CN111233966A - Glycyrrhetinic acid derivative ASBT (ascorbyl transferase) as well as preparation method and application thereof - Google Patents
Glycyrrhetinic acid derivative ASBT (ascorbyl transferase) as well as preparation method and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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Abstract
The invention discloses a glycyrrhetinic acid derivative ASBT (American society for testing health) and a preparation method and application thereof, wherein the glycyrrhetinic acid derivative ASBT has a structure shown in a general formula I:
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a glycyrrhetinic acid derivative ASBT and a preparation method and application thereof.
Background
The active ingredients of licorice include Glycyrrhizin (GL) and Glycyrrhetinic Acid (GA), and GA is the main bioactive ingredient in licorice and is the main metabolite of GL.
Compared with other synthetic sweeteners, aspartame has the advantages of pure taste, high safety, low calorie and the like.
Studies show that aspartame can cause some diseases of the nervous system, such as migraine, brain tumor, epilepsy, shock, thought disorder and digestion, and can also accelerate the occurrence of Alzheimer's disease.
The toothpaste is an essential article for daily life, and can be divided into common toothpaste and medicinal toothpaste according to functions, while the antiallergic toothpaste is an important branch of the medicinal toothpaste as a household auxiliary prevention or treatment means for Dentine Hypersensitivity (DH).
At present, a glycyrrhetinic acid derivative ASBT as a toothpaste desensitizer, and a preparation method and application thereof are lacked.
Disclosure of Invention
The invention aims to provide a novel glycyrrhetinic acid derivative ASBT as a toothpaste desensitizer, and a preparation method and application thereof.
In order to solve the problems in the prior art, the invention provides the following technical scheme: the glycyrrhetinic acid derivative ASBT has a structure shown in a general formula I:
the preparation method of the glycyrrhetinic acid derivative ASBT comprises the following steps:
(1) dissolving glycyrrhetinic acid and succinic anhydride in triethylamine, refluxing for 14-15h, after the reaction is finished, diluting with cold water, adjusting the pH value of the system to 3-4 with hydrochloric acid, filtering to obtain a brownish black solid, washing the precipitate with hot water, and separating a product by column chromatography to obtain a light yellow solid glycyrrhetinic acid acidification product ZKU;
(2) dissolving aspartame in distilled water to prepare a mixed solution, dissolving a glycyrrhetinic acid acidification product ZKU in dimethylformamide with the same volume as the distilled water, dropwise adding the dimethylformamide into the mixed solution, then dropwise adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride EDC & HCl into the system, reacting at 55-65 ℃ for 20-30h, after the reaction is finished, carrying out vacuum concentration, precipitating with acetone for 3-5 times, and sequentially washing the precipitate with acetone, ethanol and diethyl ether to prepare the final product glycyrrhetinic acid derivative ASBT.
Further, in the step (1), the molar ratio of the glycyrrhetinic acid to succinic anhydride is 1: 4.
Further, in the step (1), the molar volume ratio of the glycyrrhetinic acid to the triethylamine is 1:10 mol/l.
Furthermore, in the step (1), the volume ratio of the triethylamine to the cold water is 1: 6.
Further, in the step (1), in the column chromatography, the volume ratio of ethanol to ethyl acetate is 10: 3.
Further, in the step (2), the mass ratio of the aspartame to the glycyrrhetinic acid acidification product ZKU is 294mg:286 mg.
Further, in the step (1), 2.4g (5mmol) of glycyrrhetinic acid and 2.4g (20mmol) of succinic anhydride are dissolved in 50ml of triethylamine and refluxed for 14-15h, after the reaction is finished, the mixture is diluted by 300ml of cold water, the pH value of the system is adjusted to be 3-4 by hydrochloric acid, a brownish black solid is obtained by filtration, hot water washing is carried out on the precipitate, and a product is separated by column chromatography, so that a light yellow solid glycyrrhetinic acid compound ZKU of glycyrrhetinic acid is obtained.
Further, in the step (2), 294mg of aspartame is dissolved in distilled water to prepare a mixed solution, 286mg of glycyrrhetinic acid acidification product ZKU is dissolved in 30ml of dimethylformamide and is dropwise added into the system, then 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is dropwise added into the system, the reaction is carried out for 20-30h at 55-65 ℃, after the reaction is finished, vacuum concentration is carried out, the precipitation is carried out for 3-5 times by using acetone, ethanol and ether, and the precipitation is washed by using the acetone, the ethanol and the ether in sequence, so that the glycyrrhetinic acid derivative ASBT is prepared.
The glycyrrhetinic acid derivative ASBT disclosed by the invention is used as a desensitizer in the preparation of toothpaste.
Compared with the prior art, the invention has the following beneficial effects: (1) the method has the advantages of simple synthesis, mild reaction conditions and excellent performance of the synthesized compound, and can provide a reliable tool for further research on the compound as a toothpaste desensitizer. (2) The desensitizer is glycyrrhetinic acid derivative ASBT, has good desensitizing effect on tooth allergy symptoms, and also has good deodorization effect, so that the deodorization performance of the toothpaste can be effectively improved.
Detailed Description
The present invention is described in more detail below with reference to examples, but it should not be construed that the scope of the present invention is limited to the examples below, and any technologies implemented based on the above contents of the present invention are within the scope of the present invention.
Example 1
The glycyrrhetinic acid derivative ASBT has a structure shown in a general formula I:
the preparation method of the glycyrrhetinic acid derivative ASBT comprises the following steps:
(1) dissolving glycyrrhetinic acid and succinic anhydride in triethylamine, refluxing for 14h, after the reaction is finished, diluting with cold water, adjusting the pH value of the system to 4 with hydrochloric acid, filtering to obtain a brownish black solid, washing the precipitate with hot water, and separating the product by column chromatography to obtain a light yellow solid glycyrrhetinic acid acidification substance ZKU; the molar ratio of the glycyrrhetinic acid to the succinic anhydride is 1: 4. The molar volume ratio of the glycyrrhetinic acid to the triethylamine is 1:10mol/l, and the volume ratio of the triethylamine to the cold water is 1: 6. In the column chromatography, the volume ratio of ethanol to ethyl acetate is 10: 3.
(2) Dissolving aspartame in distilled water to prepare a mixed solution, dissolving an acidification product ZKU of glycyrrhetinic acid in 30ml of dimethylformamide, dropwise adding the mixture into the mixed solution, dropwise adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride into the system, reacting for 20 hours at 55 ℃, after the reaction is finished, carrying out vacuum concentration, precipitating for 4 times by using acetone, and washing and precipitating by using acetone, ethanol and diethyl ether in sequence to prepare the glycyrrhetinic acid derivative ASBT. The mass ratio of the aspartame to the glycyrrhetinic acid acidification matter ZKU is 294mg to 286 mg.
The glycyrrhetinic acid derivative ASBT disclosed by the invention is used as a desensitizer in the preparation of toothpaste.
Example 2
Example 2 differs from example 1 in that:
in the step (1), glycyrrhetinic acid and succinic anhydride are dissolved in triethylamine and refluxed for 15 hours, after the reaction is finished, the mixture is diluted by cold water, the pH value of the system is adjusted to 3 by hydrochloric acid, brownish black solid is obtained by filtering, hot water is used for washing and precipitating, and a product is separated by column chromatography to obtain a light yellow solid glycyrrhetinic acid acidification compound ZKU.
In the step (2), aspartame is dissolved in distilled water to prepare a mixed solution, an acidification product ZKU of glycyrrhetinic acid is dissolved in 30ml of dimethylformamide and is dropwise added into the mixed solution, then 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is dropwise added into the system, the system reacts for 25 hours at 65 ℃, after the reaction is finished, vacuum concentration is carried out, acetone is used for precipitation for 3 times, and the precipitation is washed by acetone, ethanol and ether in sequence to prepare the glycyrrhetinic acid derivative ASBT.
The glycyrrhetinic acid derivative ASBT disclosed by the invention is used as a desensitizer in the preparation of toothpaste.
Example 3
Example 3 differs from example 1 in that:
in the step (1), glycyrrhetinic acid and succinic anhydride are dissolved in triethylamine and refluxed for 14-15 hours, after the reaction is finished, the mixture is diluted by cold water, the pH value of the system is adjusted to 3.5 by hydrochloric acid, brownish black solid is obtained by filtering, hot water is used for washing and precipitating, and a product is separated by column chromatography to obtain a light yellow solid glycyrrhetinic acid acidification product ZKU.
In the step (2), aspartame is dissolved in distilled water to prepare a mixed solution, an acidification product ZKU of glycyrrhetinic acid is dissolved in 30ml of dimethylformamide and is dropwise added into the mixed solution, then 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is dropwise added into the system, the system reacts for 30 hours at the temperature of 60 ℃, after the reaction is finished, vacuum concentration is carried out, acetone is used for precipitation for 5 times, and the precipitate is washed by acetone, ethanol and ether in sequence to prepare the glycyrrhetinic acid derivative ASBT.
Example 4
The invention relates to a preparation method of glycyrrhetinic acid derivative ASBT, which comprises the following steps:
(1) 2.4g (5mmol) of glycyrrhetinic acid and 2.4g (20mmol) of succinic anhydride are dissolved in 50ml of triethylamine and refluxed for 14-15 h. After the reaction is finished, diluting with 300ml of cold water, adjusting the pH value of the system to 3-4 by using hydrochloric acid, filtering to obtain a brownish black solid, washing the precipitate by hot water, and performing column chromatography V (ethanol): v (ethyl acetate) ═ 10:3, and the product was isolated to give glycyrrhetinic acid hydrochloride ZKU as a pale yellow solid.
(2) 294mg of aspartame was dissolved in distilled water, 286mg of glycyrrhetinic acid hydrochloride ZKU was dissolved in 30ml of dimethylformamide and added dropwise to the above system, and then 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride was added dropwise to the above system, followed by reaction at 55-65 ℃ for 20-30 hours. After the reaction is finished, vacuum concentration is carried out, acetone is used for precipitation for 3-5 times, and the acetone, ethanol and ether are used for washing the precipitation in sequence to obtain the glycyrrhetinic acid derivative ASBT.
1H NMR(600MHz,DMSO-d6),0.691(3H,s),0.760(3H,s),0.911(3H,s),1.040(6H,s),1.100(3H,s),1.353(3H,s)；2.09(1H,d,J＝0.86Hz),2.33(1H,s),2.49(2H,s),2.53(1H,s),2.61(1H,s),3.0(1H,rn),3.0(1H,rn),3.19(2H,s),3.44(1H,s),4.3(1H,s),4.46(2H,s),5.4(1H,s)；7.14(4H,s).MS(ESI):832.1([M+H]+)
Test example 1
Through experimental observation, the instant effect and the long-term effect of the glycyrrhetinic acid derivative ASBT and the ultra-fast and high-cleanness special anti-sensitivity toothpaste on the dentinal tubule sealing effect are selected, the desensitizer with the best effect is selected, and a theoretical basis is provided for the reasonable clinical application of the desensitizer.
The method comprises the following steps:
140 fresh intact third molars were collected, prepared into dentinal hypersensitivity models, and then randomly divided into a blank control group (n ═ 20), a glycyrrhetinic acid derivative ASBT control group (n ═ 40), a guonine group (n ═ 40), and a high-dew group (n ═ 40). The blank control group was coated with distilled water, the remaining three groups were coated with desensitizing agent as required, and 20 samples were randomly drawn from each of the 3 desensitizing agent-coated groups for the brushing experiment. And observing the change of the dentin surface after the desensitizer is coated and after the tooth brushing experiment under a scanning electron microscope, analyzing the pictures of the scanning electron microscope by an image analysis system, calculating the average diameter and the relative area of the mouth of the open dentin tube, and performing statistical analysis on the result by using SPSS 21.0.
Results
The mean diameter of the open mouths of the dentinal tubules after application of the desensitizer was statistically different from the population (F785.274, P0.000); the average diameter of the open nozzles of the blank control group is obviously higher than that of the other three groups (P & lt0.000), the average diameter of the open nozzles of the glycyrrhetinic acid derivative ASBT control group is obviously lower than that of the other three groups (P & lt0.000), and the average diameter of the open nozzles of the gunning group is not significantly different from that of the Gaolu group (P & lt0.139). After the tooth brushing experiment, the average diameter of the open mouth of the dentinal tubule in the three groups of the glycyrrhetinic acid derivative ASBT control group, the Yongning group and the high-distillate-cleaning special-effect anti-allergy toothpaste group is statistically different (F is 564.674, and P is 0.000); the average diameter of the open nozzles of the glycyrrhetinic acid derivative ASBT comparative group is obviously lower than that of the Gaoguang group (P is 0.000), and the average diameter of the open nozzles of the Gaoguang group is obviously lower than that of the Gaoguang group (P is 0.008). The relative area of the open mouth of the dentinal tubules was statistically different between the four groups after application of the desensitizer (F5224.798, P0.000); the relative area of the open orifice was significantly higher in the blank than in the remaining three groups (P ═ 0.000),
the relative area of the open tube orifice of the glycyrrhetinic acid derivative ASBT contrast group is obviously lower than that of the Jieguing group (P is 0.000), the relative area of the open tube orifice of the glycyrrhetinic acid derivative ASBT contrast group is obviously lower than that of the Gaoguang group (P is 0.000), and the relative area of the open tube orifice of the Jieguing group is obviously lower than that of the Gaoguang group (P is 0.026). After the tooth brushing experiment, the comparative total of the relative area of the open mouth of the dentinal tubule among the glycyrrhetinic acid derivative ASBT control group, the Yongning group and the high-distillate special-effect anti-allergy toothpaste group has statistical difference (F is 336.288,
p ═ 0.000); the relative area of the small open nozzles of the glycyrrhetinic acid derivative ASBT contrast group is lower than that of the Jieguing group (P is 0.000), the relative area of the small open nozzles of the glycyrrhetinic acid derivative ASBT contrast group is obviously lower than that of the high-distillate group (P is 0.000), and the relative area of the small open nozzles of the Jieguing group is obviously lower than that of the high-distillate group (P is 0.000). The diameter and relative area of each group coated with the desensitizer before and after the tooth brushing experiment are longitudinally compared with those after the tooth brushing experiment, the diameter of the glycyrrhetinic acid derivative ASBT control group has no significant difference before and after the tooth brushing experiment (P is 0.062), and the rest groups have significant difference (P is less than 0.05).
Conclusion
The glycyrrhetinic acid derivative ASBT contrast group, the extremely firm and the highly luclean anti-allergy toothpaste can effectively seal dentinal tubules, and the sealing effect of the dentinal tubules after the brushing friction experiment is in turn from strong to weak
Glycyrrhetinic acid derivative ASBT contrast group, Jiguning, and Gaolujie anti-allergy toothpaste. The immediate desensitizing effect and the long desensitizing effect of the glycyrrhetinic acid derivative ASBT comparison group in the three desensitizers are optimal.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the foregoing description only for the purpose of illustrating the principles of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the invention as defined by the appended claims, specification, and equivalents thereof.
Claims (10)
1. A glycyrrhetinic acid derivative ASBT is characterized by having a structure shown in a general formula I:
2. the method for preparing glycyrrhetinic acid derivative ASBT of claim 1, characterized by comprising the steps of:
(1) dissolving glycyrrhetinic acid and succinic anhydride in triethylamine, refluxing for 14-15h, after the reaction is finished, diluting with cold water, adjusting the pH value of the system to 3-4 with hydrochloric acid, filtering to obtain a brownish black solid, washing the precipitate with hot water, and separating a product by column chromatography to obtain a light yellow solid glycyrrhetinic acid acidification product ZKU;
(2) dissolving aspartame in distilled water to prepare a mixed solution, dissolving a glycyrrhetinic acid acidification product ZKU in dimethylformamide with the same volume as the distilled water, dropwise adding the dimethylformamide into the mixed solution, then dropwise adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride EDC & HCl into the system, reacting at 55-65 ℃ for 20-30h, after the reaction is finished, carrying out vacuum concentration, precipitating with acetone for 3-5 times, and sequentially washing the precipitate with acetone, ethanol and diethyl ether to prepare the final product glycyrrhetinic acid derivative ASBT.
3. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (1), the molar ratio of the glycyrrhetinic acid to the succinic anhydride is 1: 4.
4. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (1), the molar volume ratio of the glycyrrhetinic acid to the triethylamine is 1:10 mol/l.
5. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein the method comprises the following steps: in the step (1), the volume ratio of the triethylamine to the cold water is 1: 6.
6. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (1), in the column chromatography, the volume ratio of ethanol to ethyl acetate is 10: 3.
7. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (2), the mass ratio of the aspartame to the glycyrrhetinic acid acidification product ZKU is 294mg to 286 mg.
8. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (1), 2.4g (5mmol) of glycyrrhetinic acid and 2.4g (20mmol) of succinic anhydride are dissolved in 50ml of triethylamine and refluxed for 14-15h, after the reaction is finished, the mixture is diluted by 300ml of cold water, the pH value of the system is adjusted to be 3-4 by hydrochloric acid, a brownish black solid is obtained by filtration, the precipitate is washed by hot water, and a product is separated by column chromatography, so that a light yellow solid glycyrrhetinic acid compound ZKU of glycyrrhetinic acid is obtained.
9. The method for preparing glycyrrhetinic acid derivative ASBT according to claim 2, wherein: in the step (2), 294mg of aspartame is dissolved in distilled water to prepare a mixed solution, 286mg of glycyrrhetinic acid acidification product ZKU is dissolved in dimethylformamide of the mixed solution and is dropwise added into the system, then 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is dropwise added into the system to react for 20-30h at 55-65 ℃, after the reaction is finished, vacuum concentration is carried out, acetone is used for precipitation for 3-5 times, and the precipitate is washed by acetone, ethanol and ether in sequence to prepare the glycyrrhetinic acid derivative ASBT.
10. Use of a glycyrrhetinic acid derivative ASBT as claimed in any one of claims 1 to 9 as a desensitizing agent in the manufacture of a toothpaste.
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| CN202011289306.5A CN112321669A (en) | 2020-03-31 | 2020-11-18 | Glycyrrhetinic acid derivative ASBT (ascorbyl transferase) as well as preparation method and application thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102579462A (en) * | 2012-01-18 | 2012-07-18 | 苏州大学 | Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs |
| CN105407718A (en) * | 2013-06-04 | 2016-03-16 | 维奥姆生物科学有限公司 | Coated particles and compositions comprising same |
| JP2018052914A (en) * | 2016-09-23 | 2018-04-05 | 小林製薬株式会社 | Composition for oral cavity |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102579462A (en) * | 2012-01-18 | 2012-07-18 | 苏州大学 | Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs |
| CN105407718A (en) * | 2013-06-04 | 2016-03-16 | 维奥姆生物科学有限公司 | Coated particles and compositions comprising same |
| JP2018052914A (en) * | 2016-09-23 | 2018-04-05 | 小林製薬株式会社 | Composition for oral cavity |
Non-Patent Citations (1)
| Title |
|---|
| 董鑫: ""三种不同脱敏剂对牙本质小管封闭作用的实验研究"", 《中国优秀硕士学位论文全文数据库（电子期刊） 医药卫生科技辑》 * |
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Application publication date: 20200605 |