CA3140143C - Beer-taste fermented malt beverage - Google Patents

Abstract

An object of the invention is to provide a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v), which has beer-like fermented feeling and robust feeling of drinking, and does not give a watery drinking feeling. The means for solving the problems is a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v), containing a wort fermented liquid, more than 5.3 ppm and less than 80 ppm of pyruvic acid, more than 29.2 ppm and less than 90 ppm of succinic acid, and having a genuine extract concentration of more than 2.0% (w/w).

Description

89167867 1 DESCRIPTION BEER-TASTE FERMENTED MALT BEVERAGE CROSS-REFERENCE TO RELATED APPLICATION 5 This application claims benefit under Article 4 of the Paris Convention based on Japanese Patent Application No. 2020- 011736 filed in Japan on January 28, 2020.

Technical Field 10

[0001] The present invention relates to a beer-taste fermented malt beverage, and particularly to a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v).

As used herein, the term "alcohol" means ethanol. 15 [0002] "Fermented malt beverage" means a beverage obtained through the process of using malt as a raw material, and fermenting the same. "Beer taste" means a taste and aroma reminiscent of beer. "Beer" means a beverage obtained through the use 20 of fermenting malt, hops, water and the like as raw materials, and fermenting these with yeast.

Background Art [0003) Low-alcohol beer made by removing alcohol from ordinary Date re9ue/Date received 2023-05-24 2 beer is known.

For example, Patent Document 1 describes a beer-taste beverage obtained by subjecting a beer after fermentation to an alcohol-removing treatment to remove alcohol component. 5

[0004] When the alcohol component is removed from beer, that is a fermented product of wort, flavor components produced in an alcoholic fermentation process may be left, and the obtained beer-taste fermented malt beverage has beer-like 10 fermented feeling.

Also, low molecular saccharides are consumed in the fermentation process, and the above beertaste fermented malt beverage hardly feels unpleasant sticky aftertaste.

In addition, high molecular weight saccharides remain even after the fermentation process, and 15 the beer-taste fermented malt beverage imparts a feeling of touchiness or catchiness felt in the throat when swallowing, that is, robust feeling of drinking.

[0005] On the other hand, the beer-taste beverage from which the 20 alcohol component has been removed does not feel stimulation coming from the alcohol component when drinking.

In particular, beer that has undergone the fermentation process is low in concentration of low molecular saccharides, and the intensity of its sweetness and 25 richness are reduced.

Due to that effects, a low-alcohol Date R99ue/Date Received 2021-11-11 3 beer-taste beverage, obtained from beer as a raw material by removing alcohol, has a problem of imparting watery drinking feeling.

Watery means a weak taste that feels much in water content. 5 [0006) Patent Document 2 describes that a sour agent such as pyruvic acid is included in a beer-taste beverage with an alcohol concentration of less than 0.005% (v/v), and, thereby, beer-like sharp aftertaste is realized, while 10 robust feeling of drinking is provided.

In Patent Document 2, the beer-taste beverage to which a sour agent such as pyruvic acid is added is specifically a liquid obtained by diluting wort using a beer-flavored flavoring, caramel coloring, and carbonated water so that the extract 15 component is 2.0% (Examples 1 to 4).

This beer-taste beverage has not undergone a fermentation process and contains low-molecular saccharides derived from wort.

Therefore, the beer-taste beverage has sweetness and richness from low-molecular saccharides, and does not 20 impart watery drinking feeling.

Prior Art Documents Patent Documents

[0007] Patent Document 1: JP 2003-250503 A 25 Patent Document 2: JP 2016-144412 A Date R99ue/Date Received 2021-11-11 89167867 4 Summary of the Invention Problems to be solved by the Invention [00081 The present invention solves the above problems, and an 5 object thereof is to provide a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v) (hereinafter may referred to as a "low-alcohol beertaste fermented malt beverage••), which has beer-like fermented feeling and robust feeling of drinking, and does 10 not impart watery drinking feeling.

Means for solving the Problems

[0009] The present invention provides a beer-taste fermented malt beverage with an alcohol concentration of less than 1% 15 (v/v), containing a wort fermented liquid, more than 5.l ppm and less than 80 ppm of pyruvic acid, more than 29.2 ppm and less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% (w/w). [0010] 20 In one embodiment, the concentration of the pyruvic acid is 20 to 75 ppm.

[0011] In one embodiment, the concentration of the succinic acid is 35 to 85 ppm. 25

[0012] Date rec;:ue/Date received 2023-10-23 89167867 In one embodiment, the wort fermented liquid is an alcoholremoved wort fermented liquid.

[0013] In one embodiment, the wort fermented liquid is a wort 5 bottom fermented liquid.

[0014] In one e:rqbodiment, the wort fermented liquid has an apparent final degree of fermentation of 80% or less. [0015] 10 In one embodiment, the beer-taste fermented malt beverage has a malt use ratio of 25% or more.

[0016] In one embodiment, the beer-taste fermented malt beverage has a real extract concentration of more than 2. 0% (w/w) . 15

[0017] Also, the present invention provides a method for producing a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v), containing more than 5.3 ppm and less than 80 ppm of pyruvic acid, more than 20 29.2 ppm and less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% (w/w), the method comprising: a step of obtaining a wort fermented liquid; and a step of reducing the alcohol concentration to less than 25 1% (v/v) by removing alcohol from the wort fermented liquid.

Date rec;:ue/Date received 2023-10-23 89167867 5a [0017a] In particular embodiments, the present invention provides: - a beer-taste fermented malt beverage with an alcohol concentration of less than 1% volume/volume, containing a wort fermented liquid, greater than 5.3 ppm to less 5 than 80 ppm of pyruvic acid, greater than 29.2 ppm to less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% weight/weight, wherein the wort fermented liquid has an apparent final degree of fermentation of 45% to 80%; the wort 10 fermented liquid contains hops or a hop extract; the beer-taste fermented malt beverage has a bitterness value of 5 to 100 BU; and the wort fermented liquid is an alcohol-removed wort fermented liquid; and - a method for producing a beer-taste fermented malt beverage 15 with an alcohol concentration of less than 1% volume/volume, containing greater than 5.3 ppm to less than 80 ppm of pyruvic acid, greater than 29.2 ppm to less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% weight/weight, the method comprising: a step of fermenting 20 a wort with yeast; a step of obtaining a wort fermented liquid; a step of reducing the alcohol concentration to less than 1% volume/volume by removing alcohol from the wort fermented liquid; and a step of adding carbon dioxide gas so that it has the same foaming property as beer, wherein the wort fermented 25 liquid has an apparent final degree of fermentation of 45% to 80%; the wort fermented liquid contains hops or a hop extract; and the beer-taste fermented malt beverage has a bitterness value of 5 to 100 BU. 6 Effect of the Invention

[0018] According to the present invention, a low-alcohol beertaste fermented malt beverage, that has beer-like fermented 5 feeling and robust feeling of drinking, does not impart watery drinking feeling, yet has excellent refreshing feeling, is provided.

As a result, the low-alcohol beertaste fermented malt beverage of the present invention has excellent palatability. 10 Brief Description of Drawing [0019) FIG. 1 is a graph showing relationship between the concentrations of pyruvic acid and succinic acid and the palatability of low-alcohol beer-taste fermented malt 15 beverages.

Description of Embodiments [0020) The beer-taste fermented malt beverage of the present invention may be produced according to a method for 20 producing a beer-taste fermented malt beverage with an alcohol concentration of less than 1% (v/v) through a process of fermenting wort, wherein the predetermined concentrations of pyruvic acid and succinic acid are allowed to generate, for example, by adjusting fermentation 25 conditions.

An example of the method for producing a low- Date R99ue/Date Received 2021-11-11 7 alcohol beer-taste fermented malt beverage will be described below.

[0021] By first, crushed malt, auxiliary raw materials such as 5 barley, and warm water are placed into a preparation tank and mixed to prepare maische.

The preparation of the maische can be performed by a conventional method.

For example, first, by holding at 35 to 60°C for 20 to 90 minutes, proteins derived from raw materials is decomposed 10 into amino acids and the like, and then, a saccharifying step is conducted.

At this stage, as necessary, an enzyme such as transglucosidase, and flavor components such as spices and herbs, and the like may be added other than the main raw materials and the auxiliary raw materials. 15 [0022) Then, by gradually raising the temperature of the maische and holding it at a predetermined temperature for a certain period 0£ time, starchy component is saccharified by utilizing an enzyme derived from malt and an enzyme added 20 to the maische.

The temperature and time during the saccharifying treatment may be appropriately determined in consideration of the type of enzyme used, the amount of maische, the quality of the intended wort fermented liquid, and the like, which may be carried out by holding, for 25 example, from 60 at 72°C for 30 to 90 minutes.

After the Date R99ue/Date Received 2021-11-11 8 saccharifying treatment, the maische is held at 76 to 78°C for about 10 minutes, and then filtered in a wort filtration tank to obtain a transparent saccharide liquid.

Further, when performing the saccharifying treatment, an 5 appropriate amount of the enzyme may be added within a necessary range.

[0023] The wort fermented liquid is a liquid obtained by fermenting wort.

The wort fermented liquid may be a wort 10 top fermented liquid or a wort bottom fermented liquid.

The wort top fermented liquid means a wort fermented liquid prepared by inoculating top fermenting yeast to wort, and fermenting under normal fermentation conditions, for example, at 15 to 25°C for several days.

The wort bottom • 15 fermented liquid means a wort fermented liquid prepared by inoculating bottom fermenting yeast to wort, and fermenting under normal fermentation conditions, for example, at around 10°C for about one week. (0024] 20 Raw materials to be saccharified contain malt.

The content of malt in raw materials to be saccharified is not particularly limited, but is 25% or more, preferably 50% or more, and more preferably 67% or more.

The malt use ratio is a ratio (% by weight) of malt to all raw materials 25 excluding water.

The raw materials to be saccharified may Date R99ue/Date Received 2021-11-11 9 be 100% malt.

In general, the higher the malt use ratio, the stronger the malt-derived umami, richness and robust feeling of drinking of the obtained wort. (0025] 5 Auxiliary raw materials mean raw materials other than malt and hops.

Examples of the auxiliary raw materials are starchy raw materials such as barley, wheat, corn starch, corn grits, rice, and Kaoliang, and saccharide raw materials such as liquid sugar and sugar.

Here, the liquid 10 sugar is produced by decomposing and saccharifying starchy component with an acid or a saccharifying enzyme, and mainly contains glucose, maltose, maltotriose and the like.

In addition, spices, herbs, fruits and the like used for the purpose of imparting or improving flavor are also 15 included in the auxiliary raw materials.

[0026] The saccharifying enzyme means an enzyme for decomposing starchy component into saccharide.

As the saccharifying enzyme, there are, for example, a-amylase, glucoamylase, 20 pullanase and the like.

[0027] Wort boiling operation may be carried out according to the method and conditions which are commonly carried out when producing beer.

For example, a saccharide liquid, the pH 25 of which has been adjusted, is transferred to a boiling Date R99ue/Date Received 2021-11-11 CA 03140143 2021-11•11 kettle, and boiled.

During the time from the start of boiling of the saccharide liquid until being left to stand, hops are added in a whirlpool.

Hop extract or a component extracted from hops may be used as the hops.

The 5 saccharide liquid is then transferred to a precipitation tank called a whirlpool.

After hop lees and curdled protein, produced by boiling, are removed, the resulting liquid is cooled to an appropriate fermentation temperature by a plate cooler.

Wort is obtained by the above wort 10 boiling operation.

[0028] The resulting wort is fermented with yeast.

As the yeast to be used, top-fermenting yeast may be used, or bottomfermenting yeast may be used, but it is preferred to use 15 bottom-fermenting yeast from the viewpoint of controlling sourness, astringency and the like.

The type of yeast and fermentation conditions are adjusted to conditions under which predetermined concentrations of pyruvic acid and succinic acid are produced in the beer-taste fermented malt 20 beverage.

The types of such yeasts and fermentation conditions are known.

For example, WO2012/077212 Al describes a method of increasing or decreasing produced amounts of pyruvic acid and succinic acid in a fermentation process for producing a beer-like fermented beverage. N. 25 Coote et al "The Concentration and Significance Pyruvate in Date R99ue/Date Received 2021-11-11 11 Beer", J.

Inst.

Brew., Vol. 79, 1973, p298-304 describes the results of studies on the factors that control the pyruvic acid content in beer. JP Hl0-117760 A describes a method of adjusting produced amounts of malic acid and 5 succinic acid in a fermentation process for producing lowmalt beer.

As a method other than adjusting the fermentation conditions, pyruvic acid and succinic acid may be added to the wort before, during or after fermentation, or the fermented liquid may be diluted so that the 10 concentrations of pyruvic acid ·and succinic acid in the beer-taste fermented malt beverage are adjusted in predetermined ranges. (0029] The beer-taste fermented malt beverage of the present 15 invention contains pyruvic acid at a concentration of more than 5.3 ppm and less than 80 ppm.

By adjusting the pyruvic acid concentration to the above range, the sourness of the beer-taste fermented malt beverage does not stand out, the watery drinking feeling is reduced, and the 20 refreshing feeling is enhanced.

The pyruvic acid concentration is preferably 20 to 75 ppm, and more preferably 25 to 70 ppm. (0030) The beer-taste fe_rmented malt beverage of the present 25 invention contains succinic acid at a concentration of more Date R99ue/Date Received 2021-11-11 12 than 29.2 ppm and less than 90 ppm.

By adjusting the succinic acid concentration within the above range, the sourness of the beer-taste fermented malt beverage does not stand out, the watery drinking feeling is reduced, and the 5 refreshing feeling is enhanced.

The succinic acid concentration is preferably 20 to 200 ppm, and more preferably 35 to 85 ppm.

[0031] The apparent final degree of fermentation of the wort 10 fermented liquid is preferably 80% or less.

When the apparent final degree of fermentation of the wort fermented liquid exceeds 80%, the robust feeling of drinking of the obtained beer-taste beverage tends to be insufficient, and the sourness tends to be strong.

The apparent final degree 15 of fermentation of the fermented wort liquid of the present invention is preferably 45 to 80%, and more preferably 50 to 75%.

[0032] The degree of fermentation is an important index which 20 indicates to what extent fermentation has progressed in beer after fermentation, i.e., the progress of fermentation.

Further, the final degree of fermentation means the ratio of the extract component that can be assimilated by beer yeast based on the raw wort extract component.

Here, the 25 extract component that can be assimilated by beer yeast is Date R99ue/Date Received 2021-11-11 89167867 13 what is obtained by subtracting an extract component contained in the produced beer (that is, an extract component remaining after fermenting all the extract components that can be used by beer yeast (referred to as a 5 final extract component)) from the raw wort extract component.

The apparent final degree of fermentation means the final degree of fermentation which is calculated by using, as the value of final extract component, the apparent extract component, that is, the extract 10 concentration (% (w/w)) derived from the specific gravity of alcohol-containing beer.

[0033] The extract means the concentration (%(w/w)) of a non- volatile solid component.

The real extract 15 concentration of the wort fermented liquid may be measured by, for example, the EBC method (BCOJ Beer Analysis Method, 7.2 (2004), edited by the Beer Brewery Association).

The term extract means the non-volatile solid component itself, the amount of the non-volatile solid component, or the 20 concentration of the non-volatile solid component depending on the context.

[0034] The apparent final degree of fermentation Vend of the wort fermented liquid may be obtained by, for example, the 25 following formula (1).

Date rec;:ue/Date received 2023-10-23 14

[0035] Vend (%) = { (P-End)/P} x 100 ( 1) wherein Pis a raw wort extract component and Eend is an apparent final extract component. 5

[0036] The raw wort extract component Pis the theoretical wort extract component value before alcoholic fermentation, which is back calculated from the alcohol concentration and the extract component value of the produced beer according 10 to Balling's formula.

Specifically, it may be obtained by the method shown in Analytica-EBC (9.4) (2007).

In addition, the apparent final extract component Eend may be determined by collecting beer in a flask, adding a large amount of fresh pressed yeast, fermenting the mixture at 15 25°C while stirring until the extract component value does not decrease any more (24 hours), and measuring the apparent extract component value in the remaining beer.

[0037] The apparent final extract component Eend may show a 20 negative value because it is calculated from the alcoholcontaining specific gravity of the final extract component.

As a result, the apparent final degree of fermentation may exceed 100%. [0038] 25 The apparent final degree of fermentation may be controlled Date R99ue/Date Received 2021-11-11 by adjusting, for example, the saccharifying conditions, whether or not the enzyme is used when saccharifying the raw material, the type and blending amount of the raw material, and the like.

For example, the apparent final 5 degree of fermentation may be reduced by reducing the amount of assimilable saccharides contained in maische.

[0039] After completion of the fermentation, furthermore, the obtained wort fermented liquid is matured as a maturing 10 process in a liquor storage tank, stored under a low temperature condition of about 0°C, and stabilized_ Next, as a filtration step, yeast, proteins and the like are removed by filtering the wort fermented liquid after maturation. 15

[0040] From the wort fermented liquid, from which yeast, protein and the like have been removed, carbon dioxide gas contained therein is removed as necessary.

In addition, the wort fermented liquid is subjected to an alcohol- 20 removing step to remove alcohol contained therein.

The alcohol-removing step is carried out until the alcohol concentration of the wort fermented liquid is, for example, less than 1% (v/v), preferably less than 0.5% (v/v}, and more preferably less than 0.1% (v/v).

The alcohol-removing 25 step is carried out using a conventionally known method.

Date R99ue/Date Received 2021-11-11 16 For example, a vacuum distillation method may be used.

In this case, it is preferred to employ a method in which flavor components produced in the alcoholic fermentation process are allowed to remain therein. 5

[0041] A pH adjusting agent is added to the alcohol-removed wort fermented liquid to lower the pH as necessary.

By sufficiently lowering the pH, bacteriostatic properties required for marketing the beverage is imparted, and the 10 beer-taste fermented malt beverage of the present invention is obtained.

The beer-taste fermented malt beverage of the present invention may have a low pH to such an extent that the spoilage prevention effect is obtained.

The specific upper limit of the pH is less than 4.2, preferably less 15 than 4.1, and more preferably less than 4.0.

On the other hand, the specific lower limit of the pH is 3.0 or more, preferably 3.3 or more, and more preferably 3.6 or more.

[0042] The types of pH adjusting agents are not limited.

Acids, 20 which are food additives and which may be used for beverages, foods or production process thereof, salts thereof, and beer raw materials having pH lowering ability, may be used as pH adjusting agents.

Examples of the beer raw materials having a pH lowering ability include sour 25 malt, dark malt and the like.

Preferred pH adjusting Date R99ue/Date Received 2021-11-11 17 agents are phytic acid, citric acid, lactic acid, lactic acid bacteria, phosphoric acid, malic acid, sulfurous anhydride, tartaric acid, gluconic acid, acetic acid, succinic acid, adipic acid, itaconic acid, fumaric acid and 5 combinations thereof.

More preferred pH adjustors are phytic acid, lactic acid, lactic acid bacteria, phosphoric acid, malic acid, sulfurous anhydride, tartaric acid and combinations thereof.

Considering the effect on the flavor o:f beer-taste beverages, phytic acid, which has less 10 sourness among these, is most preferred.

[0043] To the alcohol-removed wort fermented liquid, a bitter substance is added as necessary to adjust the bitterness value.

Isolated iso-a acids may be used as the bitter 15 substance.

The iso-a acids are contained in hops, and it may also be employed as hops or a hop extract.

The hops or hop extract means hop leaves, a ground product thereof, an extraction liquid obtained by extracting these with water or boiling water, a concentrate and a dried product of the 20 extraction liquid. [0044) The bitterness value of beer-taste beverages is adjusted to have a bitterness equivalent to beer.

Specifically, the bitterness value of the beer-taste beverage is adjusted to 25 5 to 100 BU, preferably 10 to 35 BU, and more preferably 15 Date R99ue/Date Received 2021-11-11 89167867 18 to 27 BU.

The bitterness value of beer-taste beverages may be measured by the EBC method described in BCOJ Beer Analysis Method, 8.15 (2004), edited by the Beer Brewery Association. 5

[0045] To the alcohol-removed wort fermented liquid, carbon dioxide gas is added through a carbonation step.

This results in obtaining the beer-taste fermented malt beverage of the present invention.

The amount of carbon dioxide gas 10 added is adjusted so that it has the same foaming property as beer.

Specifically, the amount of carbon dioxide gas added is adjusted so as to be 1.2 to 5.0 gas volumes, preferably 2.4 to 3.5 gas volumes, and more preferably 2.6 to 3.2 gas volumes. 15

[0046] The beer-taste fermented malt beverage of the present invention has a real extract concentration of more than 2.0% (w/w) due to the extract component derived from the wort fermented liquid.

As a result, the watery drinking 20 feeling of the beer-taste fermented malt beverage is reduced, and the robust feeling of drinking is easily enhanced.

The real extract concentration due to the extract component derived from the wort fermented liquid of the beer-taste fermented malt beverage is preferably 2.5 to 25 6.0% (w/w), and more preferably 3.0 to 5.0% (w/w).

Date rec;:ue/Date received 2023-10-23 19

[0047] The present invention will be described in more detail with reference to the following examples, but the present invention is not limited these. 5 [Examples] [0048] <Example 1> [Production Method of Beer-Taste Fermented Malt Beverage] Crushed malt, water, and corn starch were put in a 10 preparation kettle, gelatinized at 70°C, and liquefied at 100°C.

Next, crushed malt, an enzyme and warm water were put in a preparation tank, protein was decomposed at around 55°C, and then the liquid was transferred from the preparation kettle to the preparation tank, and 15 saccharifying was performed at a temperature in the range of 60°C to 76°C.

This saccharified liquid was filtered with a lauter that was a filter tank, then transferred to a boiling kettle, bitter hops were added, and boiled for 60 minutes.

After boiling, warm water equivalent to the 20 evaporated component was added, hot trub was removed in a whirlpool tank, followed by cooling to 10°C using a plate cooler to obtain cold wort.

[0049] Beer yeast was added to this wort and ferment it at around 25 10°C for 7 days, after which the beer yeast was removed.

Date R99ue/Date Received 2021-11-11 89167867 The tank was changed, the resulting wort was matured for 7 dayf:i, then cooled to around -1°C an.cl stabilized for 14 days.

After dilution by adding gas-removed water, filtration was conducted using diatomaceous earth to obtain a wort 5 fermented liquid.

[0050] Next, the obtained wort fermented liquid was sprayed into a gas-removing tank under a reduced pressure of about 90 mbar to remove carbon dioxide gas, followed by heating to about 10 50°C using a plate cooler.

Thereafter, it was brought into contact with water vapor heated to around 50°C in a column at a reduced pressure of around 90 mbar to adsorb volatile components to the water vapor so that alcohol and volatile components are removed, thereby obtaining an alcohol- 15 removed wort fermented liquid having an alcohol concentration of 0.02% (v/v).

[0051] The obtained alcohol-removed wort fermented liquid was diluted by adding gas-removed water so that the real 20 extract concentration was 5.0%, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, and pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby obtaining a beer-taste fermented malt beverage.

This was represented as sample 1-1.

On the other hand, 25 predetermined amounts of gas-removed water, pyruvic acid Date rec;:ue/Date received 2023-10-23 89167867 21 and succinic acid were added to the alcohol-removed wort fermented liquid, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, and further pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby 5 preparing beer-taste fermented malt beverages of samples 1- 2 to 1-11.

[0052] Regarding these samples, the real extract component (% (w/w)) of the beer-taste fermented malt beverage was 10 measured by using the EBC method.

Furthermore, the pH and bitterness value were measured.

[0053] The concentrations of pyruvic acid and succinic acid in the beer-taste fermented malt beverage were measured by the 15 following method.

First, a decarbonated beer-taste fermented malt beverage was appropriately diluted with distilled water, filtered through a filter, and subjected to UHPLC analysis.

The measurement conditions for UHPLC were as follows. 20

[0054] Date rec;:ue/Date received 2023-10-23 22 [Table 1] Measurement UHPLC (Shimadzu Corporation, Nexera) - MS/MS (AB Sciex, API 3200)' Instrument Column Hypercarb, 2.1 x150 mm, 3 um (Thermo Scientific) Column 80°C (Tmax=85°C) Temperature Mobile Phase Liquid A: 10 mmol/L ammonium acetate/ 0.1% acetic acid aqueous solution Liquid B: methanol Flow Rate 0.2 ml/min Gradient O min··· 0%8, 25 min··· 3%B, 40 min··· 18%B, 50 min 25%8, 65 min·· Conditions • 80%B, 75 min • • • 80%B, 75.1 min • • • 0%B, 90 min· • • 00/48 Ionization ESI positive, CUR 20, CAD 3, IS 5500, TEM 300, GS1 70, GS2 60, lhe ON Conditions Sample 10μL Amount [0055) [Sensory Evaluation Method] Sensory evaluation was performed on the prepared samples. 5 The five evaluation items of "having fermented feeling", "feeling robust feeling of drinking", "not feeling wateriness", "having refreshing feeling", and "not feeling prominent sourness" were set, and 10 trained panelists specialized in beer scored according to the criteria 10 described below.

The average score of all the panelists was used as the score for each evaluation item.

The liquid temperature of the samples used for evaluation was around 4°c. [0056) 15 [Evaluation Items and Evaluation Criteria] Having fermented feeling: The fermented feeling was defined as a beer-like complex taste. "Asahi Super Dry" (trade name) manufactured by Date R99ue/Date Received 2021-11-11 CA 03140143 2021-11-1.1 23 Asahi Breweries, Ltd. was given 5 points, and water was given 1 point, scored on a 5-levels scale.

[0057] Not feeling wateriness: 5 The wateriness was defined as a weak taste that feels much in water content. "Asahi Super Dry" (trade name) manufactured by Asahi Breweries, Ltd. was given 5 points, and water was given 1 point, scored on a 5-levels scale. [0058] 10 Feeling robust feeling of drinking: The robust feeling of drinking was defined as a feeling of touchiness or catchiness felt in the throat when swallowing. "Asahi Super Dry" (trade name) manufactured by Asahi Breweries, Ltd. was given 5 points, and water was given 1 15 point, scored on a 5-levels scale.

[0059] Having refreshing feeling: The refreshing feeling was defined as not feeling a sticky aftertaste. "Asahi Super Dry" (trade name) manufactured by 20 Asahi Breweries, Ltd. was given 5 points, a 2.0% (w/w) aqueous solution of dextrin was given 1 point, scored on a 5-levels scale. (0060] Not feeling prominent sourness: 25 The prominent sourness was defined as feeling sourness Date R99ue/Date Received 2021-11-11 • CA 03140143 2021-11-11 24 clearly. "Asahi Super Dry" (trade name) manufactured by Asahi Breweries, Ltd. was given 5 points, and a 200 ppm citric acid aqueous solution was given 1 point, scored on a 5-levels scale. 5 [00 61] Palatability: "A fermented feeling", "feeling a robust feeling of drinking", "having a refreshing feeling", "not feeling Wateriness" and "not feeling prominent sourness", all of 10 which were scored 3.5 or higher, were rated as good "A", and the others were rated as poor "X".

[0062] Date R99ue/Data Received 2021-11-11 89167867 [Table 2] Item Sample Sample Sample Sample Sample Sample 1-1 1-2 1-3 14 1-5 1-6 Analytical Real value and extract the like concentration 5.0 5.0 5.0 5.0 5.0 5.0 (%) Pyruvic acid concentration 24.7 50.0 70.0 80.0 24.7 24.7 lnom) Succinic acid concentration 40.5 40.5 40.5 40.5 60.0 80.0 lnom) oH 3.9 3,9 3.9 3.9 3.9 3.9 Bitterness 20 20 20 20 20 20 value (BU) Sensory Having a evaluation fermented 4.2 4.4 4.5 4.5 4.2 4.4 feeting Feeling a robust feeling 4.0 4.2 4.2 4.5 4.2 4.4 of drlnkina Having a refreshing 3.8 4.0 4.2 4.0 3.8 3.6 feelina Not feeling 3.8 4.2 4.4 4.4 4.0 4.2 wateriness ' Not feeling prominent 3.5 3.8 3.6 2.8 3.8 3.8 acidltv Palatabilitv A A A X A A (0063] Date rec;:ue/Date received 2023-10-23 26 [Table 3] Item Sample Sample Sample Sample Sample 1-7 1-8 1-9 1-10 1-11 Analytical Real extract value and concentration 5.0 5.0 5.0 5.0 5.0 the like (%) Pyruvic acid concentration 60.0 70.0 80.0 24.7 70.0 loom) Succinlc acid concentration 80.0 80.0 80.0 90.0 90.0 loom) PH 3.9 3.9 3.9 3.9 3.9 Bitterness value (BU) 20 20 20 20 20 Sensory Having a evaluation fermented 4.4 4.5 4.5 3.8 4.6 feelina Feeling a robust feeling 4.4 4.4 4.2 4.4 4.4 of drlnkina Having a refreshing 3.8 3.6 3.6 3.2 3.3 feeling Not feeling wateriness 4.4 4.6 4.6 4.0 4 Not feeling prominent 3.8 3.5 2.9 4.0 3.8 aciditv Palate biHtv A A X X X [0064) <Example 2> Crushed malt, an enzyme and warm water were put in a 5 preparation tank, protein was decomposed at around 55°C, and then saccharifying was performed at a temperature in the range of 60°C to 76°C.

This saccharified liquid was filtered with a lauter that was a filter tank, then transferred to a boiling kettle, bitter hops were added, 10 and boiled for 60 minutes.

After boiling, warm water equivalent to the evaporated component was added, hot trub was removed in a whirlpool tank, followed by cooling to Date R99ue/Date Received 2021-11-11 89167867 27 10°C using a plate cooler to obtain cold wort. [0065) Beer yeast was added to this wort to ferment it at around 10°C for 7 days, after which the beer yeast was removed. 5 The tank was changed, the resulting wort was matured for 7 days, then cooled to around -1°C and stabilized for 14 days.

Then, after dilution by adding gas-removed water, filtration was conducted using diatomaceous earth to obtain a wort fermented liquid. 10

[0066] Next, the obtained wort fermented liquid was sprayed into a gas-removed tank under a reduced pressure of about 90 mbar to remove carbon dioxide gas, followed by heating to about 50°C using a plate cooler.

Thereafter, it was brought into 15 contact with water vapor heated to around 50°C in a column at a reduced pressure of around 90 mbar to adsorb volatile components to the water vapor so that alcohol and volatile components are removed, thereby obtaining an alcoholremoved wort fermented liquid having an alcohol 20 concentration of 0.02% (v/v}.

[0067] The obtained alcohol-removed wort fermented liquid was diluted by adding gas-removed water so that the real extract component was 5.0% (w/w), carbon dioxide gas was 25 dissolved so as to be 2.9 gas volumes, and pH adjustment Date rec;:ue/Date received 2023-10-23 89167867 28 was conducted with phosphoric acid so that the pH was 3.9, thereby obtaining a beer-taste fermented malt beverage.

This was represented as sample 2-1.

On the other hand, predetermined amounts of gas-removed water, pyruvic acid 5 and succinic acid were added to the alcohol-removed wort fermented liquid, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, and further pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby preparing beer-taste fermented malt beverages of samples 2- 10 2 to 2-4. [ 0 0 68] Regarding these samples, the real extract concentration, pyruvic acid concentration, succinic acid concentration, pH and bitterness value were measured in the same manner as in 15 Example 1, and sensory evaluation was performed.

[0069] Date rec;:ue/Date received 2023-1Q-23 89167867 [Table 4] Item Analytical Real value and extract the like concentration {%) Pyruvic acid concentration loom) Succinic acid concentration loom) oH Bitterness value (BU) Sensory Having a evaluation fermented feelini:i Feeling a robustfeellng of drinking Havfng a refreshing feelina Not feeling wateriness Not feeling prominent acidity Palatability [0070) <Example 3> Sample 2~1 5.0 5.3 45.9 3.9 3.0 3.8 3.2 3.2 3.5 X 29 Sample Sample Sample 2~2 2~3 2~4 5.0 5.0 5.0 5.3 25.0 25.0 80.0 45.9 80.O 3.9 3.9 3.9 20 20 20 3.2 4.1 3.8 4.0 4.0 4.2 2.8 3.8 3.6 3,8 3.8 4.2 4.0 3.6 3.8 X A A The alcohol-removed wort fermented liquid obtained in 5 Example 1 was diluted by adding a predetermined amount of gas-removed water so that the succinic acid concentration was 30 ppm.

An isomerized hop extract was added so that the bitterness value was 20 BU.

Then, predetermined amounts of dextrin and pyruvic acid were added so that the 10 real extract concentration was 5.0% and the pyruvic acid concentration was 40 ppm.

Further, carbon dioxide gas was Date rec;:ue/Date received 2023-10-23 89167867 dissolved so as to be 2.9 gas volumes, and pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby obtaining a beer-taste fermented malt beverage.

This was represented as sample 3-1.

On the other hand, 5 predetermined amounts of gas-removed water, pyruvic acid and succinic acid were added to the alcohol-removed wort fermented liquid, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, and further pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby 10 preparing beer-taste fermented malt beverages of samples 3- 2 to 3~4.

[0071] Regarding these samples, the real extract concentration, pyruvic acid concentration, succinic acid concentration, pH 15 and bitterness value were measured in the same manner as in Example 1, and sensory evaluation was performed.

[0072] Date rec;:ue/Date received 2023-10-23 89167867 31 [Table 5] Item Sample Sample Sample Sample 3--1 3-2 3,-3 3-4 Analytical Real value and extract the like concentration 5.0 5.0 5.0 5.0 (%) Pyruvic acid concentration 40.5 70.0 40.5 70.0 {porn) Succinic acid concentration 29.2 29.2 40.0 40.0 loom) pH 3.9 3.9 3.9 3.9 Bitterness 20 20 20 20 value (BU) Sensory Having a evaluation fermented 4.0 4.2 4.2 4.5 feelina Feellnga robust feeling 3.4 3.4 4.2 4.2 of drinking Having a .-~fr@i:.hing 38 3.8 38 A? feetina Not feeling 3.0 3.6 3.8 4.4 wateriness Not feeling prominent 3.0 2.8 3.5 3.6 acidity Palatabilitv X X A A

[0073] FIG. 1 is a graph showing the relationship between the concentrations of pyruvic acid and succinic acid and the 5 palatability of low-alcohol beer-taste fermented malt beverages by summarizing the results of Examples 1 to 3.

In the figure, the symbol "•" indicates that the palatability of the sample was good; and the symbol "X" indicates that the palatability of the sample was poor. 10 From the relationship shown in FIG. 1, it is understood that the palatability of the low-alcohol beer-taste Date rec;:ue/Date received 2023-10-23 89167867 32 fermented malt beverage is improved by adding pyruvic acid and succinic acid in predetermined concentration ranges. [0074] <Example 4> 5 The alcohol-removed wort fermented liquid obtained in Example 1 was diluted by adding a predetermined amount of water so that the real extract concentration was 4.0%, 3.5%, 3.0%, 2.5% or 2.0%, and the bitterness value was adjusted using an isomerized hop extract so that the 10 bitterness value was 20 BU.

Thereafter, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, and further pH adjustment was conducted with phosphoric acid so that the pH was 3.9, thereby obtaining five beer-taste fermented malt beverages.

These were represented as samples 4-1, 4-2, 15 4-3, 4-4, and 4-5. [ 007 5] Regarding these samples, the real extract concentration, pyruvic acid concentration, succinic acid concentration, pH and bitterness value were measured in the same manner as in 20 Example 1, and sensory evaluation was performed. (0076] Date rec;:ue/Date received 2023-10-23 89167867 33 [Table 6J Item Sample Sample Sample Sample Sample 4-1 4.2 4-3 4-4 4-5 Analytical Real value and extract the like concentration 4.0 3.5 3.0 2.5 2.0 (%) Pyruvic acid concentration 42.7 43.0 43.0 43.0 43.0 loom) Succinic acid concentration 47.0 47.0 47.0 47.0 47.0 loom) pH 3.9 3.9 3.9 3.9 3.9 Bitterness 20 20 20 20 20 value (BU) Sensory Having a evaluation fermented 4.0 3.8 3.6 3.5 3.0 feelina Feeling a robust feeling 4.4 4.2 4.0 3.8 3.4 of drinking Having a refreshing 4.2 4.0 3.6 3.6 3.2 feelina Not feeling 4.2 4.2 3.5 3,5 2.5 wateriness Not feeling prominent 3.8 3.6 3.6 3.6 2.5 acidltv Palatability A A A A X [0077] <Reference Example> A non-fermented non-alcohol beer-taste beverage was 5 prepared and sensory evaluation was performed.

[0078] One kilogram of malt was crushed to an appropriate particle size and put in a preparation tank, 3L of warm water was added thereto, the temperature was maintained at 65°C for 10 30 minutes, the temperature was then gradually raised, and saccharifying was performed at 75°C for 30 minutes.

After Date rec;:ue/Date received 2023-10-23 89167867 34 completion of the saccharifying, the temperature was raised to 78°C, and filtration was performed using a filter paper to obtain a filtrate.

The production scale was set to 1 L, hops were added, and boiled at 100°C for 60 minutes.

The 5 liquid after boiling was filtered using a filter paper and cooled to about 2°C.

Water was added to adjust the wort as appropriate so that the real extract concentration was 2.0%. A beer flavored flavoring and a caramel coloring were added to this wort, and an isomerized hop extract was 10 added to adjust the bitterness value.

After pH adjustment with phosphoric acid was conducted on the liquid after dilution .-so that the pll wa:s 3.9, carbon dioxide gao wa::s dissolved so as to be 2.9 gas volumes, thereby preparing Sample 5-1.

On the other hand, water was added to the 15 obtained wort so that the real extract concentration was 4.0% to adjust the wort. A beer flavored flavoring and a caramel coloring were added to this wort, and an isomerized hop extract component was added to adjust the bitterness value.

After pH adjustment with phosphoric acid was 20 conducted on the liquid after dilution so that the pH was 3.9, carbon dioxide gas was dissolved so as to be 2.9 gas volumes, thereby preparing Sample 5-2.

[0079] For these samples, the real extract concentration, 25 pyruvic acid concentration, succinic acid concentration, pH Date rec;:ue/Date received 2023-10-23 89167867 and bitterness value were measured in the same manner as in Example 1, and sensory evaluation was performed. [0080] [Table 7] Item Analytical Real value and extract the like concentration (%) Pyruvic acid concentration (nom) Succinic acid concentration loom) DH Bitterness value (BU) Sensory Having a evaluation fermented feeHna Feeling a robust feeling ofdrinkino Having a refreshing feelino Not feeling wateriness Not feeling prominent aciditv Palatabilitv Sample 5-1 2.0 3.9 2.0 3.0 2.0 3.5 2.0 X Date rec;:ue/Date received 2023-10-23 Sample 5-2 4.0 3.9 2.0 3.2 2.0 . -·· 3.6 1.6 X

Claims (6)

1. 89167867 CLAIMS: 5 36 1. A beer-taste fermented malt beverage with an alcohol concentration of less than 1% volume/volume, containing a wort fermented liquid, greater than 5.3 ppm to less than 80 ppm of pyruvic acid, greater than 29.2 ppm to less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% weight/weight, wherein 10 15 20 25 30 the wort fermented liquid has an apparent final degree of fermentation of 45% to 80%; the wort fermented liquid contains hops or a hop extract; the beer-taste fermented malt beverage has a bitterness value of 5 to 100 BU; and the wort fermented liquid is an alcohol-removed wort fermented liquid.
2. 2. The beer-taste fermented malt beverage according to claim 1, wherein the concentration of the pyruvic acid is 20 to 75 ppm.
3. 3. The beer-taste fermented malt beverage according to claim 1 or 2, wherein the concentration of the succinic acid is 35 to 85 ppm.
4. 4. The beer-taste fermented malt beverage according to any one of claims 1 to 3, wherein the wort fermented liquid is a wort bottom fermented liquid.
5. 5. The beer-taste fermented malt beverage according to any one of claims 1 to 4 having a malt use ratio of 25% or more.
6. 6. A method for producing a beer-taste fermented malt beverage with an alcohol concentration of less than 1% volume/volume, 89167867 37 containing greater than 5.3 ppm to less than 80 ppm of pyruvic acid, greater than 29.2 ppm to less than 90 ppm of succinic acid, and having a real extract concentration of more than 2.0% weight/weight, the method comprising: 5 10 15 a step of fermenting a wort with yeast; a step of obtaining a wort fermented liquid; a step of reducing the alcohol concentration to less than 1% volume/volume by removing alcohol from the wort fermented liquid; and a step of adding carbon dioxide gas so that it has the same foaming property as beer, wherein the wort fermented liquid has an apparent final degree of fermentation of 45% to 80%; the wort fermented liquid contains hops or a hop extract; and the beer-taste fermented malt beverage has a bitterness value of 5 to 100 BU.