AU2021355080B2

AU2021355080B2 - Beer-flavored beverage

Info

Publication number: AU2021355080B2
Application number: AU2021355080A
Authority: AU
Inventors: Kenichiro HARUNA; Shigekuni Noba
Original assignee: Asahi Breweries Ltd; Asahi Group Holdings Ltd
Current assignee: Asahi Breweries Ltd; Asahi Group Holdings Ltd
Priority date: 2020-10-02
Filing date: 2021-09-10
Publication date: 2025-06-26
Anticipated expiration: 2041-09-10
Also published as: JP2022059997A; AU2021355080A1; WO2022070833A1; JP7655714B2

Abstract

The present invention addresses the problem of providing a beer-flavored beverage which has an excellent flavor balance and in which richness is enhanced and the usage quantity of malt is low. A means for solving this problem is a beer-flavored beverage which contains 3-methyl-2-butene-1-thiol and at least one type of 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine, which is a tautomer thereof. The concentration of 3-methyl-2-butene-1-thiol is 2.0 ng/l or more. The concentration of the 2-acetyltetrahydropyridine compound is 5.0 μg/l or more.

Description

DESCRIPTION BEER-FLAVORED BEVERAGE

Technical Field

[0001]

The present invention relates to a beer-taste beverage,

and particularly relates to a low-malt beer-taste beverage.

Background Art

[0002]

Beer-taste beverages are those with a flavor reminiscent of beer, with or without a fermentation process.

Malt is used as the main component in beer-taste beverages.

The use of malt produces a beer-taste beverage rich in malt-

derived umami and sweetness.

[0003]

In recent years, beer-taste beverages with a reduced

malt usage have been developed against the backdrop of

diverse needs including low price orientation. In the

development of the beer-taste beverage, attempts to reproduce the flavor of beer and to improve the flavor of

the beer-taste beverage itself have been made.

[0004]

One of the components contained in malt includes proline.

Patent Document 1 discloses that increasing the concentration of proline in beer-taste beverages with a reduced malt usage improves umami and sweetness, which are elements constituting richness.

[0005]

Patent Documents Patent Documents2 2and 3 disclose and 3-methy1-2-butene-1- 3 disclose 3-methyl-2-butene-1-

thiol as a flavor-improving substance for beer-taste beverages. 3-Methyl-2-butene-1-thiol is used to impart a

fermentation feeling to non-fermented beer-taste beverages

in Patent Document 2. In addition, in Patent Document 3, 3- -

methyl-2-butene-1-thiol and dimethyl sulfide are used to methy1-2-butene-1-thiol

give robust feeling of drinking (richness) to beer-taste

beverages with a low malt ratio.

[0006]

With regard to Non-Patent Document 1, the article will

first be excerpted and then explained.

Page 391, lines 15-13 from the bottom, Abstract

"Using GC-MS technology, we have identified for the

first time several compounds having bread-like aroma characteristics and very low flavor thresholds in pale and

dark malts. dark malts.""

[0007]

Page 393, lines 6-17, Introduction

"When malt is roasted or wort is boiled, [omitted]

a compound having a hitherto unknown roasted, popcorn-

like, bread-like aroma is produced. A fragrance substance

having bread-like aroma characteristics is of major importance to beer. This fragrance substance is the main component of aromas in malt, but this fragrance substance may be the cause of a bad aroma in beer stored in a high temperature environment and deteriorated. "

[0008]

Page 401, lines 12-24, Characterization of bread-like aroma

components in beer

"Bread-like bad aroma components are particularly detected

when beer is subjected to a heat load or when beer is improperly transported and stored. particularly A particularly pronounced "off-flavor" impression is felt in the case of

heat sterilization at a too high temperature and for a too

long action time. Fig. 11 shows a gas chromatogram of "excessively heat-sterilized" beer that exhibits typical

bread-like bad aromas. It is observed that there occur several chromatogram segments having sensory characteristics

showing almost equivalent retention times to those for the

characterized proline derivatives. Using preparative GC,

capillary-GC-NSD, and capillary-GC-MS, we were able to

characterize them using four 2-acetyltetrahydropyridines as

index components. "

[0009]

Fig. 1, which is Fig. 11 of Non-Patent Document 1, shows

a gas chromatogram of an "excessively heat-sterilized" beer

that exhibits typical bread-like bad aromas. The conditions for heat sterilization defined here are 0.5 to 20 hours at

80°C 80°C (p. (p. 393, 393,lines lines19-18 from 19-18 thethe from bottom) . When bottom). heated When at at heated

such high temperatures for a long time like this, beer deteriorates by heat.

[0010]

Non-Patent Document 1 discloses, in short, that (1)

when malt is heated, compounds having popcorn-like, bread-

like aromas are produced, that (2) the above aromas are "off- -

flavors", i.e., abnormal odors, which are perceived in beer

that is deteriorated due to heat loading, and that (3) the

analysis results of the above off-flavors are indicated in

the gas chromatogram of Fig. 11.

[0011]

Shown here as Fig. 1, in Fig. 11 of Non-Patent Document

1, 1, 2-acetyl-3 2-acetyl-3,4, 4,5, ,5,6-tetrahydropyridine 2-acetyl 6-tetrahydropyridine, - 1, 4, 5, 6- - 2-acetyl-1,4,5,6-

tetrahydropyridine and the like are indicated as the analysis

results of off-flavors.

[Prior Art Documents]

[Patent Documents]

[0012]

[Patent Document 1] JP 2020-103272 A

[Patent Document 2] WO 2013/080357 A1

[Patent Document 3] JP 2018-186716 A

[Non-Patent Document]

[0013]

2021355080 03 Jun 2025

5

[Non-Patent Document1]1]

[Non-Patent Document

R. Tressl et R. Tressl et al., al.,"Bildung "Bildungvon von Verbindungen Verbindungen mitmit brotigem brotigem Aromacharakter Aromacharakter ininMalz Malz und und Bier", Bier", EBC EBC Congress Congress 1981 1981 2021355080

[0013a]

5 5 The referenceto The reference toany anyprior priorart art in in this this specification specification is is

not, and should not, and should not not be be taken takenas asananacknowledgement acknowledgementororany any

form of suggestion form of suggestion that thatthe theprior prior artart forms forms part part of the of the common generalknowledge. common general knowledge.

Summary of Invention Summary of Invention

10 10 [0014]

[0014]

Proline Proline is mainly derived is mainly derived from from malt, malt, and and the the low- low-

concentration proline tends concentration proline tends totomake make beer-taste beer-taste beverages beverages have less richness. have less richness.

[0015]

15 15 3-Methyl-2-butene-1-thiol contributes to 3-Methyl-2-butene-1-thiol contributes to richness richness and and

a fermentation feeling a fermentation feeling of ofbeer-taste beer-tastebeverages. beverages. ManyMany of of these effectsare these effects areattributed attributed to to returning returning aroma aroma provided provided by by

3-methyl-2-butene-1-thiol. 3-methy1-2-butene-1-thiol.

[0016]

20 20 The returningaroma The returning aromaisisa afragrance fragrance that that passes passes fromfrom the the

mouth to mouth to the the nose. nose. In In contrast, contrast, a fragrance a fragrance thatthat enters enters directly throughthe directly through thenose noseisiscalled called top top aroma. aroma. The The returning returning

aroma and the aroma and thetop toparoma aroma can can be be distinguished distinguished as senses. as senses.

[0017]

25 25 On the other On the other hand, hand, 3-methyl-2-butene-1-thiol 3-methyl-2-butene-1-thiol develops develops

2025 6

an an off-flavor off-flavor (sunlight (sunlight odor) odor) as as the the top top aroma. Becauseof of 2021355080 03 Jun

aroma. Because such top aroma, such top aroma,there thereisis an an upper upper limit limit in the in the amount amount of 3-of 3-

methyl-2-butene-1-thiol that the methyl-2-butene-1-thiol that thebeer beer taste taste may may contain contain 2021355080

while maintaining while maintaining aa flavor flavor balance. balance. TheThe sunlight sunlight odor odor is is 5 5 particularly problematic particularly problematic in inlight-colored light-coloredbeers, beers, such such as as Pilsner-type beers,contributing Pilsner-type beers, contributingto to impairment impairment of lightness. of lightness.

[0018]

A desirable outcome of embodiments of the present A desirable outcome of embodiments of the present invention is to invention is to provide providea a beer-taste beer-taste beverage beverage having having an an 10 10 excellent flavorbalance, excellent flavor balance, enhanced enhanced richness, richness, and and a lowa malt low malt

usage. usage.

[0019]

The present invention The present invention provides providesa abeer-taste beer-tastebeverage beverage

containing 3-methyl-2-butene-1-thiol, and containing 3-methyl-2-butene-1-thiol, and at atleast leastone one2-2-

15 15 acetyltetrahydropyridine compound selected acetyltetrahydropyridine compound selected from fromthe thegroup group

consisting of 2-acetyl-3, consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and 2- 4,5, 6-tetrahydropyridine and 2-

acetyl-1,4,5,6-tetrahydropyridine that acetyl 1, 4, 5, 6-tetrahydropyridine thatis its tautomer, is its tautomer,

wherein wherein

the concentration of the concentration of the the 3-methyl-2-butene-1-thiol 3-methyl-2-butene-1-thiol is is

20 20 2.0 ng/L or 2.0 ng/L or more, more,and and

the concentration ofofthethe the concentration 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound is 5.0 compound is 5.0µg/L μg/Loror more. more.

[0019a]

According to According toone oneaspect, aspect,the the present present invention invention provides provides

25 25 a beer-tastebeverage a beer-taste beveragecontaining containing 3-methyl-2-butene-1-thiol, 3-methyl-2-butene-1-thiol,

6a 03 Jun 2025 2021355080 03 Jun 2025

6a

and at least and at leastoneone 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound compound selected from the selected from thegroup group consisting consisting of 2-acetyl-3,4,5,6- of 2-acetyl-3, 4,5,6- tetrahydropyridine tetrahydropyridine andand 2-acetyl-1,4,5,6-tetrahydropyridine 2-acetyl-1, 4, 5, 6-tetrahydropyridine 2021355080

that is its that is its tautomer, tautomer,wherein wherein

5 5 the malt ratio the malt ratio is is 50 50to to100% 100%bybyweight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 1 to 1 to 10% 10% by weight, by weight,

the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 10 10 to 20% to 20% by weight, by weight, or or

10 wort 10 wort extract extract concentration concentration is is 1 to 1 to 10%10% by by weight; weight; the beer-tastebeverage the beer-taste beverage contains contains proline; proline;

the ratio of the concentration of the 2- the ratio of the concentration of the 2- acetyltetrahydropyridine compound (μg/L) to the acetyltetrahydropyridine compound (µg/L) to the concentration concentration ofofthe theproline proline (mg/L) (mg/L) is more is more thanthan 0.02;0.02;

15 15 the concentrationofofthe the concentration the proline proline is is 400 400 mg/Lmg/L or less; or less;

the concentration of the concentration of the the 3-methy1-2-butene-1-thiol 3-methyl-2-butene-1-thiol is is

2.0 to 55 ng/L; 2.0 to ng/L;and and

the concentration ofofthethe the concentration 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound is 5.0 compound is 5.0toto1010µg/L. μg/L.

20 20 [0019b]

[0019b]

According to According to another anotheraspect, aspect, thethe present present invention invention provides a provides a method method for for producing producing a abeer-taste beer-tastebeverage beverage

containing 3-methyl-2-butene-1-thiol, and containing 3-methy1-2-butene-1-thiol, and at at least leastone one2-2-

acetyltetrahydropyridine compound selected acetyltetrahydropyridine compound selected from fromthe thegroup group

25 25 consisting of2-acetyl-3, consisting of 2-acetyl-3,4,5,6-tetrahydropyridine 4,5, 5-tetrahydropyridine andand 2- 2-

6b 03 Jun 2025 2021355080 03 Jun 2025

6b

acetyl-1,4,5,6-tetrahydropyridine acetyl 1, 4,5, 6-tetrahydropyridinethat is its that is itstautomer, tautomer,

wherein wherein

the malt ratio the malt ratio is is 50 50 to to100% 100%bybyweight, weight,and and the the original original 2021355080

5 5 the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 1 to 1 to 10% 10% by weight; by weight;

the beer-tastebeverage the beer-taste beverage contains contains proline; proline;

10 10 the ratio of the concentration of the 2- the ratio of the concentration of the 2- acetyltetrahydropyridine compound (μg/L) (µg/L) to to the the acetyltetrahydropyridine compound concentration concentration ofofthe theproline proline (mg/L) (mg/L) is more is more thanthan 0.02;0.02;

the concentrationofofthe the concentration the proline proline is is 400 400 mg/Lmg/L or less; or less;

the method including: the method including:

15 15 a step of a step of adjusting adjustingthe the concentration concentration of the of the 3-methyl- 3-methyl-

2-butene-1-thiol to 2.0 2-butene- thiol to 2.0 to to 55 ng/L, ng/L, and and

a step of a step of adjusting adjusting the theconcentration concentrationofofthethe 2- 2- acetyltetrahydropyridine compound acetyltetrahydropyridine compound to to 5.0 5.0 to µg/L. to 10 10 μg/L.

[0020]

20 20 In In one embodiment, it one embodiment, it contains contains proline, proline, and and the the ratio ratio

of the concentration of the concentration of ofthe the2-acetyltetrahydropyridine 2-acetyltetrahydropyridine

compound (μg/L) to compound (µg/L) to the the concentration concentration of of the the proline proline (mg/L) (mg/L)

is more than is more than0.02. 0.02.

[0021]

25 25 In one embodiment, In one embodiment,the theconcentration concentration of the of the proline proline is is

400 mg/L or less.

[0022]

In one embodiment, it is a fermented beer-taste beverage

produced through an alcoholic fermentation process by yeast.

[0023]

In one embodiment, the malt ratio is 50 to 100% by

weight and the original wort extract concentration is 1 to

10% by weight.

[0024]

In one embodiment, the malt ratio is 1 to 50% by weight

and the original wort extract concentration is 10 to 20% by

weight.

[0025]

In one embodiment, the malt ratio is 1 to 50% by weight

and the original wort extract concentration is 1 to 10% by

weight.

[0026]

In one embodiment, the 3-methyl-2-butene-1-thiol is

derived from an added flavoring.

[0027]

In embodiment, the 2-acetyl-3,4, 5, 6- - 2-acetyl-3,4,5,6- one

tetrahydropyridine is derived from an added flavoring.

[0028]

Also, the present invention provides a method for producing producing aabeer-taste beer-tastebeverage containing beverage 3-methyl-2- containing - - 3-methyl-2- butene-1-thiol, and butene-1-thiol, andatat least oneone least 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl- -

3, 4, 5,6-tetrahydropyridine 3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6- -

tetrahydropyridine that is its tautomer, the method including:

a step of adjusting the concentration of the 3-methyl- -

2-butene-1-thiol toto2.0 2-butene-1-thiol ng/L 2.0 or or ng/L more, and and more,

a step of adjusting the concentration of the 2- ug/L or more. acetyltetrahydropyridine compound to 5.0 µg/L

[0029]

In one embodiment, the beer-taste beverage contains

proline, and it includes a step of adjusting the ratio of

the concentration of the 2-acetyltetrahydropyridine compound

(µg/L) to the concentration of the proline (mg/L) SO (ug/L) so that

the ratio is more than 0.02.

[Effect of the Invention]

[0030]

According to the present invention, a beer-taste

beverage having an excellent flavor balance, enhanced richness, and a low malt usage is provided.

[Brief Description of Drawing]

[0031]

FIG. 1, which is FIG. 11 of Non-Patent Document 1, is

a gas chromatogram of an "excessively heat-sterilized" beer

that exhibits typical bread-like bad aromas.

[Description of Embodiments]

[0032]

The present invention will hereinafter be described in

detail.

[0033] <3-Methyl-2-butene-1-thiol> <3-Methy1-2-butene-1-thiol>

3-Methyl-2-butene-1-thiol contained in the beer-taste

beverage of the present invention is a volatile substance

having a thiol group and is contained in trace amounts in

hops hops and and the thelike. like.ItIt is is also known also to increase known or decrease to increase or decrease

in the production process of beer-taste beverages, such as

boiling. Even in trace amounts, 3-methyl-2-butene-1-thiol

reacts with radicals originating from allyl side chains of

isohumulone, which is a bitter component in beer, to produce

an odor known as a sunlight odor when irradiated with ultraviolet light at wavelengths of 350 to 550 nm. However,

containing 3-methyl-2-butene-1-thiol imparts richness to

beer-taste beverages with a low malt usage.

[0034]

In the present specification, the above 3-methyl-2-

butene-1-thiol may be referred to as "MBT". The MBT contained in the beer-taste beverage of the present invention

may be any of those isolated or extracted from natural products, those chemically synthesized by food chemically

acceptable methods, those derived from raw materials

containing containing MBT, MBT,those thosederived from derived raw raw from materials containing materials containing precursors that are converted to MBT in the production process, those commercially available as flavorings, those containing MBT as flavorings.

[0035]

In the beer-taste beverage of the present invention,

the concentration of MBT is 2.0 ng/L or more. If the concentration of MBT is less than 2.0 ng/L, richness of the

beer-taste beverage is hardly perceived. The concentration

of MBT is preferably 2.0 to 20.0 ng/L, and more preferably

3.0 to 5.0 ng/L. If the concentration of MBT is too high,

the sulfur-like top aroma becomes noticeable and the flavor

balance becomes poor.

[0036] <2-Acetyl tetrahydropyridine compound>

The 2-acetyl-3,4,5,6-tetrahydropyridine The 2-acetyl-3, contained 4,5, 6-tetrahydropyridine contained in in

the beer-taste beverage of the present invention has 2-

acetyl - 1,1, 4,4, 5,5,6-tetrahydropyridine asaatautomer. 6-tetrahydropyridine as tautomer.Therefore, Therefore,

when 2-acetyl-3,4,5,6-tetrahydropyridine is added 2-acetyl-3, 4, 5, 6-tetrahydropyridine to a is added tobeer- a beer-

taste beverage, the beer-taste beverage generally contains

both 2-acetyl-3, both 4, 5, 6-tetrahydropyridine and -acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl 2-acetyl- -

1,4,5,6-tetrahydropyridine. 1,4,5, 6-tetrahydropyridine. Their presence ratio is determined depending upon the ambient pH environment and the

like.

[0037]

In the present specification, the above 2 2--

acetyltetrahydropyridine compounds are sometimes referred to as "ATHP". The ATHP is a compound that is formed when malt is heated in the process of producing a fermented beer-taste beverage as described above. The presence of ATHP suppresses the sulfur-like top aroma of the beer-taste beverage and enhances richness. For the ATHP contained in the beer-taste beverage of the present invention, a commercially available

ATHP as a flavoring may be added.

[0038]

In the beer-taste beverage of the present invention,

the concentration of ATHP is 5.0 ug/L µg/L or more. If the µg/L, the sulfur-like concentration of ATHP is less than 5.0 ug/L,

top aroma derived from MBT may not be sufficiently suppressed.

The concentration of ATHP is preferably 5.0 to 50 ug/L, µg/L, more

preferably 6.0 to 20 ug/L, µg/L, and still more preferably 7.0 to

10 ug/L. µg/L. If the concentration of ATHP is too high, astringency is noticeable and the flavor balance becomes

poor. In particular, if its concentration is more than 1

ppm, it becomes a heated bread-like off-flavor as described

in Non-Patent Document 1.

[0039] <Proline>

Proline is an amino acid constituting a protein. Most

of the proline contained in the beer-taste beverage of the

present invention is derived from malt.

[0040]

In a usual beer-taste beverage, the concentration of proline is 500 mg/L or more. The beer-taste beverage of the present invention is a beer-taste beverage with a low proline concentration, for example, a beer-taste beverage with a proline concentration of 400 mg/L or less, 300 mg/L or less,

250 mg/L or less, 200 mg/L or less, 150 mg/L or less, or 100

mg/L or less.

[0041]

In the beer-taste beverage of the present invention,

the ratio of the concentration of ATHP [ug/L]

[µg/L] to the concentration of proline [mg/L] is preferably more than 0.02.

If the ratio is 0.02 or less, in beer-taste beverages with

a low malt ratio or a low original wort extract concentration,

the flavor balance is liable to become poor because richness

is weak or the top aroma is not sufficiently suppressed.

The ratio is preferably 0.025 or more, more preferably 0.03

or more, and still more preferably 0.04 or more. Also, the

ratio is preferably 1.5 or less. If the ratio is more than

1.5, an off-flavor of ATHP is noticeable and the flavor

balance is liable to become poor. The ratio is preferably

1.0 or less, more preferably 0.8 or less, and still more

preferably 0.5 or less.

[0042] <Beer-Taste Beverage>

The beer-taste beverage of the present invention may be

a beer-taste beverage produced through a fermentation

process or without a fermentation process. The beer-taste beverage of the present invention preferably has a low malt usage. Examples of beer-taste beverages with a low malt usage include beer-taste beverages in which the combinations of [the malt ratio (% by weight), the original wort extract concentration (% by weight) weight)]]are arerespectively respectively[50

[50to to100, 100,11

to 10], [1 to 50, 10 to 20], or [1 to 50, 1 to 10]. Here,

the malt ratio is the ratio of the weight of malt to the

weight of starchy raw materials, and the original wort

extract concentration is the concentration of extracts extracted from wort and sugars, proteins, amino acids,

vitamins, minerals, malt and hops contained therein, indicating the ratio with respect to the entire wort. The

original wort extract concentration may be adjusted by adding

water after a filtration step of the beer-taste beverage.

[0043]

Specific examples of beer-taste beverages of the present invention include sparkling liquors, low-alcohol

sparkling beverages, liqueurs and the like. More specific

examples of beer-taste beverages include beer-taste beverages produced without a fermentation process, fermented

beer-taste beverages with a low malt ratio, and fermented

beer-taste beverages with a low original wort extract concentration.

[0044] <Production Method>

The beer-taste beverage of the present invention is produced by a production process that includes the following fermentation process and a production process that does not include a fermentation process.

[0045] <Method for Producing Fermented Beer-Taste Beverage>

A crushed product of malt is prepared as a raw material.

In addition, starchy materials such as rice and corn starch,

protein or protein degradation products and the like are

prepared as auxiliary materials. The raw materials and auxiliary materials are mixed, warm water is added thereto,

and the mixture is heated to saccharify the malt. The resulting wort is filtered and additives are added. At this

time, the concentration of the original wort extract was

adjusted by adding water. The wort is then boiled in a boiling kettle. After boiling, the wort is transferred to

a settling tank (called a whirlpool and the like) to remove

hop lees and other sediments. After removal of the sediments,

the mixture is cooled to an appropriate fermentation temperature by a heat exchanger (a plate cooler). . After After

cooling, the wort is inoculated with yeast for alcoholic

fermentation and filtered to obtain a fermented beer-taste

beverage. The MBT and/or ATHP may be added respectively as

a flavoring to the resulting fermented beer-taste beverage

to adjust the concentration of each component.

[0046] <Method for Producing Non-Fermented Beer-Taste Beverage>

A starchy starchy raw rawmaterial materialsuch as as such malt is saccharified malt to is saccharified to

obtain a saccharide solution. The saccharide solution is

mixed with auxiliary materials such as a sweetener, a flavoring, grain extracts, dietary fiber, a bittering agent,

a coloring and hops, and if necessary alcohol to obtain a

liquid preparation. The order of adding the respective raw

materials to the saccharide solution is not particularly

limited. Next, carbon dioxide gas is added to the liquid

preparation to thereby obtain a non-fermented beer-taste

beverage. The addition of carbon dioxide gas may be conducted conducted by bya aconventional conventionalmethod. For For method. example, the liquid example, the liquid

preparation obtained in the preparation step and carbonated

water may be mixed, or carbon dioxide gas may be added

directly to the liquid preparation obtained in the preparation step to be dissolved. The MBT and/or ATHP may

be be added added respectively respectivelyasas a flavoring to the a flavoring resulting to the non- non- resulting -

fermented beer-taste beverage to adjust the concentration of

each component.

[0047]

The concentration of MBT may be adjusted, for example,

by controlling the type or amount of hops used, or, in the

production process such as boiling or fermentation, the time,

temperature thereof and the like. The concentration of MBT

may be adjusted, for example, by adding the MBT itself to an

intermediate or final product.

[0048]

The concentration of ATHP may be adjusted, for example,

by increasing or decreasing the amount of malt used, or by

increasing or decreasing the temperature or time at which

the malt is heated. The concentration of ATHP may be

adjusted, for example, by adding the ATHP itself to an intermediate or final product.

[0049]

The concentration of proline may be adjusted, for example, by adjusting the malt ratio and/or the concentration

of the original wort extract.

[0050]

The present invention will be further specifically

described in detail by the following examples, but the present invention is not limited to these.

[Examples]

[0051] <Example 1>

In Example 1, the effects of MBT and ATHP in beer-taste

beverages with a low malt ratio were examined.

[0052] <Reference Example 1>

[Production of Beer-Taste Beverage]

A crushed product of malt was prepared as a raw material.

In addition, starchy materials such as rice and corn starch,

protein or protein degradation products and the like were

prepared as auxiliary prepared as auxiliarymaterials. materials. The The raw raw materials and materials and auxiliary materials were mixed to prepare a starchy raw material with a malt ratio of 100%. Warm water was added to the starchy raw material, and the mixture was heated to saccharify the malt. The resulting wort was filtered and additives were added. At this time, the concentration of the original wort extract was adjusted to 12% by weight by adding water. The wort was then boiled in a boiling kettle.

After boiling, the wort was transferred to a settling tank

(called a whirlpool and the like) to remove hop lees and

other sediments. After removal of the sediments, the mixture

was cooled to an appropriate fermentation temperature by a

cooler).. After heat exchanger (a plate cooler) After cooling, cooling, the the wort wort

was inoculated with yeast for fermentation. After

fermentation, filtration was performed to obtain a fermented

malt beer-taste - beverage. beverage.

[0053]

MBT, ATHP and proline were analyzed as specifications

of the resulting fermented beer-taste beverage to determine

their concentrations concentrations.The Theanalysis analysismethod methodis isshown shownbelow. below.

The analysis results are shown in Table 1.

[0054] [Analysis of MBT]

The concentration of MBT was measured using the method

of Kishimoto et al. (Kishimoto, T. et al., Odorants including

hop aroma of beer: hop-derived odorants increased in the

beer hopped with aged hops, Proceedings of the 31st E BC

Congress, Venice 2007) 2007)..

[0055] [Analysis of ATHP]

To 20 g of beer-taste beverage, 50 uL µL of an internal

standard solution (4 ug/mL µg/mL ATHP stable isotope), and 200 uL µL

of formic acid and 10mL of distilled water were added and

loaded onto loaded ontoOASIS OASISMCX MCX500 mg/6 500 mL mL mg/6 (Waters Corporation). (Waters Corporation)

[0056]

The column was washed with 5 mL of 1% formic acid water,

followed by elution with 5 mL of 2% ammonia-methanol. The

eluate was diluted 2-fold with distilled water, and analyzed

by LC/MS/MS.

[0057]

Using LC/MS/MS (5500 QTRAP manufactured by AB-SCIEX

Corporation) Corporation),and andit itwas wasseparated separatedusing usingas asaacolumn columnACQUITY ACQUITY

UPLC BEH C18 1.7 um, µm, 2.1 X 100 mm (manufactured by Waters

Corporation) Corporation).As Asfor formoving movingphase phaseconditions, conditions,Liquid LiquidA: A:10 10

mM ammonium hydrogen carbonate, and Liquid B: acetonitrile

were used with the following conditions: (B%, t) : (10%, 1

min), (50%, 6 min), and analysis was conducted by setting

the transition at 126 -> 84 84 (collision (collision energy: energy: 23 23 V) V) forfor ATHP. ATHP.

Quantification was conducted using a calibration curve prepared by adding a standard substance.

[0058] [Analysis of Proline]

Proline in beer-taste beverages was determined by the

AccQ-TagUltra labeling method using an AcquityUPLC analyzer manufactured manufacturedbybyWaters Corporation Waters (US)(US) Corporation . . AA calibration calibration curve curve was prepared using Amino Acids Mixture Standard Solution,

Type H (Wako Pure Chemicals Co., Ltd. ) . Ltd.).

[0059] <Comparative Example 1-1>

A beer-taste beverage was obtained in the same manner

as in Reference Example 1, except that the malt ratio of the

starchy raw material was adjusted to 45%, and the specifications were analyzed. The MBT concentration was 1

ng/L, ATHP concentration was 1.5 µg/L, ug/L, and proline concentration was 200 mg/L.

[0060] <Comparative Examples 1-2, 1-3 and 1-4>

ng/1, 3 ng/L The MBT concentrations were increased to 2 ng/l,

and 5 ng/L respectively by adding MBT to the beer-taste

beverage of Comparative Example 1-1.

[0061] <Examples 1-1 and 1-2>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 1-2.

[0062] <Examples 1-3 and 1-4>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 1-3.

[0063] <Examples 1-5 and 1-6>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

pg/L µg/L respectively by adding ATHP to the beer-taste beverage of Comparative Example 1-4.

[0064]

Next, sensory evaluation of produced beer-taste beverages was conducted. The evaluation items were the top

aroma (sunlight odor) and richness of the beverages. Three

professional evaluators for beers tasted each beer-taste

beverage and scored them according to the following evaluation criteria. The average of the three evaluators'

sensory scores was used as an evaluation score. The aroma

balance was scored as "A" when the grade was 3 or higher in

two items. The evaluation results are shown in Table 1.

[0065] <Evaluation Criteria: Top Aroma (Sunlight Odor) Odor):> >

Score 4 : 4: Very weak

3: Weak Weak 2: Strong

1: Very strong

[0066] <Evaluation Criteria: Richness>

Score 4 : 4: Very Very strong strong 3: Strong

2: Weak 1: Very weak

[0067]

Ex. 1-6 Ex. 1-6

0.05 0.05 200 45 12 10 10

[Table 1] 1-5 5 4 4 A Ex. Ex. 1-5

0.03 0.03 Table 1 Evaluation in beer-taste beverages 200 200 45 with a low 45 12 malt ratio Ref. Ex. Comp. Comp. Ex. 1-1 Ex. 1-2 Ex. 1-4 Ex. 1-4 5 Comp. 5 Ex. 1-3 Ex. 1-4 3 Comp.3 A Ex. 1-5 Ex. 1-6 Comp. Comp. 0.01 0.01 Ex. 1- 1 Ex. 1-2 200 200 Ex. 1-3 1.5 1.5 Ex. 1-4 45 45 12 Malt ratio 100 Ex. 1-4 Ex. 1-4 45 45 45 45 5 45 45 45 1 45 3 45 45 0.05 0,05

[%] 200 200 45 12 10 Original wort 3 4 4 A Ex. 1-3 Ex. 1-3 extract 12 12 12 12 12 12 12 0.03 0.03 12 12 12 12 200 200 45 12

[%] Ex. 1-3 Ex. 1-3 3 5 3 3 A Proline Comp. Comp. 200 200 200 0.01 0.01 200 200 200 200 500 200 200 200 200 200 1.5 1.5

[mg/L] 45 12 3 2 2 21

MBT Ex. 1-2 Ex. 1-2

1 o o i i t t a a r r t t l l a a m m w w o o l l a a h h t t i i w w s s e e g g a a r r e e v v e e b b e e t t s s a a t t - - r r e e e e b b n n i i n n o o i i t t a a u u l l a a v v E E 1 1 e e l l b b a a T T 1 2 2 2 3 3 0.05 0.05 3 5 5 5 o i t a r t l a m w o l a h t i w s e g a r e v e b e t s a t - r e e b n i n o i t a u l a v E 1 e l b a T 200 200

[ng/L] 45 12 10 10 ATHP 2 4 4 A Ex. 1-1 Ex. 1-1 5 1.5 1.5 5 10 1.5 5 10 1.5 5 10 0.03 0.03

[µg/L] 200 200 45 12 ATHP/Proline 0.01 0.01 0.01 0.03 0.05 0.01 0.03 0.05 4 0.01 0.03 A 0.05 Ex. 1-2 Ex. 1-2 2 5 3 Comp. Comp. 0.01 0.01 Top aroma 200 200 1.5 1.5 45 12 (sunlight 4 4 3 4 4 2 3 4 1 3 4 Ex. 1-1 Ex. 1-1 2 3 2 odor) Comp. Comp. 0.01 0.01 200 200 1.5 1.5 2 452 12 3 4 2 3 4 3 3 4 Richness 4 Ref. Ex. Ref. Ex. 1 4 2 Flavor A A 0.01 0.01 A A 100 100 500 A A500 balance 12 1 Original wort Original wort 1 5 ATHP/Proline ATHP/Proline 4 4 A Top Top aroma aroma Malt ratio

[Table 1]

[Table 1] Mait ratio (sunlight (sunlight Richness Richness balance balance extract extract Proline Proline

[mg/L]

[mg/L] [ng/L] [µg/L]

[ug/L] Flavor Flavor

[ng/L] ATHP ATHP MBT MBT odor) odor)

[%] [%]

[0068]

It is understood from the evaluation results in Table

1 that richness is lacked in beer-taste beverages with a low

malt ratio by comparison between Reference Example 1 and

Comparison Example 1-1. In addition, it is understood that

the higher MBT concentration imparts richness, but the flavor

balance becomes poor due to the top aroma by comparison

between the comparative examples.

[0069]

Furthermore, it is understood from the evaluation results in Table 1 that, by the effect of ATHP, if the ATHP

concentration is 5.0 ug/L µg/L or higher, and particularly 10.0

ug/L µg/L or higher in beer-taste beverages with a low malt ratio,

the top aroma (sunlight odor) is suppressed, the richness is

enhanced, and the flavor balance is excellent.

[0070] <Example 2>

In Example 2, the effects of MBT and ATHP in beer-taste

beverages with a low original wort extract concentration

were examined.

[0071] <Comparative Example 2-1>

A beer-taste beverage was obtained in the same manner

as in Reference Example 1, except that the original wort

extract concentration was adjusted to 5%, and the specifications were analyzed. The MBT concentration was 1

ng/L, ATHP concentration was 2 ug/L, µg/L, and proline concentration was 200 mg/L.

[0072] <Comparative Examples 2-2, 2-3 and 2-4>

The MBT concentrations were increased to 2 ng/l, ng/1, 3 ng/L

and 5 ng/L respectively by adding MBT to the beer-taste beverage of Comparative Example 2-1.

[0073] <Examples 2-1 and 2-2>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 2-2.

[0074] <Examples 2-3 and 2-4>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 2-3.

[0075] <Examples 2-5 and 2-6>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L respectively by adding ATHP to the beer-taste beverage µg/L

of Comparative Example 2-4.

[0076]

Sensory evaluation of the above beer-taste beverages

was conducted in the same manner as in the beer-taste beverages listed in Table 1. The evaluation results are

shown in Table 2.

[0077]

Ex. 2-6 Ex. 2-6

0.05 0.05 100 200 200 10

[Table 2] 5 5 4 4 A Ex. 2-5 Ex. 2-5

0.03 0.03 100 Table 2 Evaluation in beer-taste beverages 200 100 with a low original wort extract concentration Ref. Ex. Comp. Ex. Ex. 2-4 2 -4 Comp. 5 Comp. 5 Ex. 2- 5 Ex. 2-4 3 Comp. 4 A Ex. 2-5 Ex. 2-6 Comp. Comp. Ex. 2-1 Ex. 2-2 3 0.01 0.01 Ex. 2 -4 Ex. 2-1 Ex. 100 2-2 200 200 Ex. 2-3 Malt ratio 100 Ex. 100 2-4 Ex. 2-4 100 5 100 100 100 5 2 100 100 1 100 3 100 100 0.05 0.05

[%] 100 200 10 Original wort 5 3 4 4 A n n o o i i t t a a r r t t n n e e c c n n o o c c t t c c a a r r t t x x e e t t r r o o w w l l a a n n i i g g i i r r o o w w o o l l a a h h t t i i w w s s e e g g a a r r e e v v e e b b e e t t s s a a t t - - r r e e e e b b n n i i n n o o i i t t a a u u l l a a v v E E 2 2 e e l l b b a a T T n o i t a r t n e c n o c t c a r t x e t r o w l a n i g i r o w o l a h t i w s e g a r e v e b e t s a t - r e e b n i n o i t a u l a v E 2 e l b a T Ex. Ex.2 -2- 5 5 5 5 5 extract 12 5 5 5 5 5 0.03 0.03 100 200 200

[%] Praline 3 Ex. 2-3 Ex. 2-3 5 3 5 3 3 A Comp. Comp. 200 200 200 0.01 0.01 200 200 200 200 500 200 200 100 200 200 200

[mg/L] 3 2 24

MBT Ex. 2-2 Ex. 2-2 5 2 2 1 1 2 2 2 3 3 0.05 0.05 3 5 5 100 200 200

[ng/L] 10 ATHP Ex. 2-1 Ex. 2-1 55 10 2 2 5 10 4 2 4 5 A 10 5 2 2 0.03 0.03

[µg/L] 100 200 200

ATHP/Proline 0.01 0.01 0.01 0.03 0.05 0.01 0.03 0.05 0.03 A 0.05 Ex. 2-2 Ex. 2-2 5 2 5 4 0.01 3 Comp. Comp. 0.01 0.01 Top aroma 100 200 200

(sunlight 4 4 3 4 4 2 4 1 3 4 2-1 5 2 23 3 2 Ex. Ex. 2-1 odor) Comp. Comp. 0.01 0.01 100 200 Richness 4 2 2 3 4 2 3 4 3 4 4 Ref. Ex. Ref. Ex. 5 1 2 4 2 Flavor A A 0.01 0.01 A A A 100 A A500 balance 12 1 Original wort Original wort 1 5 ATHP/Proline ATHP/Proline 4 4 A Top aroma Top aroma Malt ratio

[Table 2]

[Table 2] Malt ratio (sunlight (sunlight Richness Richness balance balance extract extract Proline Proline

[mg/L]

[mg/L] [ng/L] [µg/L] Flavor Flavor

[ng/L] ATHP ATHP [ug/L] odor) odor) MBT MBT

[%] [%]

[0078]

It is understood from the evaluation results in Table

2 that richness is lacked in beer-taste beverages with a low

original wort extract concentration by comparison between

Reference Example 1 and Comparison Example 2-1. In addition,

it is understood that the higher MBT concentration imparts

richness, but the flavor balance becomes poor due to the top

aroma by comparison between the comparative examples.

[0079]

Furthermore, it is understood from the evaluation results in Table 2 that, by the effect of ATHP, if the ATHP

concentration is 5.0 ug/L µg/L or higher, and particularly 10.0

ug/L µg/L or higher in beer-taste beverages with a low original

wort extract concentration, the top aroma (sunlight odor) is

suppressed, the richness is enhanced, and the flavor balance

is excellent.

[0080] <Example 3>

In Example 3, the effects of MBT and ATHP in beer-taste

beverages with a low malt ratio and proline concentration

were examined.

[0081] <Comparative Example 3-1>

A beer-taste beverage was obtained in the same manner

as in Reference Example 1, except that the malt ratio of the

starchy raw material was adjusted to 30%, and the

specifications were analyzed. The MBT concentration was 1 µg/L, and proline ng/L, ATHP concentration was 1.5 ug/L, concentration was 120 mg/L.

[0082] <Comparative Examples 3-2, 3-3 and 3-4>

ng/1, 3 ng/L The MBT concentrations were increased to 2 ng/l,

and 5 ng/L respectively by adding MBT to the beer-taste

beverage of Comparative Example 3-1.

[0083] <Examples 3-1 and 3-2>

µg/L and 10 The ATHP concentrations were increased to 5 ug/L

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 3-2.

[0084] <Examples 3-3 and 3-4>

µg/L and 10 The ATHP concentrations were increased to 5 ug/L

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 3-3.

[0085] <Examples 3-5 and 3-6>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 3-4.

[0086]

Sensory evaluation of the above beer-taste beverages

was conducted in the same manner as in the beer-taste beverages listed in Table 1. The evaluation results are are

shown in Table 3.

[0087]

Ex. 3-6 Ex. 3-6

0.08 0.08 120 30 12 10

[Table 3] 5 4 4 A Ex. 3-5 Ex. 3-5

0.04 0.04 Table 3 Evaluation in beer-taste beverages 120 120 12 malt ratio and praline concentration 30 with a low Ref. Ex. Comp. Comp. Comp. 5 5 Comp. 3 4 Ex. 3-4 Ex. 3-4 Ex. 3-2 Ex. 3-3 Ex. 3-4 Ex. 3-5 A Ex. 3-6 Ex. 3-1 Comp. Comp. Ex. 3-3 0.01 0.01 Ex. 3-4 Ex. 3-1 Ex. 3-2 120 120 1.5 1.5 30 12 Malt ratio 100 Ex. 3-4 Ex. 3-4 30 30 30 30 30 5 30 30 130 330 30 0.08 0.08

[%] 120 30 12 10 10 Original wort T a b l e 3 E v a l u a t i o n i n b e e r - t a s t e b e v e r a g e s w i T T t a a h b b l l a e e l 3 3 o w E E v v m a a a l l l u u t a a t t r i i a o o t n n i o i i n n a n b b d e e e e p r r r - - o t t l a a i s s n t t e e e c b b o e e n v v c e e e r r n a a t g g r e e a s s t i w w o i i n t t h h a a l l o o w w m m a a l l t t r r a a t t i i o o a a n n d d p p r r o o l l i i n n e e c c o o n n c c e e n n t t r r a a t t i i o o n n 3 4 A Ex. 3-3 Ex. 3-3 12 12 12 12 12 12 412 extract 12 12 12 12 0.04 0.04 120 30 12

[%] Ex. 3-3 Ex. 3-3 3 5 3 3 A Comp. Comp. Praline 0.01 0.01 120 1.5 120 120 120 120 500 120 30 120 12 120 120 120 120 120 1.5

[mg/L] 2 3 2 27

Ex. 3-2 Ex. 3-2

0.08 0.08 MBT 120 1 1 302 12 2 2 3 3 10 3 5 5 5

[ng/L] 2 4 4 A Ex. 3-1 Ex. 3-1

ATHP 0.04 0.04 120 10 1.5 5 10 5 1.5 30 1.5 12 5 10 1.5 5

[µg/L] 2 5 4 Ex. 3-2 Ex. 3-2 0.08 0.04 0.08 0.01 30.04 A Comp. ATHP/Proline 0.01 Comp. 0.01 0.01 0.04 0.08 0.01 0.01 0.01 120 120 1.5 1.5 30 12 Top aroma 4 4 Ex. 3-1 Ex. 3-1 3 4 4 2 2 3 4 31 23 4 Comp. Comp. (sunlight 0.01 0.01 120 120 1.5 1.5 odor) 30 12

Richness 4 Ref. Ex. Ref. Ex. 1 2 3 4 2 1 3 4 43 14 4 0.01 0.01 100 500 500 Flavor 12 A A A A A A balance 1 Original wort Original wort 1 5 ATHP/Proline ATHP/Proline 4 4A A Top aroma Top aroma Malt ratio

[Table

[Table 3] 3] Malt ratio (sunlight (sunlight Richness Richness balance balance extract extract Proline Proline

[mg/L]

[mg/L] [ng/L]

[ng/L] [µg/L]

[ug/L] Flavor Flavor ATHP ATHP odor) odor) MBT MBT

[%] [%]

[0088]

It is understood from the evaluation results in Table

3 that richness is lacked in beer-taste beverages with a low

malt ratio and proline concentration by comparison between

Reference Example 1 and Comparison Example 3-1. In addition,

it is understood that the higher MBT concentration imparts

richness, but the flavor balance becomes poor due to the top

aroma by comparison between the comparative examples.

[0089]

Furthermore, it is understood from the evaluation results in Table 3 that, by the effect of ATHP, if the ATHP

ug/L or higher, and particularly 10.0 concentration is 5.0 µg/L

ug/L µg/L or higher in beer-taste beverages with a low malt ratio

and proline concentration, the top aroma (sunlight odor) is

suppressed, the richness is enhanced, and the flavor balance

is excellent.

[0090] <Example 4>

In Example 4, the effects of MBT and ATHP in beer-taste

beverages with a low malt ratio and a low original wort

extract concentration were examined.

[0091] <Comparative Example 4-1>

A beer-taste beverage was obtained in the same manner as in Reference Example 1, except that the malt ratio of the

starchy raw material and the original wort extract

concentration concentrationwere wereadjusted to to adjusted 6% 6% and and 7%, 7%, respectively, and and respectively, the specifications were analyzed. The MBT concentration was

1 ng/L, ATHP concentration was 0.4 ug/L, µg/L, and proline concentration was 20 mg/L.

[0092] <Comparative Examples 4-2, 4-3 and 4-4>

The MBT concentrations were increased to 2 ng/l, ng/1, 3 ng/L

and 5 ng/L respectively by adding MBT to the beer-taste

beverage of Comparative Example 4-1.

[0093] <Examples 4-1 and 4-2>

The ATHP concentrations were increased to 5 pg/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 4-2.

[0094] <Examples 4-3 and 4-4>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 4-3.

[0095] <Examples 4-5 and 4-6>

The ATHP concentrations were increased to 5 ug/L µg/L and 10

ug/L µg/L respectively by adding ATHP to the beer-taste beverage

of Comparative Example 4-4.

[0096]

Sensory evaluation of the above beer-taste beverages

shown in Table 4.

[0097]

EExx.. 44--66

0.50

20 10

[Table 4] 6 7 5 4 4 A EExx.. 44--55

0.25 0.25 Table 4 Evaluation in beer-taste beverages with a low malt ratio and 20 a low original wort extract concentration Ref. Ex. Comp. Comp. T a b l e 4 E v Comp. T T a a a l Ex. 4-3b b u l l Ex. 4-4 a Comp. e e t i 4 4 o n E E v v i a a n l l u u b a a e t t e i i r o o - n n t a i i s n n t e b b e e b e e e r r v - - e t t r a a a s s g t t e e e s b b w e e i v v t e e h r r a a a g g e e l s s o w w w i i m t t a h h l t a a r l l a o o t w w i o m m a a a l l n t t d r r a a a t t l i i o o o w a a o n n r d d i g a a i n l l a o o l w w w o o o r r r i i t g g i i e n n x a a t l l r a w w c o o t r r t t c o e e n x x c t t e r r n a a t c c r t t a t c c i o o o n n n c c e e n n t t r r a a t t i i o o n n EExx.. 44--44 6 7 5 5 3 4 Ex. 4-5 A Ex. 4-6 Ex. 4-1 Ex. 4-2 Comp. Comp. Ex. 4-3 Ex. 4-4 0.02 Ex. 4-1 Ex. 4-2 0.4 20 Malt ratio 100 EExx.. 44--44 6 66 76 6 6 5 6 6 16 36 6 0.50

[%] 20 10 Original wort 6 7 3 4 A EExx.. 44--33 7 47 7 extract 12 7 7 7 7 7 7 0.25 0.25 7 . 20

[%] 6 7 3 5 3 3 A EExx.. 44--33 Comp. Comp. Praline 0.02 0.4 20 20 20 20 500 20 20 20 20 20 20 20

[mg/L] 6 7 3 2 2 30

EExx.. 44--22

0.50 0.50 MBT 10 1 1 2 2 2 20 3 3 3 5 5 5

[ng/L] 6 7 2 4 4 A EExx.. 44--11

ATHP 0.25

5 0.4 0.4 5 10 20 0.4 5 10 0.4 5 10

[µg/L] 2 5 4 EExx.. 44--22 6 7 30.25 A 0.50 Comp. ATHP/Proline 0.01 Comp. 0.02 0.02 0.25 0.50 0.02 0.25 0.50 0.02 0.02 0.4 0,4 20 Top aroma 4 EExx.. 44--11 62 7 4 4 2 2 3 4 21 4 Comp. Comp. (sunlight 4 0.02 23 0,02 0.4 odor) 20

Richness 4 RReeff.. EExx.. 1 62 7 3 4 2 1 3 4 43 14 4 0.01 100 500 500 Flavor 12 A A A A A A balance 1 OOrriiggiinnaall wwoorrtt 1 5 AA TT HH PP // PP rr oo ll ii nn ee 4 4A A TToopp aarroommaa Malt ratio

[[TTaabbllee 44]] Malt ratio ((ssuunnlliigghhtt RRiicchhnneessss bbaallaannccee eexxttrraacctt Proline

[mg/L]

[mg/L] [ng/L] [ug/L] Flavor Flavor

[ng/L] ATHP [µg/L] odor) MBT

[%] [%]

2025 31

[0098] 2021355080 03 Jun

[0098]

It It is understood from is understood from the the evaluation evaluation results results in in Table Table

4 4 that richnessis that richness islacked lackedininbeer-taste beer-taste beverages beverages withwith a low a low 2021355080

malt ratio malt ratio and and a a low low original original wort wort extract extract concentration concentration by by

5 5 comparison between Reference comparison between Reference Example Example 11 and andComparison Comparison

Example Example 4-1. Inaddition, 4-1. In addition,it itis isunderstood understoodthat thatthe thehigher higher

MBT concentration MBT concentration imparts imparts richness, richness, but but the the flavor flavor balance balance

becomes poordue becomes poor duetotothe the toptop aroma aroma by comparison by comparison between between the the

comparative examples. comparative examples.

10 10 [0099]

[0099]

Furthermore, Furthermore, it is understood it is understood from from the the evaluation evaluation

results in Table results in Table4 4that, that, by by thethe effect effect of ATHP, of ATHP, if ATHP if the the ATHP

concentration is 5.0 concentration is 5.0 µg/L μg/L or or higher, higher, and and particularly particularly 10.0 10.0

μg/L or higher µg/L or higherin inbeer-taste beer-taste beverages beverages with with a low a low maltmalt ratio ratio

15 15 and a low and a low original originalwort wortextract extract concentration, concentration, the the top top aroma aroma

(sunlight odor) is (sunlight odor) is suppressed, suppressed,the the richness richness is is enhanced, enhanced, and and

the flavor balance the flavor balanceisisexcellent. excellent.

[0100]

In the present In the present specification specification and and claims, claims, the the term term

20 20 ‘comprising’ 'comprising' and its derivatives and its derivatives including including 'comprises' ‘comprises’ and and

‘comprise’ 'comprise' is used to is used to indicate indicate the the presence presenceofofthe thestated stated

integers integers but does not but does not preclude preclude the thepresence presenceof of other other unspecifiedintegers. unspecified integers.

Claims

2021355080 09 Apr 2025

32

CLAIMS CLAIMS 1. 1. A A beer-taste beer-taste beverage beverage containing containing 3-methyl-2-butene-1- 3-methy1-2-butene-1- thiol, and at thiol, and atleast leastone one 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound compound

selected from the thegroup group consisting of 2-acetyl-3,4,5,6- 2021355080

selected from consisting of 2-acetyl-3,4,5,6- tetrahydropyridine tetrahydropyridine andand 2-acetyl-1,4,5,6-tetrahydropyridine 2-acetyl-1 1, 4, 5, 5-tetrahydropyridine

that is its that is its tautomer, tautomer,wherein wherein

the malt ratio the malt ratio is is 50 50 to to100% 100%bybyweight, weight,and and the the original original

wort extractconcentration wort extract concentrationis is 1 to 1 to 10% 10% by weight, by weight,

the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 10 10 to 20% to 20% by weight, by weight, or or

the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 1 to 1 to 10% 10% by weight; by weight;

the beer-tastebeverage the beer-taste beverage contains contains proline; proline;

the ratio of the concentration of the 2- the ratio of the concentration of the 2- acetyltetrahydropyridine compound (μg/L) to the acetyltetrahydropyridine compound (µg/L) to the concentration concentration ofofthe theproline proline (mg/L) (mg/L) is more is more thanthan 0.02;0.02;

the concentrationofofthe the concentration the proline proline is is 400 400 mg/Lmg/L or less; or less;

the concentration of the concentration of the the 3-methyl-2-butene-1-thiol 3-methyl-2-butene-1-thiol is is
2.0 to 55 ng/L; 2.0 to ng/L;and and

the concentration ofofthethe the concentration 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound is 5.0 compound is 5.0toto1010µg/L. μg/L.

2. The 2. The beer-taste beer-taste beverage beverage according according to to claim claim 1, 1, wherein wherein the 3-methyl-2-butene-1-thiol is the 3-methyl-2-butene-1-thiol is derived derived from an added from an added

flavoring. flavoring.
3. Thebeer-taste 3. The beer-taste beverage beverage according according to to claim claim 11 oror2,2,

2021355080 09 Apr 2025

33

wherein the wherein the2-acetyl-3, 2-acetyl-3,4,5,6-tetrahydropyridine is derived 4,5, 6-tetrahydropyridine is derived

from an added from an addedflavoring. flavoring.
4. 4. A A methodfor method forproducing producinga abeer-taste beer-tastebeverage beveragecontaining containing

3-methyl-2-butene-1-thiol, and at least one 2- 2021355080

3-methyl-2-butene-1-thiol, and at least one 2- acetyltetrahydropyridine compound selected acetyltetrahydropyridine compound selected from fromthe thegroup group

consisting of 2-acetyl-3, consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and 2- 4,5, 6-tetrahydropyridine and 2-

acetyl-1,4,5,6-tetrahydropyridine acetyl 1, 4,5, 6-tetrahydropyridinethat that is itstautomer, is its tautomer,

wherein wherein

the malt ratio the malt ratio is is 50 50to to100% 100%bybyweight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 1 to 1 to 10% 10% by weight, by weight,

the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 10 10 to 20% to 20% by weight, by weight, or or

the malt ratio the malt ratioisis1 1toto 50% 50% by by weight, weight, and and the the original original

wort extract wort extractconcentration concentrationis is 1 to 1 to 10% 10% by weight; by weight;

the beer-tastebeverage the beer-taste beverage contains contains proline; proline;

the ratio of the concentration of the 2- the ratio of the concentration of the 2- acetyltetrahydropyridine compound (μg/L) acetyltetrahydropyridine compound (µg/L)toto the the

concentration concentration ofofthe theproline proline (mg/L) (mg/L) is more is more thanthan 0.02;0.02;

the concentrationofofthe the concentration the proline proline is is 400 400 mg/Lmg/L or less; or less;

the method including: the method including:

a step of a step of adjusting adjustingthe the concentration concentration of the of the 3-methyl- 3-methyl-

2-butene-1-thiol 2-butene-1-thiol toto2.0 2.0 to to 5 ng/L, 5 ng/L, and and

a step of a step of adjusting adjusting the theconcentration concentrationofofthethe 2- 2- acetyltetrahydropyridine compound acetyltetrahydropyridine compound to to 5.0 5.0 to µg/L. to 10 10 μg/L.
5. The method for producing a beer-taste beverage 5. The method for producing a beer-taste beverage

2021355080 09 Apr 2025

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according to claim according to claim4,4,which which isis produced produced through through an alcoholic an alcoholic

fermentation processbyby fermentation process yeast. yeast.