Alcoholic beverage and method for suppressing bitterness of alcoholic beverage

Abstract

To provide an alcohol drink having suppressed bitterness due to alcohol and a bitterness suppression method of the alcohol drink.SOLUTION: The problem is solved by an alcohol drink containing a tetrasaccharide represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} and an organic acid, and a method for suppressing the bitterness of an alcohol drink by adding the cyclic tetrasaccharide and an organic acid to the alcoholic drink.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an alcoholic beverage containing a cyclic tetrasaccharide represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} and an organic acid, and a method for reducing the bitterness of an alcoholic beverage, characterized by containing an organic acid together with the cyclic tetrasaccharide. [Background technology]

[0002] Alcoholic beverages are available in a wide variety of forms, including beer, happoshu (low-malt beer), wine, sake, shochu, whiskey, brandy, vodka, gin, and rum, depending on the ingredients and production method used. These beverages are popular and highly palatable. In particular, in recent years, easy-to-drink alcoholic beverages have been available, such as chuhai and cocktails made by diluting shochu, vodka, gin, or the like with water or carbonated water and adding sweeteners, acidulants, fruit juice, flavorings, and the like, and sangria, made by adding fruit, sweeteners, spices, and the like to alcohol-containing ingredients. These beverages are consumed by adults of all ages, regardless of gender. However, because alcohol itself has a bitter taste, the bitterness of the alcohol, which is incompatible with the sweetness or acidity, is noticeable, reducing drinkability and ultimately reducing palatability, particularly in alcoholic beverages with a sweet or sour taste.

[0003] Previously, methods for reducing the bitterness of alcohol have been proposed using octanal, decanal (Patent Document 1), 2-methyl-3-furanthiol, and limonene (Patent Document 2). However, substances such as octanal, decanal, 2-methyl-3-furanthiol, and limonene themselves have distinctive tastes and aromas. Therefore, the flavors of alcoholic beverages that are suitable for these substances are limited due to their compatibility with the taste and aroma, and these methods have not been widely applicable to alcoholic beverages that exhibit a variety of flavors.

[0004] Furthermore, among the many carbohydrates available, highly branched cyclic dextrin (Patent Document 3) and indigestible glucan (Patent Document 4) are known as carbohydrates that suppress the alcoholic sensation, but these only suppress the irritating taste and odor of alcohol, and do not suppress the bitterness, which is one of the five basic tastes.Cyclodextrin (Patent Document 5) has been reported as a carbohydrate that mellows the bitterness of coffee, orange juice, dairy drinks, etc., and gives them a mild throat feel, but its effect in suppressing the bitterness of alcohol is unknown. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2018-126115 A [Patent Document 2] Japanese Patent Publication No. 2020-115900 [Patent Document 3] Japanese Patent Application Laid-Open No. 2003-289824 [Patent Document 4] Japanese Patent Application Publication No. 2017-106 [Patent Document 5] Japanese Patent Publication No. 54-145268 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide an alcoholic beverage in which the bitterness caused by alcohol is reduced, and a method for reducing the bitterness of an alcoholic beverage. [Means for solving the problem]

[0007] As a result of extensive ingenuity, the present inventors have surprisingly found that the bitterness of alcoholic beverages caused by alcohol can be significantly reduced by incorporating a cyclic tetrasaccharide having a structure represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} (hereinafter simply referred to as "cyclic tetrasaccharide") and an organic acid.

[0008] That is, the present invention solves the above problems by providing the following: (1) An alcoholic beverage containing a cyclic tetrasaccharide and an organic acid. (2) The alcoholic beverage according to (1), having an alcohol concentration of 2 to 15 v / v%. (3) An alcoholic beverage according to (1) or (2), which contains distilled alcohol as an ingredient. (4) An alcoholic beverage according to any one of (1) to (3), wherein the concentration of the cyclic tetrasaccharide contained in the alcoholic beverage is 0.1 w / v% or more. (5) An alcoholic beverage according to any one of (1) to (4), wherein the concentration of the organic acid contained in the alcoholic beverage is 0.002 w / v% or more. (6) An alcoholic beverage according to any one of (1) to (5), wherein the organic acid is citric acid and / or malic acid. (7) An alcoholic beverage described in any one of (1) to (6), having an acidity, calculated as citric acid, of 0.002 w / v% or more. (8) A method for reducing the bitterness of an alcoholic beverage, comprising adding an organic acid to the alcoholic beverage together with a cyclic tetrasaccharide. (9) The method for suppressing the bitterness of an alcoholic beverage according to (8), wherein the alcohol concentration of the alcoholic beverage is 2 to 15 v / v%.

[0009] As described above, according to the findings of the present inventors, blending a cyclotetrasaccharide with an organic acid having a sour taste significantly reduces the bitterness of alcohol in an alcoholic beverage. Cyclotetrasaccharide is a substance with a mild sweetness that harmonizes well with other sweeteners and does not leave a lingering aftertaste. On the other hand, organic acids are sometimes added to drinks such as chuhai and are naturally contained in fruit juices and wines, making them highly compatible with alcoholic beverages. In other words, the combination of cyclotetrasaccharide and organic acid discovered by the present inventors can be widely applied to many alcoholic beverages without substantially impairing the inherent sweetness and sourness of the alcoholic beverages, thereby offering the outstanding advantage of being able to provide a wide variety of alcoholic beverages with reduced bitterness and high palatability. [Effects of the Invention]

[0010] According to the present invention, an alcoholic beverage having reduced alcohol bitterness and being easy to drink is provided. Furthermore, the method for reducing the bitterness of alcohol according to the present invention can effectively reduce the bitterness of alcohol in an alcoholic beverage by adding an organic acid together with a cyclic tetrasaccharide to the alcoholic beverage. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention relates to an alcoholic beverage containing a cyclotetrasaccharide and an organic acid, and also to a method for reducing the bitterness of the alcoholic beverage. The alcoholic beverage according to the present invention will now be described in detail.

[0012] <Alcoholic beverages> As used herein, "alcoholic beverage" refers to a beverage with an alcohol content of 1% or more, i.e., a beverage containing 1% or more by volume (v / v%) of ethyl alcohol, which falls under the category of alcoholic beverages under the Liquor Tax Act. In this specification, unless otherwise specified, the percentage used to represent the alcohol concentration in an alcoholic beverage refers to volume %. On the other hand, unless otherwise specified, the concentration of substances other than alcohol contained in an alcoholic beverage is expressed in weight / volume %, i.e., w / v%.

[0013] Examples of alcoholic beverages include sake, wine, beer, happoshu, gin, vodka, tequila, rum, spirits, liqueurs, whiskey, brandy, continuously distilled shochu, pot still shochu, and raw material alcohol.Also included are cocktails, chuhai, sangria, and beer cocktails made from these alcoholic beverages, diluted with water or carbonated water, and optionally with fruit juice, flavors, or the like, to make them easier to drink.

[0014] Alcoholic beverages have a bitter taste due to alcohol (hereinafter referred to as "alcohol bitterness"). The bitter taste of alcohol is one of the five basic tastes that alcohol itself possesses, and is a taste that is mainly perceived at the back of the tongue. The bitter taste of alcohol can reduce the palatability of alcoholic beverages. However, as shown in the experimental examples described below, by adding cyclotetrasaccharide and an organic acid to an alcoholic beverage, the bitter taste of alcohol in the alcoholic beverage can be effectively reduced compared to when either cyclotetrasaccharide or an organic acid is added alone. Note that the reduction in bitterness means a reduction in the intensity of the bitterness, which can be confirmed, for example, by the sensory evaluation described in the experimental examples described below.

[0015] The alcohol content, i.e., alcohol concentration, of the alcoholic beverage of the present invention is not particularly limited, but alcoholic beverages with an alcohol concentration of less than 2% inherently have a low perception of the bitterness of alcohol, and it may be difficult to perceive the bitterness-reducing effect. Therefore, the alcohol concentration of the alcoholic beverage of the present invention is preferably 2% or more, more preferably 3% or more, and even more preferably 4% or more. On the other hand, if the alcohol concentration is too high, the bitterness of alcohol may become too strong, making it difficult to fully perceive the bitterness-reducing effect. Therefore, the alcohol concentration of the alcoholic beverage of the present invention is preferably 15% or less, more preferably 12% or less, even more preferably less than 12%, and even more preferably 9% or less.

[0016] As described above, there are no particular limitations on the type of alcoholic beverage used as the alcoholic raw material in the alcoholic beverage of the present invention. However, among the alcoholic beverages used as the raw material for alcoholic beverages, distilled alcoholic beverages contain fewer flavor components due to distillation, and therefore have a relatively pronounced alcoholic bitterness compared to brewed alcoholic beverages, which contain many flavor components derived from fermentation. Therefore, the combined use of cyclotetrasaccharide and organic acid in alcoholic beverages containing distilled alcoholic beverages as the alcoholic raw material is preferred, as it more clearly exhibits the effect of suppressing the alcoholic bitterness. Among distilled alcoholic beverages, the combined use of cyclotetrasaccharide and organic acid in alcoholic beverages containing continuously distilled shochu, vodka, and raw material alcohol as alcoholic raw materials, which have little flavor derived from the raw material and tend to have a strong alcoholic bitterness, is particularly preferred, as it significantly exhibits the effect of suppressing the alcoholic bitterness. The alcoholic beverage of the present invention may be made up of one type of alcoholic beverage, or two or more types of alcoholic beverages may be used as the alcoholic raw material.

[0017] <Cyclic tetrasaccharide> As used herein, the term "cyclic tetrasaccharide" refers to a cyclic glucotetrasaccharide in which four glucose molecules are alternately bonded via α-1,6 and α-1,3 bonds, i.e., a carbohydrate represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→}.

[0018] Cyclotetrasaccharide is a highly water-soluble carbohydrate with a molecular weight of 648, dissolving 51.9 g in 100 g of water at 30°C. Therefore, it can be easily incorporated into alcoholic beverages containing water. Cyclotetrasaccharide is a substance with a slight sweetness and no unpleasant taste, and does not interfere with the flavor or aroma of sweet alcoholic beverages, making it suitable for use in formulating alcoholic beverages. Furthermore, although cyclotetrasaccharide is a white powder, it becomes colorless and transparent when dissolved in water, which is advantageous in formulating alcoholic beverages because it does not alter the color of fruit juices or colorings in the beverage.

[0019] The method for producing cyclotetrasaccharide is not particularly limited. For example, as disclosed in International Publication No. WO 2002 / 010361, cyclotetrasaccharide can be obtained by treating a partial starch hydrolysate with α-isomaltosyltosylglucosidase and α-isomaltosyltransferase to produce a composition containing cyclotetrasaccharide, which is then purified by chromatographic separation. The cyclotetrasaccharide obtained by chromatographic separation can be crystallized and dried to form a crystalline powder. Known examples of cyclotetrasaccharide crystals include cyclotetrasaccharide pentahydrate crystals and anhydrous cyclotetrasaccharide crystals. A method for producing cyclotetrasaccharide crystals is also described in International Publication No. WO 2002 / 010361.

[0020] The above-mentioned α-isomaltosylglucosidase and α-isomaltosyltransferase used in the production of cyclotetrasaccharide may be derived from any source, as long as they are capable of producing cyclotetrasaccharide. Examples of suitable sources include microorganisms of the genus Bacillus and Arthrobacter, as disclosed in International Publication No. WO 2001 / 090338. In particular, Bacillus globisporus strain C9 (FERM BP-7143), Bacillus globisporus strain C11 (FERM BP-7144), Bacillus globisporus strain N75 (FERM BP-7591), Arthrobacter globformis strain A19 (FERM BP-7590), and mutant strains thereof are preferred. The two enzymes may be purified enzymes that have been separated and purified, or crude enzymes containing both enzymes, or may be extracts or cultures of source microorganisms, etc. When the above-exemplified microbial strains and their mutants are cultured by conventional methods, they usually produce both enzymes in the medium as well. Therefore, a concentrated solution of the filtrate obtained by filtering the cells from the culture can be used as a cyclotetrasaccharide-synthesizing enzyme preparation containing both enzymes, and such an enzyme preparation is particularly advantageous in terms of low production costs and labor. Needless to say, genes encoding the two enzymes may be isolated and used as enzymes obtained from a genetically modified microorganism into which the genes have been introduced.

[0021] The cyclotetrasaccharide blended in the alcoholic beverage of the present invention does not necessarily need to be a highly isolated and purified cyclotetrasaccharide (e.g., cyclotetrasaccharide pentahydrate crystals) but may also be a sugar composition containing cyclotetrasaccharide. An example of such a cyclotetrasaccharide-containing composition is "Tetraring (registered trademark)" (manufacturer: Hayashibara Co., Ltd.). This composition is a cyclotetrasaccharide-containing composition in a starch syrup-like form. Compared with cyclotetrasaccharide crystals prepared through purification, such as cyclotetrasaccharide pentahydrate crystals or cyclotetrasaccharide anhydrous crystals, this composition requires fewer separation and purification steps and can be produced with fewer production steps, making it inexpensive and advantageous for industrial use. In this specification, such a cyclotetrasaccharide-containing composition in a starch syrup-like form is referred to as "cyclotetrasaccharide starch syrup." The method for producing cyclotetrasaccharide starch syrup is as shown in the experimental examples described below, but is not limited thereto. In addition to the cyclotetrasaccharide, the cyclotetrasaccharide starch syrup may also contain coexisting carbohydrates, such as a branched cyclotetrasaccharide in which one or more glucose molecules are bound to the cyclotetrasaccharide, glucose, or maltose.

[0022] Although there is no particular lower limit to the concentration of cyclotetrasaccharide contained in the alcoholic beverage of the present invention, the bitterness of alcohol in the alcoholic beverage can be suitably suppressed by including 0.1% or more, preferably 0.2% or more, and more preferably 0.5% or more of cyclotetrasaccharide together with an organic acid in the alcoholic beverage. On the other hand, there is no particular upper limit to the concentration of cyclotetrasaccharide contained in the alcoholic beverage of the present invention, but if the concentration of cyclotetrasaccharide exceeds 5%, the body flavor derived from the cyclotetrasaccharide becomes dominant, which may reduce palatability, so it is desirable to keep the concentration of cyclotetrasaccharide in the alcoholic beverage at 5% or less.

[0023] <Organic acid> As used herein, "organic acid" refers to an organic compound having acidic properties. The type of organic acid used in the alcoholic beverage of the present invention is not particularly limited, but organic acids having a carboxyl group are preferably used. Specifically, adipic acid, citric acid, gluconic acid, succinic acid, tartaric acid, lactic acid, acetic acid, fumaric acid, and malic acid are preferred, with citric acid and malic acid being more preferred. These organic acids have a sour taste and are therefore used, for example, as acidulants to impart a sour taste to various beverages. The alcoholic beverage of the present invention may contain one or more of these organic acids. Furthermore, these organic acids may be added as organic acid salts. Furthermore, the organic acid blended into the alcoholic beverage of the present invention does not necessarily need to be an isolated substance, and fruit juice or the like containing the organic acid and / or a salt thereof may also be blended in. According to the findings of the present inventors, the bitterness of alcohol is significantly suppressed by adding such an organic acid that exhibits a sour taste to an alcoholic beverage together with a cyclotetrasaccharide.

[0024] As mentioned above, the type of organic acid used in the alcoholic beverage of the present invention is not particularly limited, but when the alcoholic beverage of the present invention is provided as an alcoholic beverage containing fruit juice or fruit juice flavor (e.g., chuhai or cocktail), it is preferable to use the same type of organic acid as the organic acid contained in the fruit juice or flavor blended into such alcoholic beverage, as this allows for formulation without impairing the original flavor and sweetness of the fruit juice or flavor. From this perspective, citric acid and malic acid, which are organic acids commonly contained in many fruit juices, are particularly suitable for use in the alcoholic beverage of the present invention.

[0025] Incidentally, from the perspective of increasing the palatability of alcoholic beverages, it is preferable for the pH of alcoholic beverages to be 2.8 or higher. This is because if the pH of an alcoholic beverage is too low, it becomes too irritating and reduces palatability. On the other hand, in order to make the alcoholic beverage taste sour and highly palatable, and to prevent microbial contamination, it is preferable to adjust the pH of the alcoholic beverage to less than 4.0. The pH of an alcoholic beverage can be adjusted by adjusting the amount and type of organic acid and organic acid salt. As an organic acid salt, for example, trisodium citrate, which is less likely to produce an unpleasant taste when used in alcoholic beverages, is preferably used, but is not limited to this.

[0026] The concentration of the organic acid contained in the alcoholic beverage of the present invention is not particularly limited and can be set appropriately depending on the preference of the alcoholic beverage. However, from the viewpoint of suppressing the bitterness of alcohol by synergistically acting with cyclotetrasaccharide, specifically, it is preferably 0.002% or more, more preferably 0.005% or more. On the other hand, as mentioned above, while the concentration of the organic acid can be appropriately adjusted depending on the preference of the alcoholic beverage, if the organic acid concentration is too high, the alcoholic beverage tends to have an overly strong sour taste and become less palatable. Therefore, the concentration of the organic acid contained in the alcoholic beverage is preferably 2% or less, more preferably 1% or less. The concentration of the organic acid contained in the alcoholic beverage can be calculated from the amount of organic acid and / or its salt added, but it goes without saying that it can also be measured by other chemical methods. For example, it can be determined by quantifying the organic acid in the alcoholic beverage using high-performance liquid chromatography.

[0027] Meanwhile, in this specification, the "acidity" of an alcoholic beverage refers to the "citric acid equivalent acidity" calculated based on the acidity measurement method stipulated in the Japanese Agricultural Standards for Fruit Drinks (Ministry of Agriculture, Forestry and Fisheries Notification No. 3118, December 24, 2013). The "citric acid equivalent acidity" is a value obtained by neutralizing an alcoholic beverage with sodium hydroxide at an endpoint pH of 8.1, determining the amount of sodium hydroxide required for neutralization, and converting the amount of acid contained in the aqueous solution based on that amount into the amount of citric acid, assuming that all the acid is citric acid. In this specification, the citric acid equivalent acidity is expressed as w / v%, as is customary.

[0028] The acidity of the alcoholic beverage of the present invention, calculated as citric acid, is not particularly limited, but is preferably 0.002 w / v% or more, more preferably 0.004 w / v% or more, from the viewpoint of fully obtaining the effect of suppressing the bitterness of alcohol by the cyclotetrasaccharide and organic acid. On the other hand, if the acidity of the alcoholic beverage is too high in terms of citric acid, the alcoholic beverage tends to have an overly strong sour taste and lose its palatability, so the acidity in terms of citric acid is preferably 1.5 w / v% or less, more preferably 1.0 w / v% or less.

[0029] It goes without saying that the alcoholic beverage of the present invention may contain ingredients other than the alcohol raw material, cyclotetrasaccharide, and organic acid. For example, sugars, fruit juice, flavorings, sweeteners, colorants, antioxidants, emulsifiers, preservatives, extracts, pH adjusters, bittering agents, quality stabilizers, etc. may be blended. Furthermore, the alcoholic beverage of the present invention can be made into a carbonated alcoholic beverage by adding a step of sealing in carbon dioxide gas or using carbonated water during the production of the alcoholic beverage. The carbon dioxide pressure may be adjusted to a range normally used for beverages, and is not particularly limited.

[0030] The alcoholic beverage with reduced bitterness of the present invention can be produced, for example, by diluting the alcoholic beverage as the alcohol raw material with water and dissolving or mixing a cyclotetrasaccharide and an organic acid therein. In other words, by adding an organic acid together with the cyclotetrasaccharide to the alcoholic beverage, the bitterness of the alcohol in the alcoholic beverage can be reduced. Thus, in another aspect, the present invention provides a method for reducing the bitterness of an alcoholic beverage. In this method for reducing the bitterness of an alcoholic beverage, the timing and order of adding the cyclotetrasaccharide and the organic acid to the alcoholic beverage are not important. Furthermore, the preferred amounts of each component are as already described in the description of the alcoholic beverage.

[0031] The present invention will be specifically explained below based on experimental examples, but the present invention is not limited to these experimental examples.

[0032] <Experiment 1: Preparation of cyclotetrasaccharide and cyclotetrasaccharide syrup> First, in the following experiments, cyclotetrasaccharide and cyclotetrasaccharide starch syrup to be blended into alcoholic beverages were prepared.

[0033] <Experiment 1-1: Preparation of cyclic tetrasaccharide> Cyclotetrasaccharide 5 hydrate crystals were obtained by the method described in Experiment 30 of International Publication No. WO2002 / 010361. The cyclotetrasaccharide content in the cyclotetrasaccharide 5 hydrate crystals was 88% based on molecular weight calculations (calculated assuming a molecular weight of cyclotetrasaccharide of 648 and a molecular weight of water of 18).

[0034] <Experiment 1-2: Preparation of cyclic tetrasaccharide syrup> Cyclic tetrasaccharide syrup was prepared according to the following procedure.

[0035] <Experiment 1-2-1: Preparation of cyclotetrasaccharide-forming enzyme used in the preparation of cyclotetrasaccharide syrup> First, a cyclotetrasaccharide-synthesizing enzyme was prepared for use in preparing cyclotetrasaccharide. As used herein, "cyclotetrasaccharide-synthesizing enzyme" refers to an enzyme composition containing α-isomaltosylglucosidase and α-isomaltosyltransferase, but substantially free of other enzymes. The cyclotetrasaccharide-synthesizing enzyme was obtained by culturing Bacillus globisporus C9 strain (FERM BP-7143) according to the method of Experiment 3 in International Publication WO 2002 / 010361, sterilizing the culture using an SF membrane, and concentrating the resulting filtrate using an UF membrane in the usual manner. The enzymatic activity of the resulting cyclotetrasaccharide-synthesizing enzyme was 492 units / mL.

[0036] One unit of enzyme activity of cyclotetrasaccharide-synthesizing enzyme was defined as the amount of enzyme required to purify 1 μmol of total cyclotetrasaccharide from soluble dextrin per minute. The enzyme activity of cyclotetrasaccharide-synthesizing enzyme was determined by mixing 500 μL of an appropriately diluted solution of cyclotetrasaccharide-synthesizing enzyme with 500 μL of 50 mM acetate buffer (pH 6.0) containing 2% (w / v) soluble dextrin (Pinex #100, Matsutani Chemical Industry Co., Ltd.), incubating at 40°C for 1 hour, and then boiling for 10 minutes to terminate the reaction. The resulting reaction mixture was then subjected to total cyclotetrasaccharide content analysis, and the total cyclotetrasaccharide produced in the reaction was quantified using the method described below.

[0037] In this specification, the term "total cyclotetrasaccharide" refers to not only cyclotetrasaccharide but also saccharides having a branched structure in which one or more glucose molecules are bound to a cyclotetrasaccharide via a glycosidic bond (hereinafter, also referred to as "branched cyclotetrasaccharide"). Specific examples of branched cyclotetrasaccharides include saccharides in which one glucose is bound to a cyclotetrasaccharide via an α-1,4 glycosidic bond, and saccharides in which one isomaltose is bound to a cyclotetrasaccharide via an α-1,3 glycosidic bond.

[0038] On the one hand, in this specification, when referring to the "total cyclic tetrasaccharide content", it means the cyclic tetrasaccharide content (mass%) in terms of anhydride per total solid of the sugar composition obtained when glucoamylase and α-glucosidase are allowed to act on a sugar composition containing cyclic tetrasaccharides, branched cyclic tetrasaccharides and coexisting saccharides (for example, cyclic tetrasaccharide syrup). When glucoamylase and α-glucosidase are allowed to act on a sugar composition containing cyclic tetrasaccharides, branched cyclic tetrasaccharides and coexisting saccharides, the branched structure of the branched cyclic tetrasaccharides and the coexisting saccharides contained in the sugar composition are decomposed into glucose, and a mixture substantially containing only cyclic tetrasaccharides and glucose as saccharides is obtained. Therefore, the cyclic tetrasaccharide content of the obtained mixture reflects the amount of cyclic tetrasaccharide structures originally contained in the sugar composition.

[0039] Specifically, the total cyclic tetrasaccharide content was analyzed by the following method. That is, 0.5 mL of a sugar composition solution containing cyclic tetrasaccharides and branched cyclic tetrasaccharides adjusted to a solid concentration of 2% by mass was mixed with 0.5 mL of a 50 mM acetate buffer (pH 5.0) containing 400 units / mL of α-glucosidase (trade name 'Transglucosidase L "Amano"', manufactured by Amano Enzyme Inc., 13,000 units / mL) and 10 units / mL of glucoamylase (trade name 'Denzyme GSA / R', manufactured by Nagase ChemteX Corporation, 3,800 units / g), and held at 50°C for 24 hours to completely digest the bonds between glucose other than cyclic tetrasaccharides, boiled for 10 minutes to stop the digestion reaction, and after desalting by a conventional method and subjecting to filtration through a membrane filter, the total cyclic tetrasaccharide content was determined by the area percentage method based on the chromatogram obtained by HPLC under the following conditions.

[0040] <HPLC Conditions> Column: 'Shodex Sugar KS-801 (Na type)' (manufactured by Showa Denko K.K.) Sample concentration: 1% by mass as the solid concentration Sample injection volume: 20 μL Eluent: Ultra-pure water Flow rate: 0.5 mL / min Temperature: 60°C Detection: Differential refractive index

[0041] <Experiment 1-2-2: Preparation and Analysis of Cyclic Tetrasaccharide Syrup> Next, using the cyclic tetrasaccharide-forming enzyme prepared in Experiment 1-2-1, cyclic tetrasaccharide syrup was prepared according to the method described in Example A-9 of WO2002 / 010361 pamphlet. That is, for the raw material (corn starch liquefied liquid, DE5, solid concentration 30% by mass), 2 units of the cyclic tetrasaccharide-forming enzyme prepared in Experiment 1-2-1 per 1 g of the solid and 1 unit of CGTase (manufactured by Hayashibara Co., Ltd., derived from Geobacillus stearothermophilus, 1,634 units / g) per 1 g of the solid were added, and the mixture was held at pH 6.0 and 50 °C for 48 hours to carry out the cyclic tetrasaccharide-forming reaction. Also, when 5 hours had elapsed after the start of the cyclic tetrasaccharide-forming reaction, 500 units of isoamylase (manufactured by Hayashibara Co., Ltd., derived from Pseudomonas amyloderamosa, 553,500 units / g) per 1 g of the solid of the raw material were added. Then, the reaction solution was held at 95 °C for 30 minutes to stop the reaction, cooled to room temperature, and then subjected to filtration, desalting with H-type and OH-type ion exchange resins, further decolorization with activated carbon, and concentration with an evaporator to adjust the solid concentration to 73% by mass, thereby obtaining cyclic tetrasaccharide syrup.

[0042] The content (mass%) in terms of anhydride conversion per total solid of the cyclic tetrasaccharide contained in the obtained cyclic tetrasaccharide syrup was determined by calculating by the percentage method based on the chromatogram obtained by subjecting the test sample to high performance liquid chromatography (hereinafter referred to as "HPLC") using a commercially available high performance liquid chromatography system (trade name 'Prominence', manufactured by Shimadzu Corporation) under the following conditions.

[0043] <HPLC Conditions> Column: Two 'MCI GEL CK04SS' (manufactured by Mitsubishi Chemical Corporation) connected in series Sample concentration: 1% by mass as the solid concentration Sample injection volume: 20 μL Eluent: Ultra-pure water Flow rate: 0.4 mL / min Temperature: 80 °C Detection: Differential refractive index

[0044] The cyclic tetrasaccharide content of the obtained sugar composition based on the total solid matter was 31.7% by mass, the branched cyclic tetrasaccharide content was 15.0% by mass, the total content of glucose, maltose, and isomaltose was 9.7% by mass, and the content of trisaccharides or more other than cyclic tetrasaccharide and branched cyclic tetrasaccharide was 43.6%. Furthermore, since the solid content concentration of the cyclic tetrasaccharide starch syrup was 73% by mass as described above, the cyclic tetrasaccharide content in the cyclic tetrasaccharide starch syrup was calculated to be 23% by mass.

[0045] <Experiment 2: Sensory evaluation of the bitterness of alcohol in alcoholic beverages> Next, alcoholic beverages were prepared according to the method described below, and whether the bitterness of the alcoholic beverages was changed by the cyclic tetrasaccharide and the organic acid was evaluated by a sensory test.

[0046] <Raw materials used> The following ingredients were used to prepare the alcoholic beverages. Pure water was used to dissolve and dilute these ingredients. Alcoholic ingredient: Commercially available "Wilkinson Vodka 50%" (manufacturer: Nikka Whisky Co., Ltd.) was used. The alcohol concentration was 50%. Cyclotetrasaccharide 5-hydrate crystals: The cyclotetrasaccharide 5-hydrate crystals prepared in Experiment 1-2 were used. Cyclotetrasaccharide syrup: Cyclotetrasaccharide syrup prepared in Experiment 1-1-2 was used. α-Cyclodextrin: Commercially available α-cyclodextrin (manufacturer: Serachem Co., Ltd.) was used. Maltotetraose syrup: Commercially available maltotetraose syrup (trade name "Tetrap", manufacturer: Hayashibara Co., Ltd.) was used. Citric acid: Commercially available citric acid (crystals), a food additive (manufacturer: Kenei Pharmaceutical Co., Ltd.), was used. Note that the citric acid (crystals) used was a monohydrate crystal, and the citric acid content in the citric acid (crystals) was 91% (calculated assuming a molecular weight of citric acid of 192 and a molecular weight of water of 18). Malic acid: Commercially available DL-malic acid (manufacturer: Marugo Corporation), a food additive, was used. Trisodium citrate: Commercially available trisodium citrate (manufacturer: Fujifilm Wako Pure Chemical Industries, Ltd.) was used as a food additive. Note that the trisodium citrate used is a dihydrate crystal, so the citric acid content in the trisodium citrate was 65% (calculated based on the molecular weight of citric acid: 192, the molecular weight of water: 18, and the atomic weight of sodium: 23). In the following experiments, the amount of organic acid was adjusted to an appropriate concentration, taking into consideration the balance with the sweetness and alcoholic taste. For test samples containing organic acids, the pH was adjusted to 3.1 to 3.2 using trisodium citrate, a salt of organic acid.

[0047] <Method for measuring acidity in citric acid equivalent> The acidity of the alcoholic beverages prepared in the following experiments was calculated based on the acidity measurement method stipulated in the Japanese Agricultural Standards for Fruit Juice Drinks (Ministry of Agriculture, Forestry and Fisheries Notification No. 3118, December 24, 2013). Specifically, 100 ml of alcoholic beverage was sampled and subjected to neutralization titration using a 0.1 N sodium hydroxide solution, with a pH endpoint of 8.1. The acid concentration in the aqueous solution was calculated as the acidity (unit: w / v%) in terms of citric acid, assuming that all the acid in the aqueous solution was citric acid, based on the amount of sodium hydroxide used in the neutralization titration. Carbonated alcoholic beverages were boiled for 30 seconds to completely remove the carbon dioxide before being subjected to the neutralization titration.

[0048] <Sensory evaluation> The sensory evaluation was carried out according to the following method.

[0049] <Selected panelists> Panelists with food sensory evaluation skills from the applicant company were asked to taste room-temperature liquids of "Wilkinson Vodka 50%" diluted with pure water to alcohol concentrations of 4% and 6%, and panelists who perceived the 6% alcohol concentration to have a clearly stronger bitterness were selected as panelists who could accurately detect the bitterness of alcohol. Here, the bitterness of alcohol was defined as bitterness, one of the five basic tastes felt when swallowing an alcoholic beverage, and the bitterness felt particularly at the back of the tongue.

[0050] <Sensory test method> The sensory evaluation was conducted by having selected panelists drink either a control sample or a test sample and score the bitterness of the alcohol according to the following evaluation criteria. The liquid temperature of the samples used in the sensory evaluation was room temperature. Because the test sample was alcohol, taking into consideration the influence of intoxication, a maximum of eight samples were tested per sensory evaluation test, and each sensory evaluation test was conducted with at least four hours between tests. The scores given by the panelists were totaled and an average score was calculated, which was used as the sensory evaluation score. In this evaluation, samples with an average score of 2.0 or less by the panelists were judged to have significantly reduced alcohol bitterness compared to the control.

[0051] <Sensory evaluation scores and evaluation criteria> 5: The bitterness of the alcohol is stronger than the control sample. 4: The bitterness of the alcohol is slightly stronger than the control sample. 3: The bitterness of the alcohol is similar to that of the control sample. 2: The bitterness of the alcohol is slightly weaker than the control sample. 1: The bitterness of the alcohol is weaker than the control sample. 0: No bitterness of alcohol

[0052] <Experiment 2-1: Effect of cyclotetrasaccharide and organic acids on suppressing the bitterness of alcohol> Using the above-mentioned ingredients, control sample 1 and test samples 1-1 to 1-4 were prepared based on the formulations shown in Table 1. Test samples 1-1 and 1-3 contained cyclotetrasaccharide pentahydrate crystals, and test sample 1-4 contained cyclotetrasaccharide starch syrup. The cyclotetrasaccharide concentration in each was adjusted to 1.8%. The concentration of organic acids in each alcoholic beverage was calculated based on the blend amounts of citric acid and trisodium citrate and the citric acid content (91% citric acid, 65% trisodium citrate). Sensory evaluation of the bitterness of alcohol was conducted by four panelists selected according to the sensory evaluation method described above. Each panelist voluntarily wrote a taste comment for each test sample during the sensory evaluation. The formulations of the test and control samples and the sensory evaluation results are shown in Table 1.

[0053] [Table 1]

[0054] As shown in Table 1, Test Sample 1-1, which contains only cyclotetrasaccharide in addition to alcohol and water, and Test Sample 1-2, which does not contain cyclotetrasaccharide but contains citric acid as an organic acid, received a sensory evaluation score of over 2.0, indicating no effect in suppressing the bitterness of alcohol. In contrast, Test Sample 1-3, which contains both cyclotetrasaccharide and an organic acid, received a sensory evaluation score of 1.0, indicating a significantly reduced bitterness of alcohol compared to Test Sample 1-1, which contains only cyclotetrasaccharide in addition to alcohol and water, and Test Sample 1-2, which contains only organic acid in addition to alcohol and water. Test Sample 1-4, which used cyclotetrasaccharide syrup instead of cyclotetrasaccharide 5-hydrate crystals, also received a sensory evaluation score of 0.75, indicating a similar reduction in the bitterness of alcohol to Test Sample 1-3. These results demonstrate that in alcoholic beverages containing both cyclotetrasaccharide and an organic acid, the cyclotetrasaccharide and the organic acid act synergistically to suppress the bitterness of alcohol. Furthermore, as shown in Table 1, test samples 1-3 and 1-4 were formulated so that the same amount of cyclotetrasaccharide was added, and thus the scores were almost the same, suggesting that cyclotetrasaccharide is the main agent in suppressing the bitterness of alcohol. Therefore, since cyclotetrasaccharide syrup is superior in terms of production costs as described above, in the following experiments, cyclotetrasaccharide syrup was used instead of cyclotetrasaccharide as the raw material containing cyclotetrasaccharide to be added to the test samples.

[0055] <Experiment 2-2: Effect of alcohol concentration on the bitterness-suppressing effect of alcohol by the combined use of cyclotetrasaccharide and organic acid> In Experiment 2-1, we used cyclic tetrasaccharide syrup, which has been confirmed to suppress the bitterness of alcohol when used in combination with organic acids, and evaluated the degree of alcohol bitterness in alcoholic beverages when the alcohol concentration was changed to examine the influence of alcohol concentration on the bitterness suppression effect of using cyclic tetrasaccharide and organic acids in combination.

[0056] Based on the formulations shown in Table 2, samples with varying alcohol concentrations were prepared to obtain control samples 2-1 to 2-4 and test samples 2-1 to 2-4. These control samples and test samples were subjected to sensory evaluation by four selected panelists using the same sensory evaluation method as in Experiment 2-1. The sensory evaluation was conducted for each group with the same alcohol concentration. For example, the sensory evaluation of test sample 2-1, which has an alcohol concentration of 4%, was conducted using control sample 2-1, also with an alcohol concentration of 4%, as the control sample for evaluation. The formulations of the test samples and control samples, along with the sensory evaluation results, are shown in Table 2.

[0057] [Table 2]

[0058] As shown in Table 2, when the alcohol concentration was 4 to 12%, the sensory evaluation scores for all test samples 2-1 to 2-4 containing both cyclotetrasaccharide and organic acid were 2.0 points or less, clearly indicating that the bitterness of alcohol was suppressed. These results demonstrate that the inclusion of both cyclotetrasaccharide and organic acid suppresses the bitterness of alcohol even when the alcohol concentration of the alcoholic beverage was varied within the range of 4 to 12%. Thus, the combined use of cyclotetrasaccharide and organic acid demonstrated a significant reduction in the bitterness of alcohol over a wide range of alcohol concentrations, independent of the alcohol concentration. Furthermore, test sample 2-3 achieved a sensory evaluation score of 0.75 points, demonstrating a significant reduction in the bitterness of alcohol, despite the cyclotetrasaccharide concentration of the alcoholic beverage being reduced from 1.8% to 0.9% compared to test sample 1-4 in Experiment 2-1.

[0059] <Experiment 2-3: Effect of cyclotetrasaccharide concentration on the effect of combining cyclotetrasaccharide with organic acids to suppress the bitterness of alcohol> The influence of cyclotetrasaccharide concentration on the bitterness-reducing effect of the combined use of cyclotetrasaccharide and organic acid in alcoholic beverages was investigated by varying the concentration of cyclotetrasaccharide. Specifically, the amount of cyclotetrasaccharide syrup was varied based on the formulation shown in Table 3, and control sample 3 and test samples 3-1 to 3-3 were prepared, and a sensory evaluation was performed on the resulting samples. The sensory evaluation was performed by four selected panelists using the same sensory evaluation method as in Experiment 2-1. The formulations of the test sample and control sample and the sensory evaluation results are shown in Table 3.

[0060] [Table 3]

[0061] As shown in Table 3, in test samples 3-1 to 3-3 in which the alcohol concentration was fixed at 6% and the cyclotetrasaccharide concentration was varied from 0.2% to 0.9%, the sensory evaluation score for each test sample was 2.0 points or less, indicating that the bitterness of alcohol was significantly reduced compared to control sample 3. In particular, test sample 3-1, in which the cyclotetrasaccharide concentration was as low as 0.2%, also achieved a sensory evaluation score of 2.0 points, indicating that the bitterness of alcohol was significantly reduced. Thus, the combined use of cyclotetrasaccharide and organic acid is considered to be extremely advantageous in formulation design, since the bitterness of alcohol is significantly reduced with an extremely small amount of cyclotetrasaccharide.

[0062] <Experiment 2-4: Effects of organic acids and sugars on the bitterness-suppressing effect of alcohol> To investigate the effect of combining cyclotetrasaccharide with an organic acid other than citric acid on suppressing the bitterness of alcohol in alcoholic beverages, a study was conducted using malic acid instead of citric acid as the organic acid. Patent Document 5 also reports that α-cyclodextrin, which has a cyclic structure and is known to mellow the bitterness of beverages and make them smoother, and maltotetraose starch syrup (product name "Tetrap", manufactured by Hayashibara Co., Ltd.), which, like cyclotetrasaccharide starch syrup, has glucotetrasaccharide as its main component, were tested to investigate their effects on the bitterness of alcohol. Control sample 4 and test samples 4-1 to 4-4 were prepared using the formulations shown in Table 4. Sensory evaluation was performed by four selected panelists using the same method as in Experiment 2-1. The formulations of the test and control samples and the results of the sensory evaluation are shown in Table 4.

[0063] [Table 4]

[0064] As shown in Table 4, Test Sample 4-1, which did not contain cyclotetrasaccharide but mainly contained malic acid as an organic acid, received a sensory evaluation score of 2.5 points, indicating that the bitterness of alcohol in alcoholic beverages was not suppressed, whereas Test Sample 4-2, which contained cyclotetrasaccharide and mainly contained malic acid as an organic acid, received a sensory evaluation score of 1.5 points, indicating that the bitterness of alcohol in alcoholic beverages was suppressed.The results of Test Samples 4-1 and 4-2 demonstrate that not only citric acid but also malic acid, which is an organic acid that has a carboxyl group like citric acid, can be used in combination with cyclotetrasaccharide to suppress the bitterness of alcohol.

[0065] On the other hand, as also shown in Table 4, Test Sample 4-3, which used α-cyclodextrin instead of cyclotetrasaccharide, and Test Sample 4-4, which used maltotetraose syrup instead of cyclotetrasaccharide, received sensory evaluation scores of 3.5 and 2.25, respectively, and showed no effect of suppressing the bitterness of alcohol. These results revealed that these carbohydrates that do not contain cyclotetrasaccharide, even if they contain organic acids, do not have a clear effect of suppressing the bitterness of alcohol, and that the effect of suppressing the bitterness of alcohol is a characteristic effect seen when cyclotetrasaccharide and organic acids are used in combination.

[0066] The present invention will be specifically described below based on examples, but the present invention is not limited to these examples. [Example]

[0067] <Grape Chuhai> 20g of the cyclic tetrasaccharide syrup prepared in Experiment 1-2-2, 3g of 6x concentrated clear red grape juice, 40g of high fructose corn syrup, 2g of citric acid, 1g of malic acid, 1g of trisodium citrate, and an appropriate amount of grape flavor were mixed well with a small amount of water, 120ml of vodka (Nikka Whisky Wilkinson Vodka 50%) was added, and the mixture was diluted to a total of 1000ml with carbonated water to obtain a grape chuhai with an alcohol concentration of 6%. The resulting grape chuhai was easy to drink and had no noticeable bitterness from the alcohol. [Example]

[0068] <Lemon Chuhai> 30g of the cyclic tetrasaccharide syrup prepared in Experiment 1-2-2, 2g of 7x concentrated clear lemon juice, 0.1g of acesulfame potassium, 0.02g of sucralose, 4g of citric acid, 1g of trisodium citrate, and an appropriate amount of lemon flavor were mixed thoroughly with a small amount of water, and 180ml of vodka (Nikka Whisky Company, Wilkinson Vodka 50%) was added. The mixture was then diluted with carbonated water to a total of 1000ml, yielding a lemon chuhai with an alcohol concentration of 9%. The resulting lemon chuhai was easy to drink and had no noticeable bitterness from the alcohol. [Example]

[0069] <Cocktails> 10g of the cyclic tetrasaccharide syrup prepared in Experiment 1-2-2 was thoroughly mixed with 100g of orange juice, and vodka (Nikka Whisky Wilkinson Vodka 50%) was added to a final alcohol concentration of 10%. The resulting cocktail (Screwdriver) was refreshing and easy to drink, without any bitterness from the alcohol. Orange juice is known to contain citric acid and malic acid. [Industrial Applicability]

[0070] As described above, by using the alcoholic beverage and the bitterness reduction method of the present invention, it is possible to provide an alcoholic beverage with reduced bitterness. That is, by using the present invention, it is possible to provide an alcoholic beverage with reduced bitterness that is popular with many people, thereby contributing to the realization of a richer life for people.

Claims

1. An alcoholic beverage containing a cyclic tetrasaccharide represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl(1→} and an organic acid, the alcoholic beverage has a concentration of the cyclic tetrasaccharide of 0.1 w / v% or more; The alcohol concentration is 2 to 15 v / v%. Alcoholic beverages (excluding beer and alcoholic beverages containing maltitol).

2. The alcoholic beverage according to claim 1, which contains a distilled alcoholic beverage as an ingredient.

3. The alcoholic beverage according to claim 1 or 2, wherein the concentration of the organic acid contained in the alcoholic beverage is 0.002 w / v % or more.

4. The alcoholic beverage according to any one of claims 1 to 3, wherein the organic acid is citric acid and / or malic acid.

5. The alcoholic beverage according to any one of claims 1 to 4, having an acidity calculated as citric acid of 0.002 w / v % or more.

6. A method for suppressing the bitterness of an alcoholic beverage (excluding beer and alcoholic beverages containing maltitol) having an alcohol concentration of 2 to 15 v / v%, characterized in that a cyclic tetrasaccharide represented by cyclo{→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→} and an organic acid are added to the alcoholic beverage so that the concentration of the cyclic tetrasaccharide contained in the alcoholic beverage is 0.1 w / v% or more.

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