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Synthesis method of hypericin

A technology of hypericin and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of multiple column passes, high cost, low product yield and the like

Active Publication Date: 2014-12-10
湖南世标健康科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that a lot of organic solvents need to be used, and there are many steps, resulting in low overall yield and multiple column passes
(3) Directly use crude emodin as raw material, obtain emodin anthrone through reduction, and then condense through a catalyst to obtain protohypericin, and then convert protohypericin into aureus through monochromatic light or high-power light irradiation Sericin, because it is difficult to control the light when it is illuminated, and it is difficult to concentrate, resulting in a slow reaction rate and incomplete reaction, so not only the reaction time is long, the product yield is low, and it is very unsuitable for industrial applications. It can only be used in experiments. Small-scale experiments in the laboratory
And in the process of preparing hypericin with emodin as raw material, it is necessary to obtain the intermediate product emodin anthrone first, and then carry out the dimerization condensation reaction to obtain the original hypericin, resulting in complicated process and high cost

Method used

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  • Synthesis method of hypericin
  • Synthesis method of hypericin
  • Synthesis method of hypericin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Synthesis of protohypericin from emodin

[0030] Emodin 270 mg, potassium tert-butoxide 347 mg, distilled water 30 mL, hydroquinone 230 mg, the above reactants were added to a 50 mL round bottom flask, and the N 2 , 200w microwave irradiation reaction at 95°C for 4-6h. After the reaction was initiated, the solution was quickly transferred to a reaction kettle and placed in an oven at 120°C for 8 h. After opening the reaction kettle, 3% by mass hydrochloric acid was added dropwise to adjust the solution to pH=3, the precipitate was filtered out, washed with water until neutral, and vacuum-dried to obtain prohypericin as a black powder solid with a yield of 90%.

[0031] (2) Protohypericin conversion hypericin

[0032] Weigh 100 mg of the original hypericin obtained in step (1) and add 44 mg of iodosobenzene, dissolve in 100 mL of acetone, heat at 45°C while stirring, react for 4 hours, filter, collect the filtrate, and remove the acetone by rotary evaporation . Th...

Embodiment 2

[0034] (1) Synthesis of protohypericin from emodin

[0035] Emodin 270 mg, sodium tert-butoxide 300 mg, distilled water 30 mL, hydroquinone 230 mg, the above reactants were added to a 50 mL round bottom flask, and a three-way pipe was connected to N 2 ,, 300w microwave irradiation reaction under the condition of 95 ℃ for 4 ~ 6h, after the reaction was initiated, the solution was quickly transferred to the reaction kettle, and placed in a 130 ℃ oven for 10h. After the reactor was opened, 3% sulfuric acid was added dropwise to adjust the solution to pH = 3, the precipitate was filtered off, washed with water until neutral, and vacuum-dried to obtain prohypericin as a black powder solid with a yield of 89%.

[0036] (2) Protohypericin conversion hypericin

[0037] Weigh 100 mg of the original hypericin obtained in step (1), add 30 mg of iodosobenzene, dissolve in 150 mL of acetone, heat at 50°C while stirring, react for 6 hours, filter, collect the filtrate, and remove the aceto...

Embodiment 3

[0039] (1) Synthesis of protohypericin from emodin

[0040] Emodin 270mg, Potassium tert-butoxide 350mg, distilled water 30mL, hydroquinone 330mg, add the above reactants into a 50 mL round bottom flask, connect N with a three-way tube 2 , 400w microwave irradiation reaction at 100°C for 4-6h, after the reaction was initiated, the solution was quickly transferred to a reaction kettle and placed in an oven at 140°C for 12h. After opening the reaction kettle, add 3% hydrochloric acid drop by drop, adjust the solution to pH = 3, filter out the precipitate, wash the precipitate with water until neutral, and dry it in vacuum to obtain a black powdery solid protohypericin with a yield of 90%. .

[0041](2) Protohypericin conversion hypericin

[0042] Weigh 100 mg of the original St. John's Wort obtained in step (1), add 22 mg of iodosobenzene, dissolve in 200 mL of acetone, heat at 55 ° C while stirring, and after 8 hours of reaction, filter, collect the filtrate, and remove the a...

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Abstract

The invention discloses a synthesis method of hypericin. The synthesis method comprises the following steps of (a) dissolving emodin and tert-butanol salt into water, adding hydroquinone at a protective atmosphere, carrying out microwave irradiation, reacting at the temperature of 90-100 DEG C for 4-6h, then, transferring the product into a sealed vessel, continuing to react at the temperature of 120-140 DEG C for 8-12h, after finishing the reaction, adding an inorganic acid to regulate the pH value of the solution to 3-4, settling, filtering, washing, and drying, thereby obtaining raw hypericin at one step; and (b) dissolving the obtained raw hypericin and iodosobenzene substances into acetone, reacting at the temperature of 45-55 DEG C for 4-8h, filtering after finishing the reaction, collecting filtrate, carrying out evaporative concentration, washing, filtering and recrystallizing to obtain the hypericin. The hypericin obtained by using the synthesis method is high in purity and yield; and the synthesis method is simple in step, environment-friendly, reduced in cost and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a method for synthesizing hypericin. Background technique [0002] Hypericum perforatum, also known as Hypericum perforatum, uses the whole plant as medicine. It tastes bitter, pungent, and flat in nature. It has the effects of stopping bleeding and promoting muscle growth, detoxification and anti-inflammatory. The most active ingredient in the Hypericum perforatum plant is a dianthraquinone compound-hypericin. According to reports, hypericin and pseudohypericin also have various pharmacological effects such as anti-virus, anti-depression, and anti-AIDS, making Hypericum perforatum become one of the best-selling herbal medicines in the world in recent years. In addition to Hypericum perforatum plants, hypericin also widely exists in Hypericum plants. [0003] Hypericin is a natural plant active ingredient, which has hypericin extracted from plants and is ve...

Claims

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Application Information

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IPC IPC(8): C07C50/36C07C46/00
CPCC07C46/00C07C46/10C07C2603/54C07C50/36
Inventor 钟世安周成赟苏霞张小娜朱小红李慧
Owner 湖南世标健康科技有限公司
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