Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of troxerutin

A rutin and reaction technology, applied in the field of chemical pharmacy, can solve the problems such as the difficulty of product purity, the inability to use 80-90°C, the difficulty of precise reaction conditions in industrial production control, and the like

Inactive Publication Date: 2013-05-22
NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
View PDF10 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the pKa value of the four phenolic hydroxyl groups, carefully analyze the deficiencies of the prior art: because the similar acidity of the four hydroxyl groups tries to realize the C by adjusting the pH 5 The selectivity between -OH and the other three hydroxyl groups makes it difficult to control precise reaction conditions in industrial production. The purity of the product obtained by the reaction is generally not easy to reach more than 90%, and the obtained product must rely on complicated post-treatment to improve the purity.
The patent pointed out that the reaction should be carried out below 50°C for 24 hours, and the conventional 80-90°C for hydroxyethylation reaction cannot be used.
If the reaction temperature is too high, the borax complex will decompose, reducing the protective effect of the coordination reaction
From the data of this patent, it is not known whether a suitable temperature can be found to realize the boron atom C 4 =O...B...C 5 -OH, C 3′ -OH...B...C 4′ Selectivity of Hydroxyethylation of Phenolic Hydroxyl in Complexes Formed by -OH

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of troxerutin
  • Preparation method of troxerutin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 100.0g of rutin dispersed in 300ml of water, add 1.0g of sodium hydroxide, after stirring evenly, add 220g of ethylene oxide, and react at 75°C for 3 hours. The reaction solution was taken to analyze the components, and the monohydroxyethylated product was 4%, the tetrahydroxyethylated product was 3%, and the di- and trihydroxyethylated products accounted for 93%. Add 62 g of borax, measure the pH of the reaction solution to 9.5, add 16 g of ethylene oxide, and continue to react at 70° C. for 3 hours. After the reaction was completed, the components of the reaction solution were analyzed: 88% of troxerutin, 7% of tetrahydroxyethyl product, and 3% of dihydroxyethyl product. Adjust the pH of the reaction solution to 6-7 with 6mol / L hydrochloric acid, concentrate to dryness under reduced pressure, add 400mL of methanol, then continue to adjust the pH to about 3 with dilute hydrochloric acid, heat to reflux, filter to remove insoluble matter, let it stand at room temperatur...

Embodiment 2

[0015] Dissolve 0.6g of sodium hydroxide in 150ml of water, add 53g of rutin (about 6% water content), and stir evenly. Add 12g of ethylene oxide into the reactor and react at 73°C for 3.5 hours. The reaction solution was taken for analysis, 3% of the monohydroxyethyl product, 5% of the tetrahydroxyethyl product, and 92% of the di- and tri-hydroxyethyl products. 31 g of borax was added, the pH of the reaction solution was 9.4, 4 g of ethylene oxide was added, and the reaction was continued at 70° C. for 2.5 hours. After finishing the reaction, the components of the reactant solution were analyzed: troxerutin accounted for 87%, tetrahydroxyethyl product was 9%, and dihydroxyethyl product was 2%. Use the calculated amount of concentrated hydrochloric acid to neutralize the borax to adjust the pH of the reaction solution to 5-7, concentrate and dry under reduced pressure, add 200mL of 90% ethanol, adjust the pH to about 3 with dilute hydrochloric acid, heat to about 75°C and sti...

Embodiment 3

[0017] Dissolve 0.7g of potassium hydroxide in a mixed solution of 150ml of water and 50ml of methanol, add 55g of rutin with a water content of about 6%, and stir evenly. Add 11 g of ethylene oxide into the reactor and react at 73° C. for 3 hours. Add 30 g of borax and continue to add 6 g of ethylene oxide, and continue to react at 70° C. for 3 hours. Finish reaction, analysis reactant troxerutin accounts for 90%, dihydroxyethyl product 3%, tetrahydroxyethyl product 6%. The aftertreatment is similar to Example 1, and the yield and purity are comparable.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for synthesizing troxerutin with high content. According to the invention, hydroxyethyl reaction is implemented on a phenolic hydroxyl group on a rutin flavone skelecton by using ethylene oxide in alkaline water or a mixed water and ethanol solvent. The reaction is implemented through two steps: in the first step, dihydroxyethylrutin and troxerutin (namely trihydroxyethylrutin) are mainly generated, and in the second step, borax is added and serves as a coordination catalyst to protect C5-OH, so that the generation proportion of tetrahydroxyethylrutin acquired from excessive reaction is effectively reduced and the preparation of 3',4',7-tri-beta-hydroxyethylrutin is implemented, wherein the purity of the 3',4',7-tri-beta-hydroxyethylrutin after being purified can reach 90% or higher and the yield of the 3',4',7-tri-beta-hydroxyethylrutin can reach 70% or higher.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of troxerutin with a high content of 3', 4', 7-tri-beta-hydroxyethyl rutin. Background technique [0002] Troxerutin, chemical composition 3′, 4′, 7-tri-β-hydroxyethylrutin, vitamin P4, CAS No: 7085-55-4, Merck No.: 12:9920. It can inhibit platelet aggregation and prevent thrombosis. At the same time, it can resist vascular damage caused by 5-tryptamine and bradykinin, increase capillary resistance, reduce capillary permeability, and prevent edema caused by increased vascular permeability. It has a significant protective effect on acute ischemic brain injury. It is suitable for hemiplegia, aphasia, pre-myocardial infarction syndrome, arteriosclerosis, central retinitis, thrombophlebitis, varicose veins, and edema caused by increased vascular permeability caused by cerebral thrombosis and embolism. Because of its definite curative effect on cardiovascular a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
Inventor 吴振刚刘占军刘延敏纪占林
Owner NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com