JP7738465B2 - High-alcohol beverages containing eriocitrin - Google Patents

Description

The present invention relates to a high-alcohol beverage containing eriocitrin and related methods.

With alcoholic beverages, the stimulating sensation and other alcoholic tastes that alcohol has are often a problem. Several methods are known to solve this problem. For example, a method using specific sugars is known (Patent Document 1).

Japanese Patent Application Laid-Open No. 2019-193602

The inventors recognize that beverages containing high amounts of alcohol have a characteristic bitter aftertaste. The objective of the present invention is to reduce the bitter aftertaste caused by alcohol that is characteristic of beverages containing high amounts of alcohol.

As a result of extensive research, the present inventors have found that eriocitrin can reduce the bitter aftertaste of alcohol that is characteristic of beverages containing a high amount of alcohol.
The present invention relates to, but is not limited to, the following:
(1) A beverage having an eriocitrin content of 10 to 60 ppm, a pH in the range of 3.0 to 5.0, and an alcohol content of more than 15 v/v%.
(2) The beverage according to (1), having an alcohol content of 16 to 60 v/v%.
(3) The beverage according to (1) or (2), having a pH in the range of 3.3 to 4.8.
(4) The beverage according to any one of (1) to (3), wherein the limonene content is 20 to 150 ppm.
(5) A beverage according to any one of (1) to (4), containing a citrus flavor or citrus juice.
(6) A method for reducing the bitter aftertaste of alcohol in a beverage having an alcohol content of more than 15 v/v%, the method comprising mixing ingredients so that the beverage contains 10 to 60 ppm of eriocitrin and has a pH in the range of 3.0 to 5.0.

The present invention can reduce the bitter aftertaste of alcohol that is characteristic of high-alcohol beverages.
In this specification, the "bitter aftertaste of alcohol that is characteristic of high-alcohol beverages" refers to the stimulating, bitter taste that lingers on the tongue and is felt in alcoholic beverages that contain a high concentration of alcohol.

The beverages of the present invention and related methods are described below.
Unless otherwise specified, "ppm" used in this specification means ppm by weight/volume (w/v), which is synonymous with "mg/L."

(alcohol)
The beverage of the present invention contains a high alcohol content. The alcohol content exceeds 15 v/v%, preferably 16 to 60 v/v%, and more preferably 16 to 45 v/v%. When the alcohol content is within the above range, the bitter aftertaste that is characteristic of high-alcohol beverages is produced. Note that the term "alcohol" used in this specification refers to ethanol unless otherwise specified.

In this specification, the alcohol content of a beverage can be measured by any known method, for example, using a vibration density meter. Specifically, the beverage is decarbonated by filtration or ultrasonication as necessary to prepare a sample, and the sample is then steam distilled. The density of the resulting distillate is measured and converted using "Table 2: Conversion Table of Alcohol Content, Density (15°C) and Specific Gravity (15/15°C)," an appendix to the National Tax Agency's Prescribed Analysis Methods (National Tax Agency Ordinance No. 6 of 2007, revised June 22, 2007).

The beverage of the present invention may contain alcohol by any means, but typically, the beverage of the present invention contains a distilled spirit, and thereby alcohol. The distilled spirit is not limited by its raw materials or production method. Examples of distilled spirits include whiskey, brandy, spirits (e.g., vodka, rum, tequila, gin, aquavit), neutral spirits, liqueurs, and shochu. Preferably, the distilled spirit is whiskey, brandy, or neutral spirits.

(Eriocitrin)
Eriocitrin is a compound consisting of eriodictyol, a flavanone, and a disaccharide (rutinose).

The beverage of the present invention contains eriocitrin at a content of 10 to 60 ppm, preferably 20 to 60 ppm.
In the present invention, eriocitrin can reduce the bitter aftertaste of alcohol that is specific to high-alcohol beverages.

The eriocitrin content may be measured by any known method such as GC-MS, GC, or HPLC.
Typical analytical conditions for HPLC are shown below.

<HPLC analysis conditions>
The sample beverage was subjected to high performance liquid chromatography (HPLC) under the following conditions. The HPLC analysis conditions were as follows:
Measuring equipment: Prominence (Shimadzu Corporation)
Detector: SPD-M20A (Shimadzu Corporation)
Column: TSKgel ODS-80Ts QA 150 x 4.6 mm, particle size 5 μm (manufactured by Tosoh Corporation)
Column temperature: 40°C
Detection wavelength: 280 nm
Mobile phase: Solution A: ultrapure water: acetonitrile: trifluoroacetic acid = 95:5:0.05
Solution B: ultrapure water: acetonitrile: trifluoroacetic acid = 5:95:0.05
Liquid transfer conditions:

Injection volume: 5μL
(pH)
The pH of the beverage of the present invention is 3.0 to 5.0, preferably 3.3 to 4.8, and more preferably 3.3 to 4.5. In the present invention, when the pH is within these ranges, the after-bitterness can be more effectively reduced.

In this specification, the pH of a beverage means the pH measured in a non-carbonated state.
The pH of the beverage of the present invention may be adjusted by any known method, but for example, the pH can be adjusted by adding an acid component such as citric acid (anhydrous) or phosphoric acid, or an alkaline component such as sodium citrate, as needed.

(limonene)
The beverage of the present invention may contain limonene. As used herein, the term "limonene" refers to d-limonene. The content of limonene is preferably 20 to 150 ppm, more preferably 30 to 120 ppm.

The limonene content may be measured by any known method such as GC-MS, HPLC, etc. Typical analytical conditions for GC-MS are shown below.
<GC-MS analysis conditions>
The sample beverage was subjected to gas chromatography mass spectrometry (GC-MS) under the following conditions:
GC device: Agilent Technologies GC-MSD
GC oven temperature conditions: 40°C (5 min) - 6°C/min - 240°C
Mass spectrometry (MS) conditions Quadrupole setting value: 150
Ion source setting: 230
Area value calculation conditions Total ion mode mass (LOW): 35
Mass (HIGH): 550
Column: DB-WAXETR 60 m, inner diameter 320 μm, film thickness 0.25 μm
Sample pretreatment conditions: 80 μL of sample and internal standard substance (decanoic acid methyl ester 20 ppm
20 μL of alcoholic solution was mixed in a 20 mL screw cap vial. Dynamic headspace conditioning device: Gestell MPS
Adsorbent: TENAX
Sample vaporization temperature: 80°C
Sample vaporization gas supply amount: 3000 ml
Sample vaporization gas supply rate: 100 ml/min
Sample vaporization gas type: nitrogen Peak retention time: components and concentrations are identified by MS analysis.
Standard substance: Limonene (fruit or vegetable juice)
The beverage of the present invention may contain fruit juice and/or vegetable juice. The fruit juice may be in the form of either straight fruit juice, which is obtained by squeezing fruit and using the juice as is, or concentrated fruit juice. Clear or cloudy fruit juice may also be used. Whole fruit juice obtained by crushing the whole fruit, including the outer skin, and removing only particularly hard solids such as seeds, fruit puree obtained by straining fruit, or fruit juice obtained by crushing or extracting the pulp of dried fruit may also be used. Vegetable juice may also be used in the same form as the fruit juice.

The type of fruit juice is not particularly limited, but examples include citrus fruits (orange, Unshu mandarin, grapefruit, lemon, lime, yuzu, iyokan, natsumikan, sudachi, hassaku, ponkan, shiikuwasha, kabosu, etc.), pome fruits (apple, pear, etc.), stone fruits (peach, plum, apricot, plum, cherry, etc.), citrus fruits (grape, black currant, blueberry, etc.), tropical and subtropical fruits (pineapple, guava, banana, mango, lychee, etc.), and fruit-like vegetables (strawberry, melon, watermelon, etc.). These fruit juices may be used alone or in combination of two or more. Examples of vegetable juices include tomato juice, corn juice, pumpkin juice, and carrot juice. Vegetable juices may be used alone or in combination of two or more. Fruit juices and vegetable juices may also be combined.

The content of fruit juice in the beverage of the present invention is not particularly limited, but is typically 0 to 100 w/w %, or less than 10 w/w %, in terms of fruit juice ratio.
In the present invention, the "fruit juice ratio" in a beverage is calculated using the amount of fruit juice (g) blended in 100 ml of beverage using the following conversion formula. The concentration ratio is calculated in accordance with the JAS standard, excluding the sugar refractometer readings of sugars, honey, etc. added to the fruit juice.

Fruit juice percentage (w/w%) = <amount of fruit juice (g)> x <concentration ratio> / 100 mL / <density of beverage> x 100
The vegetable juice content in the beverage of the present invention is not particularly limited, but is typically 0 to 100 w/w %, or less than 10 w/w %. Here, the vegetable juice content is determined in accordance with the fruit juice content converted into the above-mentioned fruit juice percentage.

(Citrus flavor or citrus juice)
The present invention preferably contains a citrus flavor or citrus juice. Examples of citrus fruits include oranges, Unshu mandarins, grapefruits, lemons, limes, yuzu citrus, iyokan citrus, natsumikan citrus, sudachi citrus, hassaku citrus, ponkan citrus, shiikuwasha citrus, and kabosu citrus, with oranges, lemons, grapefruits, and limes being preferred.

(carbon dioxide)
The beverage of the present invention may contain carbon dioxide gas. Carbon dioxide gas can be added to the beverage using methods commonly known to those skilled in the art, including, but not limited to, dissolving carbon dioxide in the beverage under pressure, mixing the carbon dioxide and the beverage in a pipe using a mixer such as a Zühenhagen carbonator, spraying the beverage into a tank filled with carbon dioxide to absorb the carbon dioxide, or mixing the beverage with carbonated water. Carbon dioxide pressure can be adjusted using any of these methods.

When the beverage of the present invention contains carbon dioxide, the carbon dioxide pressure is not particularly limited, but is preferably 0.7 to 4.5 kgf/cm ² , more preferably 0.8 to 2.8 kgf/cm ² . In the present invention, the carbon dioxide pressure can be measured using a gas volume measuring device GVA-500A manufactured by Kyoto Electronics Manufacturing Co., Ltd. For example, the sample temperature is set to 20°C, and the air in the container is degassed (sniffed) using the gas volume measuring device, and the container is shaken, after which the carbon dioxide pressure is measured. In this specification, unless otherwise specified, carbon dioxide pressure refers to the carbon dioxide pressure at 20°C.

(Other ingredients)
The beverage of the present invention may also contain additives that are typically added to beverages, such as flavorings, vitamins, colorings, antioxidants, preservatives, seasonings, extracts, pH adjusters, citric acid, and quality stabilizers, as long as the additives do not impair the effects of the present invention.

(Packaged beverages)
The beverage of the present invention can be provided in a container-packed form. Container forms include, but are not limited to, metal containers such as cans, PET bottles, paper cartons, bottles, pouches, etc. For example, a sterilized container-packed product can be produced by filling a container with the beverage of the present invention and then subjecting it to heat sterilization such as retort sterilization, or by sterilizing the beverage and filling it into a container.

(method)
Another aspect of the present invention is a method for producing a high-alcohol beverage. The method includes a step of mixing ingredients so that the alcohol beverage contains 10 to 60 ppm of eriocitrin and has a pH in the range of 3.0 to 5.0. The ingredients include eriocitrin or an eriocitrin-containing material (such as fruit juice or flavoring), water, and, if necessary, other ingredients such as an acidic or alkaline component for adjusting the pH. The other ingredients are obvious from the above description of the beverage. This method can reduce the bitter aftertaste that is characteristic of high-alcohol beverages, and therefore, in another aspect, also serves as a method for reducing the bitter aftertaste in the beverage.

The method for adjusting the eriocitrin content and pH in a beverage is clear from the above description of the beverage. The timing is not limited. For example, the above steps may be performed simultaneously or separately, or the order of the steps may be reversed. It is sufficient that the final beverage meets the above conditions. Furthermore, the preferred ranges for the content of the above components are as described above for beverages. Furthermore, specific examples and amounts of additional components are as described above for beverages.

(Numerical range)
For clarity, the numerical ranges herein include their endpoints, i.e., lower and upper limits. For example, a range expressed by "from 1 to 2" includes 1 and 2.

The present invention will be explained below based on test examples, but the present invention is not limited to these examples.
Test Example 1: Bitter aftertaste of alcohol in high-alcohol-containing beverages The alcohol content was varied to evaluate the bitter aftertaste of alcohol that is specific to high-alcohol-containing beverages.

Specifically, aqueous alcohol solutions with an alcohol content of 15% v/v or more were prepared (sample beverages), and sensory evaluations were conducted on these. The sensory evaluations were conducted using the following method.

Each sample beverage was tasted by three expert panelists, who evaluated the bitterness of the alcohol aftertaste according to the following criteria, and the average score was calculated.
6 points: no sensation at all, 5 points: almost no sensation, 4 points: hardly any sensation, 3 points: some sensation, 2 points: sensation, 1 point: strong sensation.

Next, the evaluation results were expressed as follows according to the average score:
"-": average score is 5 points or more; "±": average score is 4 points or more but less than 5 points; "+": average score is 3 points or more but less than 4 points; "++": average score is 2 points or more but less than 3 points; "+++": average score is 1 point or more but less than 2 points.

The results are shown in the table below. When the alcohol content was 16% v/v or higher, a distinctive bitter aftertaste was observed.

(Test Example 2) Effect of Eriocitrin Several aqueous alcohol solutions with an alcohol content of 16% v/v or more were prepared, and various concentrations of eriocitrin were added to these to prepare sample beverages, and the effect of eriocitrin on the bitter aftertaste that is characteristic of high-alcohol beverages was confirmed. For comparison, eriocitrin was also added to an aqueous alcohol solution with an alcohol content of 15% v/v to confirm the effect. The pH of the obtained sample beverages was 4.3 to 4.5. Sensory evaluation was performed using the following method.

Each sample beverage was drunk by three expert panelists, who evaluated the effect of reducing the after-bitterness according to the following criteria, and the average score was calculated.
6 points: very strong feeling, 5 points: strong feeling, 4 points: feeling, 3 points: some feeling, 2 points: slight feeling, 1 point: no feeling.

Next, the evaluation results were expressed as follows according to the average score:
"-": average score is 1 point or more but less than 2 points; "±": average score is 2 points or more but less than 3 points; "+": average score is 3 points or more but less than 4 points; "++": average score is 4 points or more but less than 5 points; "+++": average score is 5 points or more.

Samples that received a rating of "+" or higher can be said to have passed the test in terms of improving or reducing the bitter aftertaste of alcohol.
The results are shown in the table below.

When a specific amount of eriocitrin was used, the bitter aftertaste was effectively reduced.
Test Example 3: Effect of pH An aqueous alcohol solution containing 25% (v/v) alcohol and 40 ppm eriocitrin was prepared, and the pH was further adjusted to prepare several sample beverages. The effect of eriocitrin on reducing the bitter aftertaste was confirmed for these beverages. The pH was adjusted using anhydrous citric acid as the acid component and sodium citrate as the alkaline component.

The sensory evaluation was performed using the same method as in Test Example 2. The results are shown in the table below.

Eriocitrin was found to be highly effective within a specific pH range.

Claims (6)

A beverage having an eriocitrin content of 10 to 60 ppm, a pH in the range of 3.0 to 5.0, and an alcohol content of 16 to 60 v/v% . 2. The beverage according to claim 1, having an alcohol content of 16 to 45 v/v%. The beverage according to claim 1 or 2, having a pH in the range of 3.3 to 4.8. The beverage according to any one of claims 1 to 3, wherein the limonene content is 20 to 150 ppm. The beverage according to any one of claims 1 to 4, containing a citrus flavor or citrus juice. A method for reducing the bitter aftertaste of alcohol in a beverage having an alcohol content of 16 to 60 v/v% , the method comprising mixing ingredients so that the beverage contains 10 to 60 ppm of eriocitrin and has a pH in the range of 3.0 to 5.0.