JP7529488B2 - Non-fermented beer-flavored beverage and its manufacturing method - Google Patents

Description

The present invention relates to a non-fermented beer-flavored beverage, and in particular to a non-fermented beer-flavored beverage with enhanced body.

A non-fermented beer-flavored beverage is a beverage that has a beer-like flavor and taste by adding beer flavorings and hop flavorings, which are composed of aroma components contained in beer, to a base drinking liquid. A non-fermented beer-flavored beverage may be an alcoholic beverage with an alcohol content of 1% by volume or more, or may be a so-called non-alcoholic beverage or low-alcohol beverage with an alcohol content of less than 1% by volume.

The production of non-fermented beer-flavored beverages does not require a fermentation process or fermentation equipment. Therefore, non-fermented beer-flavored beverages are suitable for mass production at low cost. However, it is not yet clear what ingredients and in what amounts should be mixed to reproduce a beer-like flavor, and research and development is still ongoing.

In Example 1 of Patent Document 1, it is described that the main aroma components contained in beer were analyzed and 2-acetyl-1-pyrroline was identified as one of them. It is also described that when 2-acetyl-1-pyrroline is added to a beer-like beverage, it enhances the aroma of nuts and popcorn and the beer-like flavor.

Patent Document 2 describes a flavor improver for beer-like beverages that contains 2-acetyl-2-thiazoline. Example 1 describes that when 2-acetyl-1-pyrroline is added to a beer-like beverage, it reduces sourness and enhances the grain aroma, nutty aroma, and beer-like flavor.

Regarding Non-Patent Document 1, the description will first be excerpted and then explained.
Page 391, lines 15-13 from the bottom, Abstract: "Using GC-MS techniques, we have identified for the first time several compounds with bread-like aroma characteristics and very low flavor thresholds in light and dark malts."

Page 393, lines 6-17, preface: "When malt is roasted or wort is boiled...[omitted]... hitherto unknown compounds with roasted, popcorn, and bready aromas are produced. Odor substances with bready aroma properties are of central importance for beer. These odor substances are the main components of aroma in malt, but they can also be the cause of bad aromas in heat-pasteurized, high-temperature stored and stagnant beers."

Page 401, lines 12-24, Characterization of bready aroma components in beer: "Bready aroma components are detected in particular when beer is subjected to thermal stress or improperly transported and stored. In the case of pasteurization at too high a temperature and too long an action time, a particularly pronounced impression of "off-flavor" is felt. FIG. 11 shows a gas chromatogram of an "overpasteurized" beer showing a typical bready aroma. It can be seen that several chromatogram parts with organoleptic properties occur, showing retention times almost identical to the characterized proline derivatives. Using preparative GC, capillary-GC-NSD and capillary-GC-MS, four 2-acetyltetrahydropyridines could be characterized as indicator components."

Figure 1 shows a gas chromatogram of "overheat-sterilized" beer, which shows a typical bread-like bad aroma, as shown in Figure 11 of Non-Patent Document 1. The heat-sterilization conditions referred to here are 80°C for 0.5 to 20 hours (page 393, lines 19-18 from the bottom). When heated for a long period of time at such high temperatures, beer deteriorates.

In short, Non-Patent Document 1 describes that (1) when malt is heated, compounds with popcorn-like or bread-like aromas are produced, (2) the aromas are "off-flavors," or strange odors, that are felt in beer that has deteriorated due to thermal stress, and (3) the analysis results of the off-flavors are shown in the gas chromatogram in Figure 11.

As shown in Figure 1 here, Figure 11 in Non-Patent Document 1 shows the off-flavor analysis results for 2-acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine, etc.

WO2014/119065 JP 2016-86792 A

R. Tressl et al., "Bildung von Verbindungen mit brotigem Aromacharakter in Malz und Bier", EBC Congress 1981

Non-fermented beer-flavored beverages do not completely reproduce the types and composition of components produced during the fermentation process, and as a result have a weaker body than fermented beer-flavored beverages. Body is the quality that gives the drinker a drinking sensation that is accompanied by a "rich" or "profound" feeling. Body is a drinking sensation that includes flavor qualities that can also be described as "full-bodied," "depth," or "thickness."

The full-bodiedness of food and beverages can generally be enhanced by increasing their sweetness. In the production of non-fermented beer-flavored beverages, for example, sweeteners have traditionally been used to impart a certain degree of fullness. However, the drinking sensation, such as the strength of the fullness, varies depending not only on taste but also on other senses, such as smell and touch.

On the other hand, if sweeteners are used to enhance the body of a non-fermented beer-flavored beverage, the sweetness also becomes stronger, and the sweetness lingers after drinking, which can have a negative effect on the crispness that is characteristic of beer.

The present invention aims to solve the above problems, and its purpose is to provide a non-fermented beer-flavored beverage that has a sufficient body while suppressing the sweetness that lingers after drinking.

The present invention comprises at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, and a sweetener,
The sweetness is 3.0 to 15.0,
The present invention provides a non-fermented beer-taste beverage having a concentration of the 2-acetyltetrahydropyridine compound of 0.1 μg/L or more.

In one embodiment, the concentration of the 2-acetyltetrahydropyridine compound is 200.0 μg/l or less.

In one embodiment, the concentration of the 2-acetyltetrahydropyridine compound is 0.5 μg/l or more.

In one embodiment, the non-fermented beer-flavored beverage does not contain malt as an ingredient.

In one embodiment, the non-fermented beer-flavored beverage has a sweetness level of 10.0 or less.

In one embodiment, the 2-acetyltetrahydropyridine compound is derived from an added flavoring.

The present invention also provides a method for producing a non-fermented beer-taste beverage, which includes a step of adding at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, to a non-fermented beer-taste beverage containing a sweetener and having a sweetness level of 3.0 to 15.0, in an amount such that the concentration of the compound is 0.1 μg/l or more.

The present invention also provides a method for enhancing the body of a non-fermented beer-taste beverage and suppressing the sweetness remaining after consumption, the method comprising the step of adding at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, to a non-fermented beer-taste beverage containing a sweetener and having a sweetness level of 3.0 to 15.0, in an amount such that the concentration of the compound is 0.1 μg/l or more.

The present invention provides a non-fermented beer-flavored beverage that has a sufficient body while suppressing the sweetness that lingers after drinking.

FIG. 11 of Non-Patent Document 1 is a gas chromatogram of "overpasteurized" beer exhibiting a typical bready off-flavor.

<Sweeteners>
The sweetener contained in the non-fermented beer-flavored beverage of the present invention is a seasoning used for the purpose of sweetening food. The sweetener includes natural sweeteners and artificial sweeteners. Specific examples of sweeteners include glucose, fructose, maltose, sucrose, oligosaccharides, sugar, honey, maple syrup, agave syrup, palm sugar, molasses, starch syrup, glucose-fructose liquid sugar, stevia, xylitol, sorbitol, licorice extract, Monk fruit extract, trehalose, maltitol, palatinose, thaumatin, glycerin, curculin, monellin, monatin, erythritol, hernandurcin, aspartame, neotame, alanine, glycine, advantame, acesulfame K, sucralose, and saccharin. Sucrose, stevia, and acesulfame K are often used in beverages such as non-fermented beer-flavored beverages, and can be preferably used in the present invention. Glycine is an amino acid that has a sweet taste, but also has the effect of improving sleep quality and antibacterial action, and is therefore preferably used.

By adding a sweetener to the non-fermented beer-flavored beverage, the richness of the non-fermented beer-flavored beverage is enhanced and a full-bodied taste is imparted. The sweetener is added in an amount that results in a sweetness level of the non-fermented beer-flavored beverage of 3.0 to 15.0. If the sweetness level of the non-fermented beer-flavored beverage is less than 3.0, the full-bodied taste will be insufficient, and if it exceeds 15.0, a strong sweetness will linger after drinking. The sweetness level of the non-fermented beer-flavored beverage is preferably 4.0 to 10.0, and more preferably 5.0 to 8.0.

Sweetness is a measure of sweetness intensity. Sucrose is used as the standard substance, and sweetness is determined from the ratio of concentrations that show the same sweetness intensity as a given concentration of sucrose, or the ratio to the threshold value of sucrose determined under the same conditions. The sweetness of a beverage is calculated as the sum of the products of the concentrations (mg/l) of each sweet substance contained in the beverage and the sweetness intensity.

In this case, the sweetness of sucrose is set to 1, and the sweetness of each sweet substance can be determined using known values (Maebashi Kenji: Basic Knowledge of Sweetness, Journal of the Brewing Society of Japan (2011), Vol. 106, No. 12, pp. 818-825; McMurry Organic Chemistry (7th ed.) p. 988; Sugar Refining Association, "Comprehensive List of Sweeteners," All About Sugar, etc.). Examples of sweetness of sweet substances are shown in Table 1.

<2-Acetyltetrahydropyridine Compound>
The 2-acetyltetrahydropyridine compounds contained in the non-fermented beer-taste beverage of the present invention, i.e., 2-acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine, are aroma components, and therefore the taste quality of the non-fermented beer-taste beverage does not change significantly by using these compounds.

2-acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine are tautomers. Therefore, when 2-acetyl-3,4,5,6-tetrahydropyridine is added to a non-fermented beer-flavored beverage containing a sweetener, the non-fermented beer-flavored beverage generally contains both 2-acetyl-3,4,5,6-tetrahydropyridine and 2-acetyl-1,4,5,6-tetrahydropyridine. The ratio of their presence is determined by factors such as the surrounding pH environment.

In this specification, the 2-acetyltetrahydropyridine compound may be referred to as "ATHP." ATHP may be a commercially available fragrance.

By adding ATHP to a non-fermented beer-flavored beverage, the sweetness remaining after consumption of the non-fermented beer-flavored beverage is suppressed and the full-bodied taste is enhanced. The amount of ATHP contained is adjusted appropriately taking into consideration the type of non-fermented beer-flavored beverage whose sweetness is to be suppressed or the target sweetness level. ATHP can be added to the non-fermented beer-flavored beverage, for example, by adding a flavoring containing ATHP.

In general, ATHP is added to a non-fermented beer-taste beverage in an amount that results in an ATHP concentration of 0.1 to 200 μg/l. If the ATHP concentration in the non-fermented beer-taste beverage is less than 0.1 μg/l, the sweetness is more easily felt after drinking, and if it exceeds 200 μg/l, the aroma derived from ATHP becomes stronger, resulting in a poor balance of the overall flavor. The effect of suppressing the sweetness after drinking does not change significantly even if the ATHP concentration is increased beyond 200 μg/l. Furthermore, if the ATHP concentration is increased beyond 1 ppm, an off-flavor similar to that of cooked bread may be felt, as described in Non-Patent Document 1. The ATHP concentration in a non-fermented beer-taste beverage is preferably 0.5 to 100 μg/l, more preferably 1.0 to 80 μg/l, and even more preferably 4 to 50 μg/l.

<Non-fermented beer-flavored beverage>
A non-fermented beer-flavored beverage containing ATHP is a beverage that is not fermented during the manufacturing process, contains a sweetener, and exhibits a flavor reminiscent of beer. Specific examples of non-fermented beer-flavored beverages containing ATHP include, for example, alcoholic beverages such as happoshu, miscellaneous alcoholic beverages, liqueurs, and spirits, and non-alcoholic beverages such as low-alcohol beverages and carbonated beverages with an alcohol content of less than 1.0% by volume. Low-alcohol beer-flavored beverages and carbonated beer-flavored beverages do not have an alcoholic stimulation when drunk, so that the richness and full body are not easily felt. Therefore, these are suitable for non-fermented beer-flavored beverages containing ATHP.

A non-fermented beer-flavored beverage is produced, for example, by the following method. That is, a starchy raw material such as malt is saccharified to obtain a sugar solution. The sugar solution is mixed with auxiliary raw materials such as sweeteners, flavorings, grain extracts, dietary fiber, bittering agents, colorings, and hops, and alcohol, if necessary, to obtain a prepared liquid. The order in which each raw material is mixed with the sugar solution is not particularly limited. Carbon dioxide gas is then added to the prepared liquid. The addition of carbon dioxide gas can be carried out by a conventional method. For example, the prepared liquid obtained in the preparation process may be mixed with carbonated water, or carbon dioxide gas may be added directly to the prepared liquid obtained in the preparation process and dissolved therein.

The sugar solution is produced by adding ground malt or the like as needed, and starchy raw materials such as barley, rice, cornstarch, etc., to warm water, mixing and heating, and using mainly malt enzymes to saccharify the starch, preferably to maltose, etc. The ground malt and starchy raw materials such as barley, rice, cornstarch, etc., may be those normally used in the production of conventional beer-flavored beverages, and used in the amounts normally used.

A sugar solution of starchy raw materials containing malt may have an unpleasant grassy odor. Therefore, the ratio of malt used to the total amount of solid starchy raw materials is preferably 66% by mass or less, more preferably 50% by mass or less, and even more preferably 25% by mass or less, and it is particularly preferable that no malt is used as a raw material. The ratio of malt used is measured in accordance with the provisions of the Liquor Tax Act. When preparing a sugar solution from a starchy raw material other than malt, it is preferable to add a composition containing amylase after adding warm water to the starchy raw material.

Specific examples of non-fermented beer-like beverages that do not use malt or have a malt usage ratio of less than 25% by mass include low-sugar beer-flavored beverages such as low-sugar happoshu. For example, when producing a non-fermented low-sugar beer-flavored beverage, the blend may be produced using raw water instead of a sugar solution.

When ATHP is added to a non-fermented beer-taste beverage, there is no restriction on the timing, and it can be added at any appropriate step in the manufacturing method of the non-fermented beer-taste beverage. However, the earlier the addition step is, the more likely it is that the concentrations of the individual components of the compound group will fluctuate, so it is preferable to add it at a later step. ATHP may be added, for example, to the manufactured non-fermented beer-taste beverage.

The non-fermented beer-flavored beverage containing ATHP may contain ATHP derived from malt or the like. The concentration of this compound group in commercially available non-fermented beer-flavored beverages that contain malt is, for example, 3.0 to 4.0 μg/l. On the other hand, the concentration of this compound group in non-fermented beer-flavored beverages that do not contain malt is, for example, 0.5 μg/l or less.

The present invention will be explained in more detail with reference to the following examples, but the present invention is not limited to these.

Example 1
A non-fermented beer-taste beverage 1 (product name "Style Free Perfect" manufactured by Asahi Breweries, Ltd., alcohol content: 6%, sweetness: 0, ATHP concentration: 0.0 μg/l) was prepared. The sweetness and ATHP concentration of non-fermented beer-taste beverage 1 were determined as follows.

<Sweetener Analysis Method>
The beer-taste beverage was diluted 20-fold with distilled water and analyzed by LC/MS/MS. Separation was performed using an LC/MS/MS (AB-SCIEX 3200QTRAP) with an ACQUITY UPLC BEH C18 1.7 μm, 2.1 × 100 mm (waters) column. The mobile phase conditions were A solution: 0.1% formic acid water, B solution: 0.1% formic acid acetonitrile, (B%, t): (10%, 8 min), (28%, 11 min), (70%, 18 min), and the analysis was performed under the following conditions: acesulfame K transitions: 162→82 (collision energy: -18 V), sucralose 395→359 (collision energy: -20 (V)), aspartame 293→261 (collision energy: -16 (V)). Quantitative analysis was performed using a calibration curve prepared by adding a standard, and the sweetness was calculated as the sum of the products of the concentrations (mg/l) of each sweet component and the known sweetness values.

<ATHP Analysis Method>
50 μL of an internal standard solution (4 μg/mL ATHP stable isotope), 200 μL of formic acid, and 10 mL of distilled water were added to 20 g of the beer-flavored beverage, and the mixture was loaded onto OASIS MCX 500 mg/6 ml (Waters).
After washing the column with 5 mL of 1% formic acid water, elution was performed with 5 mL of 2% ammonia-methanol, and the eluate was diluted two-fold with distilled water and then analyzed by LC/MS/MS.

LC/MS/MS (AB-SCIEX 5500QTRAP) was used, and separation was performed using an ACQUITY UPLC BEH C18 1.7 μm, 2.1 x 100 mm (waters) column. The mobile phase conditions were A solution: 10 mM ammonium bicarbonate, B solution: acetonitrile, (B%, t): (10%, 1 min), (50%, 6 min), and the ATHP transition was 126 → 84 (collision energy: 23 V). Quantitation was performed using a calibration curve created by adding a standard.

Acesulfame K ("Sanet", manufactured by Kirin Kyowa Foods Co., Ltd., sweetness level: 200) and ATHP were added to non-fermented beer-taste beverage 1 to change their content. The sweetness of the beverage after addition was determined by converting the amount of Acesulfame K added to a concentration (mg/l), multiplying this concentration by the sweetness level of Acesulfame K, 200, and adding the resulting value to the sweetness of non-fermented beer-taste beverage 1. The ATHP concentration of the beverage after addition was determined by converting the amount of Acesulfame K added to a concentration (μg/l), and adding this concentration to the ATHP concentration of non-fermented beer-taste beverage 1.

Next, a sensory evaluation of the produced non-fermented beer-taste beverages was conducted. The evaluation items were suppression of after-drink sweetness and enhancement of body. Three beer expert evaluators tasted each non-fermented beer-taste beverage and scored it based on the following evaluation criteria. The average of the sensory scores of the three evaluators was used as the evaluation score. The evaluation results are shown in Tables 2 and 3.

Evaluation criteria: Suppression of sweetness after drinking Rating 1: Not noticeable (no difference from control)
2: Somewhat effective 3: Effective 4: Somewhat strongly effective 5: Strongly effective 6: Very strongly effective 7: Very strongly effective

From the evaluation results in Table 2, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or higher, particularly 0.5 μg/l or higher, the after-drink sweetness is suppressed.

Evaluation criteria: Strengthening of body feeling Rating 1: Very weak 7: Very strong

From the evaluation results in Table 3, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the body sensation is enhanced.

Example 2
A non-fermented beer-taste beverage was produced in the same manner as in Example 1, except that stevia ("Rebaudio J-100" manufactured by Morita Chemical Industry Co., Ltd., sweetness level: 360) was used as the sweetener instead of acesulfame K. The sweetness level and ATHP concentration were determined, and a sensory evaluation was performed. The results are shown in Tables 4 and 5, respectively.

From the evaluation results in Table 4, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the after-drink sweetness is suppressed.

From the evaluation results in Table 5, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the body sensation is enhanced.

Example 3
A non-fermented beer-taste beverage was produced in the same manner as in Example 1, except that sucrose (sweetness level: 1) was used as the sweetener instead of acesulfame K, and the sweetness level and ATHP concentration were determined and a sensory evaluation was performed. The results are shown in Tables 6 and 7, respectively.

From the evaluation results in Table 6, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the after-drink sweetness is suppressed.

From the evaluation results in Table 7, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the body sensation is enhanced.

Example 4
A non-fermented beer-flavored beverage was produced in the same manner as in Example 1, except that glycine (AHS Glycine RC, manufactured by Ajinomoto Healthy Supply Co., Inc., sweetness level 0.9) was used as the sweetener instead of acesulfame K. The sweetness level and ATHP concentration were determined, and a sensory evaluation was performed. The results are shown in Tables 8 and 9, respectively.

From the evaluation results in Table 8, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the after-drink sweetness is suppressed.

From the evaluation results in Table 11, it can be seen that in samples with a sweetness level of 3 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the body sensation is enhanced.

Example 4
A non-fermented beer-taste beverage 2 ("Dry Zero" (product name) manufactured by Asahi Breweries, Ltd., alcohol content: 0.00%, sweetness: 5.9, ATHP concentration: 0.0 μg/l) was prepared. A non-fermented beer-taste beverage was produced in the same manner as in Example 1, except that non-fermented beer-taste beverage 2 was used instead of non-fermented beer-taste beverage 1, and the sweetness and ATHP concentration were determined and a sensory evaluation was performed. The results are shown in Tables 10 and 11, respectively.

From the evaluation results in Table 10, it can be seen that in samples with a sweetness level of 7 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the after-drink sweetness is suppressed.

From the evaluation results in Table 11, it can be seen that in samples with a sweetness level of 7 to 15, when the ATHP concentration is 0.1 μg/l or more, particularly 0.5 μg/l or more, the body sensation is enhanced.

Claims (8)

The composition comprises at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, and a sweetener;
The sweetness is 3.0 to 15.0,
A non-fermented beer-flavor beverage, in which the concentration of the 2-acetyltetrahydropyridine compound is 0.1 μg/L or more. The non-fermented beer-flavor beverage according to claim 1, wherein the concentration of the 2-acetyltetrahydropyridine compound is 200.0 μg/l or less. The non-fermented beer-flavor beverage according to claim 1 or 2, wherein the concentration of the 2-acetyltetrahydropyridine compound is 0.5 μg/l or more. The non-fermented beer-flavored beverage according to any one of claims 1 to 3, which does not contain malt as an ingredient. The non-fermented beer-flavored beverage according to any one of claims 1 to 4, having a sweetness level of 10.0 or less. The non-fermented beer-taste beverage according to any one of claims 1 to 5, wherein the 2-acetyltetrahydropyridine compound is derived from an added flavoring. A method for producing a non-fermented beer-flavored beverage, comprising the step of adding at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, to a non-fermented beer-flavored beverage containing a sweetener and having a sweetness level of 3.0 to 15.0, in an amount such that the concentration of the compound is 0.1 μg/l or more. A method for enhancing the body of a non-fermented beer-flavored beverage and suppressing the sweetness remaining after consumption, comprising the step of adding at least one 2-acetyltetrahydropyridine compound selected from the group consisting of 2-acetyl-3,4,5,6-tetrahydropyridine and its tautomer, 2-acetyl-1,4,5,6-tetrahydropyridine, to a non-fermented beer-flavored beverage containing a sweetener and having a sweetness level of 3.0 to 15.0, in an amount such that the concentration of the compound is 0.1 μg/l or more.

Images