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Method for preparing (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein

A technology of methoxyphenyl and acrolein, applied in the field of medicine, can solve the problems such as the preparation and activity research of acrolein, and achieve the effects of mild conditions, simple steps and high product purity

Active Publication Date: 2014-06-04
聊城来通国际贸易有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no further research on the preparation and activity of (trans)-3-(3-hydroxy-4-methoxyphenyl)acrolein, and there is a technical gap

Method used

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  • Method for preparing (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein
  • Method for preparing (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein
  • Method for preparing (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Preparation of Eucommia Extract

[0029] Take the dried bark of Eucommia ulmoides, soak it in saturated NaCl solution for 15 minutes, take it out and dry it in the air, make small pieces or strips, bake it at 150-180°C for 4 hours, and pulverize it with a pulverizer to obtain salted eucommia powder. Take 100 grams of salt Eucommia powder, add 300ml of 60% ethanol to soak at room temperature for 10 minutes, fully swell, bathe in 60°C water for 30 minutes, add the filtrate to a chromatography column filled with neutral alumina (100-200 mesh), and the column volume is φ60mm ×80mm, the filler is pre-saturated with ethanol. Collect the effluent after passing through the column, and after all the filtrate passes through the column, wash the column with 100 ml of ethanol, and collect the effluent. Suction filter funnel filter paper was filtered under reduced pressure, the residue was bathed in water at 60°C for 30 minutes again, filtered under reduced pressure, and ...

Embodiment 2

[0030] Example 2 Preparative HPLC Separation of Eucommia Eucommia Extract

[0031] The chromatographic conditions used are: chromatographic column SHIMADZU PRC-ODS 20×250mm 15μm, the mobile phase is methanol:water=1:1, the flow rate is 15ml / min, 315nm detection, room temperature operation, and the components with a retention time of 7-8.5 minutes are collected . (See figure 1 , the peak marked by DZ_2 is (trans)-3-(3-hydroxy-4-methoxyphenyl)acrolein).

Embodiment 3

[0032] Example 3 Preparation of (trans)-3-(3-hydroxy-4-methoxyphenyl)acrolein by semi-preparative HPLC

[0033] The components obtained in Example 2 were concentrated using a rotary evaporator at a temperature of 60° C., and evaporated until figure 2 .

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Abstract

The invention provides a method for preparing (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein, comprising the following steps of: (1) by taking eucommia ulmoides as an extraction raw material, extracting by using a mixed solution of alcohol and water; (2) removing pigment from the extract obtained in the step (1) by using a neutral aluminum oxide chromatography column, collecting the eluate and concentrating the eluate; (3) extracting the eluate obtained in the step (2) by using an organic solvent; (4) separating the extract obtained in the step (3) by using preparative HPLC (High Performance Liquid Chromatography) and semi-preparative HPLC orderly, thereby obtaining the (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein. The preparation method provided by the invention is mild in conditions and simple in steps, and the prepared product is high in purity, and therefore, the method has pioneering significance for the preparation of (trans)-3-(3-hydroxy-4-methoxy phenyl) acrolein.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of (trans)-3-(3-hydroxyl-4-methoxyphenyl)acrolein. Background technique [0002] (Trans)-3-(3-Hydroxy-4-methoxyphenyl)acrolein is a cinnamic aldehyde derivative with the following structure: [0003] [0004] Literature "Cinnamaldehydes inhibit cyclin dependent kinase 4 / cyclin D1. (Jeong, H.-W.; Kim, M.-R.; Son, K.-H. et al, Bioorganic & Medicinal Chemistry Letters (2000), 10( 16), 1819-1822.)” for the first time disclosed the structure of (trans)-3-(3-hydroxy-4-methoxyphenyl)acrolein, and found that cinnamon aldehyde has the activity of inhibiting cell cycle protein kinase. (trans)- The extraction method of 3-(3-hydroxyl-4-methoxyphenyl) acrolein. At present, there is no preparation of (trans)-3-(3-hydroxyl-4-methoxyphenyl)acrolein And further research on activity, there is a technical gap. Contents of the invention [0005] The invention provi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/277C07C45/78C07C45/79C07C45/80
Inventor 谭湘陵钱晓伟潘丹岷羌利民
Owner 聊城来通国际贸易有限公司