Ethoxyl quercetin derivative, method for preparation and use

A technology of quercetin and its compounds, applied in the field of quercetin derivatives and its preparation, achieving the effects of high yield, broad market development prospects, and simple preparation methods

Inactive Publication Date: 2006-12-27
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, other derivatives of quercetin, especially tetrahydroxyethyl quercetin derivatives and their preparation have not been reported yet

Method used

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  • Ethoxyl quercetin derivative, method for preparation and use
  • Ethoxyl quercetin derivative, method for preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 500mL flask, add 4.0g NaOH and 250mL water, stir to dissolve. Add 60g of quercetin afterwards, stir to make it all dissolve. 32 mL of ethylene oxide was added dropwise with stirring, and the reaction was continued for another 30 hours under airtight conditions. The reaction solution was neutralized to neutral with 2mol / L hydrochloric acid, desalted with ion exchange resin, concentrated by heating under reduced pressure (70°C), and spray-dried to obtain 58.6g of tetrahydroxyethyl quercetin.

[0038] The chemical structure of the obtained product was identified by mass spectrometry and nuclear magnetic resonance.

[0039] The appearance of the product is light yellow powder, and the hydrochloric acid-magnesium powder reaction is positive, showing flavonoids.

[0040] Mass Spectrum (FAB-MS): m / z 478.2 [M] + , 434.1 (tetrahydroxyethyl quercetin lost a hydroxyethyl fragment).

[0041] nuclear magnetic resonance 17 CNMR (75MHz, DMSO-d 6 ), δppm: 146.7(C-2), 136.7(C...

Embodiment 2

[0043] In a 250mL flask, add 1.4gNaH, 200mL DMF, stir to dissolve. Then add 30g of quercetin and stir until dissolved. 20 mL of chloroethanol was added dropwise with stirring, and the reaction was continued for 24 hours. Neutralize the reaction liquid with 1mol / L sulfuric acid to neutral, concentrate under reduced pressure, desalt and remove DMF with a gel chromatography column, and dry under vacuum (20kPa) to obtain 26.3g of hydroxyethyl quercetin derivatives.

Embodiment 3

[0045] In a 250mL flask, add 10.2g KOH and 100mL water, stir to dissolve. Then add 15g of quercetin and stir until dissolved. 3 mL of ethylene oxide was added dropwise with stirring, and the reaction was continued for another 22 hours under airtight conditions. Use 2mol / L acetic acid to neutralize the reaction solution to neutrality, extract the water phase through n-butanol extraction, heat the n-butanol phase under reduced pressure (below 80°C) to recover n-butanol, and then vacuum-dry to obtain 13.2g of hydroxyl Ethyl quercetin derivatives.

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Abstract

The invention relates to hydroxyethylated meletin derivative with general formula (I), and the R1, R2, R3, R4, R5 are H or -CH2CH2OH, and at least one of R1, R2, R3, R4, R5 is -CH2CH2OH, but R1, R2 are not H, and R3, R4, R5 are -CH2CH2OH. The invention also relates to method for preparing said compound, comprising dissolving meletin in basic solution, adding epoxyethane or chlorethanol, stirring, neutralizing with acid to be neutral, getting coarse product; removing salt with one methodof normal chromatogram, chromatogram, hyperfiltration, ion exchange, electrodialysis and hyperfiltration; drying and getting yellow or amber-yellow powder hydroxyethylated meletin derivative. The product is widely used in preparing drug, cosmetics, health products and foodstuff.

Description

technical field [0001] The invention relates to a quercetin derivative and its preparation method and application, in particular to a tetrahydroxyethyl quercetin derivative, its preparation method and its application in the preparation of medicines, cosmetics, health care products and food. Background technique [0002] Quercetin widely exists in natural medicines, and has anti-tumor, anti-allergic, anti-oxidation, and anti-platelet aggregation effects, and has been paid more and more attention and application. However, because quercetin is insoluble in water, it is very inconvenient and sometimes limited when applying quercetin to the fields of medicine, cosmetics, health care products and food. Therefore, the development of water-soluble quercetin derivatives with the same drug function to be easily applied to the fields of medicine, cosmetics, health products, and food has become an urgent problem to be solved at present. [0003] Chinese patent application number 200410...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/352A61K8/49A23L1/30A23L33/10
Inventor 刘玉法杜华陈玉琴王锐
Owner SHANDONG NORMAL UNIV
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