Semi-synthetic method for diosmetin

A diosmin and semi-synthetic technology, applied in chemical instruments and methods, preparation of sugar derivatives, disaccharides, etc., can solve the problems of reduced efficiency and increased production cost, and achieve low production cost, easy operation, and simple synthesis process Effect

Inactive Publication Date: 2014-10-29
CHENGDU RUNDE PHARMA
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  • Abstract
  • Description
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Problems solved by technology

[0004] Since the content of diosmin in natural plants is very small, it is possible to increase the output by exploring semi-synthetic methods to prepare diosmin; the existing semi-synthetic processes of diosmin all use organic solvent / inorganic acid as the hydrolysis medium, not only Increased production costs, and because organic solvents and inorganic acids can undergo chemical reactions at high temperatures, the efficiency of synthesis is reduced

Method used

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Embodiment 1

[0025] (1) Synthesis: Add 1200L of water to the reactor, start stirring, drop in 120kg of diosmin, close the manhole of the reactor, vacuum inhale 240kg of concentrated sulfuric acid, open the vent valve of the reactor, turn on the jacket steam heating, wait When the temperature in the kettle rises to 90°C, close the vent valve and continue heating until the internal pressure of the reactor is 0.08MPa. At this time, the temperature in the kettle is 110°C. Turn down the steam pressure of the jacket to keep the temperature in the reactor at 110-115 ℃, hydrolyze for 10 hours; after the reaction, slowly remove the pressure in the kettle, lower to room temperature, vacuum filter the reaction mixture with a PTFE suction filter, after the suction filtration is completed, wash the filter cake with water until the pH value of the effluent 6-7 to obtain crude geranolin; at the same time, add sodium hydroxide to the filtrate to neutralize to a pH value of 6-7, then add 3.6kg of medicinal ...

Embodiment 2

[0029] (1) Synthesis: add 1200L of water to the reactor, start stirring, drop in 80kg of diosmin, close the manhole of the reactor, vacuum inhale 80kg of concentrated sulfuric acid, open the vent valve of the reactor, turn on the jacket steam heating, wait When the temperature in the kettle rises to 90°C, close the vent valve and continue heating until the internal pressure of the reactor is 0.08MPa. At this time, the temperature in the kettle is 118°C. Turn down the steam pressure of the jacket to keep the temperature in the reactor at 118-120°C. ℃, hydrolysis for 12 hours; after the reaction, slowly remove the pressure in the kettle, lower to room temperature, vacuum filter the reaction mixture with a PTFE suction filter, after the suction filtration is completed, wash the filter cake with water until the pH value of the effluent 6-7 to obtain crude geranolin; at the same time, add sodium hydroxide to the filtrate to neutralize to a pH value of 6-7, then add 2.4kg of medicina...

Embodiment 3

[0033] (1) Synthesis: Add 1500L of water to the reactor, start stirring, drop in 115kg of diosmin, close the manhole of the reactor, vacuum inhale 230kg of concentrated sulfuric acid, open the vent valve of the reactor, turn on the jacket steam heating, wait When the temperature in the kettle rises to 90°C, close the venting valve, continue heating until the internal pressure of the reactor is 0.08MPa, at this time, the temperature in the kettle is 100°C, and turn down the steam pressure of the jacket to keep the temperature in the reactor at 100-110°C. ℃, hydrolyze for 10 hours; after the reaction, slowly remove the pressure in the kettle, lower to room temperature, vacuum filter the reaction mixture with a PTFE suction filter, after the suction filtration is completed, wash the filter cake with water until the pH value of the effluent 6-7 to obtain crude geranolin; at the same time, add sodium hydroxide to the filtrate to neutralize to a pH value of 6-7, then add 3.45kg of me...

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Abstract

The invention discloses a semi-synthetic process for diosmetin. The semi-synthetic process comprises the following steps of adding water and concentrated sulfuric acid into diosmin for hydrolyzing and carrying out suction filtration, washing a filter cake to obtain a diosmetin crude product; adding 50-60% alcohol into the diosmetin crude product, heating and refluxing, filtering, concentrating filtrate under reduced pressure, cooling and crystallizing to obtain a primary diosmetin pure product; adding 90-95% alcohol into the primary diosmetin pure product, heating and refluxing, filtering, concentrating filtrate under reduced pressure, cooling and crystallizing to obtain diosmetin. The process disclosed by the invention takes water as solvent to prepare diosmetin by one step, so that the synthesis process is simple, materials are easily available, reaction conditions are stable, operation is simple and convenient, production cost is lower, a product yield reaches 60-65%, purity reaches 98-99%, and therefore, the semi-synthetic process can be used for preparing large-scale production of diosmetin.

Description

technical field [0001] The present invention relates to a semi-synthetic method for diosmin. Background technique [0002] diosmin, molecular formula C 16 h 12 o 6 , the molecular weight is 300.26, the CAS registration number is 520-34-3, and the melting point is 256-258 ° C. It can be extracted from the peel of lemon. It is a natural flavonoid compound that inhibits the activity of human CYP1A enzyme. It also has anti-mutagenic and anti-mutagenic properties. Anti-allergic properties, with anti-oxidation, anti-infection, anti-shock and other effects; the structural formula is: [0003] [0004] Since the content of diosmin in natural plants is very small, it is possible to increase the output by exploring semi-synthetic methods to prepare diosmin; the existing semi-synthetic processes of diosmin all use organic solvent / inorganic acid as the hydrolysis medium, not only The production cost is increased, and the efficiency of the synthesis is reduced due to the chemical ...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07H3/04C07H1/00
CPCC07D311/30C07H1/00C07H3/04
Inventor 张满力
Owner CHENGDU RUNDE PHARMA
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