Method for preparing baicalein

A technology for baicalein and a compound, which is applied in the field of preparing baicalein, can solve the problems of difficult preservation of cinnamoyl chloride, complicated synthesis steps, etc., and achieves the effects of simple separation and purification of products, low price and high yield.

Inactive Publication Date: 2010-06-16
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has a high yield and basically has the potential for large-scale production, but b...

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  • Method for preparing baicalein
  • Method for preparing baicalein
  • Method for preparing baicalein

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Step 1: Preparation of compound II

[0035] Weigh 18.4g (0.1mol) of 3,4,5-trimethoxyphenol into a reaction vessel, add about 30ml of acetic anhydride, slowly add 10ml of boron trifluoride ether solution under stirring at room temperature, and then slowly heat to 60°C for reaction 3 hours (TLC checks that the starting material has reacted completely). The above reaction solution was slightly cooled naturally, added with 100 ml of ethyl acetate and stirred, then placed in the refrigerator overnight, and filtered to obtain the precipitated yellow solid. Add 100ml of water and 10ml of ethanolamine to the yellow solid, stir well for 1-2 hours, and then extract the product twice with ethyl acetate, 80ml each time. The extracts were combined, washed once with water, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain compound II as a light yellow oil, which could solidify after refrigeration, and weighed to obtain com...

Embodiment 2

[0043] Step 1: Preparation of compound II

[0044] Weigh 18.4g (0.1mol) of 3,4,5-trimethoxyphenol into a reaction vessel, add about 30ml of acetic acid, slowly add 50g of polyphosphoric acid under stirring at room temperature, then slowly heat to 80°C for 1 hour (TLC Check that the raw material has reacted completely).

[0045] Under stirring, the above reaction solution was poured into 150 ml of ice-cold water while hot, and then the product was extracted twice with ethyl acetate, 100 ml each time. The extracts were combined, washed once with water, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain compound II as a light yellow oil, which could solidify after being refrigerated, dried and weighed, yield: 85%. 1 HNMR (CDCl 3 ):Cit.

[0046] Step 2: Preparation of compound III

[0047] Weigh 22.4g (0.1mol) of compound II and 13g (0.12mol) of benzaldehyde, put them in a 250ml round bottom flask, add 100ml of met...

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Abstract

The invention discloses a method preparing baicalein. In the method, 3,4,5-trimethoxyphenol serving as a starting raw material undergoes four steps to obtain the high-purity baicalein, and in particular, the method comprises the following steps of: 1) in the presence of lewis acid, performing acylation of the 3,4,5-trimethoxyphenol and an acetylation reagent to form an ester, and obtaining a compound II due to the rearrangement of phenolic ester; 2) under an alkaline condition, performing chalcone cyclization of the compound II and benzaldehyde to obtain a compound III; 3) in the presence of a catalyst, performing the cyclization reaction of the compound III to obtain a compound IV; and 4) under conditions of oxygen separation and acid, heating the compound IV to remove methoxyl groups to obtain the target compound I. The method has the advantages of rich raw materials, high yield, good purity quality of products, simple process, low cost and wide application prospect.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for preparing baicalein. Background technique [0002] Baicalein is systematically named as 4', 5, 6-trihydroxyflavone, and its structural formula is as shown in formula I. Baicalein (baicalein, Baicalein) is one of the active ingredients extracted from the dry root of the labiatae plant Scutellaria baicalensis, which has various pharmacological effects, such as: antibacterial, antiviral, anti-inflammatory, anti-allergic, anti-oxidant, Scavenging oxygen free radicals, anti-cancer, anti-tumor, anti-coagulation, anti-thrombosis and protection of liver, cardiovascular and cerebrovascular, neurons and other functions. Currently clinically used mainly for anti-inflammatory and antibacterial [0003] Baicalein has a wide antibacterial range. In vitro tests have proved that it has inhibitory effects on a variety of Gram-positive bacteria, Gram-negative bacteria and spirochetes, ...

Claims

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Application Information

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IPC IPC(8): C07D311/30
Inventor 杨健陈铎之杨波吴远双吴婷
Owner KUNMING UNIV OF SCI & TECH
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