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Method for preparing apigenin

A kind of apigenin and reprocessing technology, applied in the direction of organic chemistry, etc., to achieve the effect of abundant raw material sources, high yield and simple process

Inactive Publication Date: 2011-06-01
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are not many reports on the method of preparing apigenin in large quantities by chemical synthesis, and there are still no reports on the synthesis of apigenin with 2,4-dimethoxy-6-hydroxyacetophenone as raw material

Method used

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  • Method for preparing apigenin
  • Method for preparing apigenin
  • Method for preparing apigenin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Weigh 19.6g of 2,4-dimethoxy-6-hydroxyacetophenone, and the molar ratio of 2,4-dimethoxy-6-hydroxyacetophenone to p-methoxybenzaldehyde is 1 :1.2 Weigh 16.3g of p-methoxybenzaldehyde, add 356mL methanol to dissolve it according to the solid-liquid ratio of 1:10, then add sodium hydroxide to make the alkali concentration in the solution 15%, and stir at 20℃ 40h, then adjust the pH of the reaction solution to 3 with concentrated hydrochloric acid solution, filter the reaction solution with suction, wash the filter cake with distilled water, and dry the filter cake to obtain compound II; yield 90%; mp: 112~116; 1 HNMR (CDCl 3 ) Characterization: δ3.82(s, 3H), 3.85(s, 3H), 3.92(s,3H), 5.97(d,J=1.9Hz,1H), 6.11(d, J=1.9Hz, 1H), 6.93(d, J=7.5Hz, 2H), 7.56(d, J=7.5 Hz, 2H), 12.78(s, 1H);

[0035] (2) Take 15.7 g of compound II, add 15.7 mL of dimethyl sulfoxide with a solid-liquid ratio of 1:1, add 0.0785 g of iodine, heat to 150°C, stir for 3 hours, and cool; weigh 7.85 g of ...

Embodiment 2

[0038] (1) Weigh 19.6g of 2,4-dimethoxy-6-hydroxyacetophenone, and the molar ratio of 2,4-dimethoxy-6-hydroxyacetophenone to p-methoxybenzaldehyde is 1 :1. Weigh 13.6g of p-methoxybenzaldehyde, and add 332mL of ethanol according to the solid-liquid ratio of 1:10 to dissolve, then add potassium hydroxide to make the concentration of the alkali in the solution 10%, and stir at 40°C 20h, then adjust the pH of the reaction solution to 4 with concentrated hydrochloric acid solution, filter the reaction solution with suction, wash the filter cake with distilled water, and dry the filter cake to obtain compound II; yield 90%; mp: 112~116; 1 HNMR (CDCl 3 ) Characterization: δ3.82(s, 3H), 3.85(s, 3H), 3.92(s,3H), 5.97(d,J=1.9Hz,1H), 6.11(d, J=1.9Hz, 1H), 6.93(d, J=7.5Hz, 2H), 7.56(d, J=7.5 Hz, 2H), 12.78(s, 1H);

[0039] (2) Take 15.7g of compound II, add 157mL of dimethyl sulfoxide with a solid-liquid ratio of 1:10, add 0.157g of potassium iodide, heat to 80°C, stir for 30h, and cool; we...

Embodiment 3

[0042] (1) Weigh 19.6g of 2,4-dimethoxy-6-hydroxyacetophenone, and the molar ratio of 2,4-dimethoxy-6-hydroxyacetophenone to p-methoxybenzaldehyde is 1 :1. Weigh 13.6g of p-methoxybenzaldehyde, then add 332mL of ethanol according to the solid-liquid ratio of 1:10 to dissolve, and then add potassium hydroxide to make the concentration of the alkali in the solution 25%, and stir at 30°C After 30h, the pH of the reaction solution was adjusted to 3 with concentrated hydrochloric acid solution, the reaction solution was suction filtered, the filter cake was washed with distilled water, and the filter cake was dried to obtain compound II; yield 88%; mp: 112~116; 1 HNMR (CDCl 3 ) Characterization: δ3.82(s, 3H), 3.85(s, 3H), 3.92(s,3H), 5.97(d,J=1.9Hz,1H), 6.11(d, J=1.9Hz, 1H), 6.93(d, J=7.5Hz, 2H), 7.56(d, J=7.5 Hz, 2H), 12.78(s, 1H);

[0043] (2) Take 15.7g compound II, add 78.5mL dimethyl sulfoxide according to the solid-liquid ratio of 1:5, add 0.471g sodium iodide, heat to 100°C, st...

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Abstract

The invention provides a method for preparing apigenin, which comprises the following steps: performing the condensation reaction of the raw material of 2,4-dimethoxy-6-hydroxyacetophenone with p-methoxybenzaldehyde with the catalysis of an alkali to obtain a compound II; performing the cyclization reaction with the presence of a catalyst to obtain a compound III; heating to remove the methoxy group at an oxygen-isolated and acidic condition so as to obtain apigenin. The invention prepares apigenin by chemical synthesis, and has the advantages of simple process, easy processing for product separation and purification, high yield, mass production potential, abundant raw material sources, and low cost.

Description

Technical field [0001] The invention relates to a method for preparing apigenin, which belongs to the field of medicine synthesis. Background technique [0002] Apigenin, systematically named 4',5,7-trihydroxyflavone, and its structural formula is shown in formula I. Apigenin, a naturally occurring flavonoid compound, is known as "phytoestrogens". It is widely found in many fruits, vegetables, beans and tea, among which celery has the highest content. It has a variety of pharmacological effects, such as: anti-tumor, anti-inflammatory, anti-arteriosclerosis, anti-thrombotic, anti-anxiety, anti-bacterial, anti-viral, and anti-oxidant effects. At present, it is mainly used for anti-tumor clinically. [0003] [0004] Ⅰ [0005] Apigenin has a wide range of anticancer effects. In vitro experiments have shown that it has inhibitory effects on a variety of tumor cells, such as breast cancer cells, gastric cancer cells, prostate cancer cells, liver cancer cells, and ovarian cancer cells. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
Inventor 杨健吴婷杨波吴远双
Owner KUNMING UNIV OF SCI & TECH
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