JPH0725784B2 - Alcohol stimulating odor warming agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Field The present invention comprises a β-D-glucopyranoside derivative,
An alcohol stimulating odor reducing agent mainly used in cosmetics, foods and drinks, and an alcohol stimulating odor reducing agent composed of a β-D-glucopyranoside derivative and alcohol.

More specifically, various foods and drinks, for example, an alcohol solution added for the purpose of antiseptic or flavor addition, or an alcoholic beverage, by accelerating the aging action, a substance capable of alleviating an irritating odor of alcohol, and The present invention relates to an alcohol irritating odor alleviator, in which the irritating odor of alcohol is alleviated by adding a β-D-glucopyranoside derivative to these alcohols.

(Prior Art) Conventionally, ethanol is used as a preservative in a fish paste product represented by raw noodles such as buckwheat noodles, udon noodles, or kamaboko. However, although the above-mentioned effect as a preservative for foods is exhibited, ethanol has a peculiar irritating odor, so that development of alcohol with reduced irritating odor is strongly desired.

Therefore, in order to solve this problem, some proposals have been conventionally made. For example, when ethanol is used as a preservative for raw noodles such as Chinese noodles, udon, and buckwheat, spices such as garlic and wetting agents such as sorbit are added to the raw material powder to produce raw noodles without alcohol odor. Method (JP-A-57-202259) or a method for improving the flavor of distilled liquor or the like in which the tannin extracted from the wood of a beech family plant is added to and mixed with distilled liquor (JP-A-58-202259).
No. 61-195683) or a method of obtaining ethyl alcohols having no irritating offensive odor by mixing ethyl alcohol and ground pumpkin seeds and / or the outer shell thereof, filtering and distilling the mixture. Proposals such as Kai 62-29962) are known.

(Problems to be Solved by the Invention) However, the effect of removing the pungent odor of alcohol in the above-mentioned conventional proposals is not always satisfactory, and the present situation is that there is a strong demand for the development of a more excellent alcohol pungent odor eliminator. Is.

Therefore, in view of the above circumstances, the present inventors have earnestly conducted research to develop a more excellent alcohol pungent emollient. As a result, they have found that the β-D-glucopyranoside derivative represented by the following formula (a) can effectively alleviate or remove the pungent odor of alcohol, and completed the present invention.

Therefore, an object of the present invention is to effectively remove or alleviate the pungent odor of alcohol used for food and drink, and an alcohol pungent emollient capable of increasing the commercial value thereof, and
It is an object of the present invention to provide an alcohol stimulating odor-improving agent whose commercial value is enhanced by adding the alcohol stimulating odor-eliminating agent.

(Means for Solving the Problems) The present invention provides the following formula (a): (In the formula, R represents an alkyl group having 2 to 8 carbon atoms), an alcohol stimulating odor relaxing agent comprising a β-D-glucopyranoside derivative and an alcohol stimulating odor relaxing comprising a β-D-glucopyranoside derivative and an alcohol. It is an agent.

The β-D-glucopyranoside derivative of the above formula (a) used in the present invention (hereinafter referred to as β-D-alkylglucoside) is known to be contained in, for example, a component of sake in a very small amount. Is a compound of (Agricultural
and Biological Chemistry Vol.35 No.3p.321〜324,19
(See 71), as such, is a semi-solid compound that is almost odorless and has a slight sweetness and bitterness.

There are many reports on the synthesis method of the β-D-alkylglucoside of the above formula (a), and according to these methods,
It is very easy to obtain, for example Rocznikichemi
Volume 49, No. 12, pages 2113 to 2115 It can be manufactured inexpensively and easily by the method described in 1975.

Specific examples of the β-D-alkyl glucoside of the above formula (a) include, for example, β-D-ethyl glucoside, β-D-propyl glucoside, β-D-butyl glucoside, β-D.
-Isobutylglucoside, β-D-pentylglucoside, β-D-3-methylbutylglucoside, β-D-hexylglucoside, β-D-4-methylpentylglucoside, β-D-heptylglucoside, β-D-4 -Methylhexyl glucoside, β-D-5-methylhexyl glucoside, β-D-4-ethylpentyl glucoside, β
Examples thereof include -D-octyl glucoside, β-D-6-methylheptyl glucoside, β-D-5-methylheptyl glucoside, and β-D-5,5-dimethylhexyl glucoside.

The effective amount of β-D-alkyl glucoside of the present invention is
There is no particular limitation, and it is appropriately selected depending on the usage form.
A range of 0.1 to 30% by weight is often adopted. If it is less than 0.1% by weight, the effect tends to decrease, and
When it exceeds 30% by weight, the taste of β-D-alkylglucoside tends to appear strongly, so use of the above range is preferred.

The alcoholic solution referred to in the present invention means, for example, kamaboko,
Alcohol used for the purpose of preserving or adding flavor to fish paste products such as fish ham and sausages, raw noodles such as Chinese noodles, udon, and buckwheat, and confectionery such as cakes containing aluminum packs. Specifically, in addition to commercially available 95 ° undenatured ethanol, distilled liquor such as shochu, whiskey, brandy, rum, and brewed liquor such as sake, wine, fruit liquor and beer can be mentioned.

Utilization mode of the alcohol irritating odor reducing agent of the present invention, or
The method for producing an alcohol stimulating odor reducing agent for alleviating alcohol stimulating odor is very simple, and it is only necessary to dissolve an appropriate amount of the β-D-alkylglucoside of the above formula (a) in the above alcohols.

(Function) Alcohol is usually marketed in a form containing a small amount of water. In addition, when producing foods and drinks, it is almost the case that the raw material itself contains water or that water is used as the raw material.

The present invention provides β-
It is promoted by D-alkyl glucoside.

Embodiments of the present invention will be described in more detail below with reference to examples.

(Production Example) Production Example of Alkyl Glucoside To 2 g of glucose, 100 ml of 95 ° undenatured ethanol and 0.5 ml of sulfuric acid were added and refluxed for 4 hours. This solution is distilled water 300ml
After diluting with and neutralized with barium carbonate, excess barium carbonate was removed by filtration. This filtrate is Amberlite CG
It was applied to a −120 (H ⁺ ) column and then to a CG-4B (AcO ⁻ ) column to adsorb and remove ionic components. Adding distilled water again after evaporation, this time Dowex 1 (OH ^-) column, QAE-Se
It was treated with a phadex column and concentrated by evaporation to obtain a syrupy α, β-D-ethylglucoside.

The β-form was obtained by acetylating the α-β mixture, fractionating the mixture on a silica gel column, and deacetylating it.

(Examples and Comparative Examples) The sensory evaluation test method for the pungent odor mitigating effect of alcohol and the instrumental analysis method for the aging effect are as follows.

(1) Sensory evaluation test method of alcohol stimulating odor mitigating effect 200 g of an alcoholic aqueous solution was prepared, and after dividing it into two equal parts, β-D-alkyl glucoside was added to make an example, and the other was made a control example. After pouring them into separate 200 ml beakers, whether or not the pungent odor of alcohol was alleviated was compared and evaluated by 5 expert panels repeated 5 times.

(2) Instrumental analysis evaluation test method for aging effect NMR as a method for investigating the solution structure of an ethanol aqueous solution
It is known that the method using (nuclear magnetic resonance) is effective. [Journal of the Japanese Society of Agricultural Chemistry Vol.60 No.3 191-197 (198
6), Proceedings of the 50th Annual Meeting of the Chemical Society of Japan p. 9 (198
5)] Referring to these reports, when the alcohol concentration is low (about 20% by weight or less), it is ¹⁷ O (oxygen atom), and when the alcohol concentration is high (about 40% by weight or more), it is ¹ H (hydrogen atom).
Was measured and the data before and after aging were compared.

Each measurement is made by JEOL JNM GX 270 FT-NMR Spe
It is performed using a ctrometer, and the procedure is generally a method of measuring NMR. For example, the Journal of the Japanese Society of Agricultural Chemistry Vol. 60 No. 3 191-1.
97 (1986).

(Evaluation method) A solution containing the glucoside derivative or the like referred to in the present invention was comparatively evaluated on the basis of the alcohol-water solution. ¹⁷ Evaluation using O signal: For water molecules of each solution, O
The full width at half maximum of the signal of the H group was measured, and it was determined that there was an aging effect when it became narrow as shown in FIG. Evaluation using ¹ H signal: As shown in FIG. 2, when the OH group signals of alcohol and water molecules were fused, it was considered that there was a maturing effect.

Example 1 and Comparative Example 1 300 g of an aqueous alcohol solution containing 20% by weight of 95 ° undenatured ethanol and 80% by weight of water was prepared. This had a strong alcohol pungent odor. This alcoholic aqueous solution was divided into 3 equal parts, and 5% by weight of α-D-ethylglucoside and β
Comparative Example 1 and Example 1 were prepared by dissolving 5% by weight of -D-ethyl glucoside. Nothing was added to the remaining aqueous alcohol solution, which was designated as Control Example 1. Table 1 shows the sensory evaluation test and the instrumental analysis evaluation test by ¹⁷ O-NMR (36.50 MHz) for Comparative Example 1, Comparative Example 1, and Example 1.

According to this, the effect did not appear in the α form.

Example 2 200 g of an aqueous alcohol solution containing 10% by weight of 95 ° undenatured ethanol and 90% by weight of water was prepared. This alcoholic aqueous solution is divided into two equal parts, and 1% by weight of D-ethylglucoside (α-form 70
%, Β-body 30%) was dissolved (Example 2), and the remaining aqueous alcohol solution was used as Control Example 2.

The results of evaluation as in Example 1 are shown in Table 2.

From this table, it was found that even a mixture of α and β is effective as long as it contains the β form.

Example 3 200 g of an aqueous alcohol solution containing 10% by weight of 95 ° undenatured ethanol and 90% by weight of water was prepared. This aqueous alcohol solution was divided into two equal parts, and 3% by weight of β-D-octylglucoside was dissolved in one of them (Example 3). The remaining aqueous alcohol solution was used as Control Example 3.
And

The results of evaluation as in Example 1 are shown in Table 3.

As a result, it was found that an alkyl glucoside having 8 carbon atoms was also effective.

Comparative Example 2 200 g of an aqueous alcohol solution containing 20% by weight of 95 ° undenatured ethanol and 80% by weight of water was prepared. This aqueous alcohol solution was divided into two equal parts, and 3% by weight of β-D-methylglucoside was dissolved in one of them (Comparative Example 2). The remaining aqueous alcohol solution was used as Control Example 4.

The results of evaluation as in Example 1 are shown in Table 4.

As a result, it was found that the alkyl glucoside having 1 carbon atom has no effect.

Example 4 200 g of an aqueous alcohol solution containing 30% by weight of 95 ° undenatured ethanol and 70% by weight of water was prepared. This aqueous alcohol solution was divided into two equal parts, and 3% by weight of β-D-ethylglucoside was dissolved in one of them (Example 4). The remaining aqueous alcohol solution was used as Control Example 5.

Table 5 shows the results of a sensory test conducted on these aqueous alcohol solutions.

As a result, it was found that the effect was obtained even when the alcohol concentration was 30% by weight.

Examples 5 and 6 300 g of an aqueous alcohol solution of 95% undenatured ethanol 50% by weight and water 50% by weight was prepared. This alcoholic aqueous solution is divided into 3 equal parts, each containing β-D-ethylglucoside 1.3% by weight.
Was dissolved (Examples 5 and 6), and the remaining aqueous alcohol solution was used as Control Example 6.

Sensory evaluation test and ¹ H
Table 6 shows the results of the instrumental analysis and evaluation test by -NMR (270 MHz).

As a result, it was found that the effect was obtained even when the alcohol concentration was 50% by weight.

Examples 7-9 Flour 100 g, water 31 g, and β-D-ethyl glucoside 0.5 g
After adding and mixing 5 g of an ethanol solution containing, thoroughly kneading to produce raw noodle strings according to a conventional method, and then bagging them 37
It was stored at 0 ° C for 1 week (Example 7).

In addition, in the above example, β-D-butylglucoside (Example 8) and β-D-hexylglucoside (Example 9) were used in place of β-D-ethylglucoside, and Example 7 was used.
Raw noodle strings were produced in the same manner as above, and were preserved in the same manner.

On the other hand, 5 g of ethanol not containing the above β-D-alkylglucoside was added to produce a raw noodle string in exactly the same manner as in the above Example, which was also stored at 37 ° C., which was designated as Control Example 7.

Table 7 shows the results of a sensory evaluation test comparing the alcohol pungent odors of Control Example 7 and Examples 7, 8, and 9.

As a result, it was found that the raw noodle strings using the alcohol irritating odor reducing agent of the present invention had an improvement in the alcohol irritating odor as compared with Control Example 7.

Control Example 8 A synthetic sake having the following composition was produced by a conventional synthetic sake producing technique, and was designated as Control Example 8.

Alcohol (30 wt%) 670 ml Starch syrup (40 wt%) 5.6 g Sodium glutamate 220 mg Succinic acid 1.1 g Lactic acid (75 wt%) 0.33 mg Potassium acid phosphate 66 mg Calcium acid phosphate 60 mg Sodium succinate 220 mg Sodium chloride 160 mg Alanine 100 mg Glycine 110 mg Tartrazine 0.8 mg Caramel Trace amount Water was added to the above composition to make the total amount 1 liter.

Example 10 A synthetic sake according to the present invention was obtained in the same manner as in Example 10, except that 10 g of D-ethylglucopyranoside (70% α, 30% β) was added to the alcohol used in Comparative Example 8. And

As a result of sensory evaluation of alcohol pungent odor, Example 10
It was confirmed that the alcohol irritating odor was remarkably reduced.

(Effects of the Invention) By adding the alcohol pungent odor reducing agent of the present invention to alcohol, the pungent odor of alcohol is alleviated and an excellent maturing sensation is imparted. Therefore, directly distilled liquor, brewed liquor,
When used in other alcoholic beverages, the pungent odor of alcohol is alleviated as compared with the conventional ones, and it can be consumed as a rich alcoholic beverage with a rich taste. Further, for example, fish paste products such as kamaboko, fish ham and sausage, raw noodles such as Chinese noodles, udon, buckwheat, and confectionery such as cakes packed in aluminum packs are used for the purpose of preserving or adding flavor. When used for the above, not only the effect as a preservative but also the above foods in which the pungent odor of alcohol is alleviated can be obtained.

[Brief description of drawings]

FIG. 1 shows the measured ¹⁷ O-NMR of an aqueous alcohol solution. Signal of OH group of water molecule before aging Signal of OH group of water molecule after aging FIG. 2 shows ¹ H-NMR of an aqueous alcohol solution. Left figure: Alcoholic aqueous solution before aging Right figure: Alcoholic aqueous solution after aging Signal of OH group of alcohol molecule Signal of OH group of water molecule Fusion signal of two OH groups

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication location A61K 7/00 W 7/46 Z Examiner Shinji Matsuura

Claims (2)

[Claims] 1. The following formula (a): (In the formula, R represents an alkyl group having 2 to 8 carbon atoms), an alcohol irritating odor reducing agent comprising a β-D-glucopyranoside derivative. 2. The alcohol pungent odor alleviator according to claim 1, which comprises a β-D-glucopyranoside derivative represented by the above formula (a) and an alcohol.