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Enzyme-catalyzed preparation method and application of quercetin-3-o-fatty acid ester

A fatty acid ester, catalytic preparation technology, applied in the direction of medical preparations containing active ingredients, pharmaceutical formulas, blood diseases, etc., can solve the problem of multiple reaction steps, the risk of catalytic hydrogenolysis reaction, the irritation and toxicity of benzylation reagents Large and other problems, to achieve the effect of short reaction route, good anti-platelet aggregation activity, and convenient industrial production

Active Publication Date: 2017-03-22
WEIFANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Zhai Guangyu and other patents (Chinese patent 201210113907.X) used rutin as a starting material to prepare quercetin-3-O-acyl esters through four steps of benzylation, hydrolysis under acidic conditions, esterification, and catalytic hydrogenolysis Compound, many reaction steps, the benzylation reagent used is highly irritating and toxic, and the catalytic hydrogenolysis reaction is dangerous

Method used

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  • Enzyme-catalyzed preparation method and application of quercetin-3-o-fatty acid ester
  • Enzyme-catalyzed preparation method and application of quercetin-3-o-fatty acid ester
  • Enzyme-catalyzed preparation method and application of quercetin-3-o-fatty acid ester

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The enzyme-catalyzed preparation method of quercetin-3-O-fatty acid ester comprises the following steps:

[0041] (1) Add quercetin to acetonitrile, the molar concentration of quercetin is 0.01mol / L, under the condition of 10 ℃, under the catalysis of triethylamine, react with acid anhydride or acid chloride for 5 hours to obtain quercetin Cortex-3,5,7,3',4'-penta fatty acid ester;

[0042] (2) Add the quercetin-3,5,7,3',4'-penta fatty acid ester into acetonitrile, quercetin-3,5,7,3',4'-penta fatty acid The molar concentration of the ester is 0.002 mol / L, under the condition of 20°C, under the catalysis of lipase Lipozyme IM-20, it undergoes alcoholysis reaction with n-butanol for 100 hours to obtain quercetin-3-O-fatty acid ester;

[0043]

[0044] The quercetin-3-O-fatty acid ester is a compound of general formula (I), wherein R=C1-C4 alkyl.

[0045] In step (1), the molar ratio of quercetin, acid anhydride or acid chloride and the basic catalyst is 1:5:5; in ste...

Embodiment 2

[0051] The enzyme-catalyzed preparation method of quercetin-3-O-fatty acid ester comprises the following steps:

[0052] (1) Add quercetin to N,N-dimethylformamide, the molar concentration of quercetin is 0.022mol / L, under the condition of 25°C, under the catalysis of pyridine, it will react with acid anhydride or acid chloride 3.5 hours reaction to obtain quercetin-3,5,7,3',4'-penta fatty acid ester;

[0053] (2) Add the quercetin-3,5,7,3',4'-penta fatty acid ester into N,N-dimethylformamide, quercetin-3,5,7,3 The molar concentration of ',4'-penta fatty acid ester is 0.008 mol / L, under the condition of 45℃, under the catalysis of lipase Lipozyme IM-60, it undergoes alcoholysis reaction with n-butanol for 45 hours to obtain quercetin- 3-O-fatty acid esters;

[0054]

[0055] The quercetin-3-O-fatty acid ester is a compound of general formula (I), wherein R=C1-C4 alkyl.

[0056] In step (1), the molar ratio of quercetin, acid anhydride or acid chloride and the basic catal...

Embodiment 3

[0062] The enzyme-catalyzed preparation method of quercetin-3-O-fatty acid ester comprises the following steps:

[0063] (1) Add quercetin to methyl tert-butyl ether, the molar concentration of quercetin is 0.1mol / L, at 100°C, Na 2 CO 3 Under the catalysis of the catalyst, react with acid anhydride or acid chloride for 3 hours to obtain quercetin-3,5,7,3',4'-penta fatty acid ester;

[0064] (2) Add the quercetin-3,5,7,3',4'-penta fatty acid ester into methyl tert-butyl ether, quercetin-3,5,7,3',4 The molar concentration of '-penta fatty acid ester is 0.04mol / L, under the condition of 80℃, under the catalysis of lipase Lipozyme IM-60, it undergoes alcoholysis reaction with n-butanol for 30 hours to obtain quercetin-3-O - fatty acid esters;

[0065]

[0066] The quercetin-3-O-fatty acid ester is a compound of general formula (I), wherein R=C1-C4 alkyl.

[0067] In step (1), the molar ratio of quercetin, acid anhydride or acid chloride and the basic catalyst is 1:15:15; in...

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Abstract

The invention provides an enzymatic preparation method of quercetin-3-O-fatty acid ester. The preparation method comprises the steps of: (1) adding 0.01-0.1mol / L quercetin into an anhydrous organic solvent, and carrying out acylation reaction with an acid anhydride or acyl chloride for 3 to 5 hours to obtain quercetin-3,5,7,3',4'-penta fatty acid ester; (2) adding quercetin-3,5,7,3',4'-penta fatty acid ester to an anhydrous organic solvent, and at 20-80 DEG C, under the catalytic action of lipase Lipozyme IM, performing alcoholysis reaction with n-butanol for 30-100 hours to obtain quercetin-3-O-fatty acid ester. The invention relates to the technical field of medicinal chemistry; the preparation method has the characteristics of mild reaction conditions, high yield, short reaction route, simple process, simple post-processing and easiness for industrial production. The corresponding technical problems in the prior art are solved.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an enzyme-catalyzed preparation method of quercetin-3-O-fatty acid ester and its application. Background technique [0002] Quercetin is an important flavonoid compound, which exists in almost all Chinese herbal medicines with the effect of promoting blood circulation and removing blood stasis, and has low toxic and side effects, and the extraction and separation process is mature and simple. Quercetin exhibits significant anti-platelet aggregation activity, and has obvious inhibitory effects on platelet aggregation induced by ADP, AA, PAF, collagen, and thrombin. However, there are no anti-platelet aggregation quercetin drugs for clinical use, mainly due to the poor solubility, poor druggability and low bioavailability of quercetin. The 3-hydroxyl of quercetin is esterified through structural modification, and fatty acyl groups are introduced to change the molecular...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/06A61K31/352A61P7/02
Inventor 段煜
Owner WEIFANG MEDICAL UNIV