Method for improving perfuming quality of megastigmatrienone through alkali regulation and control

Abstract

The invention discloses a method for improving perfuming quality of megastigmatrienone by alkali regulation, which comprises the following steps of: performing alkali-adding heat treatment on megastigmatrienone, and neutralizing the megastigmatrienone to be neutral by using acid so as to improve the proportion of an isomer D. The alkali is one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide and potassium tert-butoxide, preferably sodium hydroxide. According to the method, alkali-adding heat treatment is carried out on the megastigmatrienone, the relative content of isomers A and B of the treated megastigmatrienone is reduced, the content of an isomer D of the treated megastigmatrienone is increased, and the megastigmatrienone is applied to cigarette perfuming and has an obvious perfuming effect. According to the regulation and control method, sodium hydroxide is used as a regulation and control reagent, water is used as a solvent, the regulation and control reagent is cheap and easy to obtain, and acetic acid is added for neutralization removal, so that the problems of various other regulation and control reagents and complex purification are solved. The regulation and control method disclosed by the invention is high in operability and easy to industrially apply. And the regulated isomer is stable in performance during re-storage.

Description

Technical Field

[0001] The invention relates to the technical field of tobacco flavors and fragrances, and in particular to a method for improving the flavoring quality of megastigmatrienone by alkali regulation. Background Art

[0002] Megastigmatrienoside is a carotenoid degradation product and an important neutral aroma component in tobacco. A small amount of addition can give the smoke a strong and lasting warm, sweet and dry aroma. It has important applications in the flavor and fragrance industry and the tobacco industry. Megastigmatrienoside mainly exists in the form of a mixture of four isomers, which have the same peak order in a common gas chromatography column and are named Megastigmatrienoside A, B, C, and D, respectively.

[0003] In recent years, studies have found that the ratio between the isomers of megastigmatrienoside will affect the flavoring effect. Generally speaking, the flavoring effect of the D isomer is the best. At present, the ratio of the content of megastigmatrienoside A, B, C, and D in tobacco leaves or artificial synthesis is about 8:50:6:36, and the content of isomer D is not high. Chinese patent CN104312723B discloses a method for improving the flavoring quality of megastigmatrienoside, in which megastigmatrienoside is subjected to ultraviolet irradiation or microwave irradiation treatment to increase the ratio of isomer D from 36% to 43%. This method places high demands on equipment and is difficult to produce. In addition, the stability of the ratio of each isomer during storage after regulation has not been reported. The document "Stereoselective synthesis of megastigmatrien-3-one using catalytic olefin isomerization as key step" and Chinese patent CN113372209B disclose a method for regulating the isomers of megastigmatrienone, which requires the use of cobalt salts, ligands, reducing agents and additives, and the solvent is dichloromethane, and the proportion of isomer D is increased from 36% to 73%. This method requires the addition of multiple substances and the use of organic solvents, which makes the post-processing complex and the production cost high. In addition, the stability of the ratio of each isomer after regulation during storage is not reported.

[0004] Therefore, it is of great significance to develop a method for regulating megastigmatrienone with simple process, low cost and good storage stability. Summary of the invention

[0005] The technical problem to be solved by the present invention is to provide a method for improving the flavoring quality of megastigmatrienone by alkali regulation, which has simple process, low equipment requirements and low cost. After regulation, the proportion of megastigmatrienone isomer D is increased and the storage stability is good.

[0006] The technical problem to be solved by the present invention is achieved through the following technical solutions:

[0007] A method for improving the flavoring quality of megastigmatrienon by alkali regulation, wherein the megastigmatrienon is first subjected to alkali heat treatment and then neutralized to neutrality with acid, thereby increasing the proportion of isomer D.

[0008] Preferably, in the above technical solution, the base is one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide and potassium tert-butoxide.

[0009] Preferably, in the above technical solution, the alkali is sodium hydroxide.

[0010] Preferably, in the above technical solution, the mass ratio of megastigmatrienone to the base is (2-8):1.

[0011] Preferably, in the above technical solution, the mass ratio of megastigmatrienone to the base is 5:1.

[0012] Preferably, in the above technical solution, the conditions of the heat treatment are: temperature 100° C., stirring for 10-15 min.

[0013] Preferably, in the above technical solution, acetic acid is used for acid neutralization to adjust the pH to neutral.

[0014] Preferably, in the above technical solution, the method is specifically:

[0015] Mix 25 mg of megastigmatrienone, 5 mg of sodium hydroxide and 1 g of deionized water, stir at 100° C. for 10-15 min, cool to room temperature, and add acetic acid to neutralize to a neutral pH.

[0016] A megastigmatrienone, wherein the megastigmatrienone is obtained by regulating according to the above-mentioned method for improving the flavoring quality of megastigmatrienone by alkali regulation, and the ratio of isomers D to B in the megastigmatrienone is greater than 85%.

[0017] The invention discloses an application of megastigmatrienone in cigarette flavoring. The application comprises the following steps: using 95% ethanol as solvent to prepare a 1% solution by mass, and then adding 2% of the solution to shredded tobacco to roll the shredded tobacco into cigarettes. The shredded tobacco has a more roasted aroma than a control.

[0018] The above technical solution of the present invention has the following beneficial effects:

[0019] (1) The present invention is the first to subject megastigmatrienone to an alkali-adding heat treatment. After the treatment, the relative contents of isomers A and B of megastigmatrienone are reduced, while the content of isomer D is increased. The invention is applied to cigarette flavoring and has an obvious flavoring effect.

[0020] (2) The control method of the present invention uses sodium hydroxide as a control reagent and water as a solvent, which is cheap and easily available, and is finally neutralized and removed by adding acetic acid, thereby solving the problem of numerous other control reagents and complicated purification.

[0021] (3) The control method of the present invention is highly operable and easy to apply industrially. Moreover, the isomers after control have stable performance when stored again. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] The accompanying drawings, which are incorporated in and constitute a part of the specification, illustrate embodiments of the invention and, together with the description, serve to explain the principles of the invention.

[0023] Figure 1 The gas chromatogram of each isomer of the starting material of megastigmatrienone of the present application is shown in FIG.

[0024] Figure 2 This is a gas chromatogram of the isomers of megastigmatrienone after regulation obtained in Example 1 of the present application.

[0025] Figure 3 This is a gas chromatogram of the isomers of megastigmatrienone after regulation obtained in Example 5 of the present application.

[0026] Figure 4 This is a gas chromatogram of the isomers of megastigmatrienone after regulation obtained in Example 6 of the present application.

[0027] Figure 5 This is a gas chromatogram of the isomers of megastigmatrienone after regulation obtained in Example 7 of the present application. DETAILED DESCRIPTION

[0028] Various exemplary embodiments of the present invention will now be described in detail with reference to the accompanying drawings. It should be noted that the relative arrangement of components and steps, numerical expressions and numerical values ​​set forth in these embodiments do not limit the scope of the present invention unless otherwise specifically stated.

[0029] The technical solution of the present invention is further described below by specific implementation methods. The reagents used in this application, unless otherwise specified, are all commercially available or obtained from commercial channels, or can be prepared by reference to existing chemical methods. Unless otherwise specified, the percentages used in the present invention are all mass percentages.

[0030] Example 1

[0031] 25 mg of megastigmatrienone, 5 mg of sodium hydroxide and 1 g of deionized water were mixed, stirred at 100° C. for 10 minutes, cooled to room temperature, and acetic acid was added to neutralize to a neutral pH.

[0032] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample after heat treatment with sodium hydroxide was 3:46:8:43, of which the D / B ratio was 94%.

[0033] Example 2

[0034] 25 mg of megastigmatrienone, 5 mg of potassium hydroxide and 1 g of deionized water were mixed, stirred at 100° C. for 10 minutes, cooled to room temperature, and acetic acid was added to neutralize to a neutral pH.

[0035] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample after heat treatment with potassium hydroxide was 3:48:8:41, of which the D / B ratio was 85%.

[0036] Example 3

[0037] 25 mg of megastigmatrienone, 5 mg of sodium tert-butoxide and 1 g of deionized water were mixed, stirred at 100° C. for 10 minutes, cooled to room temperature, and acetic acid was added to neutralize to a neutral pH.

[0038] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; after heat treatment with sodium tert-butoxide, the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample was 3:47:7:43, of which the D / B ratio was 90%.

[0039] Example 4

[0040] 25 mg of megastigmatriene, 5 mg of potassium tert-butoxide and 1 g of deionized water were mixed, stirred at 100° C. for 10 minutes, cooled to room temperature, and acetic acid was added to neutralize to a neutral pH.

[0041] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; after heat treatment with potassium tert-butoxide, the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample was 3:48:7:42, of which the D / B ratio was 87%.

[0042] Example 5

[0043] 25 mg of megastigmatrienone and 1 g of deionized water were mixed, stirred at 100° C. for 10 minutes, and then cooled to room temperature.

[0044] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D in the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample after heat treatment was 4:50:5:41, of which the D / B ratio was 82%.

[0045] Example 6

[0046] 250 mg of megastigmatrienone, 50 mg of sodium hydroxide and 10 g of deionized water were mixed, stirred at 100° C. for 15 minutes, cooled to room temperature, and acetic acid was added to neutralize to a neutral pH.

[0047] Sampling was performed and GC-MS analysis was performed using a DB-5ms column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample after heat treatment with sodium hydroxide was 3:47:6:44, of which the D / B ratio was 94%.

[0048] Example 7

[0049] The sample of Example 6 was sealed and placed at room temperature for 14 days, and then sampled and analyzed by GC-MS using a DB-5ms chromatographic column. The analysis results showed that the ratio of the four isomers A, B, C, and D of the megastigmatrienone starting material was 6:52:7:35, of which the D / B ratio was 67%; the ratio of the four isomers A, B, C, and D in the megastigmatrienone sample after heat treatment with sodium hydroxide was 3:46:8:43, of which the D / B ratio was 93%.

[0050] Example 8

[0051] The megastigmatrienone starting material and the sample after heat treatment with sodium hydroxide were sampled respectively, and 95% ethanol was used as solvent to prepare 1% solution by mass, which was added to a certain flue-cured tobacco at a dosage of 2% and rolled into cigarettes.

[0052] Comparative inhalation test showed that compared with the starting material, the samples heat-treated with sodium hydroxide had a significantly increased roasted aroma and a better sensory experience.

[0053] Although the present invention has been disclosed as above by the embodiments, it is not intended to limit the present invention. Any person skilled in the art may make various choices and modifications without departing from the spirit and scope of the present invention. Therefore, the protection scope of the present invention is limited by the claims and their equivalents.

Claims

1. A method for improving the flavoring quality of megastigmatrienone by alkali regulation, characterized in that: The method comprises the following steps: firstly subjecting megastigmatrienon to a heat treatment with alkali, and then neutralizing it with acid to neutrality, thereby increasing the proportion of isomer D.

2. The method for improving the flavoring quality of megastigmatrienone by alkali regulation according to claim 1, characterized in that: The alkali is one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide and potassium tert-butoxide.

3. The method for improving the perfuming quality of megastigmatrienone by alkali regulation according to claim 2, characterized in that: The base is sodium hydroxide.

4. The method for improving the flavoring quality of megastigmatrienone by alkali regulation according to claim 1, characterized in that: The mass ratio of megastigmatrienone to alkali is (2-8):

1.

5. The method for improving the perfuming quality of megastigmatrienone by alkali regulation according to claim 4, characterized in that: The mass ratio of megastigmatrienone to alkali is 5:

1.

6. The method for improving the perfuming quality of megastigmatrienone by alkali regulation according to claim 1, characterized in that: The heat treatment conditions are: temperature 100° C., stirring 10-15 min.

7. The method for improving the perfuming quality of megastigmatrienone by alkali regulation according to claim 1, characterized in that: The acid neutralization uses acetic acid to adjust the pH to neutral.

8. The method for improving the perfuming quality of megastigmatrienone by alkali regulation according to claim 1, characterized in that: The method is specifically as follows: Mix 25 mg of megastigmatrienone, 5 mg of sodium hydroxide and 1 g of deionized water, stir at 100° C. for 10-15 min, cool to room temperature, and add acetic acid to neutralize to a neutral pH.

9. A megastigmatrienone, characterized in that The megastigmatrienone is obtained by regulating the method for improving the flavoring quality of megastigmatrienone by alkali regulation according to any one of claims 1 to 8, and the ratio of isomers D to B in the megastigmatrienone is greater than 85%.

10. The use of megastigmatrienone in cigarette flavoring according to claim 9, characterized in that: The application is to use 95% ethanol as solvent to prepare a 1% solution by mass, then add 2% of the solution to shredded tobacco and roll it into a cigarette. The cigarette has a more roasted aroma than the control.

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