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Method for preparing 3-ester group catechin

A technology of ester catechin and catechin is applied in the field of preparation of 3-ester catechin, can solve the problems of high cost, unsuitability for industrialized production, etc., achieves good selectivity, avoids toxicity and corrosive reagents and reactions mild conditions

Active Publication Date: 2015-01-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This document uses lipase Novozym435 as a catalyst, on the one hand, the cost is high, and on the other hand, it is not suitable for industrial production

Method used

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  • Method for preparing 3-ester group catechin
  • Method for preparing 3-ester group catechin
  • Method for preparing 3-ester group catechin

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Catechin (29 mg), propionic anhydride (59 mg) and triethylamine (45 mg) were stirred and reacted at room temperature for 20 hours, extracted with ethyl acetate after the reaction, and chromatographed (eluent ethyl acetate mixed with petroleum ether) solvent) to obtain 3',4',5,7-tetrapropyl catechin (yield: 78%) after purification. Then react with lauryl chloride (44mg) and pyridine (24mg) for 24 hours, then react with hydrazine hydrate (40mg) for 8 hours, extract with ethyl acetate after the reaction, and obtain 3-dodecyl Ester catechins 72%.

[0038] Structure determination data: 1 H NMR(400MHz,DMSO)δ9.35(s,1H),9.08(s,1H),8.96(s,1H),8.90(s,1H),6.71(d,J=1.6Hz,1H),6.68 (d,J=8.4Hz,1H),6.57(dd,J=8.4,2.0Hz,1H),5.93(d,J=2.0Hz,1H),5.77(d,J=2.0Hz,1H),5.11 (q, J=6.0Hz, 1H), 4.90(d, J=6.4Hz, 1H), 2.64(dd, J=16.4, 5.2Hz, 1H), 2.54-2.46(m, 1H), 2.17(td, J=7.2,3.2Hz,2H), 1.42-1.33(m,2H), 1.32-1.03(m,16H), 0.86(t,J=7.2,3H). The mass spectrum shows the dehydrogenation molecular i...

Embodiment 2

[0040]Catechin (29 mg), acetic anhydride (46 mg) and tripropylamine (57 mg) were stirred and reacted at room temperature for 20 hours, extracted with ethyl acetate after the reaction, and purified by chromatography to obtain 3',4',5,7 - Tetraethyl catechin (yield 75%). Then react with octanoyl chloride (24mg) and pyridine (32mg) for 24 hours, then react with hydrazine hydrate (40mg) for 8 hours, extract with ethyl acetate after the reaction, and obtain 3-octyl catechin after chromatographic purification 75%. The structure detection data is consistent with the prior art (mass spectrum shows that the dehydrogenation molecular ion peak of the main component is 414.88).

[0041] The structure determination data of 3',4',5,7-tetraethyl catechin: 1 H NMR (400MHz, DMSO-d6) δ7.37-7.25 (m, 3H), 6.61 (d, J = 2.8Hz, 1H), 6.60 (d, J = 2.4Hz, 1H), 4.87 (d, J = 8.0Hz, 1H), 4.05-3.95(m, 1H), 2.78(dd, J=16.4, 5.6Hz, 1H), 2.57-2.48(m, 1H), 2.30(s, 3H), 2.29(s, 6H ), 2.24(s,3H). The mass sp...

Embodiment 3

[0043] Catechin (29 mg), butyric anhydride (71 mg) and N,N-diisopropylethylamine (52 mg) were stirred and reacted at room temperature for 20 hours. After the reaction was completed, they were extracted with ethyl acetate and purified by chromatography to obtain 3 ',4',5,7-tetrabutyl catechin (74% yield). Then react with octanoyl chloride (24mg) and pyridine (32mg) for 24 hours, then react with hydrazine hydrate (40mg) for 8 hours, extract with ethyl acetate after the reaction, and obtain 3-octyl catechin after chromatographic purification 70%. The structure detection data is the same as in Example 2.

[0044] 3',4',5,7-tetrabutyl catechin structure determination data: 1 H NMR (400MHz, DMSO) δ7.39-7.24 (m, 3H), 6.60 (d, J = 2.0Hz, 1H), 6.58 (d, J = 2.0Hz, 1H), 4.88 (d, J = 8.0Hz ,1H),4.05-3.95(m,1H),2.77(dd,J=16.4,5.6Hz,1H),2.63-2.46(m,9H),1.73-1.59(m,8H),1.02-0.92(m , 12H). The mass spectrometry showed that the molecular ion peak of sodium addition was 593.17.

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Abstract

The invention discloses a method for preparing 3-ester group catechin. The method comprises the following steps: (1) carrying out a phenolic hydroxyl selective esterification reaction on catechin and acid anhydride under a condition that tertiary amine serves as alkali and tert-butyl methyl ether serves as a solvent, and carrying out posttreatment after the reaction is completed to obtain 3,4',5,7-tetraester group catechin; (2) reacting the 3',4',5,7-tetraester group catechin with an acylating reagent to generate 3-ester group-3',4',5,7-tetraester group catechin; (3) treating the 3-ester group-3',4',5,7-tetra-ester group catechin with a selective deprotection reagent to obtain the 3-ester group catechin (I). The preparation method has a relatively good selectivity, and the selectivity and yield of intermediate and target products are relatively high; the preparation method is simple to operate, adoption of toxic or corrosive reagent is avoided, the reaction condition is mild, and thus the preparation method is suitable for industrial production application.

Description

technical field [0001] The invention belongs to the field of functional food and medicine, and in particular relates to a preparation method of 3-ester catechin. Background technique [0002] Polyphenols are a class of polyhydric phenolic substances widely present in plants. They are contained in the leaves, wood, skin, shell and pulp of plants, and the skins of fruits and grains contain high levels of plant polyphenols. Polyphenols have an excellent antioxidant effect, which is the basis of all their physiological activities. A large number of in vivo and in vitro experiments and epidemiological data show that eating a certain amount of plant polyphenols can prevent and inhibit diseases. Polyphenols have anti-arteriosclerosis, prevention and treatment of cardiovascular diseases such as coronary heart disease and stroke, as well as anti-inflammatory, anti-allergic and anti-viral effects. With the development of polyphenol chemistry and pharmacology, it is gradually recogn...

Claims

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Application Information

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IPC IPC(8): C07D311/62
CPCC07D311/62
Inventor 刘松柏洪姗
Owner ZHEJIANG UNIV
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