WO2023276493A1

WO2023276493A1 - Beer-flavored beverage flavor enhancer and beer-flavored beverage

Info

Publication number: WO2023276493A1
Application number: PCT/JP2022/021148
Authority: WO
Inventors: 重都野場; 真維寺野
Original assignee: アサヒグループホールディングス株式会社; アサヒビール株式会社
Priority date: 2021-06-30
Filing date: 2022-05-23
Publication date: 2023-01-05
Also published as: AU2022303766A1; JP2023005941A

Abstract

The present invention addresses the problem of providing an additive that can satisfactorily enhance the beer-like flavor of a beer-flavored beverage, while enhancing the grain-like aroma, alcohol taste, aftertaste, body, and fermented flavor of the beer-flavored beverage. A solution to said problem is a beer-flavored beverage flavor enhancer containing methyl 3-methyl-2-buten-1-yl disulfide.

Description

Flavor improving agent for beer-taste beverage and beer-taste beverage

The present invention relates to a beer-taste beverage flavor improving agent used to improve the flavor of a beer-taste beverage, and a beer-taste beverage to which it is used.

A beer-taste beverage is a beverage that provides a beer-like flavor, including grain-like aroma, alcoholic taste, aftertaste, body, fermentation, and sharpness. As beer-taste beverages, beer, low-malt beer, new genre, non-alcoholic beer-taste beverages, and the like are known.

Among beer-taste beverages, happoshu or new genre with a malt ratio (weight ratio of malt in raw materials to the total weight of raw materials other than hops and water) of less than 50%, and beer produced without fermenting raw materials Taste beverages tend to lack beer-like flavor.

In Patent Document 1, conventionally, sulfur-containing compounds such as 3-methyl-2-butene-1-thiol in beer and beer-taste beverages have an unpleasant odor (“skunk taste”, "Light destroyed taste", "sunstroke taste"), and unexpectedly, 3-methyl-2-butene-1-thiol (hereinafter, "MBT ) and 3-methyl-2-butanethiol are added to a non-fermented beer-taste beverage at a predetermined concentration, so that even a beer-taste beverage that has not undergone fermentation It is described that it is possible to impart a good fermented feeling while suppressing the generation of an unpleasant odor.

In addition, in the non-fermented beer-taste beverage of Patent Document 1, the concentration of the sulfur-containing compound is 1 × 10 ² ppt or more and 1 × 10 ³ ppt or less, and by setting the concentration in the above range, excellent beer It is described that a non-fermented beer-taste beverage excellent in taste, which has a flavor and a good fermented feeling, is provided.

WO2013/080357

When 3-methyl-2-butene-1-thiol and 3-methyl-2-butanethiol are added to a beer-taste beverage for the purpose of enhancing the beer-likeness and fermentation feeling, the beer-like flavor of the beer-taste beverage is reduced by the addition concentration It became clear that it is difficult to sufficiently improve depending on the

The present invention is intended to solve the above problems, and the purpose thereof is to provide a beer-taste beverage with a grain-like aroma, alcoholic feeling, aftertaste, body feeling and fermented feeling (hereinafter, these five types of sensuality are collectively referred to as "fermentation To provide an additive capable of sufficiently enhancing a beer-like flavor while enhancing the "feeling, etc.").

The “grain-like scent” is a scent reminiscent of grains. -Acetylthiazole, 4-vinylguaiacol, 2-acetyl-1-pyrroline, 2-propyl-1-pyrroline, etc. "Alcohol feeling" refers to the bitter aftertaste felt when drinking an alcoholic beverage and the sweetness of the alcohol itself. "Afterglow" is the persistence of aroma and taste felt after swallowing. “Body” is the depth of flavor that comes from the aroma and taste of beer. "Fermentation" is a complex flavor produced by yeast in the fermentation process, and the image of specific aroma components such as esters, lower alcohols, and 2-phenylethyl alcohol. "Beer-like flavor" is an overall evaluation of beer-likeness.

The present invention provides a flavor improver for beer-taste beverages containing methyl 3-methyl-2-buten-1-yl disulfide.

In one embodiment, the beer-taste beverage whose flavor is to be improved is at least one selected from the group consisting of beer, low-malt beer, new genre, and non-alcoholic beer-taste beverage. be.

In one embodiment, the beer-taste beverage whose flavor is to be improved does not use malt or has a malt usage ratio of less than 25%.

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

The present invention also provides a method for producing a beer-taste beverage, comprising adding the beer-taste beverage flavor-improving agent to a beer-taste beverage whose flavor is to be improved.

In one embodiment, the amount of methyl 3-methyl-2-buten-1-yl disulfide added to the flavor improver for beer-taste beverages is 0.01 to 0.01 for beer-taste beverages whose flavor is to be improved. It is added in an amount to give 100 ng/g.

The present invention also provides a method for enhancing the beer-like flavor of a beer-taste beverage, which comprises adding the beer-taste beverage flavor-improving agent to a beer-taste beverage whose flavor is to be improved.

The present invention also provides the use of methyl 3-methyl-2-buten-1-yl disulfide for producing a flavor improver for beer-taste beverages.

The present invention also provides a beer-taste beverage containing 0.01 to 100 ng/g of methyl 3-methyl-2-buten-1-yl disulfide.

In one embodiment, the content of methyl 3-methyl-2-buten-1-yl disulfide is 0.1 to 10 ng/g.

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

In one embodiment, the beer-taste beverage does not use malt or has a malt usage ratio of less than 25%.

In one embodiment, the beer-taste beverage is a non-fermented beer-taste beverage.

According to the present invention, an additive is provided that can sufficiently enhance beer-like flavor while enhancing the fermented feeling of beer-taste beverages.

<Flavor improving agent for beer-taste beverages>
The flavor improving agent for beer-taste beverages of the present invention is sometimes referred to as methyl 3-methyl-2-buten-1-yl disulfide (hereinafter, "MMBD"). ). MMBD has a disulfide-bonded structure of MBT and methanethiol, and can be chemically synthesized.

The flavor improving agent for beer-taste beverages is a flavoring composition and may contain flavoring compounds other than MMBD. Moreover, although its form does not matter, it is preferably a water-soluble fragrance composition that can be extracted and dissolved in a water-soluble solvent such as hydrous alcohol or propylene glycol.

MMBD is the active ingredient of the flavor improver for beer-taste beverages. The content of MMBD in the flavor improving agent for beer-taste beverages is, for example, 50 to 100% by weight, preferably 80 to 100% by weight, more preferably substantially 100% by weight.

By including MMBD, beer-taste beverages have an improved fermented feeling. The aroma of MMBD does not linger, and even when it is contained, the sharpness of the beer-taste beverage is less likely to deteriorate. The flavor improver for beer-taste beverages is 0.01 ng/g or more, preferably 0.1 ng/g or more, more preferably 1.0 ng/g for beer-taste beverages in which the amount of MMBD added is to improve the flavor. It is added in an amount to give a concentration of 1 g or more. If the amount of MMBD added is less than 0.01 ng/g, enhancement of the fermented feeling of the beer-taste beverage will be insufficient.

In addition, the beer-taste beverage flavor improver has a concentration of 100 ng/g or less, preferably 50 ng/g or less, more preferably 10 ng/g or less for beer-taste beverages whose flavor is to be improved by adding MMBD. is added in an amount that becomes If the amount of MMBD added exceeds 100 ng/g, the beer-like flavor may be impaired.

The lower limit and upper limit of the amount added to the beer-taste beverage in which the flavor of the MMBD is to be improved may be arbitrarily combined to form a numerical range.

The amount of MMBD added to a beer-taste beverage whose flavor is to be improved is, for example, such that the concentration of MMBD in the beer-taste beverage is 0.01 to 100 ng/g, preferably 0.1 to 10 ng/g, more preferably 1 0 to 10 ng/g concentration.

<Beer-taste beverage to improve flavor>
The flavor improving agent of the present invention is used to improve the flavor of beer-taste beverages. Flavor refers to aroma and taste. Improvement means modification to suit consumer tastes. Beer-taste beverages whose flavor is to be improved include beer, low-malt beer, new genre, and non-alcoholic beer-taste beverages.

“Beer” refers to alcoholic beverages with an alcohol content of less than 20% among the following alcoholic beverages (1) to (3).
(1) Fermented products using malt, hops and water as raw materials (2) Fermented products using malt, hops, water, barley and other items specified by Cabinet Order (the weight of malt in the raw materials other than hops and water 50% or more of the total weight of the ingredients, and the total weight of the articles specified by Cabinet Order does not exceed 5% of the weight of the malt.)
(3) Alcoholic beverages listed in (1) or (2) fermented by adding hops or items specified by Cabinet Order (the weight of malt in the ingredients is 5% of the total weight of ingredients other than hops and water) 10 or more, and the total weight of the items specified by Cabinet Order among the raw materials does not exceed 5% of the weight of the malt.)

In addition, "low-malt beer" refers to alcoholic beverages made from malt or barley (sake, synthetic sake, continuous distillation shochu, single distillation shochu, mirin, beer, fruit wine, sweet fruit wine, whiskey, brandy, raw materials (Except alcohol for commercial use and alcohol-containing substances distilled from malt or barley) with foaming properties (limited to those with an alcohol content of less than 20%) ).

So-called "new genres" are divided into "other fermented liquors" that achieve a beer-taste flavor without using malt or barley as part of the ingredients, and those that use malt or barley as part of the ingredients. Among alcoholic beverages, there are some that are classified as ``liqueurs'' that are partly made by distilling alcohol-containing substances made from malt or barley.

“Non-alcoholic beer-taste beverage” is a soft drink (less than 1% by volume of alcoholic beverage) that has a beer-taste flavor, and is a fermented non-fermented beverage produced by removing alcohol from a beer-taste beverage containing alcohol. There are alcoholic beer-taste beverages and non-fermented, non-alcoholic beer-taste beverages in which beer-taste flavor is realized by suppressing the production of alcohol during the fermentation process or by blending flavorings without fermenting raw materials.

The ratio of malt used in starch raw materials when brewing beer-taste beverages is not particularly limited, but can be, for example, less than 50% or less than 25%. If a strong graininess is required, the malt content may be 50% by weight or more. However, from the viewpoint of suppressing amino acids and amino acid metabolites, the proportion of malt used is preferably 80% by weight or less.

In one embodiment, the ratio of malt used in starch raw materials 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 still more preferably less than 25% by weight. . Malt may not be used as a starch raw material.

In addition, some beer-taste alcoholic beverages have a beer-like flavor and taste by adding wort, malt extract, sugars, fragrances, ethanol, etc. to drinking water. A beer-taste alcoholic beverage that is not subjected to a fermentation process or that is restricted to the extent that a substantial amount of alcohol is not produced even if a fermentation process is performed is hereinafter referred to as a "non-fermented beer-taste alcoholic beverage".

In the present invention, the target for improving the flavor is preferably a beer-taste beverage with a low malt content ratio, a beer-taste beverage that does not use malt, and a non-fermented beer-taste beverage that is produced without fermenting raw materials. Such beer-taste beverages tend to lack cereal-like aroma or alcoholic feeling, and in particular, the effect of improving the flavor can be obtained by containing/combining MMBD.

In one embodiment, the beer-taste beverage that is preferable for flavor improvement is a low-sugar beer-taste beverage. A low-sugar beer-taste beverage refers to a beer-taste beverage having a sugar content of 1.0 g/100 ml or less. This is because a low-sugar beer-taste beverage has a low grain-like aroma or alcoholic feeling due to its low content of sugars or aroma components. The low-sugar beer-taste beverage may be a low-sugar beer-taste alcoholic beverage.

In one embodiment, the beer-taste beverage that is preferable for flavor improvement is a low-purine beer-taste beverage. Low purine beer-taste beverages refer to beer-taste beverages with a purine content of 0.5 mg/100 ml or less. This is because a low-purine beer-taste beverage has a low grain-like aroma due to a low content of purines or aroma components. The low-purine beer-taste beverage may be a low-purine beer-taste alcoholic beverage.

In one embodiment, a beer-taste beverage that is preferable 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 an alcoholic feel. 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 by a membrane distillation method.

The content of iso-α acids in beer-taste beverages, which is preferable as a target for flavor improvement, is not particularly limited, and can be appropriately adjusted according to the desired bitterness quality of the product. The content of iso-α-acids in beer-taste beverages that are preferable for flavor improvement can be adjusted, for example, so that the beverage has a bitterness value of 5 or more, preferably 10 or more, and more preferably 15 or more. In addition, the upper limit of the content of iso-α acids in a beer-taste beverage that is preferable as a target for improving the flavor is not particularly limited. It can be adjusted as follows. The bitterness value of beer-taste beverages is measured, for example, according to the method described in "Revised BCOJ Beer Analysis Method 3rd Edition", edited by the International Technical Committee of Beer Brewers Association, published in November 2004.

<Method for producing beer-taste beverage>
The beer-taste beverage of the present invention can be produced in the same manner as general fermented beer-taste beverages or non-fermented beer-taste beverages, except that MMBD is contained. Therefore, a general method for producing a fermented beer-taste beverage and a non-fermented beer-taste beverage will be described.

A fermented beer-taste beverage produced through a fermentation process can generally be produced through the steps of preparation, fermentation, storage, and filtration.

In the preparation 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 sugar raw materials. Specifically, a mixture containing cereal raw materials and raw water is heated, starch is saccharified to prepare a sugar solution, the obtained sugar solution is boiled, and then at least part of the solid content is removed. It is removed to obtain a fermentation raw material liquid.

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

Grain raw materials include barley, wheat, rye, oats, barley such as these malts, beans such as rice, corn, and soybeans, and potatoes. The grain raw material can be used as a grain syrup, a grain extract, or the like, but is preferably used as a grain pulverized product obtained by pulverization. Pulverization of grains can be carried out by a conventional method. The pulverized grains may be those that have undergone conventional treatments before and after pulverization, such as pulverized malt, corn starch, and corn grits. In the present invention, the pulverized grain used is preferably pulverized malt. By using ground malt, a fermented beer-taste beverage with a more pronounced beer-like flavor can be produced. The pulverized malt product may be obtained by germinating barley, for example, two-rowed barley by a conventional method, drying it, and then pulverizing it to a predetermined particle size. In addition, the grain raw material used in the present invention may be one type of grain raw material, or may be a mixture of a plurality of types of grain raw material. For example, pulverized malt may be used as the main raw material, and pulverized rice or corn may be used as the secondary raw material.

Carbohydrate raw materials are sugars, that is, carbohydrates with relatively low molecular weights that are soluble in water and generally have a sweet taste. Carbohydrate raw materials include sugars specified in Article 3 of the Liquor Tax Law and the Notification of Interpretation of Alcoholic Beverage Administrative Laws and Regulations dated June 25, 1999, that is, "carbohydrates less than trisaccharides and generally having a sweet taste or A mixture of these is preferred. The saccharide used as the saccharide raw material may be at least one selected from the group consisting of monosaccharides, disaccharides and trisaccharides, and may further contain saccharides of tetrasaccharide or higher. Monosaccharides include, for example, glucose, fructose, galactose, xylose, arabinose, tagatose and the like. Examples of disaccharides include sucrose, lactose, maltose, isomaltose, trehalose, cellobiose and the like. Examples of trisaccharides include maltotriose, isomaltotriose, raffinose and the like. Examples of tetrasaccharides or higher sugars include stachyose and maltotetraose. The form of the saccharide may be, for example, powder, granule, paste, liquid, or the like. Liquid sugars may be, for example, liquid sugars such as high-fructose liquid sugar, fructose-glucose liquid sugar, high-fructose liquid sugar, and sugar-mixed isomerized liquid sugar. The sugar may be granulated sugar or refined sugar.

The mixture may contain sub-ingredients other than water and cereal raw materials that are usually blended as beverages, as long as the desired effects of the present invention are not impaired. Examples of such auxiliary materials include hops, dietary fiber, yeast extract, fruit juice, bittering agents, coloring agents, herbs, flavors, sweeteners, high-intensity sweeteners, antioxidants, acidulants, salts and the like. In addition, if necessary, saccharifying enzymes such as α-amylase, glucoamylase and pullulanase, and enzymatic agents such as protease can be added. For each of these raw materials, commercially available ones can be used.

As sweeteners, for example, fructose corn syrup, glucose, galactose, mannose, fructose, lactose, sucrose, maltose, glycogen and starch can be used. 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. Acidulants include, for example, adipic acid, citric acid, trisodium citrate, gluconodeltalactone, gluconic acid, potassium gluconate, sodium gluconate, succinic acid, monosodium succinate, disodium succinate, sodium acetate, DL-tartaric acid, L-tartaric acid, DL-sodium tartrate, sodium L-tartrate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, fumaric acid, monosodium fumarate, DL-malic acid, DL-sodium malate, acetic acid, Phosphoric acid or the like can be used. Examples of salts that can be used include common salt, acid potassium phosphate, acid calcium phosphate, ammonium phosphate, magnesium sulfate, calcium sulfate, potassium metabisulfite, calcium chloride, magnesium chloride, potassium nitrate, and ammonium sulfate. Examples of dietary fiber that can be used include indigestible dextrin, pectin, polydextrose, and guar gum decomposition products.

The saccharification process is performed using enzymes derived from grain raw materials, etc., or enzymes added separately. The temperature and time for saccharification are determined by considering the type of grain raw materials used, the ratio of grain raw materials to the total fermentation raw materials, the type and amount of added enzymes, the quality of the desired fermented beer-taste beverage, etc. adjusted accordingly. For example, the saccharification treatment can be carried out by a conventional method such as holding a mixture containing cereal raw materials and the like at 35 to 70° C. for 20 to 90 minutes.

A broth (boiled sugar solution) can be prepared by boiling the sugar solution obtained after the saccharification treatment. Preferably, the sugar solution is filtered before boiling, and the obtained filtrate is subjected to boiling. Moreover, instead of the filtrate of this sugar solution, malt extract added with warm water may be used and boiled. The boiling method and its conditions can be determined as appropriate.

A fermented beer-taste beverage having a desired flavor can be produced by appropriately adding herbs or the like before or during the boiling process. For example, by adding hops before or during the boiling process and boiling in the presence of the hops, the flavor and aroma components of the hops, particularly the bitterness components, can be efficiently boiled out. The amount of hops to be added, the mode of addition (for example, adding in several portions) and the boiling conditions can be determined as appropriate.

The broth obtained after boiling contains lees such as proteins caused by precipitation. Therefore, at least part of the solid matter such as lees is removed from the broth. The dregs may be removed by any solid-liquid separation treatment, but generally a tank called a whirlpool is used to remove the sediment. At this time, the temperature of the broth may be 15°C or higher, and generally about 50 to 100°C. The broth (filtrate) after removing the lees is cooled to an appropriate fermentation temperature using a plate cooler or the like. The broth from which the lees have been removed serves as the raw material liquid for fermentation.

Next, as the fermentation process, yeast is inoculated into the cooled fermentation raw material liquid to carry out fermentation. The cooled fermentation raw material liquid may be directly subjected to the fermentation process, or may be subjected to the fermentation process after being adjusted to a desired extract concentration. The yeast used for fermentation is not particularly limited, and can be appropriately selected and used from yeasts usually used for the production of alcoholic beverages. It may be a top-fermenting yeast or a bottom-fermenting yeast, but the bottom-fermenting yeast is preferable because it can be easily applied to large-scale brewing equipment.

Furthermore, as a storage step, the obtained fermented liquor is aged in a storage tank, stored under low temperature conditions of about 0 ° C and stabilized, and then filtered as a filtration step. , yeast and proteins insoluble in the temperature range are removed to obtain the desired fermented beer-taste beverage. The filtration treatment may be a method capable of removing yeast by filtration, and examples thereof include diatomaceous earth filtration and filter filtration using a filter having an average pore size of about 0.4 to 1.0 μm.

In the fermentation process, by appropriately adjusting the fermentation conditions so that the degree of fermentation is low, removing the alcohol content from the obtained fermented liquid, or diluting the obtained fermented liquid, a non-alcoholic beer-taste beverage or a low An alcoholic beer-taste beverage can be obtained.

Beer-taste beverages may be a so-called new genre, using distilled alcohol-containing substances made from malt or barley as a raw material. An alcohol-containing material obtained by distilling malt or barley as a part of the raw material can be added as a raw material in any step of the manufacturing process of a fermented beer-taste beverage.

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

The container-packed fermented beer-taste beverage filled in the container may be heat sterilized if necessary. The heat sterilization treatment should have sufficient sterilization strength to prevent the growth of microorganisms during storage, and is appropriately determined in consideration of the alcohol concentration of the beer-taste beverage. 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, more preferably at 60 to 70°C for about 5 to 15 minutes. .

Non-fermented beer-taste beverages that are produced without going through the fermentation process can generally be produced by a method (preparation method) that mixes the ingredients. For example, specifically, by mixing each raw material, it can be manufactured by a blending step of preparing a blended solution and a gas introduction step of adding carbon dioxide gas to the obtained blended solution.

First, in the compounding process, a compounded solution is prepared by mixing raw materials. In the blending step, it is preferable to prepare a blended solution by mixing all raw materials other than carbon dioxide gas. The order of mixing each raw material is not particularly limited. All raw materials may be added to the raw material water at the same time, or the raw materials may be added sequentially, such as by adding the remaining raw material after dissolving the previously added raw material. Further, for example, the raw material water may be mixed with a solid (for example, powdery or granular) raw material and, if necessary, an alcohol. Alcohol may be mixed depending on the

Raw materials include bittering agents, acidulants, sweeteners, coloring agents, flavoring agents, ethanol (raw material alcohol), emulsifiers, polysaccharides, water-soluble dietary fibers, proteins or their decomposition products.

As the acidulant, it is more preferable to use an organic acid than an inorganic acid from the viewpoint of safety and flavor. The organic acid is not particularly limited as long as it is commonly used in the production of food and drink. Examples include lactic acid, citric acid, gluconic acid, malic acid, tartaric acid, fumaric acid, succinic acid, Adipic acid, fumaric acid, salts thereof, and the like. These organic acids may be used alone or in combination of two or more.

As the bittering agent, those listed above can be used. In addition, isohumulones such as hops, iso-α-acids, tetraiso-α-acids, and β-acid oxides 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.

Sweeteners include sucrose, glucose, fructose, isomerized liquid sugar, and high-intensity sweeteners. High-intensity sweeteners include aspartame, sucralose, acesulfame potassium, neotame, stevia, enzyme-treated stevia, and the like. These sweeteners may be used alone or in combination of two or more.

Examples of coloring agents include caramel pigments. Only one colorant may be used, or two or more colorants may be used in combination.

Flavoring agents include beer extracts, beer flavors, hop flavors, and the like. These flavoring agents may be used alone or in combination of two or more.

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.

Polysaccharides include starch and dextrin. Dextrin is a saccharide obtained by hydrolyzing starch, and refers to a saccharide larger than oligosaccharide (a saccharide in which about 3 to 10 monosaccharides are polymerized). These polysaccharides may be used alone or in combination of two or more.

　Water-soluble dietary fiber means carbohydrates that dissolve in water and are not or difficult to digest by human digestive enzymes. Examples of water-soluble dietary fiber include soybean dietary fiber (soluble soybean polysaccharide), polydextrose, indigestible dextrin, galactomannan, inulin, guar gum hydrolyzate, pectin, gum arabic and the like. Only one type of these water-soluble dietary fibers may be used, or two or more types may be used in combination.

If insoluble matter is generated in the prepared liquid in the preparation step, it is preferable to subject the prepared liquid to a treatment such as filtration to remove the insoluble matter 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 a filtration method or a centrifugation method. In the present invention, insoluble matter is preferably removed by filtration, more preferably by diatomaceous earth filtration.

Next, as a gas introduction step, carbon dioxide gas is added to the prepared liquid obtained in the preparation step. Thereby, a non-fermented beer-taste beverage is obtained. By adding carbonic acid, a refreshing feeling similar to that of beer is imparted. Incidentally, the addition of carbon dioxide gas can be carried out by a conventional method. For example, the prepared liquid obtained in the preparing step and carbonated water may be mixed, or carbon dioxide gas may be directly added to the prepared liquid obtained in the preparing step and dissolved therein.

After adding carbon dioxide gas, the resulting non-fermented beer-taste beverage may be further subjected to a treatment such as filtration to remove insoluble matter. The insoluble matter removal treatment is not particularly limited, and can be performed by a method commonly used in the technical field.

The manufactured non-fermented beer-taste beverage is preferably heat sterilized after being filled in a container. The container to be filled and the heat sterilization method can be the same as those for the fermented beer-taste sparkling beverage.

When the flavor improving agent of the present invention is added to a beer-taste beverage whose flavor is to be improved, the timing is not limited, and it can be added at an appropriate step in the production process of the beer-taste beverage. For example, when adding to a fermented beer-taste beverage, it may be added in any process such as a cooling process after boiling wort, a fermentation process, or an aging process. After the post-fermentation step is desirable, because the concentration of each component in . Moreover, when it is added to liqueurs, it is required to be added before the main fermentation is completed according to the tax law.

The concentration of MMBD contained in beer-taste beverages can be measured by methods such as GC/MS analysis. For example, the following method can be adopted.

Solvent extraction is performed using 150 mL of diethyl ether for 500 g of beer-taste beverage. The obtained extract is washed once with 50 g of saturated saline. Next, the concentrate prepared by distilling off the organic solvent from the extract under normal pressure conditions is directly subjected to GC/MS analysis. The GC/MS conditions are described below.

(1) GC
Temperature rising conditions: 40° C. to 230° C., 5.0° C./min temperature rising, holding at 230° C. for 30 minutes Carrier gas: helium Linear velocity: 25 cm/sec

(2) MS
Electric ionization (EI) method, 70 eV
MS temperature: 230°C (ion source), 150°C (quadrupole)
Scan range: 35-350amu

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

The present invention will be explained more specifically by the following examples, but the present invention is not limited to these.

<Example 1>
Production of flavor improver MMBD was synthesized according to the method described below.

1-Chloro-3-methyl-2-butene (47.1 g), sodium thiosulfate pentahydrate (134 g), catalytic amount of tetra-n-butylammonium bromide, water (201 g), and toluene (141 g) were reacted. The solution was added to the container and dissolved with stirring, and stirred at 22° C. for 60 minutes. The lower layer of the reaction solution was transferred to another reaction vessel, and hexane (75.0 g) was added to the lower layer. The obtained lower layer reaction liquid was ice-cooled and a 20% sodium methanethiolate aqueous solution (158 g) was added at once at 4°C while stirring. After stirring well for 15 minutes, the upper layer was separated from the resulting reaction solution, the resulting upper layer was washed twice with 10% saline, and the solvent was distilled off using a rotary evaporator to obtain a crude product. The obtained crude product (27.9 g) was purified by distillation under reduced pressure (bp 87° C./1.5 kPa) to obtain 8.35 g of MMBD (purity 96.7%). Physical properties are shown below. In the examples below, MMBD is used as a flavor improver.

The physical property values of the obtained MMBD were as follows.

(1) MS
Electric ionization (EI) method, 70 eV
m/z: 39 (6), 41 (61), 53 (5), 67 (7), 69 (100), 70 (8), 79 (5), 80 (5), 148 (M ⁺ , 23 )

(Equipment used)
GC device: MSD5977A manufactured by Agilent Technology
MS device: MS5977A (ionization method: EI 70 eV)
Column: GL Sciences TC-1701 (length 30 m, inner diameter 0.25 mm, liquid layer thickness 0.25 μm)

(2) NMR
¹ H NMR (C ₆ D ₆ , 400 MHz, ppm) δ 1.47 (s, 3H), 1.52 (s, 3H), 2.07 (s, 3H), 3.22 (d, J=8 .0 Hz, 2 H), 5.22 (tm, J=8.0 Hz, 1 H).
¹³ C NMR (C ₆ D ₆ , 100 MHz, ppm) δ 17.8, 23.2, 25.7, 36.7, 120.1, 136.8.

(Equipment used)
NMR measurement device: JEOL RESONANCE JNM-ECX400, 400 MHz

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

A predetermined amount of the flavor improving agent (MMBD) produced in Example 1 was added to Commercial Product 1. After the temperature of the obtained beer-taste carbonated beverage was adjusted to 4° C., a sensory evaluation of the flavor was performed by a professional evaluator. At that time, the commercial product 1 to which no flavor improving agent was added was used as a control, and the average value of 6 professional evaluators was adopted as the evaluation value. The evaluation items, evaluation scores, and their semantic content standards are as follows. Table 1 shows the results of sensory evaluation.

Evaluation item 1: Enhancement of grain-like aroma 2: Enhancement of alcohol feeling 3: Enhancement of aftertaste 4: Enhancement of body feeling 5: Enhancement of fermentation feeling 6: Enhancement of beer-like flavor

Evaluation score and its meaning 1: Same level as no additive, no change 2: Slightly effective 3: Slightly effective 4: Slightly strong effect 5: Strongly effective 6: Very strong effect 7: Very strong feel a strong effect on

The effect of enhancing the afterglow and body feeling tended to become stronger as the additive concentration increased. On the other hand, the effect of enhancing grain-like aroma, alcoholic feeling, fermented feeling, and beer-like flavor tended to be high when the additive concentration was 1.0 to 10 ng/g, and decreased when the additive concentration was 100 ng/g or more.

<Example 3>
Commercial product 2: A fermented beer-taste beverage (malt ratio: less than 25%, bitterness value: 15.0) was prepared. The flavor improving function of MMBD was tested in the same manner as in Example 2 except that the commercial product 2 was used instead of the commercial product 1. Table 2 shows the results.

<Comparative example>
Commercial product 2: A fermented beer-taste beverage (malt ratio: less than 25%, bitterness value: 15.0) was prepared. The flavor improving function of MBT was tested in the same manner as in Example 2 except that commercial product 2 was used instead of commercial product 1 and MBT was used instead of MMBD. Table 3 shows the results.

MBT's lingering effect and body enhancement effect were about the same as MMBD's. On the other hand, MMBD was significantly more effective in enhancing grain-like aroma, alcoholic feeling, fermented feeling, and beer-like flavor. Moreover, MBT is known as a component that constitutes the off-flavour (sunlight smell) of beer, and although the above evaluation items were improved, the sharpness was impaired. MMBD did not linger on the scent more than MBT, and did not impair the sharpness.

Claims

A flavor improving agent for beer-taste beverages containing methyl 3-methyl-2-buten-1-yl disulfide.
The beer-taste beverage flavor improving agent 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, low-malt beer, new genre, and non-alcoholic beer-taste beverages.
The beer-taste beverage flavor improving agent according to claim 1 or 2, wherein the beer-taste beverage whose flavor is to be improved does not use malt or has a malt content of less than 25%.
The beer-taste beverage flavor improving agent according to any one of claims 1 to 3, wherein the beer-taste beverage whose flavor is to be improved is a non-fermented beer-taste beverage.
A method for producing a beer-taste beverage, comprising the step of adding the beer-taste beverage flavor-improving agent according to claim 1 to a beer-taste beverage whose flavor is to be improved.
The amount of methyl 3-methyl-2-buten-1-yl disulfide added to the beer-taste beverage flavor improver is 0.01 to 100 ng/g for the beer-taste beverage whose flavor is to be improved. The method for producing a beer-taste beverage according to claim 5, which is added at.
A method for enhancing the beer-like flavor of a beer-taste beverage, comprising the step of adding the beer-taste beverage flavor-improving agent according to claim 1 to the beer-taste beverage whose flavor is to be improved.
Use of methyl 3-methyl-2-buten-1-yl disulfide for producing a flavor improving agent for beer-taste beverages.
A beer-taste beverage containing 0.01 to 100 ng/g of methyl 3-methyl-2-buten-1-yl disulfide.
The beer-taste beverage according to claim 9, wherein the methyl 3-methyl-2-buten-1-yl disulfide content is 0.1 to 10 ng/g.
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, low-malt beer, new genre, and non-alcoholic beer-taste beverage.
The beer-taste beverage according to any one of claims 9 to 11, which does not use malt or has a malt usage ratio of less than 25%.
The beer-taste beverage according to any one of claims 9 to 12, which is a non-fermented beer-taste beverage.