatty acid esters, sorbitan fatty acid esters, and polysorbates.

[0069] Examples of polysaccharides include starch and dextrin. Dextrin is a carbohydrate obtained by hydrolyzing starch and is larger than an oligosaccharide (a carbohydrate formed by polymerizing approximately 3 to 10 monosaccharides). These polysaccharides may be used alone or in combination of two or more.

[0070] Water-soluble dietary fiber refers to carbohydrates that dissolve in water and are not or are difficult to digest by human digestive enzymes. Examples of water-soluble dietary fiber include soybean dietary fiber (soluble soybean polysaccharides), polydextrose, indigestible dextrin, galactomannan, inulin, guar gum hydrolysate, pectin, gum arabic, etc. These water-soluble dietary fibers may be used alone or in combination of two or more types.

[0071] If insoluble matter is generated in the preparation prepared in the preparation step, it is preferable to subject the preparation to a treatment to remove the insoluble matter, such as filtration, before the gas introduction step. The insoluble matter removal treatment is not particularly limited, and can be carried out by a method commonly used in the technical field, such as filtration or centrifugation. In the present invention, it is preferable to remove the insoluble matter by filtration, and more preferably by diatomaceous earth filtration.

[0072] Next, in the gas introduction step, carbon dioxide gas is added to the preparation obtained in the blending step. This results in a non-fermented beer-flavored beverage. The addition of carbon dioxide imparts a refreshing sensation similar to that of beer. The addition of carbon dioxide gas can be carried out by a conventional method. For example, the preparation obtained in the blending step and carbonated water may be mixed, or carbon dioxide gas may be directly added to and dissolved in the preparation obtained in the blending step.

[0073] After the addition of carbon dioxide, the resulting non-fermented beer-taste beverage may be further subjected to a process to remove insoluble matter, such as filtration. The process for removing insoluble matter is not particularly limited, and may be carried out by a method commonly used in the art.

[0074] The produced non-fermented, beer-taste beverage is preferably filled into containers and then subjected to heat sterilization. The containers and heat sterilization method can be the same as those for the fermented, beer-taste sparkling beverage.

[0075] When the flavor improving agent of the present invention is added to a beer-taste beverage for which flavor improvement is desired, there is no limitation on the timing, and it can be added at any appropriate step in the production process of the beer-taste beverage. For example, when it is added to a fermented beer-taste beverage, it may be added at any step, such as the cooling step after wort boiling, the fermentation step, or the maturation step. However, the earlier the step in which it is added, the more likely it is that the concentrations of the components in the flavor improving agent will fluctuate, so it is preferable to add it after the end of the post-fermentation step. Furthermore, when it is added to liqueurs, tax law requires it to be added before the end of main fermentation, so it is preferable to add it before the start of main fermentation or just before the end of main fermentation.

[0076] The concentration of DHMPO in a beer-taste beverage can be measured by GC / MS analysis or other methods. For example, the following method can be used.

[0077] Solvent extraction was performed on 500g of beer-flavored beverage using 150mL of diethyl ether. The resulting extract was washed once with 50g of saturated saline solution. The organic solvent was then distilled off from the extract under normal pressure to prepare a concentrate, which was then directly subjected to GC / MS analysis. The GC / MS conditions are as follows:

[0078] (1)GC Temperature rise conditions: 40℃ to 230℃, 5.0℃ / min temperature rise, 30 minutes at 230℃ Carrier gas: Helium Linear speed: 25cm / sec

[0079] (2) MS Electrical ionization (EI) method, 70 eV MS temperature: 230℃ (ion source), 150℃ (quadrupole) Scan range: 35-350amu

[0080] (Equipment used) GC device: GC7890B manufactured by Agilent Technology MS device: MS5977A (Ionization method: EI 70eV) Column: GL Sciences TC-WAX (length 30 m, inner diameter 0.25 mm, liquid layer thickness 0.25 μm)

[0081] The present invention will be explained in more detail with reference to the following examples, but the present invention is not limited to these examples. [Example]

[0082] Example 1 Manufacture of flavor improvers First, ethyl 5-(1-ethoxyethoxy)pent-2-ynoate was synthesized according to the method described in J. Org. Chem. 1986, 51, pp. 1077-1079.

[0083] ·Process 1 A reaction vessel was charged with magnesium (286 mg, 11.8 mmol), a trace amount of iodine, and tetrahydrofuran (9 mL) and argon atmosphere was created. A small amount of a solution of 5-bromo-2-methylpent-2-ene (1.83 g, 11.2 mmol) in dehydrated tetrahydrofuran (1 mL) was added and vigorously stirred. The iodine color disappeared within 15 minutes, and heat generation was also observed. While cooling the reaction solution in a water bath, the remaining 5-bromo-2-methylpent-2-ene tetrahydrofuran solution was added dropwise at 30°C or below. The mixture was then stirred at room temperature for 2 hours to prepare the Grignard reagent.

[0084] Copper(I) bromide-dimethyl sulfide complex (2.30 g, 11.2 mmol) and dehydrated tetrahydrofuran (10 mL) were placed in a separate reaction vessel and stirred at -78 °C under an argon atmosphere. The previously prepared Grignard reagent was added to this and stirred for 45 minutes. A solution of ethyl 5-(1-ethoxyethoxy)pent-2-ynoate (600 mg, 2.80 mmol) in dehydrated tetrahydrofuran (3 mL) was added to this and stirred for 1 hour.

[0085] The reaction mixture was quenched with ethanol at the same temperature, and after warming, aqueous ammonium chloride solution was added. The reaction mixture was extracted with diethyl ether, washed successively with saturated aqueous sodium carbonate solution and brine, dried, and concentrated to obtain a crude product. This was purified by silica gel column chromatography (hexane / ethyl acetate mixture) to obtain 785 mg (94% yield) of ethyl (Z)-3-[2-(1-ethoxyethoxy)ethyl]-7-methylocta-2,6-dienoate.

[0086] ·Process 2 Ethyl (Z)-3-[2-(1-ethoxyethoxy)ethyl]-7-methylocta-2,6-dienoate (672 mg, 2.25 mmol), tetrahydrofuran (3.0 mL), and 1 M hydrochloric acid (3.0 mL, 3.00 mmol) were placed in a reaction vessel and stirred at room temperature for 2 hours.

[0087] The reaction mixture was quenched with saturated aqueous sodium carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried, and concentrated to give a crude product. This was purified by flash silica gel column chromatography (hexane / ethyl acetate mixture) to give 409 mg (80% yield) of ethyl (Z)-3-(2-hydroxyethyl)-7-methylocta-2,6-dienoate.

[0088] ·Process 3 Ethyl (Z)-3-(2-hydroxyethyl)-7-methylocta-2,6-dienoate (345 mg, 1.52 mmol), tetrahydrofuran (5.0 mL), and 1 M hydrochloric acid (5.0 mL, 5.00 mmol) were placed in a reaction vessel and heated under reflux for 3 hours.

[0089] The reaction mixture was quenched with saturated aqueous sodium carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried, and concentrated to obtain a crude product. This was purified by flash silica gel column chromatography (hexane / ethyl acetate mixture) and further purified by Kugelrohr (0.27 kPa) to obtain 192 mg (70% yield) of DHMPO. In the following examples, DHMPO is used as a flavor improver.

[0090] The physical properties of the obtained DHMPO were as follows:

[0091] (1) MS Electrical ionization (EI) method, 70 eV m / z:41(35), 69(59), 112(100), 152(18), 180(2)

[0092] (Equipment used) GC device: GC7890B manufactured by Agilent Technology MS device: MS5977A (Ionization method: EI 70eV) Column: GL Sciences TC-1701 (length 30 m, inner diameter 0.25 mm, liquid layer thickness 0.25 μm)

[0093] (2) TOF-MS DART method m / z: Calculated value C11H17O2 [M+H]+ 181.1223, Found value 181.1222

[0094] (Equipment used) JEOL JMS-T100LP (DART-TOFMS)

[0095] <Example 2> Commercial product 1: A non-fermented, non-alcoholic beer-flavored carbonated beverage (malt ratio: 0%, bitterness value: 23.5) was prepared.

[0096] A predetermined amount of the flavor improving agent produced in Example 1 was added to Commercial Product 1. The resulting non-fermented, non-alcoholic, beer-flavored carbonated beverage was adjusted to 4°C, and then a sensory evaluation of its flavor was conducted by expert evaluators. Commercial Product 1 to which no flavor improving agent had been added was used as a control, and the evaluation score was the average of the scores from the six expert evaluators. The evaluation items, evaluation scores, and their meanings and content criteria are as follows. The results of the sensory evaluation are shown in Table 1.

[0097] Evaluation items 1: Enhanced floral 2: Increased bitterness 3: Enhanced malt flavor 4: Enhanced body feel 5: Enhanced nasal sensation after drinking 6: Enhanced aftertaste 7: Enhanced fermented flavor 8: Beer-like flavor

[0098] Evaluation scores and their meanings 1: Same level as no additives, no change 2: Somewhat effective 3: Feel the effects 4: I feel a somewhat strong effect 5: I feel a strong effect 6: I feel a very strong effect 7: I feel a very strong effect

[0099] [Table 1]

[0100] The enhancement effects of floral notes, bitterness, body, and aftertaste tended to be stronger with increasing concentrations. On the other hand, the enhancement effects of malt notes, post-nasal freshness, fermented notes, and beer-like flavors were high at concentrations of 10-100ng / g and tended to decrease at concentrations of 1000ng / g or higher.

[0101] Example 3 Commercial Product 2: A fermented beer-flavored beverage (malt ratio: less than 25%, bitterness value: 15.0) was prepared. The flavor-improving function of DHMPO was tested in the same manner as in Example 1, except that Commercial Product 2 was used instead of Commercial Product 1. The results are shown in Table 2.

[0102] [Table 2]

[0103] The enhancement effects of floral notes, bitterness, body, and aftertaste tended to be stronger with increasing concentrations. On the other hand, the enhancement effects of malt notes, post-nasal freshness, fermented notes, and beer-like flavors were high at concentrations of 10-100ng / g and tended to decrease at concentrations of 1000ng / g or higher.

Claims

1. A flavor improver for beer-taste beverages, comprising 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one.

2. 2. The flavor improver for beer-taste beverages according to claim 1, wherein the beer-taste beverage whose flavor is to be improved is at least one selected from the group consisting of beer, happoshu, new genre beverages, and non-alcoholic beer-taste beverages.

3. 3. The flavor improver for beer-taste beverages according to claim 1 or 2, wherein the beer-taste beverage to be improved in flavor does not use malt or has a malt content of 25% or less.

4. 4. The flavor improver for beer-taste beverages according to claim 1, wherein the beer-taste beverage whose flavor is to be improved is a non-fermented beer-taste beverage.

5. 10. A method for producing a beer-taste beverage, comprising the step of adding the flavor improver for beer-taste beverages according to claim 1 to a beer-taste beverage whose flavor is to be improved.

6. 6. The method for producing a beer-taste beverage according to claim 5, wherein the flavor improver for a beer-taste beverage is added in an amount of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one such that the amount of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one added is 0.1 to 1000 ng / g based on the amount of the beer-taste beverage whose flavor is to be improved.

7. A method for enhancing the malt flavor or the after-nasal finish of a beer-taste beverage, comprising the step of adding the flavor improver for beer-taste beverages according to claim 1 to a beer-taste beverage whose flavor is to be improved.

8. Use of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one for producing a flavor improver for beer-taste beverages.

9. A beer-flavored beverage containing 0.1 to 1000 ng / g of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one.

10. 10. The beer-taste beverage according to claim 9, wherein the content of 5,6-dihydro-4-(4-methyl-3-pentenyl)-2H-pyran-2-one is 4 to 20 ng / g.

11. 11. The beer-taste beverage according to claim 9 or 10, wherein the beer-taste beverage is at least one selected from the group consisting of beer, happoshu, new genre beverages, and non-alcoholic beer-taste beverages.

12. The beer-taste beverage according to any one of claims 9 to 11, which does not use malt or has a malt content of 25% or less.

13. The beer-taste beverage according to any one of claims 9 to 12, which is a non-fermented beer-taste beverage.

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