Semi-synthesis method of diosmetin

A geranyl lignin and semi-synthetic technology, applied in the direction of organic chemistry and the like, can solve the problems of low synthesis efficiency and high production cost, and achieve the effects of low production cost, high preparation purity and high yield

Active Publication Date: 2019-01-11
SHAANXI JIAHE PHYTOCHEM
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to solve the shortcomings of high production cost and low synthesis efficiency in the existing synthetic methods, and provide a semi-synthetic method of diosmin

Method used

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  • Semi-synthesis method of diosmetin

Examples

Experimental program
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Embodiment 1

[0028] A semi-synthetic method for diosmin, the steps are as follows:

[0029] Step 1) Preparation of Neodiosmin

[0030] Put 300 kilograms of neohesperidin with a liquid phase content of 95%, 1800 kilograms of pyridine, and 240 kilograms of iodine into a 3000-liter reactor, heat up to 100 ° C for 12 hours, and monitor the neohesperidin content to below 2%. Recover pyridine under reduced pressure until no liquid is evaporated to obtain neodiosmin;

[0031] Step 2) prepare the crude product of diosmin

[0032] Add 1500 kilograms of sodium hydroxide solution with a mass concentration of 32% to the neodiosmin obtained in step 1), continue to heat up to 100° C. for 40 minutes of hydrolysis reaction, and monitor the content of neodiosmin to below 2% in the liquid phase. Add hydrochloric acid to the reaction solution to neutralize the pH value to 6-7, then cool down to 15°C-25°C to cool, centrifuge, collect the precipitate, and wash the precipitate with water to obtain 120 kg of c...

Embodiment 2

[0036] A semi-synthetic method for diosmin, the steps are as follows:

[0037] Step 1) Preparation of Neodiosmin

[0038] Put 100 kilograms of neohesperidin with a liquid phase content of 95%, 500 kilograms of pyridine, and 100 kilograms of iodine into a 1000-liter reactor, heat up to 105°C and react for 10 hours, and monitor the neohesperidin content below 2% in the liquid phase. Recover pyridine under reduced pressure until no liquid is evaporated to obtain neodiosmin;

[0039] Step 2) prepare the crude product of diosmin

[0040] Add 600 kg of sodium hydroxide solution with a mass concentration of 32% to the neodiosmin obtained in step 1), continue to heat up to 95°C for hydrolysis reaction for 50 minutes, monitor the content of neodiosmin below 2% in liquid phase, and add to Add hydrochloric acid to the reaction solution to neutralize it so that the pH value is 6-7, then cool down to 15°C-25°C, cool down, centrifuge, collect the precipitate, and wash the precipitate with...

Embodiment 3

[0044] A semi-synthetic method for diosmin, the steps are as follows:

[0045] Step 1) Preparation of Neodiosmin

[0046] Put 500 kilograms of neohesperidin with a liquid phase content of 95%, 3500 kilograms of pyridine, and 410 kilograms of iodine into a 5000-liter reactor, heat up to 110 ° C for 11 hours, and monitor the neohesperidin content to below 2%. Recover pyridine under reduced pressure until no liquid is evaporated to obtain neodiosmin;

[0047] Step 2) prepare the crude product of diosmin

[0048] Add 3000 kg of sodium hydroxide solution with a mass concentration of 32% to the neodiosmin obtained in step 1), continue to heat up to 100 ° C for 30 minutes of hydrolysis reaction, and monitor the neodiosmin content below 2% in the liquid phase. Add hydrochloric acid to the reaction solution to neutralize the pH value to 6-7, then cool down to 15°C-25°C to cool, centrifuge, collect the precipitate, and wash the precipitate with water to obtain 200 kg of crude geranoli...

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Abstract

The invention provides a semi-synthesis method of diosmetin. A purpose of the present invention is to solve the problems of high production cost and low synthesis efficiency of the existing synthesismethod. According to the present invention, neohesperidin, pyridine and iodine are heated and react to prepare neodiosmin, and the neodiosmin is hydrolyzed with a sodium hydroxide solution to preparediosmetin; and the semi-synthesis method has characteristics of short process time, simple post-treatment, low production cost, high product purity and high yield, and is suitable for the industrial production of diosmetin.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a semi-synthetic method of diosmin. Background technique [0002] Diyerin is a kind of natural flavonoids, the chemical name is 3′,5,7-trihydroxy-4′-methoxyflavone. Dianophyllin is a yellow powder with a melting point of 256°C to 258°C, a CAS number of 520-34-3, and a molecular formula of C 16 h 12 o 6 , with a molecular weight of 300.26, soluble in methanol, ethanol and other organic solvents. The hydroxyl groups at the 3′, 5, and 7 positions in the structural formula and the C2=C3 double bond determine the unique chemical properties and biological activities of diosmin, in which the phenolic hydroxyl group at the 7 position can be combined with different sugar groups to undergo glycosylation response to exhibit different biological activities. [0003] Dianophyllin is widely distributed in nature and mainly exists in free form or glycoside form. Currently, it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 郭文华肖金霞赵景辉杨雪峰
Owner SHAANXI JIAHE PHYTOCHEM
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