Method for preparing baicalein

A technology of baicalein and compounds, which is applied in the field of preparation of commonly used antiviral and antibacterial anti-inflammatory drugs and medicinal active ingredient baicalein, can solve the problems of limited sources of synthetic raw materials, high prices, high technical conditions, etc., and achieve high industrial application value and Economic value, easy production control, simple and convenient operation

Active Publication Date: 2016-08-31
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has high efficiency and basically has the potential for production application, but the sources of its synthetic raw materials are mostly limited.
In 2014, Xu, Bei-hua et al. used phloroglucinol as the starting material to obtain chrysin through acetylation and ester condensation reactions, and then performed Ebls oxidation to obtain baicalein (Xu, Bei-hua; Zhou, Hui- yan; Wo, Lian-qun. Synthesis of baicalein, Guangzhou Huagong (2014), 42(9), 68-69, 73), but the technical conditions required for the preparation process of this method are relatively high, even harsh, and the multi-step reaction yield The rate is very low, it is only suitable for the application of laboratory preparation, not suitable for production application at all
In addition, in the same year, Jing, Linlin et al. used chrysin as raw material to prepare baicalein through methylation, bromination, methoxy substitution, demethylation and rearrangement reactions (Jing, Linlin; Fan, Xiaofei; Ma, Huiping; Fan, Pengcheng; Jia, Zhengping. Convenient synthesis of baicalein, Zhongguo Yiyao GongyeZazhi (2014), 45(10), 916-918), but because the source of chrysin is also very limited and its price is high, so this method prepares Scutellaria baicalensis high efficiency and cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: The specific steps of the method for preparing baicalein are as follows:

[0020](1) Synthesis of Compound 3: Weigh 16.8g (0.10mol) of 2,6-dimethoxy-p-benzoquinone (Compound 2) into a 250mL round-bottomed flask, add 10% sodium hydrosulfite aqueous solution 100mL (the molar amount of sodium hydrosulfite is 1 times the molar amount of compound 2), stirred at room temperature for about 3 hours, then filtered, washed the filter cake with a small amount of water, pressed dry, and dried under vacuum to obtain an off-white powdery solid, namely Compound 3; weighing: 17.0 g, yield: 100%. 1 HNMR (DMSO): δ5.73(s,2H), δ5.05(s,1H), δ3.77(s, 6H).

[0021] (2) Synthesis of Compound 4: Weigh 17.0g (0.10mol) of Compound 3 into a 250mL reaction bottle, add 100mL of chloroform and 25mL of acetic anhydride, then slowly add about 20mL of boron trifluoride ether solution under stirring at room temperature ( Boron trifluoride is 0.2mol); slowly heat the reaction mixture to ab...

Embodiment 2

[0025] Embodiment 2: The specific steps of the method for preparing baicalein are as follows:

[0026] (1) Synthesis of Compound 3: Weigh 16.8g (0.10mol) of 2,6-dimethoxy-p-benzoquinone (Compound 2) into a 250mL round bottom flask, add 100mL industrial methanol and no less than 3.6g ( 0.15mol) of magnesium metal, heat the mixture to 60°C under stirring for about 5-6 hours, filter, wash with a little fresh methanol, combine the filtrate, evaporate methanol under reduced pressure to obtain an off-white powdery solid, the compound 3. Colorless crystals that can be recrystallized from a methanol-water mixed solvent, dried, weighed: 16.0 g, yield: 94.0%. 1 HNMR (DMSO): same as embodiment 1 step (1);

[0027] (2) Synthesis of Compound 4: Weigh 17.0g (0.10mol) of Compound 3 into a 100mL reaction bottle, add 35mL of acetic acid, then slowly add about 10mL of phosphorus oxychloride under stirring at room temperature; slowly heat the reaction mixture to React at about 100°C for about...

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PUM

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Abstract

The invention discloses a method for preparing baicalein. According to the method, 2,6-dimethoxy-p-benzoquinone used as an initial raw material is subjected to reduction, Friedel-Crafts acetylation, claisen condensation, dehydrogenation oxidation cyclization and demethylation five reactions to obtain baicalein with high yield. The method uses low-price and easily-available initial raw material, reagent and the like, has few synthesizing steps, is easy and convenient to operate and easy for production control, has high product yield and high purity, and is suitable for large-scale preparation and production application of baicalein.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, that is, a method for preparing commonly used antiviral, antibacterial and anti-inflammatory drugs and baicalein as a medicinal active ingredient. Background technique [0002] Baicalein, also known as baicalein, English name: Baicalein, chemical name: 5,6,7-trihydroxyflavone. Baicalein is an important pharmacological active ingredient in traditional Chinese medicine Scutellaria baicalensis George and Oroxylum indicum, which has significant anti-oxidation, anti-inflammatory, anti-allergic, antibacterial, antiviral, antitumor and other pharmacological activities , and its structurally modified derivatives also show good biological activity and medicinal prospects (Wang, Yu-nong; Jin, Ye-zhi; Dong, Ying-ying; Wu, Ying; Hao, Yu. Research development of Scutellariabaicalensis and its extracts against influenza virus infection, Xiandai Shengwuyixue Jinzhan (2014), 14(27), 536...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杨健王谦崔巍廖霞俐
Owner KUNMING UNIV OF SCI & TECH
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