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Efficient hypericin synthesizing method initiated by monochromatic light

A technology for hypericin and original hypericin, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of quinones, etc., can solve the problems of cumbersome process of synthesizing hypericin, environmental pollution and high cost, and achieves The effect of reducing synthesis cost, high yield and short reaction time

Active Publication Date: 2013-09-04
NORTHWEST A & F UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the embodiments of the present invention is to provide a method for synthesizing hypericin induced by monochromatic light, aiming to solve the problems of cumbersome synthetic hypericin process, high cost, low efficiency, large energy consumption and serious environmental pollution in the prior art. question

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  • Efficient hypericin synthesizing method initiated by monochromatic light
  • Efficient hypericin synthesizing method initiated by monochromatic light

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Embodiment 1

[0055] (1) Synthesis of protohypericin

[0056] In a 10mL microwave quartz tube, accurately weigh 130mg of emodin anthrone, 10mg of ferric chloride, 250mg of pyridine nitroxide, and 30mg of sodium hydroxide, then add 2mL of deionized water and blow argon into the quartz tube, and then put reaction in a microwave reactor. The temperature was set at 105° C., the microwave power was set at 10 W, and the reaction time was set at 70 min. After the reaction was completed, the reaction mixture was cooled to room temperature and neutralized with 3% hydrochloric acid solution, left to settle and filtered. The filter cake was washed thoroughly with deionized water and dried to obtain a black precipitate. The crude product was purified by a silica gel column to obtain 122 mg of a purple-black powder product with a yield of 96%.

[0057] (2) Synthesis of hypericin

[0058] Accurately weigh 127mg of original hypericin in a 125mL conical flask and dissolve it in 100mL acetone. Irradiate ...

Embodiment 2

[0060] (1) Synthesis of protohypericin

[0061] In a 35mL quartz tube, accurately weigh 1.28g of emodin anthrone, 107mg of ferric chloride, 301mg of sodium hydroxide, 2.51g of nitrogen pyridine, and add H 2 O20mL. After blowing in argon gas, it was put into a microwave reactor for reaction. The temperature was set at 105° C., the microwave power was set at 10 W, and the reaction time was set at 70 min. After the reaction, according to the scheme one post-processing to obtain 1.16g of purple black prohypericin powder, the yield is 92%

[0062] (2) Synthesis of hypericin

[0063] In a 250mL Erlenmeyer flask, accurately weigh 1.00g of original hypericin, and add 200mL of acetone into it. Stir under the protection of argon, irradiate the reaction with 575nm monochromatic light, follow TLC, and the reaction is complete in 3 hours. Acetone was distilled off under reduced pressure to obtain a crude product, which was purified by a silica gel column to obtain 895 mg of black hype...

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Abstract

The invention discloses an efficient hypericin synthesizing method initiated by monochromatic light. The method comprises the steps as follows: emodin is reduced to emodin anthrone under an acidic condition; the emodin anthrone is condensed to protohypericin through dimerization; and the protohypericin reacts under initiation of the monochromatic light to form the hypericin. According to the method, the dimerization reaction of the emodin anthrone takes a sodium hydroxide aqueous solution as a reaction medium and is performed in a microwave reactor, and has the characteristics of short reaction time, low temperature and high yield; in a light reaction, the monochromatic light with the wavelength of 575 nm is adopted to perform a light initiation reaction on a protohypericin acetone solution to prepare the hypericin, therefore, the reaction time is shortened greatly, and two steps of yields after column chromatography purification are as high as 96%; and additionally, the hypericin synthesizing method initiated by the monochromatic light provided by the invention has the advantages of convenience in operation, mild conditions, low synthetic cost and environment protection, and has bright development prospects.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of hypericin, in particular to a method for synthesizing hypericin induced by monochromatic light. Background technique [0002] Hypericin is the most biologically active substance in Hypericum perforatum. It not only has pharmacological activities such as antidepressant, antibacterial and anti-inflammatory, anti-DNA and RNA viruses, and memory promotion, but also is an effective photosensitizer. It has a strong activity of inducing tumor cell apoptosis in the drug therapy (PDT), has broad prospects for pharmaceutical development, and has attracted widespread attention at home and abroad. [0003] However, the content of hypericin in the whole plant of Hypericum perforatum is extremely low (only a few ten-thousandths). It takes a long time to extract and separate from the whole plant of Hypericum perforatum with traditional separation methods, the yield is low, and the effect is poor. Using this ...

Claims

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Application Information

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IPC IPC(8): C07C50/36C07C46/00
Inventor 裴玉新李泽波裴志超侯勇
Owner NORTHWEST A & F UNIV
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