Method of preparing aloe-emodin

A technology of aloe-emodin and aloin, applied in the preparation of quinone oxide, organic chemistry, etc., can solve the problems of high pipeline design requirements, iron residue in products, increased risk, etc., and achieve good promotion and application prospects, high yield and purity , the effect of less solvent consumption

Inactive Publication Date: 2009-08-19
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of oxygen-containing gas in the former, the cost is high and the requirements for pipeline design are also high, so it is difficult to realize industrial production
In addition, if the oxygen-containing gas is mixed with some other gases, it is prone to explosion accidents, which increases the risk of production
The latter uses ferric chloride as an oxidant. Although the industrial operation is simple and easy, and the production cost is also low, the waste water produced contains a large amount of iron ions, which may cause iron ion pollution to the environment and iron residues in the product.

Method used

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  • Method of preparing aloe-emodin
  • Method of preparing aloe-emodin
  • Method of preparing aloe-emodin

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Put aloin (9.36g, 20mmol) and Oxone (24.59g, 40mmol) into a 150ml reaction vessel; add 20g water and 48g toluene; stir and react at 110°C for 2h. After the reaction is completed, filter while it is hot, and the filtrate is allowed to stand for layers. Take the toluene layer, dry it with anhydrous sodium sulfate, and recover part of the solvent by distillation. The residue is cooled to 0°C to crystallize, filter, and the filter cake is dried to obtain aloe-emodin 5.03g. The HPLC purity was 97.4%, and the yield was 90.7%.

Embodiment 2

[0025] Put aloin (9.36g, 20mmol) and Oxone (24.59g, 40mmol) into a 500ml reaction vessel; add 140g water and 48g toluene; stir and react at 110°C for 2h. After the reaction is completed, filter while it is hot, and the filtrate is allowed to stand for layers. Take the toluene layer, dry it with anhydrous sodium sulfate, and recover part of the solvent by distillation. The residue is cooled to 0°C to crystallize, filter, and the filter cake is dried to obtain aloe-emodin 5.18g. The HPLC purity was 96.2%, and the yield was 92.3%.

Embodiment 3

[0027] Put aloin (9.36g, 20mmol) and Oxone (24.59g, 40mmol) into a 250ml reaction vessel; add 75g water and 20g toluene; stir and react at 110°C for 2h. After the reaction is finished, filter while it is hot, let the filtrate stand to separate layers, take the toluene layer, dry it with anhydrous sodium sulfate, recover part of the solvent by distillation, cool the residue to 0°C to crystallize, filter, and dry the filter cake in vacuum to obtain aloe-emodin 5.16 g. The HPLC purity was 95.7%, and the yield was 91.5%.

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Abstract

The invention discloses a method for preparing aloe-emodin of formula (II), comprising the following steps: feeding aloin of formula (I) and an oxidizer into a reaction container, adding water and toluene into the reaction container, stirring the mixture for reaction for 1-8 hours at a temperature between 50 and 110 DEG C, and post-treating the reactants to obtain the aloe-emodin after the reaction is over, wherein the oxidizer is selected from one or a combination of more than one of potassium monopersulfate, K2S2O8, Na2S2O and CaS2O8 in any proportion, and the amount of the substance of the oxidizer is 0.5-10 times of that of the aloin. The method for preparing the aloe-emodin has the advantages of easily obtained raw materials, simple process, little usage of solvent, higher product yield and purity, no iron ion pollution to environment or iron ion residue in the product, and better popularization and application prospects.

Description

(1) Technical field [0001] The invention relates to a preparation method of aloe-emodin. (2) Background technology [0002] Aloe-emodin, also known as aloe-emodin (Rhabarberone). It crystallizes in toluene as orange needle-shaped crystals with a melting point of 223°C to 224°C. It is easily soluble in hot ethanol and can be reduced in acidic solution to produce anthracenol and its tautomer anthrone. Aloe-emodin has the functions of purging and scavenging oxygen free radicals, is a natural and efficient free radical scavenger, and also has anti-cancer effects. More importantly, recent studies have shown that aloe-emodin is a raw material intermediate for the synthesis of osteoarthritis drug diacerein. Therefore, research on the preparation of aloe-emodin has very far-reaching significance. [0003] The structural formula of aloe-emodin: [0004] [0005] The preparation of aloe-emodin mainly includes natural extraction and chemical synthesis. Natural aloe-emodin mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/34C07C46/06
Inventor 苏为科朱兴一张志敏
Owner ZHEJIANG UNIV OF TECH
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