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Method for preparing scutellarein

A technology of scutellarin aglycone and compounds, which is applied in the field of preparation of scutellarin aglycone, can solve the problems of difficult industrial application, high price, cumbersome process operation, etc., achieve high industrial application value and economic value, easy production control, The effect of high product yield

Active Publication Date: 2016-01-06
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because its synthetic starting material 2-hydroxyl-4,5,6-trimethoxyacetophenone is currently not supplied in large quantities on the market, only a small amount is imported and the price is expensive, and its original report process operation is too complicated, and the reagents used are tested. The special medicine and high price make it not easy to realize industrial application
In 2011, GiulianaRighi et al. used the natural product naringenin as the starting material to synthesize scutellarein through 5 steps of reaction conversion, and obtained a good yield of 62% (see GiulianaRighi, etal.Efficientsynthesisofscutellarein, NaturalProductResearch:FormerlyNaturalProductLetters , 2012,26(14),1278-1284), but its starting material is the natural product naringenin, which is not easy to obtain in large quantities, and the price is relatively high, which also limits the promotion and application of this method in industrial production to a certain extent. application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: The preparation method of this scutellarin aglycon is as follows:

[0032] (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 300ml of methanol and 130ml of commercially available hydrobromic acid with a concentration of 47% by mass, and then slowly Add 90ml of hydrogen peroxide with a mass percent concentration of 30% dropwise therein, and control the dropping rate so that the temperature of the reaction solution does not exceed 40°C, and the addition is completed in about 1-2 hours. After addition, continue stirring for 1-2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of methanol, press dry, and dry at 70-80°C to obtain a white powdery solid, namely compound 3; Weighing: 82.0g, yield: 98%. 1 HNMR (DMSO): δ9.92(s, 1H), δ7.46(s, 2H).

[0033] (2) Synthesis of Compound 4: Weigh 84.0g (1.5mol) of sodium methoxide into a 1000ml round bottom flask, ad...

Embodiment 2

[0041] Example 2: The preparation method of this scutellarin aglycon is as follows:

[0042] (1) (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 500ml of ethanol, 80g (0.78mol) of sodium bromide and 20ml (0.40mol) of commercially available 98% Then, under vigorous stirring at room temperature, slowly add 90ml of hydrogen peroxide with a mass percentage concentration of 30% to it, and control the dropping rate so that the temperature of the reaction solution does not exceed 45°C, and the addition is completed in about 1-2 hours; after the addition, continue After stirring for 1-2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of distilled water, press dry, and dry at 70-80°C to obtain a white powdery solid, namely compound 3. Weighing: 82.0g, yield: 99%. 1 HNMR (DMSO): same as step (1) of Example 1 above.

[0043](2) Synthesis of compound 4: Weigh 84.0g (1.5mol) of...

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PUM

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Abstract

The invention discloses a method for preparing scutellarein. The method comprises the following steps: taking phenol as a starting material, preparing a chalcone intermediate through bromination, methoxy substitution, friedel-crafts acylation and the like, performing oxidative cyclisation on the chalcone intermediate to obtain a key flavone intermediate 4',6-dihydroxy-5,7-dimethoxy flavone, and preparing high-purity scutellarein through demethylation of the key intermediate. According to the method, the adopted raw materials are all low in price and easy to obtain, the synthesis steps are less, the operation is simple and convenient, the production control is easy, the product yield and purity are high, and the method is suitable for scutellarin and scutellarein production.

Description

technical field [0001] The invention relates to a practical method for preparing scutellarin aglycone. Background technique [0002] Scutellarin aglycone, the aglycon of scutellarin, chemical name: 4',5,6,7-tetrahydroxyflavone. Scutellarin aglycon and scutellarin are the main pharmacological active ingredients in Yunnan national medicine breviscapus and its extract preparations, which can dilate blood vessels, reduce blood viscosity, reduce peripheral resistance, reduce platelet count, inhibit platelet aggregation, increase heart, brain Its preparations are mainly used in the treatment of cardiovascular and cerebrovascular diseases such as coronary heart disease, angina pectoris, myocardial ischemia, cerebral thrombosis and its sequelae, and have shown definite and excellent curative effects. Studies in recent years have shown that it can also be used as an effective therapeutic drug for pulmonary heart disease, diabetes, kidney disease, liver disease and skin diseases. St...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杨健王谦崔巍杨波廖霞俐
Owner KUNMING UNIV OF SCI & TECH
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