阅读说明：本技术 一种用于酒类饮品粘度检测的荧光化合物及其制备和应用 (Fluorescent compound for detecting viscosity of wine beverage and preparation and application thereof ) 是由 徐灵峰 刘利民 隋岩 韩润林 吴魁 黄伟 黄春芳 黄艳蓉 孙立和 于 2021-01-25 设计创作，主要内容包括：本发明公开了一种用于酒类饮品粘度检测的荧光化合物及其制备和应用,该荧光化合物具有如下结构：本发明制备的荧光化合物本身具有AIE特性,且能够在溶液粘度变大的情况下,使得原来处于激发态的电子通过辐射跃迁的方式返回基态,进而释放出荧光信号,使得粘度检测可视化,更加便捷、高效、快速、原位的检测酒类饮品中粘度的变化,对食品安全监测起到了一定的作用。(The invention discloses a fluorescent compound for detecting the viscosity of wine drinks, and a preparation method and an application thereof, wherein the fluorescent compound has the following structure: the fluorescent compound prepared by the invention has AIE characteristics, and can make electrons in an original excited state return to a ground state in a radiation transition mode under the condition that the solution viscosity is increased, so that a fluorescent signal is released, the viscosity detection is visualized, the viscosity change in the alcoholic beverage can be detected more conveniently, efficiently, quickly and in situ, and the food safety monitoring is realizedThe function of the medicine is determined.)

1. A fluorescent compound for detecting the viscosity of wine drinks is characterized by having the following structural formula:

。

2. the method of claim 1, comprising the steps of:

(1) dissolving 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde in ethanol, and uniformly stirring by ultrasonic waves to obtain a solution 1;

(2) dissolving 4-methoxyaniline in ethanol, and uniformly stirring by ultrasonic waves to obtain a solution 2;

(3) and mixing the solution 1 and the solution 2, uniformly stirring, heating for reaction, and then precipitating and purifying to obtain dark yellow powder, namely the fluorescent compound.

3. The method of claim 2, wherein the molar ratio of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-carbaldehyde in step (1) to 4-methoxyaniline in step (2) is 1 (1-20).

4. The method for preparing a fluorescent compound for use in viscosity measurement of alcoholic beverages of claim 2, wherein the mass concentration of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-carbaldehyde in the step (1) is 1M to 10M; the mass concentration of the 4-methoxyaniline in the step (2) is 1M-100M.

5. The method for preparing a fluorescent compound used for detecting the viscosity of an alcoholic beverage as claimed in claim 2, wherein the heating temperature in the step (3) is 25 ℃ to 78 ℃, and the heating reaction time is 1 h to 48 h.

6. The method of claim 2, wherein the precipitation purification step in step (3) comprises: removing the reaction solvent, washing with ethanol, standing for 2-3 times, and vacuum drying.

7. Use of the fluorescent compound of claim 1 in the viscosity detection of an alcoholic beverage.

8. The use of a fluorescent compound according to claim 7 in the detection of the viscosity of an alcoholic beverage, for the detection of the degree of deterioration of an alcoholic beverage.

9. The use of a fluorescent compound according to claim 7 or 8 in the viscosity detection of alcoholic beverages, wherein the substance concentration of said fluorescent compound is 1-20 μ M.

10. The use of the fluorescent compound of claim 7 or 8 in the viscosity detection of an alcoholic beverage, wherein the alcoholic beverage is beer, red wine or wine.

Technical Field

The invention relates to the technical field of food safety monitoring, in particular to a fluorescent compound for detecting the viscosity of an alcoholic beverage as well as preparation and application thereof.

Background

Wine, an alcoholic beverage made by fermentation using starch or sugar-containing substances such as grains, fruits, etc., has a long brewing history and a constantly innovative brewing process, and various kinds of alcoholic beverages have been derived, including: beer, wine, white spirit, yellow wine, and the like, and even some medicated liquors have been developed for health care and adjuvant therapy. As a widely-existing beverage, the beverage plays an extremely important role in the mass life and can be applied to various occasions. However, as a kind of fermented food, it is very easy to deteriorate during ordinary storage, especially beer, wine, fruit wine, etc. with low alcohol degree exposed in the air continuously react with oxygen in the air to promote the rapid oxidation and decay of alcoholic beverages, and meanwhile some strains such as acetic acid bacteria in the air can enter alcoholic beverages to cause the beverages to be rancid, which leads to the alcoholic beverages to finally go bad. In addition, poor temperature control during production, storage, transportation, retail and the like can cause wine beverage deterioration. Such deterioration not only causes great loss to the wine industry, but also causes unnecessary economic loss to consumers, and even deteriorated wine drinks can cause great harm to the health of people. However, during the deterioration of alcoholic beverages, the viscosity generally increases as the degree of deterioration increases.

Viscosity, the property of fluid resisting deformation or preventing adjacent fluid layers from generating relative motion, and the size of the viscosity is viscosity, and the viscosity is used as a physical index, and has a deep internal relation with apparent feelings such as mouthfeel, mellow degree and the like in the alcoholic beverage. In the deterioration process of the alcoholic beverage, the viscosity of the alcoholic beverage is generally changed, and the change process is displayed in a visual mode, so that the important guarantee is provided for food safety monitoring. In the field of analysis and detection, the fluorescence technology has the advantages of high response sensitivity, rapidness and convenience in operation, simplicity and easiness in preparation, and good detection effect, and is applied to various fields, but most of fluorescent compounds are applied to the biological field, particularly the detection of viscosity change of intracellular micro-regions aiming at the physical index of viscosity. Most of the prepared fluorescent compounds at present are complex in preparation process, high in raw material price and limited in final yield, can be almost only used in micro environments such as biology and the like, are not suitable for industrial large-scale preparation, and are not beneficial to releasing fluorescence due to the fact that a large number of hydrophobic aromatic conjugated structures exist on the chemical structure of the fluorescent compounds, the ACQ effect is easily caused.

Therefore, it is urgently needed to develop a fluorescent compound capable of rapidly and efficiently detecting the viscosity of alcoholic beverages, and even visually detecting the deterioration degree of alcoholic beverages, so as to promote the development of food safety monitoring technology.

Disclosure of Invention

In order to overcome the defects and shortcomings of the prior art, the invention provides a fluorescent compound for detecting the viscosity of an alcoholic beverage, wherein the fluorescent compound has a plurality of freely rotatable aromatic rings and other structures in a molecule, is sensitive to the environmental viscosity of a solvent and has an Aggregation Induced Emission (AIE) effect.

Another object of the present invention is to provide a method for preparing the above fluorescent compound.

The invention further aims to provide the application of the fluorescent compound in the detection of the viscosity of the alcoholic beverage.

The purpose of the invention is realized by the following technical scheme:

wine for wineThe fluorescent compound for detecting the viscosity of the beverage is 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl]-4-amine, abbreviated as MIMDBA, of formula C₃₂H₂₆N₂O, molecular weight of 454.20, and the specific structural formula is shown as follows:

。

the invention provides a preparation method of the fluorescent compound for detecting the viscosity of the alcoholic beverage, which comprises the following steps:

(1) dissolving 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde in ethanol, and uniformly stirring by ultrasonic waves to obtain a solution 1;

(2) dissolving 4-methoxyaniline in ethanol, and uniformly stirring by ultrasonic waves to obtain a solution 2;

(3) and mixing the solution 1 and the solution 2, uniformly stirring, heating for reaction, and then precipitating and purifying to obtain dark yellow powder, namely the fluorescent compound for detecting the quality of the wine beverage.

The reaction equation for the preparation is as follows:

preferably, the molar ratio of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-carbaldehyde in step (1) to 4-methoxyaniline in step (2) is 1 (1-20).

Preferably, the mass concentration of the 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde in the step (1) is 1M-10M; the mass concentration of the 4-methoxyaniline in the step (2) is 1M-100M.

Preferably, the heating temperature in the step (3) is 25 ℃ to 78 ℃, and the heating reaction time is 1 h to 48 h.

Preferably, the precipitation purification step described in step (3) comprises: removing the reaction solvent, washing with ethanol, standing for 2-3 times, and vacuum drying.

The invention also provides application of the fluorescent compound in detecting the viscosity of alcoholic beverages, which belongs to the technical field of food safety monitoring.

When the fluorescent compound provided by the invention is used for detecting the viscosity of the alcoholic beverage, the fluorescent compound is prepared into a monomolecular dispersion solution to obtain a test mother solution; when testing is carried out, a certain amount of test mother liquor is extracted and dropped into the alcoholic beverage, and the final quantity concentration of the fluorescent compound is controlled to be 1-20 mu M; the environment for viscosity detection is constructed by blending the volume ratio of glycerol to ethanol; the liquor viscosity detection is to drop the fluorescent compound mother liquor into different liquor drinks, including beer, red wine and fruit wine.

The fluorescent compound 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl provided by the invention]-4-amine of formula C₃₂H₂₆N₂O, relative molecular weight 454.20. The fluorescent compound MIMDBA is dark yellow solid powder and is easily dissolved in solvents such as dichloromethane, tetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide and the like. The fluorescent compound is powdery, has good light stability and chemical stability, is nontoxic and is suitable for long-term storage. Meanwhile, the fluorescent compound MIMDBA contains a plurality of aromatic rings and other structures which can rotate freely, the fluorescent compound MIMDBA can rotate freely in a solution with lower viscosity, excited state energy is dissipated in a mechanical motion mode, fluorescence is weak, however, the free rotation is limited along with the increase of the viscosity of the solution, the excited state energy excited by light cannot be dissipated in a mechanical motion mode, and the excited state energy returns to a ground state in a radiation transition mode to release a fluorescent signal, so that the fluorescent compound MIMDBA can be used as a molecular tool for sensing the environmental viscosity of the solution; in addition, it has AIE properties, does not cause fluorescence quenching in the aggregated state, and avoids negative effects on the release of fluorescent signals. The fluorescent compound MIMDBA emits strong fluorescence near 516 nm wavelength under 365 nm excitation wavelength, and can be used for detecting the viscosity change of the wine beverage. The specific mechanism is schematically shown in fig. 1.

The invention provides a fluorescent compound (MIMDBA) for detecting the viscosity of wine drinks, which can gradually increase the fluorescence intensity along with the increase of the viscosity, and realize in-situ, sensitive and efficient turn-on type signal release and visual detection.

Compared with the prior art, the invention has the following advantages and beneficial effects:

1) the fluorescent compound (MIMDBA) provided by the invention contains a plurality of freely rotatable aromatic ring structures and the like, can fully sense the change of the viscosity of the solution, can effectively detect the deterioration degree of the alcoholic beverage and provides effective reference for the quality safety control of the alcoholic beverage;

2) the fluorescent compound (MIMDBA) provided by the invention has the characteristics of Aggregation Induced Emission (AIE), can be used at high concentration, does not cause fluorescence quenching in an aggregation state, and can avoid the negative effect of fluorescence quenching caused by organic fluorescent molecules with large conjugated structures in the aggregation state;

3) the fluorescent compound (MIMDBA) provided by the invention has strong luminescence, Stokes shift of 196 nm, good anti-interference performance, good light stability and chemical structure stability, and is suitable for complex solution environment in wine drinks;

4) the fluorescent compound (MIMDBA) provided by the invention is prepared by a simple one-step method, is simple, efficient and high in yield, has a green process (only ethanol is used as a process reaction solvent), is suitable for large-scale industrial production, and has the advantages of convenient design of a chemical process, simple and convenient post-treatment, readily available raw materials and low price.

Drawings

FIG. 1 is a schematic diagram of the mechanism of the fluorescent compound (MIMDBA) applied to the detection of the viscosity change of the alcoholic beverage;

FIG. 2 shows the NMR chart of the fluorescent compound 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl ] -4-amine obtained in example 1;

FIG. 3 is a mass spectrum of the fluorescent compound 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl ] -4-amine obtained in example 1;

FIG. 4 is a graph of the fluorescence spectra of MIMDBA described in example 4 in various volume ratios of tetrahydrofuran/water mixed solutions;

FIG. 5 is a graph showing the change in fluorescence intensity of MIMDBA in example 4 in tetrahydrofuran/water mixed solutions at 516 nm in different volume ratios;

FIG. 6 is a graph of the fluorescence spectra of MIMDBA in example 4 in varying ratios of glycerol/ethanol mixed solution in response to viscosity;

FIG. 7 is a graph of the linear relationship of the log function of fluorescence intensity and the log function of viscosity at 516 nm for MIMDBA in example 4;

FIG. 8 is a bar graph of the fluorescence intensity of MIMDBA in different solvents in example 4;

FIG. 9 is a graph showing the change of fluorescence intensity and viscosity (degree of deterioration) with time in different alcoholic beverages of MIMDBA in example 5.

Detailed Description

The present invention is further illustrated by the following examples, which are not intended to limit the embodiments of the present invention, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions and alterations are intended to be included in the scope of the present invention.

The following examples the chemical reaction formula for preparing fluorescent compounds for measuring the viscosity of wines is shown below:

。

example 1

A preparation method of a fluorescent compound for detecting the viscosity of an alcoholic beverage comprises the following steps:

(1) 349 mg of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is dissolved in ethanol, and the solution is ultrasonically stirred uniformly, wherein the concentration of the 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is controlled to be 1M, so that a solution 1 is obtained;

(2) dissolving 123 mg of 4-methoxyaniline in ethanol, uniformly stirring by ultrasonic waves, and controlling the concentration of the 4-methoxyaniline to be 1M to obtain a solution 2;

(3) mixing solution 1 and solution 2, stirring, heating to 25 deg.C, reacting for 48 h, removing reaction solvent, washing with ethanol, standing for 2-3 times, and vacuum drying to obtain dark yellow powder (354.28 mg, yield 78%) to obtain fluorescent compound (MIMDBA).

The product is characterized by hydrogen nuclear magnetic resonance spectroscopy,¹H NMR (400 MHz, CDCl₃) δ 8.53 (s, 1H), 7.98 (d, J = 7.3 Hz, 2H), 7.70 (d, J = 8.3 Hz, 2H), 7.56 (d, J = 8.6 Hz, 2H), 7.36-7.29 (m, 6H), 7.17 (d, J = 8.5 Hz, 6H), 7.08 (t, J = 7.3 Hz, 2H), 6.97 (d, J= 8.8 Hz, 2H), 3.87 (s, 3H), wherein chemical shifts at 8.53 ppm correspond to proton peaks on schiff bases, chemical shifts at 7.98 ppm, 7.70 ppm and 7.56 ppm correspond to proton peaks near benzene rings on schiff bases, chemical shifts at 7.36-7.08 ppm correspond to proton peaks on triphenylamine, chemical shifts at 6.97 ppm correspond to proton peaks near benzene rings near methyl ether, and chemical shifts at 3.87 ppm correspond to proton peaks on methyl groups on methyl ether. The NMR spectrum is shown in FIG. 2. In addition, the molecular mass is verified by mass spectrometry to obtain MS (ESI) M/z 454.2055[ M + H ]]⁺As shown in fig. 3. The synthesized target product can be determined to be the target fluorescent compound 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl by nuclear magnetic and mass spectrum analysis]-4-amine of formula C₃₂H₂₆N₂O。

Example 2

A preparation method of a fluorescent compound for detecting the viscosity of an alcoholic beverage comprises the following steps:

(1) 349 mg of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is dissolved in ethanol, and the solution is ultrasonically stirred uniformly, wherein the concentration of the 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is controlled to be 5M, so that a solution 1 is obtained;

(2) 1230 mg of 4-methoxyaniline is dissolved in ethanol, the mixture is stirred uniformly by ultrasonic, and the concentration of the 4-methoxyaniline is controlled to be 50M, so that a solution 2 is obtained;

(3) mixing solution 1 and solution 2, stirring, heating to 50 deg.C, reacting for 24 h, removing reaction solvent, washing with ethanol, standing for 2-3 times, and vacuum drying to obtain dark yellow powder (376.99 mg, yield 83%) to obtain fluorescent compound (MIMDBA).

The characterization results of the fluorescent compound MIMDBA obtained in this example are the same as those of example 1, and reference is made to fig. 2 and 3.

Example 3

A preparation method of a fluorescent compound for detecting the viscosity of an alcoholic beverage comprises the following steps:

(1) 349 mg of 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is dissolved in ethanol, and the solution is ultrasonically stirred uniformly, wherein the concentration of the 4'- (diphenylamino) - [1,1' -biphenyl ] -4-formaldehyde is controlled to be 10M, so that a solution 1 is obtained;

(2) dissolving 2460 mg of 4-methoxyaniline in ethanol, and ultrasonically stirring uniformly to control the concentration of the 4-methoxyaniline to be 100M to obtain a solution 2;

(3) mixing solution 1 and solution 2, stirring, heating to 78 deg.C, reacting for 1 h, removing reaction solvent, washing with ethanol, standing for 2-3 times, and vacuum drying to obtain dark yellow powder (404.25 mg, yield 89%), to obtain fluorescent compound (MIMDBA).

The characterization results of the fluorescent compound MIMDBA obtained in this example are the same as those of example 1, and reference is made to fig. 2 and 3.

Example 4

Optical performance testing of fluorescent compounds (MIMDBA).

(1) Aggregation-induced emission characterization of MIMDBA fluorescent compounds:

0.91 mg of the fluorescent compound 4'- (((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl ] -4-amine (MIMDBA, prepared in example 1) was dissolved in tetrahydrofuran and prepared as a 1 mM stock solution to be tested. During testing, the fluorescent compound is diluted to 10 mu M, the total volume of the testing system is kept at 3 mL, the fluorescent compound is dropwise added into solutions with different tetrahydrofuran/water volume fractions (0% -90%), the testing is carried out at room temperature, the excitation wavelength is set to 365 nm, the measured spectrum is shown in the attached figure 4, and the change rule of the specific fluorescence intensity along with the water volume fraction is shown in the attached figure 5. As can be seen from fig. 4 and 5, in the solution system with the water volume fraction below 50%, the fluorescence of the solution is weak, which indicates that MIMDBA can be sufficiently dissolved in tetrahydrofuran so that the excited state energy can be dissipated by mechanical free rotation, and thus the fluorescence is weak. However, when the volume fraction of water is gradually increased, the fluorescence intensity is gradually enhanced, and particularly when the volume fraction of water reaches 90%, the fluorescence intensity reaches a maximum value, which indicates that the solubility of the fluorescent compound MIMDBA in a solution is gradually reduced along with the increase of the volume fraction of water, so that aggregation is easily generated, a channel for excited state electron radiation to jump back to a ground state is opened, and fluorescence is released, thereby fully embodying the characteristics of aggregation-induced emission phenomenon.

(2) Response test of MIMDBA fluorescent compounds to solution viscosity:

glycerol with different volumes is added into methanol, wherein the volume fraction of the glycerol in a test system is controlled to be 10% -99%, the total volume is controlled to be 3 mL, the test is carried out at room temperature, the excitation wavelength is set to be 365 nm, and the change rule of the fluorescence intensity of the test along with the viscosity is shown in figure 6. Generally, the viscosity of methanol is only 0.6 cP (25 ℃), while the viscosity of glycerol is as high as 945.0 cP (25 ℃), and it can be seen from fig. 6 that when the volume fraction of methanol in the solution is high, i.e. in the solution system in which the volume fraction of glycerol is only 10%, the fluorescence intensity is low, and as the volume fraction of glycerol is gradually increased, i.e. the viscosity of the solution system is gradually increased, the fluorescence intensity is gradually increased, particularly when the volume fraction of glycerol is increased to 99%, the fluorescence intensity at 516 nm reaches a maximum value, and the fluorescence intensity is significantly increased by a factor of 25 compared with the solution system containing 10% volume fraction of glycerol. In addition, the linear relation between the logarithmic function of the viscosity and the logarithmic function of the fluorescence intensity is shown in 7, and it can be seen that the log value of the fluorescence intensity at 516 nm and the log value of the viscosity show a better linear relation, namely, the fluorescence intensity also obviously rises along with the increase of the viscosity, the viscosity sensitivity coefficient of the fluorescence intensity is 0.50 through calculation of a Forster-Hoffman equation, and the fitting decision coefficient is 0.99. The test result shows that the fluorescent compound prepared by the invention has better response to viscosity and is suitable for detecting the viscosity change of the wine.

(3) Fluorescence testing of MIMDBA fluorescent compounds in different solvent systems:

a series of test systems of solvents with different polarities (including glycerol, acetone, dichloromethane, N-dimethylformamide, dimethyl sulfoxide, toluene, ethyl acetate, acetonitrile and methanol) are prepared to verify the solvent stability of MIMDBA, the excitation wavelength is set to 365 nm, and the test correlation fluorescence intensity chart is shown in figure 8. Generally, at room temperature (25 ℃), the viscosity values of the solvents with different polarities are all in the range of 0.3 cP to 2.0 cP except that the viscosity of glycerol is relatively large, and the fluorescent compound MIMDBA shows lower fluorescence intensity in the solvent atmosphere with similar viscosity but different polarities, compared with the fluorescence intensity of the fluorescent compound MIMDBA greatly increased in the glycerol solvent atmosphere with relatively large viscosity. The result shows that the fluorescent compound MIMDBA has good solvent stability, can be widely applied to alcoholic beverages with complex solvent atmosphere, has obvious viscosity response effect, and is suitable for actual scenes for detecting viscosity in alcoholic beverages with complex solvent atmosphere.

Example 5

Viscosity detection of fluorescent compounds (MIMDBA) in alcoholic beverages:

the fluorescent compound is dripped into three alcoholic beverages (including beer, red wine and fruit wine), the total test volume is controlled to be 3 mL, the quantity concentration of the fluorescent compound is controlled to be 10 mu M, then the viscosities of the three alcoholic beverages in the air for 0 day, 2 days and 5 days are respectively tested, the test is carried out at room temperature, the excitation wavelength is set to be 365 nm, and the test fluorescence intensity and viscosity change are shown in figure 9. Generally, the viscosity of beer, red wine and fruit wine just opened is low and is close to 1.0 cP, but the three kinds of wine after opening are easily deteriorated in the air, the viscosity of the three kinds of wine is obviously increased along with the increase of the number of days for placing, correspondingly, the fluorescence intensity is also gradually increased, and therefore, the fluorescent compound MIMDBA can generate the change on a fluorescence signal aiming at the change of the viscosity of the alcoholic drink, namely, the viscosity change of the alcoholic drink can be effectively detected.

The invention provides a fluorescent compound 4'- ((4-methoxyphenyl) imino) methyl) -N, N-diphenyl- [1,1' -biphenyl ] -4-amine (MIMDBA), which can detect the change of the viscosity of alcoholic drinks, wherein the probe molecule has AIE characteristics, and can make the electrons originally in an excited state return to a ground state in a radiation transition mode under the condition that the solution viscosity is increased, so as to release a fluorescent signal, so that the viscosity detection is visualized, the change of the viscosity in the alcoholic drinks can be detected more conveniently, efficiently, quickly and in situ, and a certain monitoring effect on food safety is achieved. The test result shows that the fluorescent compound is simple to prepare, high in yield, green in process, good in solvent stability and good in detection effect on the viscosity of the alcoholic beverage, and the fluorescence intensity is enhanced along with the increase of the viscosity under the irradiation of a 365 nm ultraviolet lamp, so that the fluorescent compound can be used for detecting the viscosity of the alcoholic beverage, and particularly can be used for detecting the deterioration degree of the alcoholic beverage.