Cantharidin preparation method

A technology of cantharidin and carotene, which is applied in the directions of organic chemistry and chemical recovery, can solve the problems of low yield of cantharidin and large environmental pollution, and achieves the effects of good oxidation effect, high yield and reduced consumption.

Active Publication Date: 2021-03-26
XIAMEN KINGDOMWAY VI TAMIN INC +1
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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 overcome the disadvantages of low yield and high environmental pollution in the preparation of c

Method used

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Experimental program
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Effect test

Embodiment 1

[0044] Dissolve 0.30g (0.0018mol) of potassium iodide, 0.46g (0.0036mol) of manganese chloride, and 19.43g (0.1825mol) of sodium chlorate in 250mL of water, and adjust the pH value of the resulting aqueous solution to 4 with 5% dilute hydrochloric acid.

[0045] Add 20g of β-carotene (98.0%, 0.0365mol) and 500mL of dichloromethane into a 1000mL reactor, start stirring, add the above aqueous solution, pump nitrogen three times, cool down to 0-5°C, and keep warm for 3h. After the heat preservation is over, let it stand for stratification, wash the oil layer once with 150mL 2.5% w / v sodium thiosulfate solution, wash once with water, then concentrate to dryness, add 200mL ethanol, heat isomerization at 70°C for 8h, drop to room temperature, reduce Press filtration and dry to obtain 19.91 g of all-trans cantharidin with a content of 95.5% and a yield of 92.2%.

Embodiment 2

[0047] Dissolve 0.18g (0.0011mol) of potassium iodide, 0.28g (0.0022mol) of manganese chloride, and 11.66g (0.1095mol) of sodium chlorate in 250mL of water, and adjust the pH of the resulting aqueous solution to 4 with 5% dilute hydrochloric acid.

[0048] Add 20g of β-carotene (98.0%, 0.0365mol) and 500mL of dichloromethane into a 1000mL reactor, start stirring, add the above aqueous solution, pump nitrogen three times, cool down to 0-5°C, and keep warm for 3h. After the heat preservation is over, let it stand for stratification, wash the oil layer once with 150mL 2.5% w / v sodium thiosulfate solution, wash once with water, then concentrate to dryness, add 200mL ethanol, heat isomerization at 70°C for 8h, drop to room temperature, reduce After pressure filtration and drying, 19.71 g of all-trans cantharidin was obtained, the content was 90.5%, and the yield was 86.5%.

Embodiment 3

[0050] Dissolve 0.61g (0.0037mol) of potassium iodide, 0.92g (0.0073mol) of manganese chloride, and 19.43g (0.1825mol) of sodium chlorate in 250mL of water, and adjust the pH of the resulting aqueous solution to 4 with 5% dilute hydrochloric acid.

[0051] Add 20g of β-carotene (98.0%, 0.0365mol) and 500mL of dichloromethane into a 1000mL reactor, start stirring, add the above aqueous solution, pump nitrogen three times, cool down to 0-5°C, and keep warm for 3h. After the heat preservation is over, let it stand for stratification, wash the oil layer once with 150mL 2.5% w / v sodium thiosulfate solution, wash once with water, then concentrate to dryness, add 200mL ethanol, heat isomerization at 70°C for 8h, drop to room temperature, reduce After pressure filtration and drying, 20.11 g of all-trans cantharidin was obtained, the content was 93.2%, and the yield was 90.9%.

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Abstract

The invention belongs to the field of compound synthesis, and relates to a cantharidin preparation method, which comprises: carrying out an oxidation reaction on beta carotene in a solvent in the presence of an oxidizing agent, a catalyst and a strong acid salt of divalent manganese ions, performing standing for layering after the oxidation reaction is finished, washing and purifying the oil layer, and concentrating to remove the solvent, and then adding an isomerization solvent to carry out isomerization reaction, and filtering and drying after the isomerization reaction is finished to obtainthe all-trans cantharidin. The cantharidin prepared by adopting the method provided by the invention has the advantages of good oxidation effect, lower oxidant dosage and higher cantharidin yield (upto 86% or above), and the obtained cantharidin is a purple red acicular crystal with the content of more than 90%. Then, a water layer is treated by adopting the method provided by the invention andthen is recycled, so that the consumption of an oxidant can be reduced, the cost is reduced, and meanwhile, the discharge of halogen-free acid salt wastewater is realized.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a preparation method of cantharidin. Background technique [0002] Canthaxanthin is a kind of carotenoid, which naturally exists in mushrooms, algae, animal shells, fish and shrimp, poultry eggs, etc., and its content is relatively small. Its structure is shown in formula (1). In the food industry, cantharidin is widely used in beverages, ice cream, biscuits, sauces, meat products and other products. At the same time, cantharidin is also widely used in the feed additive industry, mainly to improve the color quality of poultry eggs and the growth of specific fish and shrimp. In recent years, in the pharmaceutical and health care products industry, the role of cantharidin has also begun to be valued by people. A large number of studies have shown that cantharidin has preventive and therapeutic effects on various diseases. These effects are related to its antioxidant p...

Claims

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Application Information

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IPC IPC(8): C07C403/24
CPCC07C403/24C07C2601/16Y02P20/584
Inventor 马瑞达汤镇伟谢德刚赵家宇
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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