Classifications

• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
  • C12C5/00—Other raw materials for the preparation of beer
  • C12C5/02—Additives for beer
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
  • C12G3/00—Preparation of other alcoholic beverages
  • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs

Definitions

• the present invention relates to a beer-flavored alcoholic beverage and a method for producing the same.
• Patent Document 1 In beer, it is necessary to impart a moderate richness to the drink. Techniques that achieve this effect include the addition of alcohols, aldehydes, various sweeteners, etc. (Patent Document 1).
• Non-Patent Document 1 peptides with molecular weights of 1,000 to 5,000 Da, which are products of the Maillard reaction, contribute to enhancing richness (Non-Patent Document 1), but the specific contributing components have not been identified.
• the inventors focused on the problem that when attempting to impart richness to beer-flavored alcoholic beverages, particularly those with a high malt ratio, the cost of raw materials increases due to the use of extracts, and excessive heating can cause a rough texture that impairs the flavor balance.
• MRPs Maillard reaction products
• the present invention therefore provides a beer-flavored alcoholic beverage with enhanced richness and reduced roughness, and a method for producing the same.
• the present invention includes the following inventions.
• a beer-flavored alcoholic beverage in which the total content of free carboxymethyllysine (CML), free carboxyethyllysine (CEL), and free methylglyoxal-derived hydroimidazolone-1 (MG-H1) in the beverage is 500 to 903 ppb, and the total content of bound CML, bound CEL, and bound MG-H1 in the beverage is 200 ppb or less;
• a beer-taste alcoholic beverage wherein the bound CML, bound CEL and bound MG-H1 are contained in a peptide fraction having a molecular weight of 400 to 3,000 Da.
• a beer-taste alcoholic beverage according to (1) above in which the total content of free CML, free CEL, and free MG-H1 in the beverage is 540 to 903 ppb.
• a beer-taste alcoholic beverage according to (1) or (2) above in which the total content of bound CML, bound CEL, and bound MG-H1 in the beverage is 185 ppb or less.
• a method for producing a beer-taste alcoholic beverage comprising the steps of: the total content of free CML, free CEL and free MG-H1 in the beverage is adjusted to 500-903 ppb, and the total content of bound CML, bound CEL and bound MG-H1 in the beverage is adjusted to 200 ppb or less; The method, wherein the bound CML, bound CEL and bound MG-H1 are contained in a peptide fraction having a molecular weight of 400 to 3,000 Da. (6) The method according to (5) above, wherein the malt usage ratio is 50 to 100% by mass.
• a method for enhancing richness and reducing roughness in a beer-taste alcoholic beverage comprising the steps of: the total content of free CML, free CEL and free MG-H1 in the beverage is adjusted to 500-903 ppb, and the total content of bound CML, bound CEL and bound MG-H1 in the beverage is adjusted to 200 ppb or less; The method, wherein the bound CML, bound CEL and bound MG-H1 are contained in a peptide fraction having a molecular weight of 400 to 3,000 Da.
• the present invention it is possible to enhance the richness and reduce roughness in a beer-flavored alcoholic beverage.
• the present invention is particularly advantageous in that such effects can be obtained in beer-flavored alcoholic beverages that contain a high proportion of malt.
• FIG. 1 is a bubble plot showing the magnitude of full-bodiedness as represented by the sensory evaluation scores for samples having various F-MRP and B-MRP concentrations.
• FIG. 2 is a bubble plot showing the magnitude of roughness as represented by the sensory evaluation scores for samples having various F-MRP and B-MRP concentrations.
• FIG. 3 is a calibration curve showing the relationship between retention time and molecular weight in HPLC gel filtration analysis, prepared using peptides with known molecular weights.
• CML carboxymethyllysine
• CEL carboxyethyllysine
• MG-H1 methylglyoxal-derived hydroimidazolone-1
• the three free substances above exist in the beverage as the above structures themselves or in a partially ionized state.
• the three bound substances above exist in the beverage as residues contained in peptide fractions with a molecular weight of 400-3,000 Da, and have glycated lysine or arginine side chains.
• the amounts and concentrations of the above substances shown in this invention are the masses and concentrations of compounds having the above structures for both the free and bound forms.
• the three free substances above are sometimes referred to as the "three free active ingredients”
• the three bound substances above are sometimes referred to as the "three bound active ingredients”.
• beer-taste alcoholic beverage refers to beer (an alcoholic beverage obtained by fermenting malt and hops as ingredients with brewer's yeast) or an alcoholic beverage having a flavor similar to that of beer.
• alcoholic beverage refers to a beverage having an alcohol (ethanol) concentration of 1 v/v% or more.
• the beer-taste alcoholic beverage of the present invention is preferably a fermented beverage to which hops are used as an ingredient to impart a hop aroma.
• the beer-taste alcoholic beverage of the present invention is preferably a fermented malt beverage, that is, a beverage using at least malt as an ingredient.
• fermented malt beverages examples include beer, happoshu, and liqueur (e.g., beverages classified as "liqueur (sparkling) (2)" under the Liquor Tax Act).
• the beer-taste alcoholic beverage of the present invention is preferably a fermented malt beverage with a malt content of 0% by mass or more and 100% by mass or less, more preferably 25% by mass or more and 100% by mass or less, and even more preferably 50% by mass or more and 100% by mass or less.
• “Malt usage ratio” refers to the value calculated in accordance with the Liquor Tax Act and the Interpretation Notice on Liquor-related Administrative Laws and Regulations, etc., which came into effect on April 1, 2018.
• “richness” refers to a flavor determined by a comprehensive evaluation of the strength, complexity, and persistence of the flavor.
• roughness refers to the irritation and stickiness that remains on the tongue.
• the unit "ppm” is synonymous with “mg/L” and the unit “ppb” is synonymous with “ ⁇ g/L”.
• the beer-flavored alcoholic beverage of the present invention has a total content of three free active ingredients and a total content of three bound active ingredients in the beverage each within a specified range.
• Such a beer-flavored alcoholic beverage can be obtained by adjusting the total content of the three free active ingredients and the total content of the three bound active ingredients during production.
• Specific means for adjusting the concentrations of the three free active ingredients and the three bound active ingredients are not particularly limited, and examples include adding the three free active ingredients or the bound active ingredients, increasing or decreasing the amount of raw materials containing the three free active ingredients or the bound active ingredients, increasing or decreasing the amount of raw materials that generate the three free active ingredients or the bound active ingredients in the final product, and adjusting the concentration of a substance that is converted to the three free active ingredients or the bound active ingredients by fermentation with yeast.
• the total content of the three free active ingredients in the beer-taste alcoholic beverage of the present invention is 500-903 ppb, and preferably 540-903 ppb.
• the three free active ingredients may be derived from the raw materials, may be added separately from the plant raw materials, or may be produced by fermentation.
• the concentration of the three free active ingredients can be controlled, for example, by controlling the composition of the raw materials and the fermentation conditions. According to one embodiment of the present invention, the upper limit of the total content of the three free active ingredients is 850 ppb.
• the total content of the three bound active ingredients in the beer-taste alcoholic beverage of the present invention is 200 ppb or less, and preferably 185 ppb or less.
• the lower limit of the total content of the three bound active ingredients in the beer-taste alcoholic beverage is not particularly limited as long as the effects of the present invention are achieved, and may be 0 ppb.
• the three bound active ingredients may be derived from the raw materials, may be added separately from the plant raw materials, or may be produced by fermentation.
• the concentration of the three bound active ingredients can be controlled, for example, by controlling the composition of the raw materials and the fermentation conditions.
• the upper limit of the total content of the three bound active ingredients is 170 ppb.
• the amount of the three free and bound active ingredients in a beer-flavored alcoholic beverage can be determined by LC-MS/MS analysis as described in the Examples below. Furthermore, for more accurate concentration measurements, it is desirable to use a calibration curve created based on the measured values of several control samples with known concentrations.
• the alcohol concentration in the beer-taste alcoholic beverage of the present invention is not particularly limited, but is preferably more than 1% by volume (v/v%), more preferably 2% by volume (v/v%) or more, even more preferably 3% by volume (v/v%) or more, even more preferably 3.5% by volume or more, and even more preferably 4% by volume or more.
• the upper limit of the alcohol concentration in the beer-taste alcoholic beverage is not particularly limited as long as the effects of the present invention are achieved, but is, for example, 20% by volume, preferably 10% by volume, and more preferably 7% by volume.
• the alcohol concentration in the beer-taste alcoholic beverage of the present invention is preferably 2-10% by volume or less, more preferably 3-10% by volume or less, and even more preferably 3-7% by volume.
• the beer-taste alcoholic beverage of the present invention can be a carbonated beverage.
• the carbon dioxide pressure can be adjusted as desired, for example, within the range of 0.05 to 0.4 MPa (gas pressure at 20°C).
• the pH of the beer-taste alcoholic beverage of the present invention can be adjusted to, for example, 2.0 to 5.0, preferably 2.3 to 4.8, and more preferably 2.9 to 4.8.
• the pH of the beverage can be easily measured using a commercially available pH meter.
• the beer-taste alcoholic beverage of the present invention is preferably provided as a packaged beverage.
• the container used for the beer-taste alcoholic beverage of the present invention may be any container normally used for filling beverages, such as a metal can, a barrel container, a plastic bottle (e.g., a PET bottle, a cup), a paper container, a bottle, or a pouch container, with metal cans, barrel containers, plastic bottles (e.g., a PET bottle), or bottles being preferred.
• Nitrogen can also be added to the beer-taste alcoholic beverage of the present invention in addition to carbon dioxide gas.
• the nitrogen concentration can be adjusted as appropriate according to preference.
• the form of nitrogen used when adding nitrogen to the beverage can 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) (gauge pressure). There are many purposes for adding nitrogen, for example, to make the foam of the beer-taste alcoholic beverage creamier.
• the container used for the beer-taste alcoholic beverage of the present invention may contain a hollow insert, separate from the container, for example a so-called "widget” that is used to efficiently supply nitrogen or the like to the beverage in the container.
• the widget may have a variety of shapes, such as a sphere or a cube, and any shape may be used.
• the widget may be either fixed or unfixed to the container. Before the container is opened, the widget contains gas, including pressurized nitrogen gas, that is in equilibrium with the total pressure of the container, which is higher than the atmosphere. When the container is opened from this state to serve the beverage, the empty space in which no beverage is present is released, resulting in a pressure difference and causing the nitrogen sealed in the widget to be sprayed into the container. It is desirable that the container and the widget are arranged in such a way that the nitrogen in the widget is sprayed directly into the liquid when the container is opened.
• methods for incorporating nitrogen into the beer-taste alcoholic beverage of the present invention include spraying nitrogen using a small object, and using nitrogen that is originally contained in the beverage, or by dripping liquid nitrogen or the like into the container to fill the empty space with nitrogen and saturate the beverage with nitrogen. This dripping of liquid nitrogen can be done at the same time that the beer-taste alcoholic beverage is sealed in the container.
• These methods can produce the so-called cascade foam phenomenon in the beer-taste alcoholic beverage of the present invention, generating more distinctive foam.
• the beer-taste alcoholic beverage of the present invention can be produced according to a normal method for producing a beer-taste alcoholic beverage, except for adjusting the concentrations of the three free active ingredients and the three bound active ingredients in the beverage.
• a normal production method includes, for example, a method of fermenting a pre-fermentation liquid containing at least water and malt, that is, a method of adding fermentation yeast to wort (pre-fermentation liquid) prepared from brewing raw materials such as malt to carry out fermentation, storing the fermented liquid at low temperature as desired, and then removing the yeast by a filtration process.
• hops can be added at any step.
• the amount of hops added can typically be adjusted to 0.1 to 5 g/L relative to the volume of the pre-fermentation liquid in the fermentation step, preferably 0.1 to 2 g/L, and more preferably 0.2 to 1.5 g/L.
• brewing ingredients in addition to malt, hops, and water, other brewing ingredients can be used, such as rice, corn, sorghum, potatoes, starch, sugars (e.g., liquid sugar), fruit, coriander, and other auxiliary ingredients stipulated 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 regulators, and fermentation aids.
• ungerminated wheat e.g., ungerminated barley (including extracts), ungerminated wheat (including extracts)
• ungerminated wheat can also be used as a brewing ingredient.
• a method for enhancing richness and reducing roughness in a beer-taste alcoholic beverage in which the total content of free CML, free CEL and free MG-H1 in the beverage is adjusted to 500-903 ppb, and the total content of bound CML, bound CEL and bound MG-H1 in the beverage is adjusted to 200 ppb or less.
• the bound CML, bound CEL and bound MG-H1 are contained in a peptide fraction having a molecular weight of 400-3,000 Da.
• the concentration of free Maillard reaction products is the sum of the concentrations of free CML, free CEL, and free MG-H1.
• concentration of bound Maillard reaction products is the sum of the concentrations of bound CML, bound CEL, and bound MG-H1.
• Example 1 Identification of Maillard reaction product fractions imparting appropriate body to beer-taste beverages (1) Preparation of beer-taste beverages Milled barley malt and polysaccharide decomposing enzymes were added to a brewing tank containing hot water maintained at 50-60°C, and the temperature was raised stepwise to prepare a saccharified liquid. The saccharified liquid was then filtered to remove malt residue, and wort was obtained. Hops were added to the obtained wort, and the water was boiled, followed by solid-liquid separation treatment, and cooled to obtain clear wort. Yeast was added, and the fermentation temperature and fermentation time were adjusted, and the obtained fermented liquid was filtered to prepare test beverages, which were beers.
• evaluation item 1 the strength of flavor (an overall evaluation consisting of flavor strength, complexity, and duration) was rated on a nine-point scale from 1 (weak flavor) to 9 (strong flavor).
• evaluation item 2 roughness (irritation or stickiness on the tongue) was rated on a nine-point scale from 1 (weak) to 9 (strong).
• evaluation item 3 negative elements in aftertaste and bitterness were qualitatively evaluated, and the number of panelists who pointed them out was recorded. For the sensory evaluation, commercially available sample 1 was used as the control.
• samples 1 and 2 which are commercially available beer-flavored alcoholic beverages, had low levels of full-bodiedness, negative aftertaste/bitterness, and roughness.
• Sample 11 had a significantly stronger full-bodied flavor than sample 1, but also had a strong negative aftertaste and bitterness, and could not be described as having a good flavor.
• Sample 4 was rougher than sample 1 and showed a tendency to be more irritating and sticky.
• Figure 1 shows a graph plotting the results of the sensory evaluation of full-bodiedness. Samples for which the full-bodiedness score was 5.0 or higher and less than half of the panelists reported a negative aftertaste or bitterness are boxed.
• Figure 2 shows a graph plotting the results of the sensory evaluation of roughness. Samples with a roughness score of less than 6.0 are boxed.
• Tables 2 and 3 show the combinations of samples with roughly equal sums of F-MRP or B-MRP but different compositions of individual components, and the results of the sensory evaluation.
• sample 6 contained more free CEL and CML and less MG-H1, but the total amount of the three components and the strength of the flavor were about the same.
• Sample 7 had more bound MG-H1 and less CEL than sample 2, but the total amount of the three components and the roughness were about the same.
• Example 2 Purification of free and bound MRP fractions (1) Quantification of free Maillard reaction products (F-MRP) Quantification of free Maillard reaction products fractions was performed by LC-MS/MS. Ultrapure water was added to the liquid sample or lyophilized product to redissolve it. An equal amount of 6N sulfosalicylic acid was added thereto and stirred, and centrifuged at 13,000 rpm for 5 minutes. The resulting supernatant was taken and mixed with 1/3 the amount of 20% (v/v) methanol. The analysis sample was loaded onto a solid-phase extraction column (Bond Elute C18, Agilent Technologies), followed by loading an equal amount of 10% methanol, and the resulting eluate was mixed together and stirred.
• F-MRP free Maillard reaction products
• the sample was mixed 1:1 with a separately prepared standard solution (CEL, CML: 0, 50, 100, 200 ppb/MG-H1: 0, 100, 200, 400 ppb) and subjected to LC-MS/MS under the following conditions.
• CEL, CML: 0, 50, 100, 200 ppb/MG-H1: 0, 100, 200, 400 ppb a separately prepared standard solution
• the peak areas of the two ions obtained were used to calculate the concentrations of Maillard reaction products in the samples by the standard addition method.
• B-MRP Quantitation of bound Maillard reaction products
• the fractions collected in (2) were dialyzed with a 1 kDa dialysis membrane for 24 hours, and the internal solution was freeze-dried. Then, they were dissolved in 0.02 M hydrochloric acid containing pepsin, and reacted at 37°C for 24 hours. Next, Tris buffer (pH 8.2) containing pronase E was added and mixed, and reacted at 37°C for 24 hours. Furthermore, aminopeptidase M and prolidase were added and mixed, and reacted at 37°C for 24 hours to cleave the peptide bonds. A blank was used to add a buffer containing no enzyme during this enzyme reaction, and the reaction was carried out three times at 37°C for 24 hours.
• the sample was freeze-dried and redissolved in ultrapure water. An equal amount of 6N sulfosalicylic acid was added thereto, stirred, and centrifuged at 13,000 rpm for 5 minutes. The resulting supernatant was collected and mixed with 1/3 of the amount of 20% (v/v) methanol.
• the analytical sample was loaded onto a solid-phase extraction column (Bond Elute C18), followed by loading an equal volume of 10% methanol, and the resulting eluates were combined and stirred.
• the sample was then mixed 1:1 with a separately prepared standard solution (CEL, CML: 0, 50, 100, 200 ppb/MG-H1: 0, 100, 200, 400 ppb) and subjected to LC-MS/MS under the same conditions as in (1), and the concentration of bound Maillard reaction products in the sample was calculated by the standard addition method.
• CEL CML: 0, 50, 100, 200 ppb/MG-H1: 0, 100, 200, 400 ppb
• Example 3 Tasting with the addition of purified MRP fraction (1) Purification of Maillard reaction product fraction From the test product corresponding to the scope of the invention described in Example 1, the fraction obtained by the method of Example 2 (2) was adsorbed onto a C18 solid-phase extraction column (Bond Elute C18). After washing with pure water, the obtained non-stick fraction and washing solution were further adsorbed onto a Diaion HP20 (manufactured by Mitsubishi Chemical) column, and washed with pure water. The adsorbate of the C18 solid-phase extraction column was eluted with a 50% (v/v) aqueous ethanol solution. The eluate of the C18 solid-phase extraction column was concentrated to dryness, and then rehydrated with pure water to obtain a purified product of bound Maillard reaction products.
• the fraction that passed through the Diaion HP20 column was freeze-dried and concentrated, and then dialyzed for about 10 hours using a dialysis membrane with a molecular weight of 100 to 500 until the electrical conductivity due to NaCl decreased.
• the dialysis external solution was replaced and dialysis was continued for another 20 hours. After removing NaCl, the dialysis external solution was freeze-dried and then rehydrated with pure water to obtain a concentrated solution. This was used as a purified product of free Maillard reaction products.
• B-MRP bound Maillard reaction products
• F-MRP free Maillard reaction products
• Samples 12 to 14 which have a B-MRP concentration of 200 ppb or less, were found to have low roughness with a sensory evaluation score of 6.0 or less.
• Example 2(4) Tasting with the addition of purified F-MRP fraction Similarly, the purified free Maillard reaction product fraction obtained in Example 2(4) was added to Sample 1 so as to achieve the Maillard reaction product concentration shown in Table 10, and a sensory evaluation was performed by a panel of five trained individuals using the intensity of body as an indicator.
• the F-MRP concentration range in which these samples received favorable ratings matched the concentration range of the test product in Example 1, which received a favorable rating for full-bodied flavor.

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• 2023
  • 2023-12-07 WO PCT/JP2023/043845 patent/WO2024122615A1/ja not_active Ceased
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