AU2021337053B2

AU2021337053B2 - Non-fermented beer-flavor beverage and method for producing same

Info

Publication number: AU2021337053B2
Application number: AU2021337053A
Authority: AU
Inventors: Daiki Honma; Shigekuni Noba
Original assignee: Asahi Breweries Ltd; Asahi Group Holdings Ltd
Current assignee: Asahi Breweries Ltd; Asahi Group Holdings Ltd
Priority date: 2020-09-04
Filing date: 2021-08-19
Publication date: 2025-06-26
Anticipated expiration: 2041-08-19
Also published as: JP2022043839A; JP7529488B2; AU2021337053A1; WO2022050067A1

Abstract

The present invention addresses the problem of providing a nonfermented beer-flavor beverage that has a full body while suppressing sweet aftertaste. The solution to this problem is a nonfermented beer-flavor beverage that includes a sweetener and at least one type of 2-acetyl tetrahydropyridine 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, wherein the degree of sweetness is 3.0-15.0, and the concentration of the 2-acetyl tetrahydropyridine compound is 0.1 μg/l or more.

Description

1

DESCRIPTION DESCRIPTION DESCRIPTION NON-FERMENTED BEER-FLAVOR NON-FERMENTED BEER-FLAVOR BEVERAGE BEVERAGE AND AND METHOD METHOD FOR FOR PRODUCING PRODUCING SAME SAME

Technical Technical Field Field Technical Field

[0001]

The The present invention The present present inventionrelates invention relates to to to relates a non-fermented non-fermented a non-fermented a beer-taste beer-taste beer-taste beverage, and beverage, andparticularly particularly relates relates to atonon-fermented a non-fermented beer-beer-

taste beverage taste beveragewith withanan enhanced enhanced body body feeling. feeling.

BackgroundArt Background Art

[0002]

Non-fermented beer-taste Non-fermented beer-taste beverages beverages are arebeverages beveragesfinished finished

with aa beer-like with beer-like flavor flavorand andtaste tastequality quality by by adding adding beer beer flavor agents and flavor agents and hop hop flavor flavor agents, agents, which which are are composed composed of of

fragrance components and fragrance components and the the like like contained containedininbeer, beer,totoa a

drinking liquid drinking liquid serving serving as as the thebase. base.Non-fermented Non-fermented beer- beer- taste beverages may taste beverages may be bealcoholic alcoholicbeverages beverageshaving having an an alcohol contentofof1%1% alcohol content byby volume volume or or more, more, or they or they maySO- may be be- so- so-

called non-alcoholic ororlow-alcohol called non-alcoholic low-alcohol beverages beverages having having an an

alcohol content alcohol contentofofless less than than 1% 1% or or 0% volume. 0% by by volume.

[0003]

The production The production of of non-fermented non-fermentedbeer-taste beer-tastebeverages beveragesdoes does

not require not require aafermentation fermentationprocess process andand does does not not require require fermentation fermentation equipment. Therefore, non-fermented equipment. Therefore, non-fermented beer- beer- -

taste beverages taste beverages are are suitable suitable for for mass massproduction productionatata alow low

2

cost. However,ititisisstill cost. However, still notnot clear clear what what components components andand in what amounts in what amounts they they should should be be blended blended SO so as so as to to be be able able to to

reproduce reproduce aa beer-like beer-like flavor, flavor,which whichisisinin thethe process process of of research anddevelopment. research and development.

[0004]

Patent Patent Document Document 11 discloses discloses as Example 1 that main as Example 1 that main fragrance fragrance components componentsinin fragrance components beer beer in were were beer analyzed analyzed were and and and analyzed that thatthat 2- 2 - 2- acetyl-1-pyrroline -pyrroline was acetyl-1-pyrroline acetyl- was identified identified as as one of them. one of them. It It It

discloses that, discloses that, when when 2-acetyl-1-pyrroline 2-acetyl-1-pyrrolinewas wasadded added to to a a

beer-like beverage, beer-like beverage, fragrances fragrances of of nuts, nuts, popcorn, popcorn, and and beer- beer-

likeness wereenhanced. likeness were enhanced.

[0005]

Patent Document 22 discloses Patent Document discloses aa flavor flavor improvement improvement agent agent for for

beer-like beverages beer-like beverages containing containing 2-acetyl-2-thiazoline. 2-acetyl-2-thiazoline.It It

discloses in discloses in Example Example 11 that, that, when when 2-acetyl-1-pyrroline 2-acetyl-1-pyrroline was was

added to aa beer-like added to beer-likebeverage, beverage,sourness sourness waswas reduced, reduced, and and grain smell, grain smell, fragrance fragrance of of nuts, nuts, and and beer-likeness beer-likeness were were

enhanced. enhanced.

[0006]

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

first be excerpted first be excerptedand and then then explained. explained.

Page 391, lines Page 391, lines15-13 15-13from from thethe bottom, bottom, Abstract Abstract

"Using GC-MS technology, "Using GC-MS technology, we we have have identified identifiedfor forthe thefirst first

time several compounds having bread-like aroma time several compounds having bread-like aroma

characteristics and very characteristics and very low low flavor flavor thresholds thresholds in in pale pale and and

3

dark dark malts." dark malts. malts.""

[0007]

Page 393, lines Page 393, lines6-17, 6-17,Introduction Introduction

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

[omitted] ···

a compound having a compound havinga ahitherto hitherto unknown unknown roasted, roasted, popcorn-like, popcorn-like,

bread-like aroma bread-like aroma is is produced. produced. AAfragrance fragrancesubstance substancehaving having

bread-like aroma bread-like aroma characteristics characteristics is is of of major major importance importance to to

beer. This beer. Thisfragrance fragrance substance substance is is the the mainmain component component of of aromas in malt, aromas in malt, but butthis thisfragrance fragrance substance substance may may be the be the

cause of aa bad cause of bad aroma aroma in in beer beerstored storedinina ahigh hightemperature temperature

environment anddeteriorated. environment and deteriorated." "

[0008]

Page 401, lines Page 401, lines12-24, 12-24, Characterization Characterization of bread-like of bread-like aromaaroma

components inbeer components in beer

"Bread-like bad aroma "Bread-like bad aroma components components are are particularly particularly detected detected

when beer when beer is is subjected subjected to to aa heat heat load load or orwhen whenbeer beerisis

improperly transported and improperly transported and stored. stored. A particularly A particularly particularly pronounced "off-flavor" pronounced "off-flavor" impression impression is is felt feltininthe thecase caseof of

heat sterilization heat sterilization at at aa too too high high temperature temperature and and for for aatoo too

long action time. long action Fig.1111shows time. Fig. showsa agas gaschromatogram chromatogramofof

"excessively heat-sterilized" beer "excessively heat-sterilized" beerthat thatexhibits exhibits typical typical bread-like bad bread-like bad aromas. It is aromas. It is observed observed that that there there occur occur

several chromatogram segments having sensory several chromatogram segments having sensory characteristics showing almost characteristics showing almost equivalent equivalentretention retentiontimes times

to those for to those for the the characterized characterized proline proline derivatives. derivatives. Using Using

4

preparative GC, preparative GC, capillary-GC-NSD, capillary-GC-NSD, and andcapillary-GC-MS, capillary-GC-MS,we we

were able were able to to characterize characterize them them using using four four kinds kinds ofof2-2-

acetyltetrahydropyridines acetyltetrahydropyridines as as index index components." components. components.""

[0009]

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

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

that exhibits typical that exhibits typicalbread-like bread-likebadbad aromas. aromas. The The

conditions for heat conditions for heat sterilization sterilization defined definedhere hereare are0.5 0.5toto

20 hours at 20 hours at 80°C 80oC (p. (p.393, 393,lines lines 19-18 19-18 from from the the bottom). bottom) .

When heated When heated at at such such high high temperatures temperatures for for aa long long time timelike like

this, beer deteriorates this, beer deterioratesby by heat. heat.

[0010]

Non-Patent Document Non-Patent Document 11 discloses, discloses,ininshort, short, that that (1)(1) when when malt is malt is heated, heated, compounds compoundshaving havingpopcorn-like, popcorn-like,bread-like bread-like

aromas are aromas are produced, produced, that that(2) (2)the theabove above aromas aromas areare "off- "off- flavors", i.e.,abnormal flavors", i.e., abnormal odors, odors, which which are are perceived perceived in beer in beer

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

analysis results of analysis results of the the above above off-flavors off-flavors are are shown shown in in the the

gas chromatogram gas chromatogramofofFig. Fig. 11.11.

[0011]

Although shown Although shown here here asasFig. Fig.1, 1, in in Fig. Fig. 11 Non-Patent 11 of of Non-Patent

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

1,4,5,6-tetrahydropyridine 1, 1,4,5, 5-tetrahydropyridine and 4, ,5,6-tetrahydropyridine and the and the likeare thelike like are shown shown are as as shown asthe the the

results of off-flavor results of off-flavoranalysis. analysis.

[Prior Art Documents]

5 16 Apr 2025 2021337053 16 Apr 2025

[Patent Documents]

[0012]

[Patent Document1]1]WOWO2014/119065

[Patent Document 2014/119065 A1 A1

[Patent Document2]2]JPJP2016-86792 2016-86792 A A 2021337053

[Patent Document

5 5 [Non-Patent Document]

[Non-Patent Document]

[0013]

[Non-Patent Document1]1]

[Non-Patent Document

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

10 10 [0013a]

[0013a]

The referencetotoany The reference anyprior prior artart in in this this specification specification is not, is not,

and should not and should not be be taken taken as as an anacknowledgement acknowledgementororany anyform form

of suggestion that of suggestion that the the prior prior art art forms formspart partofofthe thecommon common

general knowledge. general knowledge.

15 15 [Summary of Invention]

[Summary of Invention]

[0014]

Non-fermented beer-taste beverages Non-fermented beer-taste beverages do donot notfully fullyreproduce reproduce

the types and the types and compositions compositionsofofcomponents components produced produced during during the fermentation process, the fermentation process, and and have have the the problem problem of of having having aa

20 20 weaker body feeling weaker body feeling compared comparedto to fermented fermented beer-taste beer-taste beverages. The beverages. Thebody bodyfeeling feeling means means thethe property property of of giving giving drinkers a drinking drinkers a drinking feeling feeling that that accompanies accompanies a a"thick "thick

feeling" feeling" or a "heavy or a "heavy feeling". feeling". The Thebody bodyfeeling feelingis is a a drinking feeling that drinking feeling that includes includestaste taste qualities qualities alsoalso 25 25 expressed as"richness," expressed as "richness," "depth," "depth," or "thickness". or "thickness".

6 16 Apr 2025 2021337053 16 Apr 2025

[0015]

The The richness richness of of food food and and beverage beverage may may be be generally enhanced generally enhanced by increasing by increasing sweetness. sweetness. Sweeteners, Sweeteners, for for example, example, have have

been conventionally conventionally used used in in the the production production of of non-fermented non-fermented 2021337053

been 5 5 beer-taste beverages, beer-taste beverages, which which impart impart a a certain certain degree degree of of body body

feeling. However, the feeling. However, the drinking drinking feeling feeling such such as as strength strength or or

weakness of the weakness of the body body feeling feeling changes changes depending depending not not only only on on

taste, but also taste, but also on on other other sensory sensory actions actions such such as as smell smell and and

touch. touch.

10 10 [0016]

[0016]

On the other On the other hand, hand, when when aa sweetener sweetener is is used used to to enhance enhance the the

body feeling body feeling of of a anon-fermented non-fermentedbeer-taste beer-taste beverage, beverage, its its sweetness also becomes sweetness also becomes stronger, stronger, and and the the sweetness sweetness remains remains

after drinking, which poses a problem of adversely after drinking, which poses a problem of adversely 15 15 affecting affecting aa sharp sharpfeeling feeling characteristic characteristic of beer. of beer.

[0017]

The present invention The present invention solves solves or or at at least least substantially substantially

ameliorates ameliorates the above problem, the above problem, and and aa desirable desirable outcome outcome

thereof is to thereof is to provide provide a anon-fermented non-fermentedbeer-taste beer-tastebeverage beverage

20 20 with suppressed sweetness with suppressed sweetness that that remains remains after after drinking, drinking,

while having while havinga asufficient sufficient body body feeling. feeling.

[0018]

The present invention The present invention provides providesa anon-fermented non-fermentedbeer-taste beer-taste

beverage comprising beverage comprisingatat least least oneone 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine

25 25 compound selected from compound selected from the thegroup groupconsisting consisting of of 2-acetyl- 2-acetyl-

6a 16 Apr 2025 2021337053 16 Apr 2025

6a

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

tetrahydropyridine that is tetrahydropyridine that is its its tautomer, tautomer,and anda asweetener, sweetener,

and having aadegree and having degreeofofsweetness sweetness of of 3.0 3.0 to 15.0, to 15.0, wherein wherein

the concentration of of the the 2-acetyltetrahydropyridine 2021337053

the concentration 2-acetyltetrahydropyridine

7

compound is0.1 compound is g/Loror 0.1ug/L µg/L more. more.

[0019]

In one embodiment, the concentration of the 2- In one embodiment, the concentration of the 2 2-- acetyltetrahydropyridine compound acetyltetrahydropyridine compound is 200.0 µg/Lg/L is 200.0 ug/L or less. or less.

[0020]

In In one embodiment, the concentration of the 2- one embodiment, In one embodiment, the the concentration concentration of of the the 2- 2-- acetyltetrahydropyridine compound acetyltetrahydropyridine compound is is µg/Lg/L 0.5 0.5 ug/L or more. or more.

[0021]

In one embodiment, In one embodiment, the thenon-fermented non-fermented beer-taste beer-taste beverage beverage

contains nomalt contains no maltasasa araw raw material. material.

[0022]

In one embodiment, In one embodiment,the thenon-fermented non-fermented beer-taste beer-taste beverage beverage has aa degree has degreeofofsweetness sweetness of of 10.0 10.0 or less. or less.

[0023]

In one embodiment, In one embodiment, the the 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine compound compound

is derived from is derived fromananadded added flavor flavor agent. agent.

[0024]

Also, the Also, the present present invention invention provides provides a a method method for for producing producing

a non-fermented a non-fermentedbeer-taste beer-taste beverage, beverage, comprising comprising the step the step of of

adding to aa non-fermented adding to non-fermented beer-taste beer-taste beverage beverage comprising comprising a a

sweetener, and having sweetener, and having aa degree degree of of sweetness sweetness of of 3.0 3.0 to to 15.0 15.0

at least one at least one 2-acetyltetrahydropyridine 2-acetyltetrahydropyridinecompound compoundselected selected

from thegroup from the group consisting consisting of 2-acetyl-3,4,5,6- of 2-acetyl-3,4, - 5, 6- - from the group consisting of 2-acetyl-3,4,5,6- tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine

that is its tautomer in an amount such that its thatisisits 25 that itstautomer tautomerininananamount amountsuch suchthat thatits its

8

concentration concentration isis0.1 0.1ug/L μg/L µg/L or or more. more.

[0025]

Also, the Also, Also, the present the presentinvention present invention provides provides invention a method method a method provides a for enhancing enhancing for enhancing for the body feeling the body feeling and and suppressing suppressingsweetness sweetnessafter afterdrinking drinking

of of aa non-fermented non-fermentedbeer-taste beer-taste beverage, beverage, comprising comprising the step the step

of adding to of adding toa anon-fermented non-fermented beer-taste beer-taste beverage beverage comprising comprising

a sweetener, and a sweetener, and having havinga adegree degree of of sweetness sweetness of 3.0 of 3.0 to to 15.0 at least 15.0 at leastone one 2-acetyltetrahydropyridinecompound 2-acetyltetrahydropyridine compound

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

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

that is its tautomer in an amount such that its that is its tautomer in an amount such that its concentration concentration isis0.1 0.1µg/L μg/L ug/L or or more. more.

[Effect of the

[Effect of the Invention] Invention]

[0026]

According to According to the thepresent presentinvention, invention, there there is provided is provided a a

non-fermented beer-taste non-fermented beer-taste beverage beverage with with suppressed suppressed sweetness sweetness

that that remainsafter that remains remains afterdrinking, after drinking, while while drinking, having having while a sufficient sufficient a sufficient having a body body body

feeling. feeling.

[Brief DescriptionofofDrawings]

[Brief Description Drawings]

[0027]

FIG. 1, which FIG. 1, whichisisFIG. FIG.1111 of of Non-Patent Non-Patent Document Document 1, is1,a is gasa gas

chromatogram of an chromatogram of an "excessively "excessively heat-sterilized" heat-sterilized" beer beer that that

exhibits typical exhibits typicalbread-like bread-like badbad aromas. aromas.

Description ofEmbodiments Description of Embodiments

[0028]

9 9

The sweetener The sweetener contained containedin in thethe non-fermented non-fermented beer-taste beer-taste beverage is beverage is aa seasoning seasoning used used for for the the purpose purpose of ofsweetening sweetening

foods. foods. Sweeteners include natural Sweeteners include naturalsweeteners sweeteners and and

artificial sweeteners. artificial Specific examples sweeteners. Specific examples of of sweeteners sweeteners

include, for example, include, for example, glucose, glucose, fructose, fructose, maltose, maltose, sucrose, sucrose,

oligosaccharides, sugar, honey, oligosaccharides, sugar, honey, maple maplesyrup, syrup,agave agavesyrup, syrup,

palm sugar, palm sugar, molasses, molasses, starch starch syrup, syrup, fructose-glucose fructose-glucose liquid liquid

sugar (i.e., high-fructose sugar (i.e., high-fructosecorn cornsyrup), syrup), stevia, stevia, xylitol, xylitol,

sorbitol, licoriceextract, sorbitol, licorice extract, luoluo hanhan guo guo extract, extract, trehalose, trehalose,

maltitol, palatinose, maltitol, palatinose, thaumatin, thaumatin, glycerin, glycerin,curculin, curculin,

monellin, monatin, monellin, monatin,erythritol, erythritol, hernandulcin, hernandulcin, aspartame, aspartame, neotame, alanine, neotame, alanine, glycine, glycine,advantame, advantame,acesulfame acesulfame K, K, sucralose, saccharin and sucralose, saccharin and the thelike. like.Sucrose, Sucrose, stevia, stevia, and and

acesulfame acesulfame KK are are commonly commonlyused usedininbeverages beverages such such as as non- non- fermented beer-taste beverages fermented beer-taste beverages and and may mayalso alsobebepreferably preferably

used in used in the the present present invention. invention.Glycine Glycine is amino is an an amino acidacid that exhibitssweetness that exhibits sweetnessandand hashas thethe effect effect of enhancing of enhancing the the

quality of sleep quality of sleep and and the the antimicrobial antimicrobial activity, activity, which which may may

also be also be preferably preferablyused. used.

[0029]

Containing aa sweetener Containing sweetener inina non-fermented a non-fermented beer-taste beer-taste beverage enhances beverage enhances the the richness richnessofofthe thenon-fermented non-fermented beer- beer- taste beverage and taste beverage and imparts imparts aa body bodyfeeling. feeling.TheThe sweetener sweetener

is contained is contained in inanan containedin amount anamount amount such such such that the the that that the non-fermented beer-beer- non-fermented non-fermented beer

10

taste beverage taste beverage has has aa degree degreeofofsweetness sweetness of of 3.03.0 to to 15.0. 15.0. When the When the degree degreeofofsweetness sweetness of of the the non-fermented non-fermented beer- beer- taste beverage is taste beverage is less less than than 3.0, 3.0,the thebody bodyfeeling feelingbecomes becomes

insufficient, insufficient, and and when the sweetness when the sweetness exceeds exceeds 15.0, 15.0, the the

sweetness that sweetness that remains remains after after drinking drinking becomes becomes strong. strong. The The

sweetness of the sweetness of the non-fermented non-fermented beer-taste beer-taste beverage beverage isis

preferably 4.0 preferably 4.0toto10.0, 10.0, andand more more preferably preferably 5.08.0. 5.0 to to 8.0.

[0030]

The degree The degree of of sweetness sweetness isisa ameasure measure of of thethe intensity intensity of of

sweetness. Sucroseisisused sweetness. Sucrose usedasasa astandard standardsubstance substanceand and isis determined from determined from the the ratio ratio ofofthe theconcentration concentrationexhibiting exhibiting

equivalent intensity equivalent intensity of of sweetness sweetness to tosucrose sucroseatatany anygiven given

concentration concentration or the ratio or the ratio to to the the threshold threshold value valuefor for

sucrose determined under sucrose determined under the thesame same conditions. conditions. The The

sweetness of aa beverage sweetness of beverageisisdetermined determined as as thethe sum sum of the of the product of product of the the concentration concentration (mg/L) (mg/L) ofofeach eachsweetness sweetness

substance inthe substance in thebeverage beverageandand thethe degree degree of sweetness. of sweetness.

[0031]

In that case, In that case, the the degree degree of of sweetness sweetness of of sucrose sucrose is is set set to to

1, and publicly 1, and publicly known knownvalues values (Kenji (Kenji Maebashi: Maebashi: Basic Basic Knowledge of Knowledge of Sweetness, Sweetness,Journal Journalof of thethe Japanese Japanese Brewers Brewers Association (2011), Association (2011), Vol. Vol. 106, 106, No. No.12, 12,p.p.818-825, 818-825,McMurry McMurry

Organic Chemistry Organic Chemistry (7th (7thEdition), Edition), p. p. 988,988, "Comprehensive "Comprehensive List of List of Sweeteners" Sweeteners" This This and and That ThatofofSugar SugarbybyJapan Japan Sugar Sugar

Refiners' Association, Refiners' Association, and and the thelike) like) maymay be be usedused as the as the

11

degree of sweetness degree of sweetnessofof respective respective sweetness sweetness substances. substances.

Examples of Examples ofthe thedegree degreeof of sweetness sweetness of sweetness of sweetness substances substances

are shown in are shown inTable Table1.1.

[0032]

[Table 1]

[Table 1] Degree Degree of of sweetness sweetnessof of each each sweetness sweetness component component Degree Degree of of Sweetnesssubstance Sweetness substance sweetness sweetness Glycine Glycine 0.9 0.9

Sucrose Sucrose 1 1

Stevioside Stevioside 150 150 Aspartame Aspartame 200 200 Acesulfame K Acesulfame K 200 200 Sucralose Sucralose 600 600 Kenji MAEHASHI: Kenji A Basic MAEHASHI: A Basic Knowledge Knowledge of Sweetness, of Sweetness, Journalofofthe Journal theSociety SocietyofofBrewing Brewing (2011), (2011), Vol.Vol. 106,106, No.p.12, No. 12, p. 818-825 818-825

[0033]

<2-Acetyltetrahydropyridine compound> <2-Acetyltetrahydropyridine compound>

The 2-acetyltetrahydropyridine The 2-acetyltetrahydropyridine compound compoundcontained contained in in the the non-fermentedbeer-taste non-fermented beer-taste beverage, beverage, namely namely 2-acetyl-3,4,5,6- 2-acetyl-3,4,5,6-

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

are fragrance components. are fragrance components. Therefore, Therefore,the thetaste tastequality quality ofof the non-fermented beer-taste the non-fermented beer-taste beverage beverage is is not not significantly significantly

changed by using changed by usingthese. these.

[0034]

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

tetrahydropyridine tetrahydropyridine are are tautomers. Thus, when tautomers. Thus, when 2-acetyl- 2-acetyl- 2-acetyl--

3,4,5,6-tetrahydropyridine 3,4,5,6-tetrahydropyridine 3,4,5, is 6-tetrahydropyridine is addedto is added added toto a non-fermented aa non-fermented non-fermented beer-taste beverage beer-taste beverage containing containing aa sweetener, sweetener,the the non- non-

12

fermented beer-taste beverage fermented beer-taste beverage generally generallycontains contains both both 2 -2- 2- acetyl-3,4,5,6-tetrahydropyridine acetyl - 3,3, 4,5,6-tetrahydropyridine andand 4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6- 2-acetyl-1,4 4, 5, 2-acetyl-1, 6- - 4,5,6-

tetrahydropyridine. Theirpresence tetrahydropyridine. Their presenceratio ratioisisdetermined determined byby the ambientpH the ambient pHenvironment environmentandand thethe like. like.

[0035]

In In the present specification, the above 2- 2 - thepresent In the present specification, specification, the the above above 2- acetyltetrahydropyridine compound is acetyltetrahydropyridine compound is sometimes sometimes referred referred to to

as as "ATHP". AsATHP, "ATHP". As ATHP,those thosewhich whichare arecommercially commerciallyavailable available

may be may be used usedasasa aflavor flavor agent. agent.

[0036]

Containing ATHP Containing ATHP in inthe thenon-fermented non-fermented beer-taste beer-taste beverage beverage suppresses the sweetness suppresses the sweetness that thatremains remainsafter after drinking drinking thethe non-fermented beer-taste beverage, non-fermented beer-taste beverage, SO so that so thata abody bodyfeeling feeling

is enhanced. The is enhanced. Thecontent content of of ATHP ATHP should should be be appropriately appropriately

adjusted considering adjusted considering the the type typeofofnon-fermented non-fermentedbeer-taste beer-taste

beverage of beverage which sweetness of which sweetness is to be is to be suppressed suppressed or or the the

target target sweetnesslevel. target sweetness sweetness level. ATHP level. ATHP maycontained maymay ATHP be bebecontained containedinin in the the non- the - non- non- fermented beer-taste beverage, fermented beer-taste beverage,for forexample, example, by by adding adding a a

flavor agentcontaining flavor agent containing ATHP. ATHP.

[0037]

Generally, ATHP Generally, Generally, ATHP ATHPisis containedin in iscontained contained the thethe in non-fermented non-fermented beer- beer- non-fermented beer taste beverage taste beverage in in an an amount amount such such that that the the concentration concentrationof of

ATHP in ATHP in the thenon-fermented non-fermented beer-taste beer-taste beverage beverage is to is 0.1 0.1200 to 200

µg/L. Whenthe ug/L. When µg/L. theconcentration concentrationofofATHP ATHPininthe the non-fermented non-fermented

beer-taste beverage beer-taste beverage is isless lessthan than 0.10.1 μg/L, ug/L, µg/L, sweetness sweetness is is

13

easily easily perceivedafter easily perceived perceived after after drinking, drinking, and andand drinking, when whenwhen the the the concentration concentration concentration exceeds 200 ug/L, exceeds 200 μg/L, ananATHP-derived µg/L, ATHP-derivedodor odor becomes becomes stronger, stronger, resulting in a resulting in a poor poor overall overall flavor flavor balance. balance. The Theeffect effect ofof suppressing the sweetness suppressing the sweetness after afterdrinking drinkingdoes does notnot change change significantly

significantly even even if the concentration of ATHP is if the concentration of ATHP is increased increased beyond beyond 200 200 μg/L. Also, when ug/L. Also, µg/L. when the the concentration concentrationof of

ATHP increases ATHP increases beyond beyond 1 1 ppm, ppm, a a heated heated bread-like bread-like off-flavor off-flavor

may be may be perceived perceivedasasdescribed described in in Non-Patent Non-Patent Document Document 1. 1. The ATHP The ATHP concentration concentration in in the the non-fermented non-fermented beer-taste beer-taste

beverage is beverage is preferably preferably 0.5 0.5 to to 100 100 ug/L, μg/L, more µg/L, more preferably preferably 1.0 1.0

to 80 ug/L, to 80 μg/L,and µg/L, andstill stillmore more preferably preferably 4 to4 50 to ug/L. 50 μg/L. µg/L.

[0038]

<Non-fermented beer-taste <Non-fermented beer-taste beverage> beverage>

The non-fermented beer-taste The non-fermented beer-taste beverage beverage containing containing ATHP ATHP is is aa

beverage that beverage that is is not not fermented fermentedininthe theproduction production process, process, comprises comprises aa sweetener, sweetener, and and exhibits exhibits a flavor a flavor reminiscent reminiscent of of

beer. Specific beer. Specific examples examples of of the the non-fermented non-fermented beer-taste beer-taste beverage containing beverage containing ATHP ATHPinclude, include, forfor example, example, low-malt low-malt beer, miscellaneous beer, miscellaneous liquors, liquors, liqueurs, liqueurs, and and spirits spirits asas

alcoholic beverages; alcoholic beverages; and and include include low-alcohol low-alcohol beverages beverages and and

carbonated beverageshaving carbonated beverages having an an alcohol alcohol content content of less of less than than

1.0% by volume 1.0% by volume as asnon-alcoholic non-alcoholicbeverages. beverages.In the In the beer- beer- taste low-alcohol beverage taste low-alcohol beverage and andbeer-taste beer-taste carbonated carbonated beverage, richness beverage, richness and and aa body bodyfeeling feelingare aredifficult difficulttoto be be

perceived because perceived perceived becausethere because there is is is there no no no stimulation stimulation caused caused stimulation by alcohol alcohol by alcohol caused by

14

when drinking. when when drinking. Therefore, drinking. Therefore,they Therefore, theyare they are are suitable suitable suitable for for for non- non- non- fermented beer-tastebeverages fermented beer-taste beverages that that contain contain ATHP. ATHP.

[0039]

The non-fermented The non-fermented beer-taste beer-taste beverage beverage is is produced, produced, for for

example, by example, by the the following following method. method. That That is,is, a starchy a starchy rawraw material such as malt is saccharified to obtain a material such as malt is saccharified to obtain a saccharide saccharide solution. Thesaccharide solution. The saccharidesolution solutionis ismixed mixedwith with

auxiliary materials such auxiliary materials such as asa asweetener, sweetener, a flavor a flavor agent, agent, grain extracts, grain extracts, dietary dietary fiber, fiber, a a bittering bittering agent, agent, a a

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

liquid liquid preparation. The order preparation. The order of of adding adding the the respective respective

components to the components to the saccharide saccharide solution solutionisisnot notparticularly particularly

limited. Next,carbon limited. Next, carbondioxide dioxidegas gas is is added added to to thethe liquid liquid preparation. The preparation. The addition addition of of carbon carbon dioxide dioxide gas gas may may be be

conducted conducted by by aa conventional conventional method. method. ForFor example, example, thethe liquid preparation obtained liquid preparation obtained inina aliquid liquid preparation preparation step step and carbonated water and carbonated water may maybebemixed, mixed,oror carbon carbon dioxide dioxide gasgas may be may be added added directly directly to to the the liquid liquid preparation preparation obtained obtained in in

the liquid preparation the liquid preparation step step to to be be dissolved. dissolved.

[0040]

The saccharide The saccharidesolution solutionis is produced produced by adding by adding warm warm waterwater to to

a crushed product a crushed product and the like and the like of of malt malt and and the the like like as as

necessary, and necessary, and starchy starchy raw rawmaterials materialssuch such as as wheat, wheat, rice rice and corn starch and corn starch as asnecessary, necessary,mixing mixingand and heating heating them them to to

saccharify the starchy saccharify the starchymaterials materialspreferably preferably into into maltose maltose

15

and the like and the like mainly mainly using using aa malt malt enzyme. enzyme. ForFor thethe rawraw materials such materials such as as a acrushed crushedproduct productof of malt, malt, starchy starchy raw raw materials such materials such as as wheat, wheat, rice riceand andcorn corn starch, starch, those those usually used usually used in in the the production productionofofconventional conventionalbeer-taste beer-taste

beverages may beverages maybebeused used inin thethe usual usual amounts. amounts.

[0041]

The saccharide The saccharide solution solution of of the thestarchy starchyrawraw materials materials containing containing malt may exhibit malt may exhibit aa grassy, grassy, unpleasant unpleasant odor. odor.

Therefore, it is Therefore, it is preferable preferable that that the the malt malt use use ratio ratio to to the the

total amount of total amount of solid solid starchy starchyraw rawmaterials materialsisispreferably preferably

66% by mass 66% by mass or or less, less, more more preferably preferably50% 50%bybymass massororless, less,

still more preferably still more preferably 25% 25%bybymass mass or or less, less, and and using using no no malt as malt as aa raw raw material material is is particularly particularly preferable. The preferable. The malt use ratio is measured in accordance with the malt use ratio is measured in accordance with the

provisions of the Liquor Tax Law. When preparing a provisions of the Liquor Tax Law. When preparing a saccharide solution from saccharide solution from starchy starchy raw rawmaterials materialsother otherthan than

malt, it malt, it is is preferable preferable to to add add a acomposition composition containing containing

amylase after adding warm water to the starchy raw amylase after adding warm water to the starchy raw materials. materials.

[0042]

Specific examplesofofnon-fermented Specific examples non-fermented beer-like beer-like beverages beverages that that

use no use no malt malt or or have have a amalt maltuse useratio ratio of of less less than than 25%25% by by mass include mass include low-sugar low-sugar beer-taste beer-taste beverages beverages such such as as aalow- low-

sugar low-malt beer. sugar low-malt beer. ForFor example, example, when when producing producing a non- a non- -

fermented low-sugar beer-taste fermented low-sugar beer-taste beverage, beverage, and and the the like, like, the the

16

saccharide solutionisis saccharide solution not not used, used, andand raw raw material material waterwater may may

be used be used instead insteadtotoproduce produce a liquid a liquid preparation. preparation.

[0043]

When ATHP When ATHP is is added added to to aa non-fermented non-fermented beer-taste beer-tastebeverage, beverage,

there is no there is no restriction restriction on on the the timing, timing, and and it it may may be be added added

at at aa suitable suitable step step in in the the method method for forproducing producing a anon- non-

fermented beer-taste beverage. fermented beer-taste beverage. However, However, the the earlier earlier the the adding step, adding step, the the more more rises rises and and falls falls in in the the concentration concentration

of each component of each each componentofof component ofthe the compound compound the group group compound are are are group considered, considered, and and and considered,

therefore, it is therefore, it is preferably preferably added addedatata alater later step. step. ATHPATHP may be may be added, added, for for example, example, totonon-fermented non-fermented beer-taste beer-taste

beverages produced. beverages produced.

[0044]

Non-fermented beer-taste Non-fermented beer-taste beverages beverages containing containingATHP ATHPmay maybe be

those containing ATHP those containing ATHP derived derived from from malt malt and and the the like. like. The The

concentration concentration of this compound of this compound group groupin in commercially commercially available non-fermentedbeer-taste available non-fermented beer-taste beverages beverages containing containing malt is, malt is, for for example, example, 3.0 3.0 to to 4.0 4.0 ug/L. μg/L. OnOn µg/L. the the other other hand, hand, the concentration of the concentration of this this compound compoundgroup groupininnon-fermented non-fermented

beer-taste beverages beer-taste beverages containing containingnonomalt maltis,is, forfor example, example, less than 0.5 less than 0.5ug/L. μg/L. µg/L.

[0045]

The present The present invention invention will will be befurther furtherdescribed describedinindetail detail

by the by the following following examples, examples, but but the the invention invention is is not not limited limited

to these. to these.

17

[Examples]

[0046]

Non-fermented beer-taste Non-fermented beer-taste beverage beverage 11 (Asahi (Asahi Breweries, Breweries,Ltd. Ltd.

"Style Free Perfect" "Style Free Perfect"(trade (tradename), name), name) alcohol ,alcohol alcohol content: content: content: 6%,6%, 6%, degree of degree of sweetness: sweetness: 0, 0, ATHP ATHPconcentration: concentration:0.0 0.0ug/L) μg/L)was µg/L) was

prepared. prepared. The method for for determining determining the thedegree degree of prepared. The Themethod method for determining the degreeofof sweetness andATHP sweetness and ATHPconcentration concentration of of the the non-fermented non-fermented beer-beer-

taste beverage taste beverage1 1isisasas follows. follows.

[0047]

The beer-taste The beer-taste beverage beverage was was diluted diluted 20-fold 20-fold with with distilled distilled

water and water and analyzed analyzed by by LC/MS/MS. LC/MS/MS. Using UsingLC/MS/MS LC/MS/MS(3200 (3200QTRAP QTRAP

manufactured by manufactured by AB-SCIEX AB-SCIEX Pte. Pte. Ltd.), Ltd.), it it was was separated separated using using

as as aa column column ACQUITY ACQUITY UPLC UPLC BEH BEH C18 C18 1.7 m, 2.1 1.7 um, µm, 2.1 X x100 100mmmm

(manufactured (manufactured by by Waters Corporation). Waters Corporation) AsAs Corporation).As for for for moving moving moving phase phase phase conditions, LiquidA:A:0.1% conditions, Liquid 0.1% formic formic acid acid water, water, and Liquid and Liquid B: B:

0.1% acetonitrile formate 0.1% acetonitrile formate were used with were used with the the following following

conditions (B%, t) conditions (B%, t) :: (10%, (10%, 88 min), min), (28%, (28%, 11 11 min), min), (70%, (70%, 18 18

min), and min), and analysis analysis was was conducted conductedunder underthe thecondition condition that that the transitions were the transitions were at at 162 162 82 → (collision 82 (collision energy: energy: -18V) -18V) for for acesulfame for acesulfame K,395 acesulfameK,K, 395 →359 -> 359 395 359 (collision (collision (collision energy: energy: energy: -20 -20 -20(V) (V) forfor (V)for sucralose, sucralose, and sucralose, and 293 and293 →261 293-> 261(collision 261 (collision energy: (collision energy:-16 energy: -16(V) -16 (V)) for ) for (V)) for aspartame. Quantification was conducted using aspartame. Quantification was conducted using aa

calibration curve prepared calibration curve prepared by by adding adding aa standard standard substance, substance,

18

and the degree and the degree of of sweetness sweetnesswas wascalculated calculatedas as thethe sumsum of of the product of the concentration of each sweetness the product of the concentration of each sweetness component (mg/L)and component (mg/L) andthe the value value of of the the publicly publicly knownknown degree degree

of sweetness. of sweetness.

[0048]

To 20 To 20 gg of of the thebeer-taste beer-tastebeverage, µL L beverage,5050 uL of of an an internal internal standard standard solution g/mL solution(4(4ug/mL µg/mL ATHP ATHP stable stable isotope); isotope) ; and and µL L 200 200 UL

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

loaded into OASIS loaded into OASIS MCX MCX 500 500 mg/6 mg/6mLmL(manufactured (manufacturedbybyWaters Waters

Corporation). Corporation) Corporation)..

The column The column was was washed washed with with5 5mLmLofof 1% 1% formic formic acid acid water, water, followed by elution followed by elution with with 55 mL mL of of 2% 2% ammonia-methanol. ammonia-methanol. The The The

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

analyzed byLC/MS/MS. analyzed by LC/MS/MS.

[0049]

Using LC/MS/MS Using LC/MS/MS (5500 (5500QTRAP QTRAP manufactured manufactured by AB-SCIEX by AB-SCIEX Corporation), and Corporation), it was and it was separated separated using usingasasa column a column

ACQUITY UPLC ACQUITY UPLC BEH BEH C18 C18 1.7 m, 2.1 1.7 um, µm, 2.1 Xx 100 100 mm mm (manufactured (manufacturedby by

Waters Corporation) Waters Corporation). . As Corporation). Asfor As for for moving moving moving phase phase phase conditions, conditions, conditions, Liquid A: Liquid A: 10 10 mM mM ammonium ammonium hydrogen hydrogen carbonate, carbonate, and and Liquid Liquid B: B:

acetonitrile were used acetonitrile were used with with the the following following conditions: conditions: (B%, (B%,

t) t) :: t) (10%, (10%,11 : (10%, min), 1min), (50%, min),(50%, 6 6 min), 6 min), (50%, andand min), analysis analysis and was was conducted was conducted analysis conducted by setting by by settingthe setting thetransition the transition transition at at at 126 126126 → 84 -> 84 84 (collision (collision (collision energy: energy: energy:2323 23

V) V) for for ATHP. ATHP. Quantification was Quantificationwas conducted using wasconducted conducted using a a for ATHP. Quantification using a

19

calibration curveprepared calibration curve prepared by by adding adding a standard a standard substance. substance.

[0050]

AcesulfameKK Acesulfame Acesulfame K(manufactured (manufactured (manufactured by by by Kirin Kirin Kyowa Kirin Kyowa Foods Kyowa Foods Co., Co. ,Co., Foods Ltd., Ltd.Ltd., ,

"Sanet", degree of "Sanet", degree of sweetness: sweetness: 200) 200) and andATHP ATHPwere wereadded addedtoto

the non-fermented beer-taste the non-fermented beer-tastebeverage beverage1 to 1 to change change these these contents. Thedegree contents. The degree of of sweetness sweetness of of the the beverage beverage after after addition addition was determined by was determined by adding adding aa value valueobtained obtainedbyby

converting the amount of acesulfame K added to converting the amount of acesulfame K added to concentration (mg/L) and concentration (mg/L) and multiplying multiplying this this concentration concentration by by

200 that was 200 that was the the degree degree of ofsweetness sweetnessofofacesulfame acesulfameK,K,and and

adding this value adding this value to to the thedegree degreeofofsweetness sweetness of of thethe non- non- fermented fermented beer-taste beer-taste beverage beverage 1. TheATHP 1. The ATHPconcentration concentrationof of

the beverage after the beverage after addition additionwas wasdetermined determined by by converting converting the amount of the amount of ATHP ATHP added added totoconcentration concentration(ug/L), (µg/L),and (µg/L), and

adding this adding this concentration concentration to to the the ATHP ATHP concentration concentration of of the the

non-fermented beer-taste non-fermented beer-taste beverage beverage 1. 1.

[0051]

Next, sensory Next, sensory evaluation evaluationofofproduced produced non-fermented non-fermented beer- beer- taste beverages was taste beverages was conducted. conducted. TheThe evaluation evaluation items items were were

the suppression of the suppression of sweetness sweetnessafter afterdrinking drinking andand the the enhancement of a abody enhancement of body feeling. feeling. Three Three professional professional enhancement of a body feeling. Three professional evaluators for evaluators for beers beers tasted tastedeach eachnon-fermented non-fermentedbeer-taste beer-taste

beverage and beverage and scored scored them themaccording accordingto to the the following following evaluation criteria. evaluation criteria. The Theaverage averageofofthe thethree three evaluators' evaluators'

sensory scores was sensory scores was used used as as ananevaluation evaluationscore. score. The The

20

evaluation resultsare evaluation results are shown shown in in Tables Tables 2 and 2 and 3. 3.

[0052]

Evaluation Criteria: Evaluation Criteria: Suppression Suppression ofof sweetness sweetness after after after drinking drinking

Scores Scores

1: Feel no 1: Feel no effect effect(no (nodifference difference from from control) control)

2: Somewhatfeel 2: Somewhat feelananeffect effect

3: Feel an 3: Feel an effect effect

4: 4 Somewhat 4:: Somewhat stronglyfeel Somewhat strongly strongly feel feel anan an effect effect effect

5: Strongly feel 5: Strongly feelananeffect effect

6: Very strongly 6: Very stronglyfeel feelanan effect effect

7: Exceedinglystrongly 7: Exceedingly strongly feel feel an an effect effect

[0053]

[Table 2]

[Table 2] Evaluation results：Suppression Evaluation results of sweetness : Suppression of sweetness after drinking after drinking (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

3 3 1.3 1.3 1.7 1.7 2 2 2 2 2.7 2.7 2.7 2.7 2.7 2.7 2.7 2.7 2.7 3 3 3 3 4 4 1.3 1.3 2 2 2.7 2.7 4 4 4.3 4.3 4.3 4.3 4.3 4.3 5 5 5 5 5 5

Degree of 55 Degree of 1.7 1.7 2 2 2.7 2.7 4 4 6 6 6 6 6 6 6.7 6.7 7 7 7 7 sweetness 77 sweetness 1.7 1.7 2 2 3 3 4 4 6 6 6.3 6.3 6.3 6.3 6.3 6.7 6.7 6.7 6.7 6.7 6.7 6.7

10 10 1.7 1.7 2.3 2.3 3 3 4 4 6.7 6.7 7 7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 6.7

15 15 1.7 1.7 2 2 2 2 2.7 2.7 3 3 3 3 3 3 3 3 3.7 3.7 3.7 3.7

20 20 1 1 1 1 1 1 1 1 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.3 1.3

[0054]

From the evaluation From the evaluation results resultsininTable Table2,2, it it is is understood understood that the sweetness that the sweetness after afterdrinking drinkingisis suppressed suppressed when when thethe

21

ATHP concentration ATHP concentration is is 0.1 0.1ug/L μg/Loror µg/L more, more, particularly particularly 0.5 0.5 μg/L ug/L or more µg/L or more in in samples samples having havinga adegree degreeofofsweetness sweetnessofof 3 3 to 15. to 15.

[0055]

Evaluation criteria: Enhancement Evaluation criteria: Enhancement of body of body feeling feeling

Score Score 1: 1: Very weak Very weak 7: 7: Very strong Very strong

[0056]

[Table 3]

[Table 3] Evaluation results:Enhancement Evaluation results: Enhancement of body of body feeling feeling (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1.3 1.3 1.7 1.7 2 2 2 2 2.3 2.3 3 3 3.7 3.7 3.7 3.7 3.7 4 4 4 4 3 3 1.3 1.3 2 2 3.3 3.3 3.3 4 4 4 4 4.3 4.3 4.7 4.7 4.7 4.7 5.3 5.3 5.3 5 5 4 4 1.7 1.7 2.3 2.3 4 4 5 5 5 5 5 5 5 5 5.7 5.7 5.7 5.7 5.7 5.7 5.7

of 55 Degree of Degree 2 2 3 3 4.3 4.3 5 5 5 5 6 6 7 7 7 7 7 7 7 7 sweetness sweetness 7 7 2 2 3.3 3.3 3.3 5 5 5 5 5.3 5.3 6 6 6 7 7 7 7 7 7 7 7 10 10 3.3 3.3 3.3 4 4 5.3 5.3 5.3 5.3 5.3 5.3 5.7 5.7 5.7 6.3 6.3 7 7 7 7 7 7 7 7 15 15 4 4 4.7 4.7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 20 20 4.7 4.7 5.3 5.3 5.3 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7

[0057]

From the evaluation From the evaluation results resultsininTable Table3,3, it it is is understood understood

that the body feeling is enhanced when the ATHP that the body feeling is enhanced when the ATHP concentration concentration isis0.1 0.1ug/L μg/L µg/L or or more, more, particularly particularly 0.5 μg/L 0.5 ug/L µg/L or or

more in more in samples sampleshaving having a degree a degree of sweetness of sweetness of 3 of to 315. to 15.

[0058]

Non-fermented beer-taste Non-fermented beer-taste beverages beverageswere were produced produced in the in the

22

same manner as same manner as in in Example Example 1, 1, except except that that stevia stevia ("Rebaudio ("Rebaudio

J-100" J-100" manufactured byby J-100" manufactured manufactured by Morita Morita Kagaku Kagaku Morita Kogyo Kogyo Kagaku Co.,Ltd., Co.,Co., Kogyo Ltd., Ltd., , degree of degree of sweetness: sweetness: 360) 360) was was used used in in place place of of acesulfame acesulfame K K

as the sweetener, as the sweetener, the the degree degree of of sweetness sweetness and and the the ATHP ATHP

concentration were determined, concentration were determined, and andsensory sensoryevaluation evaluationwas was

conducted. The conducted. Theresults resultsare areshown shownin in Tables Tables 4 and 4 and 5, 5, respectively. respectively.

[0059]

[Table 4]

[Table 4] Evaluation results:Suppression Evaluation results: Suppression of sweetness of sweetness after after drinking drinking (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 11 1 1

3 3 1.3 1.3 1.7 1.7 2 2 2 2 2.7 2.7 2.7 2.7 2.7 2.7 2.7 2.7 3 3 3 3 4 4 1.3 1.3 2 2 2.7 2.7 4.7 4.7 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5 5 5 5

Degree of 5 of 5 1.7 1.7 2 2 2.7 2.7 4.7 4.7 6 6 6 6 6 6 6.7 6.7 7 7 7 7 Degree sweetness sweetness 7 1.7 1.7 2 3 3 4.7 4.7 6 6.3 6.3 6.3 6.3 7 7 7 7 7 7 7 2 6 10 10 1.7 1.7 2.3 2.3 3 3 4.7 4.7 6.7 6.7 7 7 6.7 6.7 6.7 7 7 7 7 7 7 15 15 1.7 1.7 2 2 2 2 2.7 2.7 3 3 3 3 3 3 3 3 3.7 3.7 3.7 3.7

20 20 1 1 1 1 1 1 1 1 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.3 1.3

[0060]

From the evaluation From the evaluation results resultsininTable Table4,4, it it is is understood understood that the sweetness that the sweetness after afterdrinking drinkingisis suppressed suppressed when when thethe ATHP concentration ATHP concentration is is 0.1 0.1ug/L μg/Loror µg/L more, more, particularly particularly 0.5 0.5 μg/L ug/L or more µg/L or more in in samples samples having having a adegree degreeofofsweetness sweetnessofof 3 3

to 15. to 15.

[0061]

23

[Table 5]

[Table 5] Evaluation results:Enhancement Evaluation results: Enhancement of body of body feeling feeling (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1.3 1.3 1.7 1.7 2 2 2 2 2.3 2.3 2.3 3 3 3.7 3.7 3.7 3.7 3.7 4 4 4.7 4.7

3 3 1.3 1.3 2 2 3.3 3.3 3.7 3.7 3.7 3.7 4 4 4.3 4.3 4.3 4.3 4.7 4.7 5 5 4 4 1.7 1.7 2.3 2.3 4 4 5 5 5 5 5 5 5 5 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7 Degree of Degree of 5 5 2 2 3 3 4.3 4.3 5 5 5 5 6 6 7 7 7 7 7 7 7 7 sweetnes sweetnes s S 7 7 2 2 3.3 3.3 5 5 5 5 5.3 5.3 6 6 7 7 7 7 7 7 7 7 10 10 3.3 3.3 4 4 5.3 5.3 5.3 5.3 5.3 5.7 5.7 5.7 6.3 6.3 7 7 7 7 7 7 7 7 15 15 4 4 4.7 4.7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 20 20 4.7 4.7 5.3 5.3 5.3 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7

[0062]

From the evaluation From the evaluation results resultsininTable Table5,5, it it is is understood understood that the body feeling is enhanced when the ATHP that the body feeling is enhanced when the ATHP

concentration concentration isis0.1 0.1ug/L μg/L µg/L or or more, more, particularly particularly 0.5 μg/L 0.5 ug/L µg/L or or

[0063]

same manner as same manner asininExample Example 1, 1, except except thatthat sucrose sucrose (degree (degree of of

sweetness: sweetness: 1) 1) was was used in place used in place of of acesulfame acesulfame K K as as the the

sweetener, sweetener, the the degree degree of sweetness of sweetness and the and the ATHP ATHP concentration were concentration were determined, determined, and andsensory sensoryevaluation evaluationwas was

conducted. The conducted. Theresults resultsare areshown shownin in Tables Tables 6 and 6 and 7, 7,

respectively. respectively.

[0064]

24

[Table 6]

[Table 6] Evaluationresults: Evaluation results:Suppression Suppression of sweetness of sweetness after drinking after drinking (N=3) (N=3) ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

3 3 1.3 1.3 1.7 1.7 2 2 2 2 2.7 2.7 2.7 2.7 2.7 2.7 2.7 2.7 3 3 3 3 4 4 1.3 1.3 2 2 2.7 2.7 4.3 4.3 4.3 4.3 4.3 4.3 4.3 4.3 5 5 5.3 5.3 5.3 5.3

Degree of Degree of 5 5 1.7 1.7 2 2 2.7 2.7 5 5 6 6 6 6 6 6 6.7 6.7 7 7 7 7 sweetness sweetness 7 1.7 1.7 2 3 3 5.3 5.3 6.3 6.3 6.3 6.3 6.3 6.3 6.7 6.7 6.7 6.7 6.7 6.7 7 2 10 10 1.7 1.7 2.3 2.3 3 3 5.3 5.3 6.7 6.7 7 7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 6.7

15 15 1.7 1.7 2 2 2 2 2.7 2.7 3 3 3 3 3 3 3 3 3.7 3.7 3.7 3.7

20 20 1 1 1 1 1 1 1 1 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.3 1.3

[0065]

From the evaluation From the evaluation results resultsininTable Table6,6, it it is is understood understood that the sweetness that the sweetness after afterdrinking drinkingisis suppressed suppressed when when thethe

[0066]

25

[Table 7]

[Table 7] Evaluation results:Body Evaluation results: Body feeling feeling (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1.3 1.3 1.7 1.7 2 2 2 2 2.3 2.3 3 3 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7

3 3 1.3 1.3 2 2 3.3 3.3 4 4 4 4 4.3 4.3 4.7 4.7 4.7 4.7 5.3 5.3 5.3 5 5 4 4 1.7 1.7 2.3 2.3 4 4 4.7 4.7 4.7 4.7 5 5 5.3 5.3 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7

of 5 Degree of Degree 5 2 2 3 3 4.3 4.3 5 5 5 5 6.3 6.3 7 7 7 7 7 7 7 7 7 sweetness sweetness 7 7 2 2 3.3 3.3 5 5 5 5 5.3 5.3 6.3 6.3 7 7 7 7 7 7 7 7 7 7 10 10 3.3 3.3 4 4 4 5.3 5.3 5.3 5.3 5.7 5.7 5.7 6.3 6.3 7 7 7 7 7 7 7 7 15 15 4 4 4.7 4.7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 20 20 4.7 4.7 5.3 5.3 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7

[0067]

From the evaluation From the evaluation results resultsininTable Table7,7, it it is is understood understood that the body feeling is enhanced when the ATHP that the body feeling is enhanced when the ATHP

[0068]

same manner as same manner as in in Example Example 1, 1, except except that that glycine glycine ("AHS ("AHS

Glycine RC", Glycine RC", degree degree ofofsweetness sweetness0.9 0.9 manufactured manufactured by by AJINOMMOTO HEALTHY AJINOMMOTO HEALTHY SUPPLY SUPPLY CO., CO., ,INC.) wasused INC.was INC.) was usedin used inplace in place place of of of

acesulfame K as acesulfame K as the the sweetener, sweetener, the the degree degree of of sweetness sweetness and and

the ATHP concentration the ATHP concentration were weredetermined, determined, and and sensory sensory

evaluation was evaluation was conducted. conducted. The Theresults resultsare areshown shown inin Tables Tables 8 and 9, 8 and 9, respectively. respectively.

[0069]

26

[Table 8]

[Table 8] Evaluation results:Suppression Evaluation results: Suppression of sweetness of sweetness after after drinking drinking (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1 1 1 1 1 1 1 1 1 1 1 1 11 1 1 1 1 1 1 1

Degree of 55 Degree of 1.7 1.7 2 2 2.7 2.7 5 5 6 6 6 6 6 6 6.7 6.7 7 7 7 7 sweetness 77 sweetness 1.7 1.7 2 3 3 5.3 5.3 6.3 6.3 6.3 6.3 6.3 6.3 6.7 6.7 6.7 6.7 6.7 6.7 6.7 7 2 10 10 1.7 1.7 2.3 2.3 3 3 5.3 5.3 6.7 6.7 6.7 7 7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 6.7

15 15 1.7 1.7 2 2 2 2 2.7 2.7 3 3 3 3 3 3 3 3 3.7 3.7 3.7 3.7

20 20 1 1 1 1 1 1 1 1 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.3 1.3

[0070]

From the evaluation From the evaluation results resultsininTable Table8,8, it it is is understood understood that the sweetness that the sweetness after afterdrinking drinkingisis suppressed suppressed when when thethe

ATHP concentration ATHP concentration is is 0.1 0.1ug/L μg/Loror µg/L more, more, particularly particularly 0.5 0.5 μg/L ug/L or more µg/L or more in in samples samples having having a adegree degreeofofsweetness sweetnessofof 3 3 to 15. to 15.

[0071]

[Table 9]

[Table 9] Evaluation results:Enhancement Evaluation results: Enhancement of body of body feeling feeling (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 2 2 1.3 1.3 1.7 1.7 2 2 2 2 2.3 2.3 2.3 3 3 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7

3 3 1.3 1.3 2 2 3.3 3.3 4 4 4 4 4.3 4.3 4.7 4.7 4.7 4.7 5.3 5.3 5 5 4 4 1.7 1.7 2.3 2.3 4 4 4.7 4.7 4.7 4.7 5 5 5.3 5.3 5.7 5.7 5.7 5.7 5.7 5.7 Degree of 55 Degree of 2 3 3 4.3 4.3 5 5 5 5 6.3 6.3 7 7 7 7 7 7 7 7 2 sweetnes sweetnes s 77 2 2 3.3 3.3 5 5 5 5 5.3 5.3 6.3 6.3 7 7 7 7 7 7 7 7 S 10 10 3.3 3.3 4 4 5.3 5.3 5.3 5.3 5.7 5.7 5.7 6.3 6.3 7 7 7 7 7 7 7 7 15 15 4 4 4.7 4.7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 20 20 4.7 4.7 5.3 5.3 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7

27

[0072]

From the evaluation From the evaluation results resultsininTable Table9,9, it it is is understood understood that the body feeling is enhanced when the ATHP that the body feeling is enhanced when the ATHP concentration concentration isis0.1 0.1ug/L μg/L µg/L or or more, more, particularly particularly 0.5 μg/L 0.5 ug/L µg/L or or

[0073]

Non-fermented beer-taste Non-fermented beer-taste beverage beverage 22 ("Dry ("Dry Zero" Zero" (trade (trade

name) manufactured name) manufactured by by Asahi AsahiBreweries, Breweries,Ltd. Ltd., Ltd., alcohol , alcohol alcohol

content: 0.00%, degree of sweetness: 5.9, ATHP content: 0.00%, degree of sweetness: 5.9, ATHP concentration: 0.0 g/L) concentration: 0.0 ug/L) was µg/L) was prepared. Non-fermentedbeer- prepared. Non-fermented beer-

taste beverages were taste beverages were produced produced in the same in the same manner manner as as in in

Example 1, Example 1, except exceptthat that the the non-fermented non-fermented beer-taste beer-taste beverage 22 was beverage wasused usedinin place place of of the the non-fermented non-fermented beer- beer-

taste taste beverage beverage 1. The degree 1. The degree of of sweetness sweetness and and the the ATHP ATHP

conducted. The results conducted. The results are are shown shown in inTables Tables 1010and and11, 11,

respectively. respectively.

[0074]

[Table 10]

[Table 10] Evaluation results:Suppression Evaluation results: Suppression of sweetness of sweetness after after drinking drinking (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[ug/L]

[µg/L]

0.1 0.1 0.5 0.5 1 1 2 2 5 5 10 10 20 20 50 50 100 100 200 200 7 7 1.7 1.7 2 2 3 3 4.7 4.7 6 6 6.3 6.3 6.3 6.3 6.7 6.7 6.7 6.7 6.7 6.7 6.7

Degree of 10 Degree of 10 1.7 1.7 2.3 2.3 3 3 4.7 4.7 6.7 6.7 7 7 7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 6.7 sweetness 15 sweetness 15 1.7 1.7 2 2 3 3 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7 3.7 4 4 4 4 20 20 1 1 1 1 1 1 1 1 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.7 1.3 1.3

2021337053 16 Apr 2025

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[0075]

From the evaluation From the evaluation results results in in Table Table10, 10,ititisisunderstood understood

that the sweetness that the sweetness after afterdrinking drinkingisissuppressed suppressed when when thethe ATHP concentration concentration is is 0.1 0.1µg/L μg/Loror more, particularly 0.5 0.5 2021337053

ATHP more, particularly 5 5 μg/L or more µg/L or more in in samples samples having having a adegree degreeofofsweetness sweetnessofof7 7

to 15. to 15.

[0076]

[Table 11]

[Table 11] Evaluation results:Enhancement Evaluation results: Enhancement of body of body feeling feeling (N=3) (N=3)

ATHPConcentration ATHP Concentration [μg/L]

[µg/L]

0.1 0.1 0.5 0.5 11 2 2 5 5 10 10 20 20 50 50 100 100 200 200 7 7 1.3 1.3 1.7 1.7 2 2 2 2 2.3 2.3 3 3 3.7 3.7 4.3 4.3 5 5 5.7 5.7

Degree of 10 Degree of 10 1.7 1.7 2.3 2.3 4 4 4.7 4.7 4.7 4.7 5 5 5.3 5.3 6 6 6.7 6.7 7 7 sweetness sweetness 15 15 4 4.7 4.7 5.7 5.7 6 6 6.7 6.7 7 7 7 7 7 7 7 7 7 7 4 20 20 4.7 4.7 5.3 5.3 6.7 6.7 7 7 7 7 7 7 7 7 7 7 7 7 7 7

[0077]

10 10 From the evaluation From the evaluation results results in in Table Table11, 11,ititisisunderstood understood

that the body feeling is enhanced when the ATHP that the body feeling is enhanced when the ATHP concentration concentration isis0.1 0.1µg/L μg/L or or more, more, particularly particularly 0.5 μg/L 0.5 µg/L or or

more in more in samples sampleshaving having a degree a degree of of sweetness sweetness of 7 of to 715. to 15.

[0078]

15 15 InInthethe present specification and claims, the term present specification and claims, the term ‘comprising’ 'comprising' and its derivatives and its derivatives including including 'comprises' ‘comprises’ and and

‘comprise’, 'comprise', is is used to indicate used to indicate the the presence presence of of the the stated stated

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

Claims

2021337053 16 Apr 2025

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CLAIMS CLAIMS 1. 1. A Anon-fermented non-fermentedbeer-taste beer-tastebeverage beveragecomprising comprisingat at

least one 2-acetyltetrahydropyridine least one 2-acetyltetrahydropyridine compound compound selected selected from from

the group consisting consistingofof 2-acetyl-3,4,5,6-tetrahydropyridine 2021337053

the group 2-acetyl-3, 4,5, -tetrahydropyridine

5 5 andand 2-acetyl-1,4,5,6-tetrahydropyridine 2-acetyl- that isisits its 1, 4, 5, -tetrahydropyridine that tautomer, anda asweetener, tautomer, and sweetener,andand having having a degree a degree of sweetness of sweetness

of 3.0 to of 3.0 to 15.0, 15.0,

wherein wherein

the concentration of of the concentration the the 2-acetyltetrahydropyridine 2-acetyltetrahydropyridine 10 compound 10 compound is is 0.10.1 g/L µg/L or or more. more.
2. The non-fermented beer-taste beverage according to 2. The non-fermented beer-taste beverage according to claim 1, wherein the concentration of the 2- claim 1, wherein the concentration of the 2- acetyltetrahydropyridine compound acetyltetrahydropyridine compound is is µg/Lg/L 200.0 200.0 or less. or less.
3. Thenon-fermented 3. The non-fermentedbeer-taste beer-taste beverage beverage according according toto

15 claim 1 or 2, wherein the concentration of the 2- 15 claim 1 or 2, wherein the concentration of the 2- acetyltetrahydropyridine compound acetyltetrahydropyridine compound is is µg/Lg/L 0.5 0.5 or more. or more.
4. The 4. The non-fermented non-fermented beer-taste beer-taste beverage beverage according according toto any any one of claims one of claims1 1toto3,3,containing containing no no maltmalt as aas a material. raw raw material.
5. The 5. The non-fermented non-fermented beer-taste beer-taste beverage beverage according according toto any any 20 20 oneone of of claims claims 1 4, 1 to to having 4, having a degree a degree of sweetness of sweetness of 10.0 of 10.0 or less. or less.
6. The 6. The non-fermented non-fermented beer-taste beer-taste beverage beverage according according toto any any one of claims 1 to 5, wherein the 2- one of claims 1 to 5, wherein the 2- acetyltetrahydropyridine compound is acetyltetrahydropyridine compound is derived derived from from an an added added

25 flavor 25 flavor agent. agent.

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7. 7. A Amethod methodforfor producing producing a non-fermented a non-fermented beer-taste beer-taste beverage, comprising beverage, comprising the the step step of of adding adding to to aa non-fermented non-fermented

beer-taste beverage beer-taste beverage comprising comprising a asweetener, sweetener,andand having having a a degree degree of sweetness of 3.0 to 15.0 at least one 2- 2021337053

of sweetness of 3.0 to 15.0 at least one 2- 5 5 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 isisitsits acetyl 1, 4, 5, 6-tetrahydropyridine that tautomer tautomer in in

an amount such an amount suchthat thatits its concentration concentration is 0.1 is 0.1 µg/Lμg/L or more. or more.
8. A method for enhancing the body feeling and 8. A method for enhancing the body feeling and 10 suppressing 10 suppressing sweetness sweetness that that remains remains after after drinking drinking of of a non- a non- fermented beer-taste beverage, comprising the step of fermented beer-taste beverage, comprising the step of adding to aa non-fermented adding to non-fermented beer-taste beer-taste beverage beverage comprising comprising aa

sweetener, sweetener, and having aa degree and having degree of of sweetness sweetness of of 3.0 3.0 to to 15.0 15.0

at least one at least one 2-acetyltetrahydropyridine 2-acetyltetrahydropyridinecompound compoundselected selected

15 from the group consisting of 2-acetyl-3,4,5,6- 15 from the group consisting of 2-acetyl-3,4,5,6- tetrahydropyridine tetrahydropyridine andand 2-acetyl-1,4,5,6-tetrahydropyridine 2-acetyl-1, 4,5, 5-tetrahydropyridine

that is its tautomer in an amount such that its that is its tautomer in an amount such that its concentration concentration isis0.1 0.1µg/L μg/L or or more. more.
9. 9. AA non-fermented non-fermented beer-taste beer-taste beverage beverageproduced producedaccording according

20 20 to to the the methodofofclaim method claim 7. 7.