Beer-taste alcoholic beverage and production method therefor

Abstract

The purpose of the present invention is to provide a beer-taste alcoholic beverage having a rich flavor, a favorable aftertaste, and a favorable amount of flavor. The present invention provides: a beer-taste alcoholic beverage in which the total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) is 280-1,400 ppb; and a beer-taste alcoholic beverage in which the total concentration of free CML, free CEL, and free MG-H1 is 280-1,600 ppb, the total concentration of bound CML, bound CEL, and bound MG-H1 is 150-900 ppb, and the bound CML, the bound CEL, and the bound MG-H1 are included in a peptide fraction having a molecular weight of 1,060-3,080 Da (gel filtration method for HPLC analysis).

Description

Beer-flavored alcoholic beverage and its manufacturing method REFERENCE TO RELATED APPLICATIONS

[0001] This application benefits from the priority of an earlier Japanese application, Patent Application No. 2024-95489 (filing date: June 12, 2024), the entire disclosure of which is incorporated herein by reference.

[0002] The present invention relates to a beer-taste alcoholic beverage and a method for producing the same.

[0003] Beers are required to have a moderate richness. Techniques for achieving this effect include the addition of alcohols, aldehydes, various sweeteners, etc. (Patent Document 1). However, all of these techniques inevitably affect the balance of flavors other than the richness, and many problems remain.

[0004] It has also been reported that peptides with molecular weights of 1,000 to 5,000 Da, which are products obtained by the Maillard reaction, contribute to enhancing richness (Non-Patent Document 1), but the specific contributing components have not been identified.

[0005] JP 2016-214262 A

[0006] Food Chemistry, 99, 600-604

[0007] The present invention aims to provide a beer-taste alcoholic beverage that has a strong body, a clean finish, and a good degree of intonation.

[0008] The present inventors have found that by including free Maillard reaction products (F-MRPs) in a beer-taste alcoholic beverage within a predetermined concentration range, or by including free Maillard reaction products (F-MRPs) and bound Maillard reaction products (B-MRPs) in a beer-taste alcoholic beverage within a predetermined concentration range, the beer-taste alcoholic beverage can have a good full-bodied flavor, clean aftertaste, and intonation. The present invention is based on these findings.

[0009] The present invention provides the following: [1] A beer-flavored alcoholic beverage having a total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) of 280 ppb or more and 1,400 ppb or less. [2] A beer-flavored alcoholic beverage having a total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) of 280 ppb or more and 1,600 ppb or less, a total concentration of bound CML, bound CEL, and bound MG-H1 of 150 ppb or more and 1,400 ppb or less, and wherein bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction having a molecular weight of 1,060 Da to 3,080 Da (gel filtration method for HPLC analysis). [3] The beer-taste alcoholic beverage according to [2] above, wherein the total concentration of free CML, free CEL, and free MG-H1 is from 280 ppb to 1,500 ppb. [4] The beer-taste alcoholic beverage according to [2] or [3] above, wherein the total concentration of bound CML, bound CEL, and bound MG-H1 is from 200 ppb to 850 ppb. [5] The beer-taste alcoholic beverage according to any of [1] to [4] above, wherein the malt usage ratio is 50% or more. [6] A method for producing a beer-taste alcoholic beverage, comprising a step of incorporating free CML, free CEL, and free MG-H1 so that the total concentration is from 280 ppb to 1,400 ppb. [7] A method for producing a beer-flavored alcoholic beverage, comprising the steps of: adding free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1600 ppb or less; and adding bound CML, bound CEL, and bound MG-H1 so that the total concentration is 150 ppb or more and 1400 ppb or less, wherein the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction having a molecular weight of 1060 Da to 3080 Da (gel filtration method for HPLC analysis).[8] A method for improving the flavor of a beer-taste alcoholic beverage, comprising the steps of: adding free CML, free CEL, and free MG-H1 to the beverage so that the total concentration is 280 ppb to 1400 ppb; and adding bound CML, bound CEL, and bound MG-H1 to the beverage so that the total concentration is 150 ppb to 1400 ppb; and wherein the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction with a molecular weight of 1060 Da to 3080 Da (gel filtration for HPLC analysis).

[0010] According to the present invention, by incorporating free Maillard reaction products (F-MRPs) within a predetermined concentration range in a beer-taste alcoholic beverage, or by incorporating free Maillard reaction products (F-MRPs) and bound Maillard reaction products (B-MRPs) within a predetermined concentration range, it is possible to provide the beer-taste alcoholic beverage with a strong body, a clean finish, and a good degree of intonation, which is advantageous in that it can meet the diverse tastes and needs of consumers.

[0011] FIG. 1 shows a calibration curve prepared from the retention times of gel filtration for HPLC analysis and the molecular weights of known substances, which was carried out in the example (Example 1). Specific Description of the Invention

[0012] In the present invention, the term "beer-taste alcoholic beverage" refers to a beverage having a beer-like flavor and fermented with yeast using ingredients such as a carbon source, a nitrogen source, and water, and includes beer and happoshu (including those containing distilled alcohol as ingredients and those containing no malt or hops). Preferred embodiments of beer-taste alcoholic beverages include beer-taste fermented alcoholic beverages that use malt and / or ungerminated barley and wheat as at least a portion of the ingredients, and more preferably beer-taste alcoholic beverages that use malt as at least a portion of the ingredients. In addition, in the present invention, beer can mean a product obtained by fermenting malt, hops, and water, or a product obtained by fermenting malt, hops, and water with the addition of certain auxiliary ingredients, and which meets the following two conditions (limited to products with an alcohol content of less than 20%:) - The malt ratio is 50 / 100 or more - The weight of the used fruit (including dried, boiled, or concentrated fruit juice) and certain flavorings does not exceed 5 / 100 of the weight of the malt (including products that do not use any flavorings) (see the Liquor Tax Act (Act No. 6 of 1953), which came into effect on October 1, 2024).

[0013] The beer-taste alcoholic beverage of the present invention can contain malt and / or ungerminated barley or wheat as at least a portion of its ingredients, and preferably uses at least malt (e.g., wheat malt, barley malt) as the barley-derived ingredient, and can also use malt extract. When the beer-taste alcoholic beverage of the present invention uses malt as at least a portion of an ingredient, the malt usage ratio may be, for example, 10% or less, 10% or more, 15% or less, 15% or more, 20% or less, 20% or more, 25% or less, 25% or more, 30% or less, 30% or more, 40% or less, 40% or more, 50% or less, 50% or more, 55% or less, 55% or more, 60% or less, 60% or more, 65% or less, 65% or more, 70% or less, 70% or more, 75% or less, 75% or more, 80% or less, 80% or more, 85% or less, 85% or more, 90% or less, 90% or more, 95% or more, 95% or more, 100% or less, or 100% or less, and "or less" may be interpreted as "less than," and "or greater than or equal to" may be interpreted as "greater than." These upper and lower limits may be combined as desired. In the present invention, the "ratio of malt used" refers to the ratio of the mass of malt to the mass of all raw materials excluding hops and brewing water.

[0014] The alcohol concentration of the beer of the present invention can be set arbitrarily. %、1. / v%、2.5v / v%、2.6v / v%、2.7v / v%、2.8v / v%、2.9v / v%、3.0v / v%、3.1v / v%、3.16 / v% v / v%、3.3v / v%、3.4v / v%、3.5v / v%、3.5v / v%、3.7v / v%、3.9v / v%、2.9v / v%2.2.6 / v%2. %、19、7v / v%、19.66 / v%、19.5v / v%、19.1v / v%、19.36 / v%、19.2 / / v% v%、19.0v / v%、18.9v / v%、18.8v / v%、1.77v / v%、18.6 / v%、18.5 / / v%、1..5 / v% v%, 18.3v / v%, 18.2v / v%, 18.1v / v%, 18.0v / v%, 17.9v / v%, 17.8v / v%, 17.7v / v%, 17.6v / v%, 17.5v / v%, 17.4v / v%, 17.3v / v%, 17.2v / v%, 17.1v / v%, 17.0 v / v%, 16.9v / v%, 16.8v / v%, 16.7v / v%, 16.6v / v%, 16.5v / v%, 16.4v / v%, 16.3v / v%, 16.2v / v%, 16.1v / v%, 16.0v / v%, 15.9v / v%, 15.8v / v%, 15.7v / v%, 15. 6v / v%, 15.5v / v%, 15.4v / v%, 15.3v / v%, 15.2v / v%, 15.1v / v%, 15.0v / v%, 14.9v / v%, 14.8v / v%, 14.7v / v%, 14.6v / v%, 14.5v / v%, 14.4v / v%, 14.3v / v%, 1 4.2v / v%, 14.1v / v%, 14.0v / v%, 13.9v / v%, 13.8v / v%, 13.7v / v%, 13.6v / v%, 13.5v / v%, 13.4v / v%, 13.3v / v%, 13.2v / v%, 13.1v / v%, 13.0v / v%, 12.9v / v%,12.8v / v%, 12.7v / v%, 12.6v / v%, 12.5v / v%, 12.4v / v%, 12.3v / v%, 12.2v / v%, 12.1v / v%, 12 .0v / v%, 11.9v / v%, 11.8v / v%, 11.7v / v%, 11.6v / v%, 11.5v / v%, 11.4v / v%, 11.3v / v%, 11.2 v / v%, 11.1v / v%, 11.0v / v%, 10.9v / v%, 10.8v / v%, 10.7v / v%, 10.6v / v%, 10.5v / v%, 10.4v / v%, 10.3v / v%, 10.2v / v%, 10.1v / v%, 10.0v / v%, 9.9v / v%, 9.8v / v%, 9.7v / v%, 9.6v / v%, 9.5 v / v%, 9.4v / v%, 9.3v / v%, 9.2v / v%, 9.1v / v%, 9.0v / v%, 8.9v / v%, 8.8v / v%, 8.7v / v%, 8.6v / v%, 8.5v / v%, 8.4v / v%, 8.3v / v%, 8.2v / v%, 8.1v / v%, 8.0v / v%, 7.9v / v%, 7.8v / v%, 7.7v / v% , 7.6v / v%, 7.5v / v%, 7.4v / v%, 7.3v / v%, 7.2v / v%, 7.1v / v%, 7.0v / v%, 6.9v / v%, 6.8v / v%, 6 .7v / v%, 6.6v / v%, 6.5v / v%, 6.4v / v%, 6.3v / v%, 6.1v / v% or 6.0v / v%. These lower and upper limits can be combined in any desired manner, and the alcohol concentration of the beer-taste alcoholic beverage of the present invention can be, for example, 1.0 to 20.0 v / v%, 1.0 to 19.0 v / v%, 1.0 to 18.0 v / v%, 1.0 to 17.0 v / v%, 1.0 to 16.0 v / v%, 1.0 to 15.0 v / v%, 1.0 to 14.0 v / v%, 1.0 to 13.0 v / v%, 1.0 to 12.0 v / v%, 1.0 to 1 ... 10.0 v / v%, 1.0 to 9.0 v / v%, 1.0 to 8.0 v / v%, 1.0 to 7.0 v / v%, 1.0 to 6.0 v / v%, 2.0 to 20.0 v / v%, 2.0 to 19.0 v / v%, 2.0 to 18.0 v / v%, 2.0 to 17.0 v / v%, 2.0 to 16.0 v / v%, 2.0 to 15.0 v / v%, 2.0 to 14.0 v / v%, 2.0 to 13.0 v / v%, 2.0 to 12.0 v / v%, 2.0 to 11.0 v / v%, 2.0 to 10.0 v / v%,2.0-9.0v / v%, 2.0-8.0v / v%, 2.0-7.0v / v%, 2.0-6.0v / v%, 3.0-20.0v / v%, 3 .0-19.0v / v%, 3.0-18.0v / v%, 3.0-16.0v / v%, 3.0-15.0v / v% , 3.0-14.0v / v%, 3.0-13.0v / v%, 3.0-12.0v / v%, 3.0-11.0v / v%, 3.0-10.0v / v%, 3.0-9.0v / v%, 3.0-8.0v / v%, 3.0-7.0v / v% or 3.0-6.0v / v%. ,

[0015] The alcohol concentration (ethanol concentration) in a beverage can be measured, for example, by the method described in the "National Tax Agency Prescribed Analysis Method."

[0016] The beer-taste alcoholic beverage of the present invention has the following chemical structure: The composition is characterized by containing at least carboxymethyllysine (CML), carboxyethyllysine (CEL), and methylglyoxal-derived hydroimidazolone-1 (MG-H1), which have the following chemical structure: In the present invention, the above-mentioned chemical structures themselves or those present in a partially ionized state are referred to as free CML, free CEL, and free MG-H1 (in this specification, free CML, free CEL, and free MG-H1 may be referred to as "free Maillard reaction products (F-MRPs)").

[0017] In the present invention, peptides having the above chemical structures in which the side chains of lysine and / or arginine are glycosylated residues and are present in the peptide fraction, i.e., peptides having the above chemical structures in which the side chains of lysine and / or arginine are glycosylated residues and constitute part of their structure, are referred to as bound CML, bound CEL, and bound MG-H1 (herein, bound CML, bound CEL, and bound MG-H1 may be referred to as "bound Maillard reaction products (B-MRPs)"). Bound CML, bound CEL, and bound MG-H1 are contained in peptide fractions having a molecular weight of 1,060 Da to 3,080 Da (gel filtration method for HPLC analysis) in the beer-taste alcoholic beverage of the present invention.

[0018] According to the present invention, there is provided a beer-taste alcoholic beverage having a total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) of 280 ppb or more and 1400 ppb or less. In this case, the lower limit of the total concentration of free CML, free CEL, and free MG-H1 (above or below the lower limit) is 280 ppb, but it can be any of the following: 285 ppb, 290 ppb, 295 ppb, 300 ppb, 305 ppb, 310 ppb, 315 ppb, 320 ppb, 325 ppb, 330 ppb, 335 ppb, 340 ppb, 345 ppb, 350 ppb, 355 ppb, 360 ppb, 365 ppb, 370 ppb, 375 ppb, 380 ppb, 385 ppb, 390 ppb, 400 ppb, 405 ppb, 410 ppb, 415 ppb, 420 ppb, 425 ppb, 430 ppb, 435 ppb, 440 ppb, 445 ppb, 450 ppb, 455 ppb, 460 ppb, 465 ppb, 470 ppb, 475 ppb, 480 ppb, 485 ppb, 490 ppb, 500 ppb, 510 ppb, 515 ppb, 520 ppb, 525 It can also be 75 ppb, 380 ppb, 385 ppb, 390 ppb, 395 ppb, 400 ppb, 405 ppb, 410 ppb, 415 ppb, 420 ppb, 425 ppb, 430 ppb, 435 ppb, 440 ppb, 445 ppb, 450 ppb, 455 ppb, 460 ppb, 465 ppb, 470 ppb, 475 ppb, 480 ppb, 485 ppb, 490 ppb, 495 ppb or 500 ppb. The upper limit (less than or equal to) is 1400 ppb, but may be any of the following: 1390 ppb, 1380 ppb, 1370 ppb, 1360 ppb, 1350 ppb, 1340 ppb, 1330 ppb, 1320 ppb, 1310 ppb, 1300 ppb, 1290 ppb, 1280 ppb, 1270 ppb, 1260 ppb, 1250 ppb, 1240 ppb, 1230 ppb, 1220 ppb, 1210 ppb, 1200 ppb, 1190 ppb, 1180 ppb, 1170 ppb, 1160 ppb, 1150 ppb, 1140 ppb, 1130 ppb, 1120ppb, 1110ppb, 1100ppb, 1090ppb, 1080ppb, 1070ppb, 1060ppb, 1050ppb, 1040ppb, 1030ppb, 1020ppb, 1010ppb, 1000ppb, 990ppb, 980pp b, 970ppb, 960ppb, 950ppb, 940ppb, 930ppb, 920ppb, 910ppb, 900ppb, 89 0ppb, 880ppb, 870ppb, 860ppb, 850ppb, 840ppb, 830ppb, 820ppb, 810ppb,The total concentration of free CML, free CEL, and free MG-H1 in the beer-taste alcoholic beverage of the present invention may be, for example, 800 ppb, 790 ppb, 780 ppb, 770 ppb, 760 ppb, 750 ppb, 740 ppb, 730 ppb, 720 ppb, 710 ppb, or 700 ppb. These lower and upper limits can be combined in any desired manner, and the total concentration of free CML, free CEL, and free MG-H1 in the beer-taste alcoholic beverage of the present invention may be, for example, 280 ppb or more and 1400 ppb or less, 290 ppb or more and 1400 ppb or less, 300 ppb or more and 1400 ppb or less, 310 ppb or more and 1400 ppb or less, 320 ppb or more and 1400 ppb or less, 330 ppb or more and 1400 ppb or less, 340 ppb or more and 1400 ppb or less, 350 ppb or more and 1400 ppb or less. 0 ppb or less, 360 ppb to 1400 ppb, 370 ppb to 1400 ppb, 380 ppb to 1400 ppb, 390 ppb to 1400 ppb, 400 ppb to 1400 ppb, 410 ppb to 1400 ppb, 420 ppb to 1400 ppb, 430 ppb to 1400 ppb, 440 ppb to 1400 ppb, 450 ppb to 1400 ppb, 460 ppb to 1400 ppb, 470 ppb to 1400 ppb, 4 80ppb to 1400ppb, 490ppb to 1400ppb, 500ppb to 1400ppb, 280ppb to 1300ppb, 290ppb to 1300ppb, 300ppb to 1300ppb, 310ppb b - 1300ppb or more, 320ppb or more and 1300ppb or less, 330ppb or more and 1300ppb or less, 340ppb or more and 1300ppb or less, 350ppb or more and 1300ppb or less, 360ppb or more and 1300ppb or less, 370ppb or more1 300 ppb or less, 380 ppb to 1300 ppb or less, 390 ppb to 1300 ppb or less, 400 ppb to 1300 ppb or less, 410 ppb to 1300 ppb or less, 420 ppb to 1300 ppb or less, 430 ppb to 1300 ppb or less, 440 ppb to 1300 ppb or less, 450 ppb to 1300 ppb or less, 460 ppb to 1300 ppb or less, 470 ppb to 1300 ppb or less, 480 ppb to 1300 ppb or less, 490 ppb to 1300 ppb or less,500 ppb to 1300 ppb, 280 ppb to 1200 ppb, 290 ppb to 1200 ppb, 300 ppb to 1200 ppb, 310 ppb to 1200 ppb, 320 ppb to 1200 ppb, 330 ppb to 1200 ppb, 340 ppb to 1200 ppb, 350 ppb to 1200 ppb, 360 ppb to 1200 ppb, 370 ppb to 1200 ppb, 380 ppb to 1200 ppb, 390 ppb to 1200 ppb, 400 ppb to 1200 ppb Below 1 ppb, 410 ppb to 1200 ppb, 420 ppb to 1200 ppb, 430 ppb to 1200 ppb, 440 ppb to 1200 ppb, 450 ppb to 1200 ppb, 460 ppb to 1200 ppb, 470 ppb to 1200 ppb, 480 ppb to 1200 ppb, 490 ppb to 1200 ppb, 500 ppb to 1200 ppb, 280 ppb to 1100 ppb, 290 ppb to 1100 ppb, 300 ppb to 1100 ppb, 310 ppb to 1200 ppb Below 100 ppb, 320 ppb to 1100 ppb, 330 ppb to 1100 ppb, 340 ppb to 1100 ppb, 350 ppb to 1100 ppb, 360 ppb to 1100 ppb, 370 ppb to 1100 ppb, 380 ppb to 1100 ppb, 390 ppb to 1100 ppb, 400 ppb to 1100 ppb, 410 ppb to 1100 ppb, 420 ppb to 1100 ppb, 430 ppb to 1100 ppb, 440 ppb to 1100 ppb, 450 ppb ppb above 1100 ppb, 460 ppb above 1100 ppb, 470 ppb above 1100 ppb, 480 ppb above 1100 ppb, 490 ppb above 1100 ppb, 500 ppb above 1100 ppb, 280 ppb above 1000 ppb, 290 ppb above 1000 ppb, 300 ppb above 1000 ppb, 310 ppb above 1000 ppb, 320 ppb above 1000 ppb, 330 ppb above 1000 ppb, 340 ppb above 1000 ppb, 350 ppb above 1000 ppb360 ppb to 1000 ppb, 370 ppb to 1000 ppb, 380 ppb to 1000 ppb, 390 ppb to 1000 ppb, 400 ppb to 1000 ppb, 410 ppb to 1000 ppb, 420 ppb to 1000 ppb, 430 ppb to 1000 ppb, 440 ppb to 1000 ppb, 450 ppb to 1000 ppb, 460 ppb to 1000 ppb, 470 ppb to 1000 ppb, 480 ppb to 1000 ppb, 490 ppb to 1000 ppb Below, 500 ppb to 1000 ppb, 280 ppb to 900 ppb, 290 ppb to 900 ppb, 300 ppb to 900 ppb, 310 ppb to 900 ppb, 320 ppb to 900 ppb, 330 ppb to 900 ppb, 340 ppb to 900 ppb, 350 ppb to 900 ppb, 360 ppb to 900 ppb, 370 ppb to 900 ppb, 380 ppb to 900 ppb, 390 ppb to 900 ppb, 400 ppb to 900 ppb, 410 ppb to 900 ppb Below 00 ppb, 420 ppb to 900 ppb, 430 ppb to 900 ppb, 440 ppb to 900 ppb, 450 ppb to 900 ppb, 460 ppb to 900 ppb, 470 ppb to 900 ppb, 480 ppb to 900 ppb, 490 ppb to 900 ppb, 500 ppb to 900 ppb, 280 ppb to 850 ppb, 290 ppb to 850 ppb, 300 ppb to 850 ppb, 310 ppb to 850 ppb, 320 ppb to 850 ppb, 330 ppb ppb above 850ppb, 340ppb above 850ppb, 350ppb above 850ppb, 360ppb above 850ppb, 370ppb above 850ppb, 380ppb above 850ppb, 390ppb above 850ppb, 400ppb above 850ppb, 410ppb above 850ppb, 420ppb above 850ppb, 430ppb above 850ppb, 440ppb above 850ppb, 450ppb above 850ppb, 460ppb above 850ppb, 470ppb above 850ppb480 ppb to 850 ppb, 490 ppb to 850 ppb, 500 ppb to 850 ppb, 280 ppb to 800 ppb, 290 ppb to 800 ppb, 300 ppb to 800 ppb, 310 ppb to 800 ppb, 320 ppb to 800 ppb, 330 ppb to 800 ppb, 340 ppb to 800 ppb, 350 ppb to 800 ppb, 360 ppb to 800 ppb, 370 ppb to 800 ppb, 380 ppb to 800 ppb, 390 ppb and above 800ppb or less, 400ppb or more, 800ppb or less, 410ppb or more, 800ppb or less, 420ppb or more, 800ppb or less, 4 30ppb or more and 800ppb or less, 440ppb or more and 800ppb or less Below, 450ppb or more, 800ppb or less, 460ppb or more, 800pb Below pb, above 470ppb, below 800ppb, above 480ppb8 Below 00ppb, above 490ppb, below 800ppb, 500ppb Above 800ppb and below, 280ppb and above 750ppb and below, 290 ppb above 750ppb below, 300ppb above 750ppb below, 310 ppb to 750 ppb, 320 ppb to 750 ppb, 330 ppb to 750 ppb, 340 ppb to 750 ppb, 350 ppb to 750 ppb, 360 ppb to 750 ppb, 370 ppb to 750 ppb, 380 ppb to 750 ppb, 390 ppb to 750 ppb, 400 ppb to 750 ppb, 410 ppb to 750 ppb, 420 ppb to 750 ppb, 430 ppb to 750 ppb, 440 ppb to 750 ppb, 450 ppb and above Below 750 ppb, 460 ppb to below 750 ppb, 470 ppb to below 750 ppb, 480 ppb to below 750 ppb, 490 ppb to below 750 ppb, 500 ppb to below 750 ppb, 280 ppb to below 700 ppb, 290 ppb to below 700 ppb, 300 ppb to below 700 ppb, 310 ppb to below 700 ppb, 320 ppb to below 700 ppb, 330 ppb to below 700 ppb, 340 ppb to below 700 ppb, 350 ppb to below 700 ppb, 360 ppb to below 700 ppbThe concentration can be 370 ppb or more and 700 ppb or less, 380 ppb or more and 700 ppb or less, 390 ppb or more and 700 ppb or less, 400 ppb or more and 700 ppb or less, 410 ppb or more and 700 ppb or less, 420 ppb or more and 700 ppb or less, 430 ppb or more and 700 ppb or less, 440 ppb or more and 700 ppb or less, 450 ppb or more and 700 ppb or less, 460 ppb or more and 700 ppb or less, 470 ppb or more and 700 ppb or less, 480 ppb or more and 700 ppb or less, 490 ppb or more and 700 ppb or less, or 500 ppb or more and 700 ppb or less. In the present invention, the unit "ppb" is synonymous with "μg / L".

[0019] The present invention provides a beer-flavored alcoholic beverage in which the total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) is from 280 ppb to 1600 ppb, the total concentration of bound CML, bound CEL, and bound MG-H1 is from 150 ppb to 900 ppb, and the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction having a molecular weight of 1060 Da to 3080 Da (gel filtration method for HPLC analysis). In this case, the lower limit (or higher) of the total concentration of free CML, free CEL, and free MG-H1 is 280 ppb, but the following limits are also available: 285 ppb, 290 ppb, 295 ppb, 300 ppb, 305 ppb, 310 ppb, 315 ppb, 320 ppb, 325 ppb, 330 ppb, 335 ppb, 340 ppb, 345 ppb, 350 ppb, 355 ppb, 360 ppb, 365 ppb, 370 ppb, 375 ppb, 376 ppb, 377 ppb, 378 ppb, 379 ppb, 380 ppb, 381 ppb, 382 ppb, 383 ppb, 384 ppb, 385 ppb, 386 ppb, 387 ppb, 388 ppb, 389 ppb, 390 ppb, 391 ppb, 392 ppb, 393 ppb, 394 ppb, 395 ppb, 396 ppb, 397 ppb, 398 ppb, 399 ppb, 400 ppb, 401 ppb, 402 ppb, 403 ppb, 404 ppb, 405 ppb, 406 ppb, 407 ppb, 408 ppb, 409 ppb, 410 ppb, 411 ppb, 412 ppb, 413 ppb, 414 ppb It can also be 75 ppb, 380 ppb, 385 ppb, 390 ppb, 395 ppb, 400 ppb, 405 ppb, 410 ppb, 415 ppb, 420 ppb, 425 ppb, 430 ppb, 435 ppb, 440 ppb, 445 ppb, 450 ppb, 455 ppb, 460 ppb, 465 ppb, 470 ppb, 475 ppb, 480 ppb, 485 ppb, 490 ppb, 495 ppb or 500 ppb. The upper limit (less than or equal to) is 1600 ppb, but also includes 1590 ppb, 1580 ppb, 1570 ppb, 1560 ppb, 1550 ppb, 1540 ppb, 1530 ppb, 1520 ppb, 1510 ppb, 1500 ppb, 1490 ppb, 1480 ppb, 1470 ppb, 1460 ppb, 1450 ppb, 1440 ppb, 1430 ppb, 1420 ppb, 1410 ppb b, 1400ppb, 1390ppb, 1380ppb, 1370ppb, 1360ppb, 1350ppb, 1340ppb, 1330ppb, 1320ppb, 1310ppb, 1300ppb , 1290ppb, 1280ppb, 1270ppb, 1260ppb, 1250ppb, 1240ppb, 1230ppb, 1220ppb, 1210ppb, 1200ppb, 1190ppb,It can also be 1180 ppb, 1170 ppb, 1160 ppb, 1150 ppb, 1140 ppb, 1130 ppb, 1120 ppb, 1110 ppb, 1100 ppb, 1090 ppb, 1080 ppb, 1070 ppb, 1060 ppb, 1050 ppb, 1040 ppb, 1030 ppb, 1020 ppb, 1010 ppb, 1000 ppb, 990 ppb, 980 ppb, 970 ppb, 960 ppb, 950 ppb, 940 ppb, 930 ppb, 920 ppb, 910 ppb or 900 ppb. These lower and upper limits can be combined in any desired manner, and the total concentration of free CML, free CEL, and free MG-H1 in the beer-taste alcoholic beverage of the present invention can be, for example, from 280 ppb to 1600 ppb, from 290 ppb to 1600 ppb, from 300 ppb to 1600 ppb, from 310 ppb to 1600 ppb, from 320 ppb to 1600 ppb, or from 330 ppb to 1600 ppb. 0ppb or less, 340ppb or more and 1600ppb or less, 350ppb or more and 1600ppb or less, 360ppb or more and 1600ppb or less, 370ppb or more and 1600ppb or less, 380ppb or more and 1600ppb Below, 390ppb to 1600ppb, 400ppb to 1600ppb, 410ppb to 1600ppb, 420ppb to 1600ppb, 430ppb to 1600ppb, 4 40ppb to 1600ppb, 450ppb to 1600ppb, 460ppb to 1600ppb, 470ppb to 1600ppb, 480ppb to 1600ppb, 490ppb b - 1600ppb or less, 500ppb or more and 1600ppb or less, 280ppb or more and 1500ppb or less, 290ppb or more and 1500ppb or less, 300ppb or more and 1500ppb or less, 310ppb or more1 500ppb or less, 320ppb or more and 1500ppb or less, 330ppb or more and 1500ppb or less, 340ppb or more and 1500ppb or less, 350ppb or more and 1500ppb or less, 360ppb or more and 1500p pb or less, 370 ppb or more and 1500 ppb or less, 380 ppb or more and 1500 ppb or less, 390 ppb or more and 1500 ppb or less, 400 ppb or more and 1500 ppb or less, 410 ppb or more and 1500 ppb or less,420 ppb to 1500 ppb, 430 ppb to 1500 ppb, 440 ppb to 1500 ppb, 450 ppb to 1500 ppb, 460 ppb to 1500 ppb, 470 ppb to 1500 ppb, 480 ppb to 1500 ppb, 490 ppb to 1500 ppb, 500 ppb to 1500 ppb, 280 ppb to 1400 ppb, 290 ppb to 1400 ppb, 300 ppb to 1400 ppb, 310 ppb to 1400 ppb, 320 ppb to 1400 ppb Below 1 ppb, 330 ppb to 1400 ppb, 340 ppb to 1400 ppb, 350 ppb to 1400 ppb, 360 ppb to 1400 ppb, 370 ppb to 1400 ppb, 380 ppb to 1400 ppb, 390 ppb to 1400 ppb, 400 ppb to 1400 ppb, 410 ppb to 1400 ppb, 420 ppb to 1400 ppb, 430 ppb to 1400 ppb, 440 ppb to 1400 ppb, 450 ppb to 1400 ppb, 460 ppb to 1400 ppb Below 400 ppb, 470 ppb to 1400 ppb, 480 ppb to 1400 ppb, 490 ppb to 1400 ppb, 500 ppb to 1400 ppb, 280 ppb to 1300 ppb, 290 ppb to 1300 ppb, 300 ppb to 1300 ppb, 310 ppb to 1300 ppb, 320 ppb to 1300 ppb, 330 ppb to 1300 ppb, 340 ppb to 1300 ppb, 350 ppb to 1300 ppb, 360 ppb to 1300 ppb, 370 ppb ppb above 1300 ppb, 380 ppb above 1300 ppb, 390 ppb above 1300 ppb, 400 ppb above 1300 ppb, 410 ppb above 1300 ppb, 420 ppb above 1300 ppb, 430 ppb above 1300 ppb, 440 ppb above 1300 ppb, 450 ppb above 1300 ppb, 460 ppb above 1300 ppb, 470 ppb above 1300 ppb, 480 ppb above 1300 ppb, 490 ppb above 1300 ppb, 500 ppb above 1300 ppb280 ppb to 1200 ppb, 290 ppb to 1200 ppb, 300 ppb to 1200 ppb, 310 ppb to 1200 ppb, 320 ppb to 1200 ppb, 330 ppb to 1200 ppb, 340 ppb to 1200 ppb, 350 ppb to 1200 ppb, 360 ppb to 1200 ppb, 370 ppb to 1200 ppb, 380 ppb to 1200 ppb, 390 ppb to 1200 ppb, 400 ppb to 1200 ppb, 410 ppb to 1200 ppb Below 1 ppb, 420 ppb to 1200 ppb, 430 ppb to 1200 ppb, 440 ppb to 1200 ppb, 450 ppb to 1200 ppb, 460 ppb to 1200 ppb, 470 ppb to 1200 ppb, 480 ppb to 1200 ppb, 490 ppb to 1200 ppb, 500 ppb to 1200 ppb, 280 ppb to 1100 ppb, 290 ppb to 1100 ppb, 300 ppb to 1100 ppb, 310 ppb to 1100 ppb, 320 ppb to 1200 ppb Below 100 ppb, 330 ppb to 1100 ppb, 340 ppb to 1100 ppb, 350 ppb to 1100 ppb, 360 ppb to 1100 ppb, 370 ppb to 1100 ppb, 380 ppb to 1100 ppb, 390 ppb to 1100 ppb, 400 ppb to 1100 ppb, 410 ppb to 1100 ppb, 420 ppb to 1100 ppb, 430 ppb to 1100 ppb, 440 ppb to 1100 ppb, 450 ppb to 1100 ppb, 460 ppb ppb above 1100 ppb, 470 ppb above 1100 ppb, 480 ppb above 1100 ppb, 490 ppb above 1100 ppb, 500 ppb above 1100 ppb, 280 ppb above 1000 ppb, 290 ppb above 1000 ppb, 300 ppb above 1000 ppb, 310 ppb above 1000 ppb, 320 ppb above 1000 ppb, 330 ppb above 1000 ppb, 340 ppb above 1000 ppb, 350 ppb above 1000 ppb, 360 ppb above 1000 ppb370 ppb or more and 1000 ppb or less, 380 ppb or more and 1000 ppb or less, 390 ppb or more and 1000 ppb or less, 400 ppb or more and 1000 ppb or less, 410 ppb or more and 1000 ppb or less, 420 ppb or more and 1000 ppb or less, 430 ppb or more and 1000 ppb or less, 440 ppb or more and 1000 ppb or less, 450 ppb or more and 1000 ppb or less, 4 60ppb to 1000ppb, 470ppb to 1000ppb, 480ppb to 1000ppb, 490ppb to 1000ppb, 500ppb to 100 0ppb or less, 280ppb or more and 900ppb or less, 290ppb or more and 900ppb or less, 300ppb or more and 900ppb or less, 310ppb or more and 900ppb or less, 320ppb or less Upper 900ppb or less, 330ppb or more and 900ppb or less, 340ppb or more and 900ppb or less, 350ppb or more and 900ppb or less, 360ppb or more and 900ppb or less, 370 ppb or more and 900ppb or less, 380ppb or more and 900ppb or less, 390ppb or more and 900ppb or less, 400ppb or more and 900ppb or less, 410ppb or more and 900ppb or less, It can be 420 ppb or more and 900 ppb or less, 430 ppb or more and 900 ppb or less, 440 ppb or more and 900 ppb or less, 450 ppb or more and 900 ppb or less, 460 ppb or more and 900 ppb or less, 470 ppb or more and 900 ppb or less, 480 ppb or more and 900 ppb or less, 490 ppb or more and 900 ppb or less, or 500 ppb or more and 900 ppb or less.

[0020] In the beer-taste alcoholic beverage of the present invention, the lower limit (or higher) of the total concentration of bound CML, bound CEL, and bound MG-H1 is 150 ppb, but may be any of the following: 155 ppb, 160 ppb, 165 ppb, 170 ppb, 175 ppb, 180 ppb, 185 ppb, 190 ppb, 195 ppb, 200 ppb, 205 ppb, 210 ppb, 215 ppb, 220 ppb, 225 ppb, 230 ppb, 235 ppb, 240 ppb, 245 ppb, 250 ppb, 260 ppb, 270 ppb, 275 ppb, 280 ppb, 285 ppb, 290 ppb, 300 ppb, 305 ppb, 310 ppb, 315 ppb, 320 ppb, 325 ppb, 330 ppb, 335 ppb, 340 ppb, 345 ppb, 350 ppb, 355 ppb, 360 ppb, 365 ppb, 370 ppb, 375 ppb, 380 ppb, 385 ppb, 390 ppb, 400 ppb, 405 ppb, 410 ppb, 415 ppb, 420 ppb, 425 ppb, 430 ppb, 435 ppb, 440 ppb, 445 ppb, 450 ppb, 460 It can also be 55 ppb, 260 ppb, 265 ppb, 270 ppb, 275 ppb, 280 ppb, 285 ppb, 290 ppb, 295 ppb, 300 ppb, 305 ppb, 310 ppb, 315 ppb, 320 ppb, 325 ppb, 330 ppb, 335 ppb, 340 ppb, 345 ppb, 350 ppb, 355 ppb, 360 ppb, 365 ppb, 370 ppb, 375 ppb, 380 ppb, 385 ppb, 390 ppb, 395 ppb or 400 ppb. The upper limit (or less than) is 900 ppb, but the following limits are also available: 895 ppb, 890 ppb, 885 ppb, 880 ppb, 875 ppb, 870 ppb, 865 ppb, 860 ppb, 855 ppb, 850 ppb, 845 ppb, 840 ppb, 835 ppb, 830 ppb, 825 ppb, 820 ppb, 815 ppb, 810 ppb, 805 ppb, 800 ppb, 795 ppb, 790 ppb, 785 ppb, 780 ppb, 775 ppb, 770 ppb, 765 ppb, 760 ppb, 755 ppb , 750 ppb, 745 ppb, 740 ppb, 735 ppb, 730 ppb, 725 ppb, 720 ppb, 715 ppb, 710 ppb, 705 ppb, 700 ppb, 695 ppb, 690 ppb, 685 ppb, 680 ppb, 675 ppb, 670 ppb, 665 ppb, 660 ppb, 655 ppb, 650 ppb, 645 ppb, 640 ppb, 635 ppb, 630 ppb, 625 ppb, 620 ppb, 615 ppb, 610 ppb, 605 ppb or 600 ppb. These lower and upper limits can be combined in any desired manner, and the total concentration of bound CML, bound CEL, and bound MG-H1 in the beer-taste alcoholic beverage of the present invention can be, for example,150 ppb to 900 ppb, 160 ppb to 900 ppb, 170 ppb to 900 ppb, 180 ppb to 900 ppb, 190 ppb to 900 ppb, 200 ppb to 900 ppb, 210 ppb to 900 ppb, 220 ppb to 900 ppb, 230 ppb to 900 ppb, 240 ppb to 900 ppb, 250 ppb to 900 ppb, 260 ppb to 900 ppb, 270 ppb to 900 ppb, 280 ppb to 900 ppb, 290 ppb and above Below 900 ppb, 300 ppb to 900 ppb, 310 ppb to 900 ppb, 320 ppb to 900 ppb, 330 ppb to 900 ppb, 340 ppb to 900 ppb, 350 ppb to 900 ppb, 360 ppb to 900 ppb, 370 ppb to 900 ppb, 380 ppb to 900 ppb, 390 ppb to 900 ppb, 400 ppb to 900 ppb, 150 ppb to 800 ppb, 160 ppb to 800 ppb, 170 ppb to 800 ppb 180 ppb to 800 ppb, 190 ppb to 800 ppb, 200 ppb to 800 ppb, 210 ppb to 800 ppb, 220 ppb to 800 ppb, 230 ppb to 800 ppb, 240 ppb to 800 ppb, 250 ppb to 800 ppb, 260 ppb to 800 ppb, 270 ppb to 800 ppb, 280 ppb to 800 ppb, 290 ppb to 800 ppb, 300 ppb to 800 ppb, 310 ppb to 800 ppb, 320 ppb and above Below 800 ppb, 330 ppb to 800 ppb, 340 ppb to 800 ppb, 350 ppb to 800 ppb, 360 ppb to 800 ppb, 370 ppb to 800 ppb, 380 ppb to 800 ppb, 390 ppb to 800 ppb, 400 ppb to 800 ppb, 150 ppb to 700 ppb, 160 ppb to 700 ppb, 170 ppb to 700 ppb, 180 ppb to 700 ppb, 190 ppb to 700 ppb, 200 ppb to 700 ppb210ppb to 700ppb, 220ppb to 700ppb, 230ppb to 700ppb, 240ppb to 700ppb, 250ppb to 700ppb, 260ppb to 700ppb Below, 270ppb to 700ppb, 280ppb to 700ppb, 290ppb to 700ppb, 300ppb to 700ppb, 310ppb to 700ppb, 320ppb to 700ppb ppb or less, 330 ppb or more and 700 ppb or less, 340 ppb or more and 700 ppb or less, 350 ppb or more and 700 ppb or less, 360 ppb or more and 700 ppb or less, 370 ppb or more and 700 ppb or less, 380 ppb or more 700ppb or less, 390ppb or more and 700ppb or less, 400ppb or more and 700ppb or less, 150ppb or more and 600ppb or less, 160ppb or more and 600ppb or less, 170ppb or more and 600ppb or less, 180ppb b - 600ppb, 190ppb - 600ppb, 200ppb - 600ppb, 210ppb - 600ppb, 220ppb - 600ppb, 230ppb - 600ppb, 24 0ppb to 600ppb, 250ppb to 600ppb, 260ppb to 600ppb, 270ppb to 600ppb, 280ppb to 600ppb, 290ppb to 600ppb , 300 ppb or more and 600 ppb or less, 310 ppb or more and 600 ppb or less, 320 ppb or more and 600 ppb or less, 330 ppb or more and 600 ppb or less, 340 ppb or more and 600 ppb or less, 350 ppb or more and 600 ppb or less, 360 ppb or more and 600 ppb or less, 370 ppb or more and 600 ppb or less, 380 ppb or more and 600 ppb or less, 390 ppb or more and 600 ppb or less, or 400 ppb or more and 600 ppb or less.

[0021] In the beer-taste alcoholic beverage of the present invention, the lower limit (or higher) of the total concentration of six components, namely, free CML, free CEL, free MG-H1, and bound CML, bound CEL, and bound MG-H1, is 430 ppb, but it is also possible to obtain a beer-taste alcoholic beverage containing 440 ppb, 450 ppb, 460 ppb, 470 ppb, 480 ppb, 490 ppb, 500 ppb, 510 ppb, 520 ppb, 530 ppb, 540 ppb, 550 ppb, 560 ppb, 570 ppb, 580 ppb, 590 ppb, 600 ppb, 610 ppb, 620 ppb, 630 ppb, 640 ppb, 650 ppb, 660 ppb, 670 ppb, 680 ppb, 690 ppb, 700 ppb, 710 ppb, 720 ppb, 730 ppb, 740 ppb, 750 ppb, 760 ppb, 770 ppb, 780 ppb, 790 ppb, 800 ppb, 810 ppb, 820 ppb, 830 ppb, 840 ppb, 850 ppb, 860 ppb, 870 ppb, 880 ppb, 890 ppb, 900 ppb, 910 ppb, 920 ppb, 930 ppb, 940 ppb, 950 ppb, 960 0ppb, 530ppb, 540ppb, 550ppb, 560ppb, 570ppb, 580ppb, 590ppb, 600ppb, 610ppb, 620ppb, 630ppb, 640 ppb, 650ppb, 660ppb, 670ppb, 680ppb, 690ppb, 700ppb, 710ppb, 720ppb, 730ppb, 740ppb, 750ppb, 760pp b, 770ppb, 780ppb, 790ppb, 800ppb, 810ppb, 820ppb, 830ppb, 840ppb, 850ppb, 860ppb, 870ppb, 880ppb , 890ppb, 900ppb, 910ppb, 920ppb, 930ppb, 940ppb, 950ppb, 960ppb, 970ppb, 980ppb, 990ppb, 1000ppb, It can also be 1010 ppb, 1020 ppb, 1030 ppb, 1040 ppb, 1050 ppb, 1060 ppb, 1070 ppb, 1080 ppb, 1090 ppb, 1100 ppb, 1110 ppb, 1120 ppb, 1130 ppb, 1140 ppb, 1150 ppb, 1160 ppb, 1170 ppb, 1180 ppb, 1190 ppb or 1200 ppb. The upper limit (or less than) is 2500 ppb, but also includes 2490 ppb, 2480 ppb, 2470 ppb, 2460 ppb, 2450 ppb, 2440 ppb, 2430 ppb, 2420 ppb, 2410 ppb, 2400 ppb, 2390 ppb, 2380 ppb, 2370 ppb, 2360 ppb, 2350 ppb, 2340 ppb, 23 30ppb, 2320ppb, 2310ppb, 2300ppb, 2290ppb, 2280ppb, 2270ppb, 2260ppb, 2250ppb, 2240ppb, 2 230ppb, 2220ppb, 2210ppb, 2200ppb, 2190ppb, 2180ppb, 2170ppb, 2160ppb, 2150ppb, 2140ppb,2130ppb, 2120ppb, 2110ppb, 2100ppb, 2090ppb, 2080ppb, 2070ppb, 2060ppb, 2050pp b, 2040ppb, 2030ppb, 2020ppb, 2010ppb, 2000ppb, 1990ppb, 1980ppb, 1970ppb, 1960p pb, 1950 ppb, 1940 ppb, 1930 ppb, 1920 ppb, 1910 ppb, 1900 ppb, 1890 ppb, 1880 ppb, 1870 ppb, 1860 ppb, 1850 ppb, 1840 ppb, 1830 ppb, 1820 ppb, 1810 ppb or 1800 ppb. These lower and upper limits can be combined in any desired manner, and the total concentration of the six components, F-MRP and B-MRP, in the beer-taste alcoholic beverage of the present invention can be, for example, 430 ppb or more and 2500 ppb or less, 430 ppb or more and 2400 ppb or less, 430 ppb or more and 2300 ppb or less, 430 ppb or more and 2200 ppb or less, 430 ppb or more and 2100 ppb or less, 430 ppb or more and 2300 ppb or less, 2000ppb or less, 430ppb or more and 1900ppb or less, 430ppb or more and 1800ppb or less, 500 or more and 2500ppb or less, 500ppb or more and 2400ppb or less, 500ppb or more23 18 00ppb or less, 600 or more and 2500ppb or less, 600ppb or more and 2400ppb or less, 600ppb or more and 2300ppb or less, 600ppb or more and 2200ppb or less, 600ppb or more and 2100 ppb or less, 600ppb or more and 2000ppb or less, 600ppb or more and 1900ppb or less, 600ppb or more and 1800ppb or less, 700 or more and 2500ppb or less, 700ppb or more and 2400ppb Below, 700ppb to 2300ppb, 700ppb to 2200ppb, 700ppb to 2100ppb, 700ppb to 2000ppb, 700ppb to 1900ppb Below, 700 to 1800 ppb, 800 to 2,500 ppb, 800 to 2,400 ppb, 800 to 2,300 ppb, 800 to 2,200 ppb,800ppb to 2100ppb, 800ppb to 2000ppb, 800ppb to 1900ppb, 800ppb to 1800ppb, 900 to 2500ppb b or less, 900 ppb or more and 2,400 ppb or less, 900 ppb or more and 2,300 ppb or less, 900 ppb or more and 2,200 ppb or less, 900 ppb or more and 2,100 ppb or less, 900 ppb or more 2000ppb or less, 900ppb or more and 1900ppb or less, 900ppb or more and 1800ppb or less, 1000 or more and 2500ppb or less, 1000ppb or more and 2400ppb or less, 100 0ppb to 2300ppb, 1000ppb to 2200ppb, 1000ppb to 2100ppb, 1000ppb to 2000ppb, 1000ppb to 19 00ppb or less, 1000ppb or more and 1800ppb or less, 1100 or more and 2500ppb or less, 1100ppb or more and 2400ppb or less, 1100ppb or more and 2300ppb or less, 110 0ppb to 2200ppb, 1100ppb to 2100ppb, 1100ppb to 2000ppb, 1100ppb to 1900ppb, 1100ppb to 18 100 ppb or less, 1200 to 2500 ppb, 1200 to 2400 ppb, 1200 to 2300 ppb, 1200 to 2200 ppb, 1200 to 2100 ppb, 1200 to 2000 ppb, 1200 to 1900 ppb, or 1200 to 1800 ppb.

[0022] In the present invention, the concentrations of F-MRP and B-MRP can be quantified by LC-MS / MS analysis (see Examples 1(1) d and o in the Examples section below). Furthermore, for more accurate concentration measurement, it is desirable to use a calibration curve prepared based on the measured values ​​of several control samples with known concentrations.

[0023] In the present invention, the molecular weight of B-MRP is measured by a gel filtration method using high performance liquid chromatography (sometimes referred to herein as "gel filtration for HPLC analysis"). Specifically, the molecular weight can be calculated from the retention time using a calibration curve for gel filtration for HPLC analysis (see Example 1(1)B in the Examples below and Figure 1).

[0024] The beer-taste alcoholic beverage of the present invention is characterized by having a good full-bodied flavor, a crisp aftertaste, and a good degree of intonation. Here, "full-bodied flavor" refers to an overall flavor consisting of strong, complex, and persistent flavor. "Clear aftertaste" refers to a refreshing aftertaste that has a moderate lingering aftertaste but is not lingering. "Degree of intonation" refers to the degree to which the flavor has a good degree of intonation that is commensurate with the overall strength of the flavor.

[0025] The beer-taste alcoholic beverage of the present invention can be produced according to a typical production procedure for a beer-taste alcoholic beverage, so long as the F-MRP concentration is within a predetermined range, or the F-MRP and B-MRP concentrations are within a predetermined range. In the present invention, the F-MRP and B-MRP concentrations can be adjusted by selecting the raw materials or production conditions. Non-limiting examples of such raw materials and production conditions include mashing conditions, selection of yeast (including strains), adjustment of the amount of yeast used, adjustment of fermentation conditions, and selection and amount of filter aid used. For example, these concentrations can be adjusted by appropriately setting the set temperature and retention time when obtaining the saccharified solution, and the boiling temperature and time.

[0026] In the present invention, the preparation of the brewing liquid can be carried out according to a conventional method, for example, by sequentially carrying out the steps of: (a) saccharifying a mixture of water and raw materials containing malt, followed by filtering to obtain wort; (b) adding hops to the obtained wort and then boiling it; and (c) cooling the boiled wort.

[0027] In the present invention, in addition to malt, hops, and water, other brewing raw materials can be used, such as rice, corn, koryang (rice bran), potato, starch, sugars (e.g., liquid sugar), fruit, and coriander, as defined by the Liquor Tax Act, as well as other additives such as protein hydrolysates, nitrogen sources such as yeast extract, colorants, foaming and foam retention improvers, water quality adjusters, and fermentation aids. Ungerminated barley (e.g., ungerminated barley (including extracts) and ungerminated wheat (including extracts)) can also be used as brewing raw materials.

[0028] In the present invention, degradation treatment can also be performed by adding proteolytic enzymes, carbohydrate-degrading enzymes, and cellulolytic enzymes individually or in combination at any time before the completion of the fermentation process (e.g., during mashing, fermentation, or both mashing and fermentation). Examples of proteolytic enzymes include enzymes derived from brewing raw materials such as malt and commercially available protease enzyme preparations. Examples of carbohydrate-degrading enzymes include enzymes derived from brewing raw materials such as malt and commercially available enzyme preparations (α-amylase, β-amylase, glucoamylase, α-glucosidase, pullulanase, isoamylase, etc.). Examples of cellulolytic enzymes include enzymes derived from brewing raw materials such as malt and commercially available enzyme preparations (β-glucanase, xylanase, hemicellulase, etc.). The addition of these enzymes can adjust the F-MRP concentration and B-MRP concentration.

[0029] In the present invention, malt with high endoprotease activity and / or an enzyme preparation possessing endoprotease activity can be used in the saccharification step to promote proteolysis, and malt with low endoprotease activity can be used to inhibit proteolysis. By carrying out such steps, the amounts of F-MRP and B-MRP contained in the beer-taste alcoholic beverage can be adjusted to fall within a predetermined range, thereby enabling the production of a beer-taste alcoholic beverage that has a strong, full-bodied flavor, a crisp aftertaste, and a good degree of intonation.

[0030] In the present invention, the saccharification temperature can be, for example, 30°C to 100°C, 35°C to 100°C, or 40°C to 100°C. The saccharification time can be appropriately set taking into account the saccharification temperature, and can be, for example, 30 minutes to 180 minutes, 50 minutes to 150 minutes, or 60 minutes to 140 minutes. In the present invention, the boiling conditions can be set according to conventional methods.

[0031] In the present invention, the boiling temperature can be, for example, 100° C. to 150° C., 100° C. to 140° C., or 100° C. to 130° C. The boiling time can be appropriately set in consideration of the boiling temperature, and can be, for example, 10 minutes to 180 minutes, 20 minutes to 150 minutes, or 30 minutes to 120 minutes.

[0032] In the present invention, the fermentation conditions are not particularly limited, and the fermentation can be carried out according to a conventional method.

[0033] Furthermore, in the present invention, by adding F-MRP to a beer-taste alcoholic beverage, the F-MRP concentration can be adjusted to within a predetermined range, or by adding F-MRP and B-MRP to a beer-taste alcoholic beverage, the F-MRP concentration and B-MRP concentration can be adjusted to within a predetermined range, thereby producing a beer-taste alcoholic beverage with a strong body, a clean finish, and a good intonation. That is, the present invention provides a method for producing a beer-taste alcoholic beverage, which includes adding F-MRP to a beer-taste alcoholic beverage, and a method for producing a beer-taste alcoholic beverage, which includes adding F-MRP and B-MRP to a beer-taste alcoholic beverage. The addition of F-MRP and B-MRP to a beer-taste alcoholic beverage can be carried out at any stage during the production process of the beverage. In the present invention, F-MRP and B-MRP can be derived from the raw materials or can be added separately from the plant raw materials. As shown in the Examples (Example 1) below, a fraction containing F-MRP and B-MRP can be prepared from a beverage, purified, and added to a beer-taste alcoholic beverage.

[0034] The pH (measured at 25°C) of the beer-taste alcoholic beverage of the present invention is not limited, but the lower limit (above or below) can be 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, or 3.0, and the upper limit (below or below) can be 5.0, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, or 4.3. These lower and upper limits can be arbitrarily combined, for example, 2.0 to 5.0, 2.0 to 4.5, 2.5 to 5.0, 2.5 to 4.5, 3.0 to 5.0, or 3.0 to 4.5. The pH of the beer-taste alcoholic beverage of the present invention can be adjusted using a pH adjuster. The pH of the beer-taste alcoholic beverage can be measured using a commercially available pH meter (e.g., a benchtop pH meter, manufactured by Horiba, Ltd.).

[0035] The beer-taste alcoholic beverage of the present invention can be provided as a carbonated beverage. The carbon dioxide pressure (gas pressure at 20°C) of the beer-taste alcoholic beverage of the present invention is not limited, but the lower limit (greater than or equal to) can be 0.05 MPa, 0.06 MPa, 0.07 MPa, 0.08 MPa, 0.09 MPa, or 0.1 MPa, and the upper limit (less than or equal to) can be 0.4 MPa, 0.39 MPa, 0.38 MPa, 0.37 MPa, 0.36 MPa, or 0.35 MPa. These upper and lower limits can be combined in any manner, and can be, for example, 0.05 MPa to 0.4 MPa, 0.07 MPa to 0.38 MPa, or 0.1 MPa to 0.35 MPa.

[0036] The bitterness value (BU) of the beer-taste alcoholic beverage of the present invention is not limited, but the lower limit (not less than or exceeding) can be, for example, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, and the upper limit (not more than or less than) can be, for example, 120, 115, 110, 100, 95, 90, 85, 80, 75, 70, 65, 60, 59, 58, 57, 56, 55, 54, 53, 52, 51, 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, or 40. These lower and upper limits can be combined arbitrarily, for example, from 5 to 120, from 5 to 115, from 5 to 110, from 5 to 105, from 5 to 100, from 5 to 95, from 5 to 90, from 5 to 85, from 5 to 80, from 5 to 75, from 5 to 70, from 5 to 65, from 5 to 60, from 5 to 59, from 5 to 58, from 5 to 57, from 5 to 56, from 5 to 55, from 5 to 5 5 to 54, 5 to 53, 5 to 52, 5 to 51, 5 to 50, 5 to 49, 5 to 48, 5 to 47, 5 to 46, 5 to 45, 6 to 120, 6 to 120 115 or less, 6 or more and 110 or less, 6 or more and 105 or less, 6 or more and 100 or less, 6 or more and 95 or less, 6 or more and 90 or less, 6 or more and 85 or less, 6 or more and 80 or less, 6 or more and 75 or less, 6 or more and 70 or less, 6 or more and 65 or less, 6 or more 60 or less, 6 or more and 59 or less, 6 or more and 58 or less, 6 or more and 57 or less, 6 or more and 56 or less, 6 or more and 55 or less, 6 or more and 54 or less, 6 or more and 53 or less, 6 or more and 52 or less, 6 or more and 51 or less, 6 or more and 50 or less, 6 or more and 49 or less Lower, 6 to 48, 6 to 47, 6 to 46, 6 to 45, 7 to 120, 7 to 115, 7 to 110, 7 to 105, 7 to 100, 7 to 95, 7 to 9 It can be 0 or less, 7 to 85 or less, 7 to 80 or less, 7 to 75 or less, 7 to 70 or less, 7 to 65 or less, 7 to 60 or less, 7 to 59 or less, 7 to 58 or less, 7 to 57 or less, 7 to 56 or less, 7 to 55 or less, 7 to 54 or less, 7 to 53 or less, 7 to 52 or less, 7 to 51 or less, 7 to 50 or less, 7 to 49 or less, 7 to 48 or less, 7 to 47 or less, 7 to 46 or less, or 7 to 45 or less.The bitterness value of the beer-taste alcoholic beverage of the present invention can be adjusted by the variety, amount, and timing of addition of hops. The bitterness value of the beer-taste alcoholic beverage can be measured by the method specified in the "Analysis Method Designated by the National Tax Agency."

[0037] The original wort extract (°P) of the beer-taste alcoholic beverage of the present invention is not limited, but its lower limit (not less than or exceeding) can be, for example, 5.0, 5.5, 6.0, 6.5, 7.0, or 7.5, and its upper limit (not more than or below) can be, for example, 50.0, 49.0, 48.0, 47.0, 46.0, 45.0, 44.0, 43.0, 42.0, or 50.0. 0, 41.0, 40.0, 39.0, 38.0, 37.0, 36.0, 35.0, 34.0, 33.0, 32.0, 31.0, 30.0, 29.0, 28.0, 27.0, 26.0, 25.0, 24.0, 23.0, 22.0, 21.0, 20.0, 19.0, 18.0, 17.0, 16.0, 15.5, 15.0, 14.5 or 14.0.These lower and upper limits can be combined arbitrarily, and examples thereof include 5.0 or more and 50.0 or less, 5.0 or more and 49.0 or less, 5.0 or more and 48.0 or less, 5.0 or more and 47.0 or less, 5.0 or more and 46.0 or less, 5.0 or more and 45.0 or less, 5.0 or more and 44.0 or less, 5.0 or more and 43.0 or less, 5.0 or more and 42.0 or less, 5.0 or more and 41.0 or less, 5.0 or more and 40.0 or less, 5.0 or more and 39.0 or less, 5.0 or more and 38.0 or less, 5.0 or more and 37.0 or less, 5.0 or more and 36.0 or less, 5.0 or more and 35.0 or less, and 5.0 or more and 34.0 or less. .. 0 or less, 5.0 to 33.0, 5.0 to 32.0, 5.0 to 31.0, 5.0 to 30.0, 5.0 to 29.0, 5.0 to 28.0, 5.0 to 27.0, 5.0 to 26.0, 5.0 to 25.0, 5.0 and below 24.0 or less, 5.0 or more and 23.0 or less, 5.0 or more and 22.0 or more, 5.0 or more and 21.0 or less, 5.0 or more and 20.0 or less, 5.0 or more and 19.0 or less, 5.0 or more and 18.0 or less, 5.0 or more and 17.0 or less, 5.0 or more and 16.0 or less, 5 or more and 15.5 or less, 5. 5 to 16.0, 5.5 to 15.5, 6.0 to 50.0, 6.0 to 49.0, 6.0 to 48.0, 6.0 to 47.0, 6.0 to 46.0, 6.0 to 45.0, 6.0 to 44.0, 6.0 to 43.0 Lower, 6.0 to 42.0, 6.0 to 41.0, 6.0 to 40.0, 6.0 to 39.0, 6.0 to 38.0, 6.0 to 37.0, 6.0 to 36.0, 6.0 to 35.0, 6.0 to 34.0, 6.0 to 3 The viscosity may be 3.0 or less, 6.0 to 32.0, 6.0 to 31.0, 6.0 to 30.0, 6.0 to 29.0, 6.0 to 28.0, 6.0 to 27.0, 6.0 to 26.0, 6.0 to 25.0, 6.0 to 24.0, 6.0 to 23.0, 6.0 to 22.0, 6.0 to 21.0, 6.0 to 20.0, 6.0 to 19.0, 6.0 to 18.0, 6.0 to 17.0, 6.0 to 16.0, or 6.0 to 15.5. The viscosity of the raw wort extract for the beer-taste alcoholic beverage of the present invention can be adjusted by adjusting the amount of raw materials used and the fermentation and filtration conditions.The original wort extract of a beer-flavored alcoholic beverage can be measured in accordance with the "BCOJ Beer Analysis Method."

[0038] The beer-taste alcoholic beverage of the present invention can be provided as a packaged beverage. The container used for the beverage of the present invention may be any container commonly used for filling beverages, such as a metal can, a barrel, a plastic bottle (e.g., a PET bottle or cup), a paper container, a bottle, or a pouch, with metal cans, barrels, plastic bottles (e.g., a PET bottle), or a bottle being preferred.

[0039] Nitrogen can also be added to the beer-taste alcoholic beverage of the present invention in addition to carbon dioxide. In this case, the nitrogen concentration can be adjusted as appropriate according to preference. The form of nitrogen used when adding nitrogen to a beverage may be any form known to those skilled in the art, such as nitrogen gas or liquid nitrogen, but liquid nitrogen is preferred. The total gas pressure, including nitrogen, in the beer-taste alcoholic beverage of the present invention can be adjusted within the range of 0.05 to 0.4 MPa (gas pressure at 20°C) (when no nitrogen is separately sealed in). There are many purposes for adding nitrogen, but one example is to make the foam of the beer-taste alcoholic beverage creamier.

[0040] The container used for the beer-taste alcoholic beverage of the present invention may also contain a hollow insert, such as a so-called "widget," separate from the container and used to efficiently supply nitrogen or other gases to the beverage contained in the container. The widget may have a variety of shapes, including a sphere and a cube, and any shape is acceptable. The widget may be either fixed or unfixed to the container. Before opening the container, the widget contains a gas containing pressurized nitrogen gas that is in equilibrium with the total pressure of the container, which is higher than atmospheric pressure. When the container is opened to serve the beverage, the empty space where no beverage is present is released, creating a pressure difference and causing the nitrogen sealed in the widget to be sprayed into the container. The container and widget are preferably arranged so that the nitrogen in the widget is sprayed directly into the liquid when the container is opened.

[0041] Furthermore, methods for incorporating nitrogen into the beer-taste alcoholic beverage of the present invention include spraying nitrogen using a small object, or adding nitrogen originally contained in the beverage, or by dripping liquid nitrogen into the container to fill the empty space with nitrogen and saturate the beverage with nitrogen. This dripping of liquid nitrogen can be carried out simultaneously with the sealing of the beer-taste alcoholic beverage into the container. These methods produce the so-called cascade foam phenomenon in the beer-taste alcoholic beverage of the present invention, allowing for the generation of more distinctive foam.

[0042] According to another aspect of the present invention, there is provided a method for producing a beer-taste alcoholic beverage having an improved flavor, the method comprising the steps of adding free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1400 ppb or less. According to another aspect of the present invention, there is also provided a method for producing a beer-taste alcoholic beverage having an improved flavor, the method comprising the steps of adding free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1600 ppb or less, and adding bound CML, bound CEL, and bound MG-H1 so that the total concentration is 150 ppb or more and 900 ppb or less, the bound CML, bound CEL, and bound MG-H1 being contained in a peptide fraction having a molecular weight of 1060 Da to 3080 Da (gel filtration for HPLC analysis). In the present invention, "improved flavor" or "flavor improvement" of a beer-taste alcoholic beverage means that a good full-bodied flavor, clean finish, and intonation are achieved. The production method of the present invention described above is preferably a production method of a beer-taste alcoholic beverage that has a good full-bodied flavor, clean finish, and intonation. The production method of the present invention described above can be carried out in accordance with the description of the beer-taste alcoholic beverage of the present invention.

[0043] According to another aspect of the present invention, there is provided a flavor improving agent for a beer-taste alcoholic beverage, which comprises free CML, free CEL, and free MG-H1 as active ingredients. According to another aspect of the present invention, there is also provided a flavor improving agent for a beer-taste alcoholic beverage, which comprises free CML, free CEL, and free MG-H1 as well as bound CML, bound CEL, and bound MG-H1 as active ingredients. The flavor improving agent of the present invention can be produced according to the description of the beer-taste alcoholic beverage and the production method thereof of the present invention.

[0044] Another aspect of the present invention provides a method for improving the flavor of a beer-taste alcoholic beverage. The flavor improving method of the present invention can be carried out by, in the production of a beer-taste alcoholic beverage, adding free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1400 ppb or less. The flavor improving method of the present invention can also be carried out in the production of a beer-taste alcoholic beverage by adding free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1600 ppb or less, and adding bound CML, bound CEL, and bound MG-H1 so that the total concentration is 150 ppb or more and 900 ppb or less. The flavor improving method of the present invention can be carried out according to the description of the beer-taste alcoholic beverage of the present invention and the production method thereof.

[0045] The present invention will be described in more detail based on the following examples, but the present invention is not limited to these examples.

[0046] Measurement of Alcohol Concentration The alcohol concentration (ethanol concentration) was measured according to the method described in the "National Tax Agency Prescribed Analysis Method."

[0047] Example 1: Production of a beer-taste alcoholic beverage and purification of Maillard reaction products (MRPs) In Example 1, a beer-taste alcoholic beverage was produced, and Maillard reaction products (MRPs) were purified from the beverage.

[0048] (1) Method A: Production of a Beer-Taste Alcoholic Beverage Milled barley malt and cellulose-degrading enzymes were added to a mash tank containing warm water maintained at 45 to 70°C, and the temperature was then raised in stages to prepare a saccharified solution. The saccharified solution was then filtered to remove malt residue, yielding a wort. Hops were added to the resulting wort, and the resulting wort was boiled, followed by solid-liquid separation and cooling to yield a clear wort. A beer-taste alcoholic beverage with an alcohol concentration of 5% (100% malt usage ratio) was produced by adding yeast, adjusting the fermentation temperature and fermentation time, and filtering the resulting fermented solution. This beer-taste alcoholic beverage fell within the range of the beverage of the present invention (F-MRP concentration: 521 ppb, B-MRP concentration: 319 ppb). When producing beer-taste alcoholic beverages using the same methods as in Examples 2 and 3, the blend of raw malt, the set temperature, the retention time, and other factors used to obtain the saccharified solution were appropriately adjusted.

[0049] A beer-taste alcoholic beverage was weighed and freeze-dried, and the resulting product was dissolved in 100 mM NaCl solution to prepare a 5-fold concentrated solution. The resulting concentrate was subjected to gel filtration fractionation under the conditions shown in Table 1, and a fraction with a molecular weight of 1,060 Da to 3,080 Da was collected.

[0050] Prior to fraction collection, molecular weight analysis was performed using HPLC gel filtration to identify the gel filtration fractionation range (elution time). The specific procedure is as follows. Under the conditions shown in Table 1, 40 fractions were collected in 5 mL increments starting from the elution position where UV absorption at 215 nm began. Each fraction was diluted with 50 mM sodium phosphate buffer (pH 7.0, containing 150 mM NaCl) and filtered through a 0.45 μm filter. 100 μL of each fraction was injected and analyzed under the conditions shown in Table 2. The molecular weights of each fraction were calculated from the retention time of the UV absorption peak in each analysis chart and the calibration curve. To determine the molecular weight under the analytical conditions shown in Table 2, 50 μL of peptides with known molecular weights shown in Table 3, dissolved at 0.1 to 5 mg / mL in 50 mM sodium phosphate (pH 7.0) and 150 mM NaCl, were injected, and HPLC gel filtration analysis was performed under the same conditions. A calibration curve was created from the retention time and molecular weight using a regression equation based on power approximation (Figure 1). In this way, the start and end positions (elution times) of fractionation for molecular weights of 1060 Da to 3080 Da under the fractionation conditions in Table 1 were identified.

[0051]

[0052]

[0053]

[0054] C. Purification of Maillard Reaction Products (MRPs) The fractions obtained from the beer-flavored alcoholic beverage by the method described above were adsorbed onto a C18 solid-phase extraction column (Bond Elut C18, Agilent Technologies). After washing with pure water, the resulting flow-through fraction and wash solution were further adsorbed onto a Diaion HP20 (Mitsubishi Chemical) column and washed with pure water. The adsorbed material from the C18 solid-phase extraction column was eluted with a 50 v / v% aqueous ethanol solution. The eluate from the C18 solid-phase extraction column was concentrated to dryness and reconstituted with pure water to obtain B-MRPs. This B-MRP was used to prepare the test samples of Examples 2 and 3.

[0055] The fraction that passed through the Diaion HP20 column was freeze-dried and concentrated, and then dialyzed for approximately 10 hours using a dialysis membrane with a molecular weight of 100 to 500 until the electrical conductivity due to NaCl decreased. The external dialysis solution was replaced and dialyzed for another 20 hours. The external dialysis solution after removing NaCl was freeze-dried and then rehydrated with pure water to obtain F-MRP. This F-MRP was used to prepare the test samples of Examples 2 and 3.

[0056] Quantification of free Maillard reaction products (F-MRP) Quantification of free Maillard reaction products (F-MRP) was performed by LC-MS / MS. The specific procedure is as follows: An equal volume of 6N sulfosalicylic acid was added to the beer-flavored alcoholic beverage or the F-MRP purified in (a) (appropriately diluted to within the quantification range), and the mixture was stirred. The mixture was centrifuged at 13,000 rpm for 5 minutes, and the resulting supernatant was mixed with one-third of the volume of 20% v / v methanol. This mixture was loaded onto a solid-phase extraction column (Bond Elut C18, Agilent Technologies), followed by loading an equal volume of 10% methanol, and the resulting eluate was stirred. The solution was then mixed 1:1 with separately prepared standard solutions (CEL: 0 ppb, 50 ppb, 100 ppb, 200 ppb; CML: 0 ppb, 50 ppb, 100 ppb, 200 ppb; MG-H1: 0 ppb, 100 ppb, 200 ppb, 400 ppb) and subjected to LC-MS / MS under the conditions shown in Tables 4 and 5. The peak areas of the two ions obtained were used to calculate the F-MRP concentration by the standard addition method. The F-MRP concentration was also quantified in Examples 2 to 4 in the same manner. In the present Examples (Examples 1 to 4), the F-MRP concentration refers to the sum of the concentrations of free CML, free CEL, and free MG-H1 (total concentration).

[0057]

[0058]

[0059] E. Quantification of B-bound Maillard Reaction Products (B-MRP) The fractions isolated by the method described in (A) above or B-MRP purified by the method described in (C) above were dialyzed for 24 hours using a 1 kDa dialysis membrane, and the resulting solution was lyophilized. The solution was then dissolved in 0.02 M hydrochloric acid containing pepsin and reacted at 37°C for 24 hours. Subsequently, a Tris buffer solution (pH 8.2) containing pronase E was added, mixed, and reacted at 37°C for 24 hours. Aminopeptidase M and prolidase were then added, mixed, and reacted at 37°C for 24 hours to obtain a reaction solution in which the peptide bond had been cleaved (enzyme-treated). Separately, a buffer solution containing no enzyme was added during these enzymatic reactions to serve as an enzyme blank, and the reaction was repeated three times at 37°C for 24 hours to obtain a reaction solution (without enzyme treatment). Subsequently, each reaction solution was lyophilized and redissolved in ultrapure water. An equal volume of 6N sulfosalicylic acid was added to the mixture, followed by stirring. The mixture was centrifuged at 13,000 rpm for 5 minutes. The resulting supernatant was then mixed with 1 / 3 of the volume of 20% (v / v) methanol. This mixture was then loaded onto a solid-phase extraction column (Bond Elut C18), followed by an equal volume of 10% methanol. The resulting eluate was stirred. It was then mixed 1:1 with separately prepared standard solutions (CEL: 0 ppb, 50 ppb, 100 ppb, 200 ppb; CML: 0 ppb, 50 ppb, 100 ppb, 200 ppb; MG-H1: 0 ppb, 100 ppb, 200 ppb, 400 ppb) and subjected to LC-MS / MS analysis under the same conditions as in (e) above. The difference between the reaction solution (with enzyme treatment) and the reaction solution (without enzyme treatment) was calculated by the standard addition method as the B-MRP concentration in the beverage. Note that the B-MRP concentration was quantified in the same manner in Examples 2 to 4. Furthermore, in the present Examples (Examples 1 to 4), the B-MRP concentration represents the sum of the concentrations of bound CML, bound CEL, and bound MG-H1 (total concentration).

[0060] Example 2: Production and Evaluation of Beer-Taste Alcoholic Beverages (1) In Example 1, an evaluation test was conducted on each test sample of a beer-taste alcoholic beverage (5% alcohol concentration). A. Preparation of Test Samples A beer-taste alcoholic beverage (100% malt, 5% alcohol concentration) of Test Plot 1 was produced in the same manner as in Example 1(1)A. Test Plots 2 to 14 were prepared by adding F-MRP and B-MRP to the beer-taste alcoholic beverage of Test Plot 1 to achieve the concentrations shown in Table 6.

[0061] (i) Evaluation Test An evaluation test was conducted on the test samples of test plots 1 to 14 by five trained panelists. Specifically, the three evaluation items of "full body," "aftertaste," and "degree of intonation" were rated on a scale of 1 to 9 in increments of 0.5, and the average evaluation scores of the five panelists were calculated. Here, "full body" refers to the overall flavor consisting of flavor strength, complexity, and persistence, with a higher score indicating a stronger full body. "Aftertaste" refers to the degree of aftertaste, meaning that the flavor is not lingering while still having a moderate aftertaste, with a higher score indicating a better aftertaste. "Degree of intonation" refers to the degree to which the intonation is commensurate with the overall flavor strength, with a higher score indicating a better degree of intonation. Test plots 2 to 14 were also evaluated based on the evaluation of test plot 1.

[0062] (2) Results The results are shown in Table 6. For beer-taste alcoholic beverages, a full-bodiedness rating of 4.0 or higher indicated a favorable flavor, a refreshing aftertaste rating of 3.0 or higher indicated a good aftertaste, and a desirable intonation rating of 3.5 or higher indicated a favorable intonation rating. Specifically, in all of Test Plots 2 to 14, the "full-bodiedness" rating was 4 points or higher and the "aftertaste" rating was 3.5 or higher, while in Test Plots 3 to 9 and 11 to 14, the "inflation rating" rating was 3.6 or higher. On the other hand, when the B-MRP concentration in Test Plot 10 was 130 ppb, the full-bodiedness rating was 8.4, the refreshing aftertaste rating was 4.5, but the intonation rating was 2.6. These results indicated that beer-taste alcoholic beverages with F-MRP concentrations of 280 to 1,400 ppb and beer-taste alcoholic beverages with F-MRP concentrations of 280 to 1,600 ppb and B-MRP concentrations of 150 to 900 ppb had good "full-bodied flavor," "clean aftertaste," and "degree of intonation."

[0063]

[0064] Furthermore, the test samples in Test Groups 7 and 8 had different compositions containing different concentrations of each component of F-MRP (the total concentration of each component was the same), as shown in Table 7, but similar evaluation results were obtained. These results showed that the "full body," "aftertaste," and "degree of intonation" were good regardless of the components of F-MRP.

[0065]

[0066] Example 3: Production and Evaluation of Beer-Taste Alcoholic Beverage (2) In Example 3, an evaluation test was carried out on each test sample of a beer-taste alcoholic beverage (alcohol concentration 3.5%).

[0067] (1) Method A Preparation of Test Samples A beer-taste alcoholic beverage (malt ratio 100%, alcohol concentration 3.5%) was produced in Test Plot 15 in the same manner as in Example 1(1)A. Test Plots 16 and 17 were prepared by adding F-MRP and B-MRP to the beer-taste alcoholic beverage of Test Plot 15 to achieve the concentrations shown in Table 8.

[0068] B. Evaluation test Evaluation tests were conducted in the same manner as in Example 2 (1) B. Evaluations of test plots 15 to 17 were based on test plot 1.

[0069] (2) Results The results are shown in Table 8. These results indicate that, regardless of the alcohol concentration of a beer-taste alcoholic beverage, when the F-MRP concentration and B-MRP concentration are within predetermined values, the "full-body flavor," "aftertaste," and "degree of intonation" are favorable.

[0070]

[0071] Example 4: Production and evaluation of beer-taste alcoholic beverages (3) In Example 4, test samples of beer-taste alcoholic beverages were produced and evaluation tests were carried out.

[0072] (1) Method A. Production of Test Samples (i) Test Plots 18 to 22 Beer-taste alcoholic beverages (malt ratio 100%, alcohol concentration 5%) were produced in the same manner as in Example 1(1)A for Test Plots 18 to 22. The F-MRP and B-MRP concentrations were as shown in Table 9.

[0073] (ii) Test Plots 23 and 24: The proportion of malt used was adjusted by appropriately adjusting the blending ratio of pulverized barley malt and non-malt grain raw materials (rice or corn). A cellulose-degrading enzyme was added to a mash tank containing hot water maintained at 45 to 70°C, and the temperature was gradually increased to prepare a saccharified solution. The saccharified solution was then filtered to remove malt residue, yielding a wort. Hops were added to the resulting wort, followed by boiling, solid-liquid separation, and cooling to yield a clear wort. Yeast was added, and the fermentation temperature and fermentation time were adjusted. The resulting fermented solution was then filtered to produce a beer-flavored alcoholic beverage (85% malt, 5% alcohol) for Test Plot 23 and a beer-flavored alcoholic beverage (92% malt, 5.5% alcohol) for Test Plot 24. The blending ratio of raw malt, the set temperature, and the holding time for preparing the saccharified solution were appropriately adjusted. The F-MRP and B-MRP concentrations were as shown in Table 9.

[0074] Evaluation test: Evaluation tests were conducted in the same manner as in Example 2 (1) (a). Evaluations of test plots 18 to 24 were based on test plot 1.

[0075] (2) Results The results are shown in Table 9. These results indicate that in beer-taste alcoholic beverages with each malt usage ratio, when the F-MRP concentration and B-MRP concentration were within the specified range, the "full-bodied flavor," "clean aftertaste," and "degree of intonation" were favorable.

[0076]

Claims

1. A beer-flavored alcoholic beverage having a total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) of 280 ppb or more and 1,400 ppb or less.

2. A beer-flavored alcoholic beverage in which the total concentration of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) is 280 ppb or more and 1600 ppb or less, the total concentration of bound CML, bound CEL, and bound MG-H1 is 150 ppb or more and 900 ppb or less, and the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction with a molecular weight of 1060 Da to 3080 Da (gel filtration method for HPLC analysis).

3. A beer-flavored alcoholic beverage according to claim 2, wherein the total concentration of free CML, free CEL, and free MG-H1 is 280 ppb or more and 1500 ppb or less.

4. A beer-flavored alcoholic beverage according to claim 2 or 3, wherein the total concentration of bound CML, bound CEL, and bound MG-H1 is 200 ppb or more and 850 ppb or less.

5. A beer-flavored alcoholic beverage according to claim 1 or 2, in which the malt content is 50% or more.

6. A method for producing a beer-flavored alcoholic beverage, comprising a step of incorporating free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1400 ppb or less.

7. A method for producing a beer-flavored alcoholic beverage, comprising: a step of incorporating free CML, free CEL, and free MG-H1 so that the total concentration is 280 ppb or more and 1600 ppb or less; and a step of incorporating bound CML, bound CEL, and bound MG-H1 so that the total concentration is 150 ppb or more and 900 ppb or less, wherein the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction having a molecular weight of 1060 Da to 3080 Da (gel filtration method for HPLC analysis).

8. A method for improving the flavor of a beer-taste alcoholic beverage, comprising a step of adding free CML, free CEL, and free MG-H1 to the beverage so that the total concentration of the free CML, free CEL, and free MG-H1 is 280 ppb or more and 1400 ppb or less during the production of the beverage.

9. A method for improving the flavor of a beer-taste alcoholic beverage, comprising the steps of: adding free CML, free CEL, and free MG-H1 to the beverage so that the total concentration is 280 ppb or more and 1600 ppb or less; and adding bound CML, bound CEL, and bound MG-H1 to the beverage so that the total concentration is 150 ppb or more and 900 ppb or less, and wherein the bound CML, bound CEL, and bound MG-H1 are contained in a peptide fraction having a molecular weight of 1060 Da to 3080 Da (gel filtration method for HPLC analysis).

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