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Method for synthesizing crataegolic acid

A technology of maslinic acid and oleanolic acid, applied in the direction of steroids, organic chemistry, etc., can solve problems such as complicated steps, extreme reaction conditions, and cumbersome process routes, and achieve easy control of reaction conditions, satisfactory reaction conditions, and excellent reaction environment friendly effect

Inactive Publication Date: 2011-02-16
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In the prior art: maslinic acid is prepared by plant extraction, the extraction efficiency is low, the cycle is long, and the waste of raw material resources is serious
The disadvantage of the chemical synthesis method is that the acylation protection is carried out first, and then the deprotection is used to achieve the purpose of synthesis. The steps are complicated and the process route is cumbersome.
In addition, using m-chloroperoxybenzoic acid to react, the cost of raw materials is high, the reaction conditions are extreme, and DCC is used for post-treatment, which pollutes the environment

Method used

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  • Method for synthesizing crataegolic acid
  • Method for synthesizing crataegolic acid
  • Method for synthesizing crataegolic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Step 1) in N 2 Under protection, 14.07g of oleanolic acid was dissolved in a mixed solvent of 300ml of acetone and 100ml of DMF in a 1000ml four-necked flask. 45ml of Jones reagent was slowly added dropwise at 0°C. After the addition, it was raised to room temperature and reacted for 1 hour; monitoring the completion of the reaction, Cool down to 0°C and slowly add 300ml isopropanol dropwise. After the dripping was completed, the reaction system was poured into ice water to precipitate solids, washed repeatedly with water, filtered with suction, and dried under vacuum at 50°C to obtain 12.63 g of white solids with a yield of 90.1%.

[0027] Step 2) In a 1000ml four-necked flask, 12.63g of the product of Step 1), dissolve it in 300ml of methanol, slowly add 500ml of 0.05% sulfuric acid-methanol solution at room temperature, add 13.44g of potassium hydrogen persulfate after the addition, protect from light After reacting for 7 hours, the reaction solution was extracted with ...

Embodiment 2

[0032] Step 1) in N 2 Under protection, 16g of oleanolic acid is dissolved in a mixed solvent of 300ml of acetone and 20ml of DMF in a 1000ml four-necked bottle. 48ml of Jones reagent is slowly added dropwise at 0°C. After the dropwise addition, it is raised to room temperature and reacted for 3 hours; monitor the completion of the reaction and cool down To 0°C, slowly add 320ml isopropanol dropwise. After the dripping was completed, the reaction system was poured into ice water to precipitate solids, washed repeatedly with water, filtered with suction, and dried under vacuum at 50°C to obtain 13.52 g of white solids with a yield of 84.5%.

[0033] Step 2) In a 1000ml four-necked flask, 13.52g of the product of step 1), dissolve it in methanol, slowly add 406ml of 0.05% sulfuric acid-methanol solution at room temperature, add 10.8g of potassium hydrogen persulfate after the addition is complete, and react in the dark After 5 hours, the reaction solution was extracted with dichlor...

Embodiment 3

[0037] Step 1) in N 2 Under protection, 14g of oleanolic acid is dissolved in a mixed solvent of 280ml of acetone and 140ml of DMF in a 1000ml four-necked flask, 70ml of Jones reagent is slowly added dropwise at 0°C, after the dropwise addition, warm up to room temperature and react for 2 hours; monitor the completion of the reaction and cool down To 0°C, slowly drop 490ml of isopropanol. After the addition was completed, the reaction system was poured into ice water to precipitate solids, washed repeatedly with suction and filtered, and dried under vacuum at 50°C to obtain 11.74 g of white solids, with a yield of 83.87.

[0038] Step 2) In a 1000ml four-necked flask, 11.74g of the product of Step 1), dissolve in methanol, slowly add 587ml of 0.05% sulfuric acid-methanol solution at room temperature, add 15.26g of potassium hydrogen persulfate after the addition is complete, and react in the dark After 8 hours, the reaction solution was extracted with dichloromethane and dried at...

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Abstract

The invention belongs to the field of chemical synthesis, and relates to a chemical synthesis method for crataegolic acid with low content in plants, which is suitable for industrialized production. The method comprises the following steps of: performing oxidation reaction on oleanolic acid serving as a raw material and Jones reagent to form 3-carbonyl oleanolic acid; then reacting the 3-carbonyloleanolic acid and potassium hydrogen persulfate to form 2alpha-hydroxy-3-carbonyl oleanolic acid; and finally, performing reduction reaction on the 2alpha-hydroxy-3-carbonyl oleanolic acid and sodium borohydride to obtain a crataegolic acid product. The method for preparing the crataegolic acid has the advantages of simple reaction step, simplified process route and low loss; the reaction conditions are easy to meet and control; and the reaction is environment-friendly, and the method is suitable for industrialized production.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a chemical synthesis method of maslinic acid with low content in plants, which is suitable for industrial production. Background technique [0002] Maslinic acid (MA) is an oleanane-type pentacyclic triterpene acid, mainly found in natural plants such as olive, hops, salicaria, mint, cloves, red dates, hawthorn, pomegranate, and sage . Recent studies have shown that maslinic acid has many pharmacological activities, such as anti-AIDS virus, anti-tumor, anti-oxidation, antibacterial, anti-parasitic, weight loss, health and beauty, etc., especially in the treatment of type 2 diabetes. The structure of the compound is as follows: [0003] [0004] The main sources of maslinic acid are: 1) Plant extraction. 2) Prepared by semi-synthetic route. [0005] On February 14, 2002, International Patent WO0212159 disclosed a plant extraction and preparation process of maslinic acid. [0006] On Octo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
Inventor 王霞时晨黄悦陈婕蒋学超丁佩佩丁慧美龚祝南
Owner NANJING NORMAL UNIVERSITY
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