JP7801100B2 - Containerized alcoholic beverages and their manufacturing method - Google Patents

Description

The present invention relates to a bottled alcoholic beverage and a method for producing the same, and in particular to a bottled citrus-flavored alcoholic beverage and a method for producing the same.

Packaged alcoholic beverages, such as chuhai and cocktail-flavored drinks, are known. Packaged alcoholic beverages are typically beverages prepared by adding sweeteners, acidulants, fruit flavors, and the like to alcohol.
Among bottled alcoholic beverages, there are alcoholic beverages that have been imparted with the flavor of citrus fruits by adding citrus juice, citrus extract, or a flavoring having a citrus flavor. Such citrus-flavored beverages are popular with many people because of the distinctive citrus fruit aroma and refreshing acidity.

Packaged alcoholic beverages are typically heat-sterilized during production. In the case of citrus-flavored alcoholic beverages, heat sterilization can reduce the citrus-specific flavor components (e.g., citral, limonene, etc.) or convert them into other components with unpleasant odors, making it difficult to maintain the fresh, pleasant flavor characteristic of citrus. In other words, the citrus-specific flavor components can deteriorate. This deterioration can also occur due to changes over time during storage.

As a technology for preventing the deterioration of flavor components unique to citrus fruits, for example, Patent Document 1 (JP 2008-280539 A) discloses an agent for inhibiting the formation of the deterioration odor of citral or citral-containing products, which contains a solvent extract of at least one species selected from the group consisting of angelica tree, avocado, plantain, semi-fermented tea leaves, sickleberry, and hawthorn.

Furthermore, Patent Document 2 (JP 2001-061461 A) describes that eriocitrin or substances containing eriocitrin exhibit an inhibitory effect on the decomposition of citral.

Furthermore, Patent Document 3 (JP 2018-184600 A) discloses a citral decomposition inhibitor containing a specific plant extract such as Chinese quince extract.

JP 2008-280539 A Japanese Patent Application Laid-Open No. 2001-061461 JP 2018-184600 A

As described in Patent Documents 1 to 3, techniques for using specific ingredients to prevent the deterioration of aroma components specific to citrus fruits, such as citral, are known. However, when such ingredients are used, the added ingredients themselves may affect the taste of the beverage.
Therefore, an object of the present invention is to provide a technology that can suppress the deterioration of citrus flavor without adversely affecting the taste of citrus fruits.

The present inventors have discovered that citronellal has the effect of suppressing the deteriorated odor of citrus flavors, and have completed the present invention. Specifically, the present invention provides the following.
[1] A citrus-flavored bottled alcoholic beverage containing citronellal.
[2] The bottled alcoholic beverage according to [1], wherein the citronellal content is 30 to 3,000 ppb.
[3] A bottled alcoholic beverage according to [1] or [2], having an acidity, converted to citric acid, of 0.20 g/100 ml or more.
[4] A bottled alcoholic beverage according to any one of [1] to [3], containing citrus juice.
[5] A bottled alcoholic beverage according to any one of [1] to [4], containing a Japanese pepper-infused distilled liquor.
[6] The bottled alcoholic beverage according to [5], wherein at least a portion of the citronellal is derived from the Japanese pepper-infused distilled liquor.
[7] A bottled alcoholic beverage according to any one of [1] to [6], having an alcohol content of 0.5 v/v% or more and 9 v/v% or less.
[8] A bottled alcoholic beverage according to any one of [1] to [7], having a sweetness level of 1.0 or more and 7.0 or less.
[9] A bottled alcoholic beverage according to any one of [1] to [8], which is a carbonated beverage.
[10] A method for producing a bottled alcoholic beverage, comprising a step of adding 30 to 3000 ppb of citronellal to a citrus-flavored alcoholic beverage.
[11] A method for improving the flavor of a bottled alcoholic beverage, comprising the step of adding 30 to 3,000 ppb of citronellal to a citrus-flavored alcoholic beverage.

The present invention provides a technology that can suppress the deterioration odor of citrus flavor without adversely affecting the citrus flavor.

An embodiment of the present invention will be described in detail below. The beverage according to this embodiment is a bottled alcoholic beverage with a citrus flavor that contains citronellal.

(citrus flavor)
In this specification, a "citrus-flavored" beverage refers to a beverage to which a citrus flavor has been imparted by some means. The means for imparting the citrus flavor is not particularly limited. For example, the citrus flavor can be imparted by using citrus juice, citrus flavoring, or the like.
Specifically, examples of citrus-flavored beverages include beverages containing citral and/or limonene.
The citral content in the beverage is, for example, 1 to 1000 ppm, preferably 1 to 100 ppm, and more preferably 3 to 30 ppm.
The limonene content in the beverage is, for example, 0.1 to 100 ppm, preferably 0.1 to 50 ppm, and more preferably 0.3 to 10 ppm.

Even when citrus juice is used, it is preferable that the amount of citrus juice used is not too large, for example, 10% by mass or less, preferably 5% by mass or less, more preferably 3% by mass or less, and most preferably 1% by mass or less, calculated as pure citrus juice.
Examples of citrus fruits include oranges, Unshu mandarins, grapefruits, lemons, limes, yuzu, iyokan, natsumikan, hassaku oranges, ponkan oranges, shikuwasa, and kabosu, and are preferably sour citrus fruits. Sour citrus fruits have a strong sour taste, a distinctive fragrance, and a unique refreshing feeling, and are not usually eaten raw but are used primarily as seasonings for flavoring and sourness, such as lemons, limes, yuzu, sudachi, and kabosu.

(citronellal)
Citronellal is used to suppress the deterioration odor of citrus flavors. The chemical name of citronellal is "3,7-dimethyloct-6-en-1-al." Citronellal exists as optically active d- and l-isomers. In this embodiment, "citronellal" encompasses both optically active isomers.

Citronellal also has the effect of imparting a fruit peel feel (a flavor that gives a refreshing and fresh impression, like the feeling you get when you peel a fruit). By using citronellal, it is possible to suppress the stale smell of citrus flavors and also to impart a fruit peel feel, resulting in a beverage with a good citrus flavor.

The citronellal content is, for example, 30 to 3,000 ppb, preferably 30 to 1,000 ppb, more preferably 30 to 500 ppb, and even more preferably 50 to 200 ppb. Within these ranges, the deterioration odor of citrus flavor can be sufficiently suppressed. It also provides a sufficient fruit peel flavor. Furthermore, the taste of citronellal itself is unlikely to affect the beverage.

Citronellal can be obtained, for example, by subjecting essential oils from plants such as harp and spices (such as citronella essential oil, lemon balm essential oil, and Japanese pepper essential oil) to reduced pressure distillation and subsequent purification processes. Alternatively, citronellal can be added to beverages by using a maceration spirit made from plants such as harp and spices. "Matured plant spirit" refers to a spirit obtained by macerating a plant in an alcohol-containing liquid and then distilling the resulting maceration liquid.

(Distilled liquor steeped in Japanese pepper)
In a preferred embodiment, the beverage contains a Japanese pepper-infused spirit. That is, at least a portion of the citronellal is derived from the Japanese pepper-infused spirit. The citronellal content in the Japanese pepper-infused spirit is, for example, 10 to 100 ppm, preferably 30 to 80 ppm.
The amount of the Japanese pepper-infused distilled liquor in the alcoholic beverage is, for example, 0.01 to 3.0 ml/L, preferably 0.03 to 0.5 ml/L.

The Japanese pepper-infused distilled liquor can be prepared, for example, by the following method.
First, Japanese pepper is soaked in an alcohol-containing solution. While the fruit, stem, leaves, etc. of Japanese pepper can be used, dried Japanese pepper kernels are preferred. The amount of Japanese pepper used is, for example, 1 to 100 g, preferably 5 to 40 g, per 1000 mL of alcohol-containing solution. The alcohol-containing solution can have an alcohol content of, for example, 25 vol% or more, preferably 25 to 95 vol%. The soaking time for the Japanese pepper is, for example, 5 to 48 hours, preferably 12 to 30 hours.
Next, the resulting Japanese pepper infusion liquid is distilled. The distillation may be vacuum distillation or atmospheric distillation. The temperature during distillation is, for example, 70°C or less, preferably 50°C or less.
In this manner, a Japanese pepper-infused distilled liquor containing citronellal can be obtained.

(Citronellal analysis method)
The citronellal content can be measured by the following method.
The sample is diluted to an appropriate ratio with ultrapure water. 200 μL of internal standard (10 ppm linalool-d5) is added to 1 mL of the diluted sample, and then the sample is diluted 50 times with ultrapure water. The aroma components of the diluted sample are adsorbed onto Twister (40 ° C, 2 hours), analyzed by GC-MS, and quantified using the internal standard method.
[GC conditions]
Apparatus: Temperature-programmed vaporization inlet (CIS4, manufactured by Gerstel), thermal desorption unit (TDU, manufactured by Gerstel), GC System (7890B, manufactured by Agilent Technologies), Mass Selective Detector (5977, manufactured by Agilent Technologies)
LTM column (1st: DB-WAX, 20 m x 0.18 mm; 0.3 μm, 2nd: DB-5, 10 m x 0.18 mm; 0.4 μm, manufactured by Agilent Technologies)
・TDU: 20℃ (1min) - (720℃/min) -250℃ (3min)
・CIS4: -50℃ (1.5min) - (12℃/sec) -240℃ (45min)
Split ratio: 30:1
・Inlet pressure: 508.28kPa
Vent pressure: 314.11 kPa
1st column temperature: 40 ° C (3 min) - (5 ° C / min) - 180 ° C (0 min)
・ 2nd column temperature: 40 ° C (31 min) - (5 ° C / min) - 180 ° C (0 min)
・MSD: SCAN mode, m/z 29-230, 20Hz, EI
Quantitative ion: citronellal (m/z 154)

(alcohol)
The alcohol content (ethanol concentration) of the alcoholic beverage according to this embodiment is, for example, 0.5 v/v % or more and 9 v/v % or less, preferably 3.0 to 7.5 v/v %.
The alcohol source is not particularly limited. Preferably, the beverage according to this embodiment contains a distilled alcoholic beverage as the alcohol source. For example, 50 vol% or more, preferably 70 vol% or more, and more preferably 90 vol% or more of the total alcohol contained in the beverage is derived from the distilled alcoholic beverage. Preferred examples of the distilled alcoholic beverage include continuously distilled shochu, raw material alcohol, brewer's alcohol, and spirits.

(carbon dioxide pressure)
The alcoholic beverage according to this embodiment is preferably a carbonated beverage, the carbon dioxide pressure of which is, for example, 1.5 to 3.5 gas volumes, preferably 1.7 to 3.0 gas volumes.
"Gas volume" refers to the ratio of the volume of carbon dioxide dissolved in a bottled carbonated alcoholic beverage under standard conditions to the volume of the beverage (using GV as a unit). In practice, 1 GV gas volume is obtained when 1 L of carbon dioxide is dissolved in 1 L of liquid under standard conditions (1 atmosphere, 25°C). "Gas volume" can be obtained by stabilizing a carbonated alcoholic beverage sample under standard conditions (1 atmosphere, 25°C), attaching an internal gas pressure gauge, opening the stopcock once to release gas (sniff), immediately closing the stopcock, and shaking vigorously, and then determining the value when the pressure becomes constant.

(sweetener)
Preferably, the alcoholic beverage contains a sweetener. Examples of sweeteners include sugars and high-intensity sweeteners. Sugars refer to monosaccharides and disaccharides. Examples of monosaccharides include glucose, fructose, and high-fructose corn syrup. Examples of disaccharides include sucrose, maltose, lactose, and isomerized lactose. Examples of high-intensity sweeteners include sucralose, acesulfame potassium, aspartame, and stevia sweetener.

The sweetener is preferably used in an amount such that the sweetness of the alcoholic beverage is 1.0 or more and 7.0 or less, and more preferably 2.0 to 5.0.
The "sweetness of an alcoholic beverage" is a parameter that indicates the degree of sweetness based on the sweetness of sucrose, and represents the sucrose concentration (% by mass) of a sucrose aqueous solution that has the same sweetness as the target beverage. For example, a sweetness of "2" means that the target beverage has the same sweetness as a 2% by mass sucrose aqueous solution.
The sweetness of a beverage can be calculated based on the type and content of sweeteners contained in the beverage. When a beverage contains a sweetener other than sucrose, the sweetness of the beverage can be calculated by multiplying the concentration of the sweetener used by the sweetness of that sweetener. Examples of sweetness values that can be used include the "sweetness" values listed in "Sweetener Directory," published by the Sugar Refining Industry Association in May 1990, pp. 17-18, and "Beverage Terminology Dictionary," published by Beverage Japan Co., Ltd. on June 25, 1999, Reference 11, 4-2, "Classification of Sweeteners, Classification by Sweetness Intensity," column. When values for the same sweetener are listed in multiple documents, the value listed in "Sweetener Directory" takes precedence. When the sweetness values listed in these documents have a range of values, the median value is used as the sweetness.
The sweetness of typical sweeteners is as follows:
Fructose: 1.35
Glucose: 0.65
55% fructose glucose syrup: 1
Acesulfame potassium: 200
Sucralose: 600

(acidulant)
Preferably, the alcoholic beverage contains an acidulant, such as at least one selected from the group consisting of citric acid, trisodium citrate, adipic acid, glucono-delta-lactone, gluconic acid, potassium gluconate, sodium gluconate, succinic acid, monosodium succinate, disodium succinate, sodium acetate, DL-tartaric acid, L-tartaric acid, sodium DL-tartrate, sodium L-tartrate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, fumaric acid, monosodium fumarate, DL-malic acid, sodium DL-malate, and phosphoric acid.

Preferably, the acidity of the alcoholic beverage, calculated as citric acid, is 0.20 g/100 ml or more. The acidity, calculated as citric acid, is more preferably 0.25 to 0.50 g/100 ml, and even more preferably 0.30 to 0.50 g/100 ml. In particular, when the acidity is 0.20 g/100 ml or more, a large amount of deterioration odor derived from citrus flavor is generated, and the deterioration odor masking effect of citronellal is significantly exhibited.
The acidity converted into citric acid is calculated based on the method for measuring acidity specified in the National Tax Agency's Analytical Methods (National Tax Agency Ordinance No. 6 of 2007), page 8, for total acid (free acid). More specifically, the acidity can be measured by the following method.
Accurately measure 1 to 50 ml of sample and dilute it with water as needed. Titrate it with 0.1 mol/L sodium hydroxide solution, set the endpoint to 8.2 on the pH meter, and calculate the pH using the following formula:
(Formula 1): Acidity (%) = A × f × 100 / W × 0.0064
A: Titration volume (ml) of 0.1 mol/L sodium hydroxide solution
f: Titer of 0.1 mol/L sodium hydroxide solution W: Sample weight (g)
In addition, in Equation 1, "0.0064" is the "weight (g) of anhydrous citric acid equivalent to 1 ml of 0.1 mol/L sodium hydroxide solution."

(others)
The alcoholic beverage may contain other ingredients as needed, such as a deterioration odor generation inhibitor, a deterioration odor deodorizer, a colorant, a pH adjuster, an antioxidant, a preservative, a stabilizer, and an emulsifier.

Alcoholic beverages are packaged beverages. There are no particular limitations on the containers, but examples include metal cans, glass bottles, and plastic bottles.

The method for producing an alcoholic beverage according to this embodiment is not particularly limited as long as it includes a step of adding 30 to 3,000 ppb of citronellal to a citrus-flavored alcoholic beverage. For example, a component that imparts a citrus flavor, such as citrus juice, and the like, citronellal, and other components as needed are added to a distilled alcoholic beverage that serves as the alcohol source, and water is added as needed. Carbonation is then carried out as needed, and the resulting liquid is filled into a container and sealed. Heat sterilization is then carried out as needed. This allows an alcoholic beverage to be obtained.
Citronellal may be added as a single ingredient, or may be contained in the beverage by adding a raw material containing citronellal, such as a distilled liquor steeped in Japanese pepper.

To more specifically explain the present invention, examples carried out by the inventors are described below. However, the present invention should not be construed as being limited to the following examples.

(Test 1) Sensory Evaluation Results of Citrus-Flavored Alcoholic Beverages with Added Citronellal A base solution was prepared by mixing brewer's alcohol (ethanol concentration 95 v/v%), 55% fructose glucose liquid sugar, citric acid (anhydrous), trisodium citrate, and citrus flavor according to the formula shown in Table 1. The alcohol content (ethanol concentration) of the base solution was 5.1 v/v%. The acidity, calculated as citric acid, was 0.30 g/100 ml. The sweetness was 4.0. The carbon dioxide pressure was 2.3 gas volumes (GV).
The citrus flavor used contained 3,355 ppm limonene and 36,222 ppm citral. That is, the limonene content in the base solution was about 1 ppm. The citral content in the base solution was about 11 ppm.
Citronellal was added in different amounts to the prepared base liquid to obtain beverages according to Samples 1-1 to 1-7. The compositions of Samples 1-1 to 1-7 are shown in Table 2. Sample 1-1 is the base liquid itself.

The prepared beverages were subjected to a sensory evaluation. Five trained panelists evaluated the citrus-derived stale odor, pleasant peel flavor, and overall citrus flavor. Specifically, the evaluation was based on the following criteria:

"Stale citrus-derived odor"
Each sample was stored at 65° C. for 3 days and then evaluated for flavor. Sample 1-1, to which citronellal was not added, was used as a control (score 0).
+3 points: Much stronger than the control +2 points: Stronger than the control +1 point: Slightly stronger than the control 0 point: Same as the control -1 point: Slightly weaker than the control -2 points: Weaker than the control -3 points: Much weaker than the control

"A pleasant fruit peel feel"
Sample 1-1 was used as a control and evaluated according to the following criteria.
+3 points: Much stronger than the control +2 points: Stronger than the control +1 point: Slightly stronger than the control 0 point: Same as the control -1 point: Slightly weaker than the control -2 points: Weaker than the control -3 points: Much weaker than the control

"Overall rating of citrus flavor"
Sample 1-1 was used as a control and evaluated according to the following criteria.
+3 points: Much better than the target +2 points: Better than the target +1 point: Slightly better than the target 0 points: Same as the target -1 point: Slightly worse than the target -2 points: Worse than the target -3 points: Much worse than the target

The results, along with comments, are shown in Table 2. As shown in Table 2, Samples 1-2 to 1-7 had a weaker citrus-derived aged odor and a stronger, more pleasant fruit peel flavor than Sample 1-1. This confirmed that citronellal has the effect of masking the citrus-derived aged odor and enhancing the pleasant fruit peel flavor. Sample 1-7, which contained 10,000 ppb (10 ppm) of citronellal, had a stronger spicy scent derived from citronellal, resulting in a lower overall rating of citrus flavor. In contrast, Samples 1-2 to 1-6, which contained citronellal in the range of 30 to 3,000 ppb, were less affected by the taste of citronellal itself, unlike Sample 1-7, and received a good overall rating.

(Test 2) Study of Japanese pepper 40 g of Japanese pepper was soaked in 2000 mL of 45% alcohol for a day to obtain Japanese pepper alcohol extract (A).
The resulting Japanese pepper alcohol extract (A) was distilled to obtain Japanese pepper infused distilled liquor (B).
To the base solution used in Test 1, 0.1 v/v % of Japanese pepper alcohol extract (A) and Japanese pepper infused distilled liquor (B) were added, respectively, and the flavor was confirmed.
As a result, when the Japanese pepper alcohol extract (A) was used, the pungent taste and aroma specific to Japanese pepper was imparted, and the citrus flavor was lost.
On the other hand, when the Japanese pepper infused distilled liquor (B) was added, the Japanese pepper flavor was not felt as much, and the fresh citrus flavor was felt more strongly, improving the palatability.
In other words, it was found that by adding a distilled liquor steeped in Japanese pepper to an alcoholic beverage having a citrus flavor, the palatability of the citrus flavor can be increased without making the pungent smell and flavor of Japanese pepper too noticeable.

(Test 3) Study of a citrus-flavored alcoholic beverage using Japanese pepper infused distilled liquor Using the findings obtained in Test 2, the amount of Japanese pepper infused distilled liquor to be used was studied.
The Japanese pepper infused spirit (B) obtained in Test 2 contained citronellal at a concentration of 53 ppm. Therefore, different amounts of Japanese pepper infused spirit (B) were added to the base liquid to obtain beverages according to Samples 2-1 to 2-6. Table 3 shows the compositions of Samples 2-1 to 2-6. Sample 2-1 is the base liquid itself.
Then, the prepared samples 2-1 to 2-6 were subjected to a sensory evaluation test according to the same criteria as in Test 1.

Table 3 shows the results of the sensory evaluation together with the comments obtained.
Compared to sample 2-1, samples 2-2 to 2-6 had a weaker citrus-derived deteriorated odor and a stronger, more pleasant fruit peel feel. In addition, samples 2-2 to 2-6 also received a higher overall rating than sample 2-1.

Claims (10)

A citrus-flavored bottled alcoholic beverage containing citronellal,
The citronellal content is 30 to 10,000 ppb,
The citral content is 1 to 100 ppm and/or the limonene content is 0.1 to 100 ppm,
A bottled alcoholic beverage having an alcohol content of 0.5 v/v% or more and 9 v/v% or less. The bottled alcoholic beverage according to claim 1, having a citronellal content of 30 to 3,000 ppb. The bottled alcoholic beverage according to claim 1 or 2, having an acidity, converted to citric acid, of 0.20 g/100 ml or more. The bottled alcoholic beverage according to any one of claims 1 to 3, containing citrus fruit juice. The bottled alcoholic beverage according to any one of claims 1 to 4, containing a distilled liquor infused with Japanese pepper. The bottled alcoholic beverage according to claim 5, wherein at least a portion of the citronellal is derived from the Japanese pepper-infused distilled liquor. The bottled alcoholic beverage according to any one of claims 1 to 6, having a sweetness level of 1.0 or more and 7.0 or less. The bottled alcoholic beverage according to any one of claims 1 to 7, which is a carbonated beverage. A method for producing a bottled alcoholic beverage, comprising a step of adding 30 to 3000 ppb of citronellal to a citrus-flavored alcoholic beverage,
The containerized alcoholic beverage has a citral content of 1 to 100 ppm and/or a limonene content of 0.1 to 100 ppm,
A production method in which the alcohol content of the bottled alcoholic beverage is 0.5 v/v% or more and 9 v/v% or less. A method for improving the flavor of a bottled alcoholic beverage, comprising the step of adding 30 to 3,000 ppb of citronellal to a citrus-flavored alcoholic beverage,
The containerized alcoholic beverage has a citral content of 1 to 100 ppm and/or a limonene content of 0.1 to 100 ppm,
A flavor improving method for a bottled alcoholic beverage having an alcohol content of 0.5 v/v% or more and 9 v/v% or less.