Preparation method of betulinic acid polymer

A technology for betulinic acid and polymers, which is applied in the field of preparing betulinic acid polymers and pentacyclic triterpenoid polymers by using ball mills, and can solve the problems of low contact probability between alcoholic hydroxyl groups and carboxyl groups, complex experimental conditions, etc. , to achieve the effects of low chemical synthesis cost, high application potential, and simple separation

Inactive Publication Date: 2021-01-29
南京江北新区生物医药公共服务平台有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on poly- or oligo-betulinic acid, because the monomolecular structure of betulinic acid is relatively complex. During the polymerization process, the contact probability of alcoholic hydroxyl and carboxyl groups in different molecular structures is low, although betulinic acid is soluble in Most of the organic solvents, but the inventor found that the solution polymerization under normal temperature and high temperature reflux is difficult to control during the experiment
In addition, due to the high melting point of betulinic acid monomer, the melt bulk polymerization temperature is above 300 °C, which is difficult to achieve under conventional experimental conditions.

Method used

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  • Preparation method of betulinic acid polymer
  • Preparation method of betulinic acid polymer
  • Preparation method of betulinic acid polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 4.56 g of betulinic acid, 3.8 µL of ammonium hydroxide, 0.022 g of hydroquinone, and 0.022 g of powdered calcium chloride, put them into a ball mill jar, select 8 agate balls of Φ5 mm, 4 agate balls of Φ 10 mm, and Φ Two 20mm agate balls. Start the ball mill at a speed of 400 r / min. After running for 25 minutes, the ball mill pauses for 5 minutes, and exhausts the pressure once. After 1 hour, that is, after the second suspension of pressure relief, stop the ball mill after running for another 25 minutes. Open the ball mill tank, transfer the solids and agate balls in the tank into 20 mL of acetone, the solids are completely dissolved, and there is no residual solid on the surface of the agate balls, pour the acetone solution into 200 mL of methanol, and a white solid is precipitated, and the white The solid was dried at 45° C. for 4 hours in a forced air drying oven, and the obtained solid was detected by NMR, infrared and gel permeation chromatography.

Embodiment 2

[0025] Weigh 4.56 g of betulinic acid, 85.7 mg of barium hydroxide, 10.4 µL of benzyl alcohol, and 0.011 g of powdered calcium chloride, put them into a ball mill jar, select 8 agate balls of Φ5 mm, 4 agate balls of Φ 10 mm, and Φ 20 mm 2 standard agate balls. Start the ball mill at a speed of 400 r / min. After running for 25 minutes, the ball mill pauses for 5 minutes, and exhausts the pressure once. After 1 hour, that is, after the second suspension of pressure relief, stop the ball mill after running for another 25 minutes. Open the ball mill tank, move the solids and agate balls in the tank into 20 mL of acetone, the solids are completely dissolved, and there is no residual solid on the surface of the agate balls, the acetone solution is poured into 200 mL of methanol, a white solid is precipitated, and the white The solid was dried at 45° C. for 4 hours in a forced air drying oven, and the obtained solid was detected by NMR, infrared and gel permeation chromatography.

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Abstract

The invention belongs to the technical field of high polymer materials, and relates to a method for preparing a betulinic acid polymer by using a ball mill. The method comprises the steps of adding betulinic acid, a basic catalyst, a stabilizer and a water removal agent into a ball tank of a ball mill, starting the ball mill to react, dissolving a product with an organic solvent, pouring into methanol to separate out, filtering, collecting solids, and performing vacuum drying to obtain a betulinic acid polymer. High temperature is not needed in the reaction, no solvent is needed in the reaction process, the cost is low, the separation is simple, and certain pilot scale test and industrialization prospects are achieved. The obtained polybetulinic acid is a novel high-molecular compound andis not reported before.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a method for preparing pentacyclic triterpenoid polymers, in particular to a method for preparing betulinic acid polymers by using a ball mill. Background technique [0002] Betulinic acid (BA) is a typical natural medicine, which belongs to pentacyclic triterpenoids. Betulinic acid is extracted from a variety of plants, including trees, shrubs, such as Betula (Betuaceae), Persimmon (Pysimmonaceae), Jujube (Rhamnaceae) , Carmine (Myrtaceae) and so on. Even carnivorous plants such as the yellow pitcher plant (Sarraceniaceae). Betulinic acid is used as a traditional folk remedy. People soak birch bark into tea or other drinks to treat diarrhea, dysentery and other gastrointestinal diseases. Betulinic acid also has significant anti-tumor and anti-HIV activities, and also has the advantages of specific mechanism of action, small molecular weight, low toxicity, etc., and ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08H99/00
CPCC08H99/00
Inventor 朱旨昂阚苏立吕兴祥陈云智绪崔汉立王丹
Owner 南京江北新区生物医药公共服务平台有限公司
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