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Hypericin synthesis method

A technology of hypericin and a synthesis method is applied in chemical instruments and methods, preparation of organic compounds, preparation of quinones, etc., can solve the problems of inability to large-scale production, low yield and the like, and achieves low cost, high yield, The effect of a short synthetic route

Active Publication Date: 2017-04-26
陕西嘉禾药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to provide a synthetic method of hypericin, which mainly solves the problem that the yield in the prior art is low and cannot be produced on a large scale

Method used

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Examples

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Effect test

Embodiment 1

[0032] (1) Put 30kg of emodin, 1500kg of glacial acetic acid, and 100kg of stannous chloride dihydrate into a 2-ton reaction kettle. 283kg of concentrated hydrochloric acid was added and reacted for two hours. Cool down to below 20 degrees, plate and frame filter and wash with water until neutral. Dried to obtain 27 kg of emodin enone.

[0033] (2) 30 kg of emodin anthrone, 600 kg of pyridine, 51.6 kg of piperidine, 60 kg of pyridine nitrogen oxide, and 3 kg of ferrous sulfate are dropped into 1 ton of reactor, and after adding, reflux reaction is carried out for 3 hours, and pyridine is reclaimed under reduced pressure to a small volume. After cooling, add dilute hydrochloric acid to neutralize the pH value at about 5-6, centrifuge or plate-and-frame filter and wash with water until neutral to obtain prohypericin, and dry at 50 degrees to obtain 30 kg for later use.

[0034] (3) 15kg of former hypericin is dissolved in 1500L concentration and is that the sodium hydroxide so...

Embodiment 2

[0036] (1) Emodin 20kg glacial acetic acid 1000kg stannous chloride dihydrate 68kg is thrown into 2 tons of reactor, after adding, the temperature is raised to reflux, then slowly add 55.3kg concentrated hydrochloric acid and react for one hour after adding, then slowly add 188.7 kg concentrated hydrochloric acid. The reaction was completed for two hours. Cool down to below 20 degrees, plate and frame filter and wash with water until neutral. Dry to obtain 19 kilograms of emodin enquinone.

[0037] (2) 20 kg of emodin anthrone, 400 kg of pyridine, 34.4 kg of piperidine, 40 kg of pyridine nitrogen oxide, and 2 kg of ferrous sulfate are put into 1 ton of reactor, and after adding, reflux reaction is carried out for 3 hours, and pyridine is reclaimed under reduced pressure to a small volume. After cooling, add dilute hydrochloric acid to neutralize the pH value at about 5-6, centrifuge or plate and frame filter and wash with water until neutral to obtain prohypericin, and dry a...

Embodiment 3

[0040](1) Emodin 10kg glacial acetic acid 450kg stannous chloride dihydrate 35kg into a 1-ton reaction kettle, after the addition, the temperature was raised to reflux, then slowly added dropwise 28kg concentrated hydrochloric acid, reacted for one hour after the addition, and then slowly added dropwise 94kg Concentrated hydrochloric acid. The reaction was completed for two hours. Cool down to below 20 degrees, plate and frame filter and wash with water until neutral. Dried to obtain 9 kg of emodin enone.

[0041] (2) 9 kg of emodin anthrone, 200 kg of pyridine, 17.2 kg of piperidine, 20 kg of pyridine nitrogen oxide, and 1 kg of ferrous sulfate are put into a 1 ton reactor, and after the addition, the reflux reaction is carried out for 3 hours, and the pyridine is recovered under reduced pressure to a small volume. After cooling, add dilute hydrochloric acid to neutralize the pH value at about 5-6, centrifuge or plate and frame filter and wash with water until neutral to ob...

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Abstract

The invention provides a hypericin synthesis method. The hypericin synthesis method includes the steps of firstly, mixing emodin, glacial acetic acid and stannous chloride dihydrate prior to heating reflux, adding concentrated hydrochloric acid prior to cooling and filtering, washing a filtered product until the filtered product is neutral, and drying the neutral filtered product so as to obtain emodin anthrone; mixing the emodin anthrone, pyridine, piperidine, pyridine N-oxide and ferrous sulfate prior to reflux reaction, performing pressure reduction to recover the pyridine prior to cooling, adding hydrochloric acid for neutralizing prior to filtering, washing a filtered product until the filtered product is neutral, and drying the neutral filtered product so as to obtain protohypericin; dissolving the protohypericin into a sodium hydroxide solution, reacting under the action of lighting, and adding hydrochloric acid for neutralizing prior to suction filtration, washing and drying so as to obtain hypericin. The hypericin synthesis method has the advantages that the hypericin is prepared from the emodin through chemical synthesis and is synthesized through a process route including reduction, condensation and lighting reaction, and accordingly the method is high in yield, low in cost, simple and convenient to operate, high in hypericin chemical synthesis route applicability and suitable for enlarged production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a method for synthesizing hypericin. Background technique [0002] Hypericin is the most biologically active substance in Hypericum perforatum L. Hypericin is not only present in Hypericum perforatum, but also widely distributed in other plants of the genus Hypericum. Hypericin was first isolated by Dietrich in 1891. In 1911, S.Czerny named it "Hypericin". fully synthetic work. Decomposition point is 320°C, easily soluble in pyridine or other organic amines, orange-red with red fluorescence, insoluble in most organic solvents, soluble in alkaline aqueous solution, red solution when pH is lower than 11.5, pH higher than At 11.5, it is a green solution with red fluorescence. The chemical formula of Hypericin is 4,4',5,5',7,7'-hexahydroxy-2,2'-dimethyl-meso-naphthodianthrone. [0003] The structural formula of Hypericin is as follows: [0004] [0005] Hypericin is a dianthron...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/36C07C46/00
Inventor 郭文华赵景辉肖金霞
Owner 陕西嘉禾药业有限公司
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