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A method for artificially synthesizing curcumin and derivatives thereof

A curcumin derivative, artificial synthesis technology, applied in the field of medicine, can solve the problems of difficult continuous production, unstable active site selectivity, low production efficiency, etc., and achieves a simple post-processing method, stable properties, and less three wastes. Effect

Active Publication Date: 2020-05-05
GREAT FOREST BIOMEDICAL LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the method for this synthetic curcumin and its derivatives has the unstable active site selectivity of the intermediate; the reaction process is restricted by various factors such as temperature, water content and reaction time; it is not easy to realize continuous production and Disadvantages such as low production efficiency

Method used

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  • A method for artificially synthesizing curcumin and derivatives thereof
  • A method for artificially synthesizing curcumin and derivatives thereof
  • A method for artificially synthesizing curcumin and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Firstly, the calcium acetylacetonate was dried in a vacuum at 60°C; the water content was measured by the Fischer reagent method, and the source of acetylacetonate-calcium acetylacetonate was obtained after passing the test.

[0025] Put 49.1Kg of calcium acetylacetonate, 125Kg of vanillin, 1500Kg of dimethylformamide, and 460Kg of tri-n-butyl borate into the reactor, raise the temperature to 55°C, and stir to dissolve. Heat 15Kg of n-butylamine to 40°C with a heater, drop it into the reactor within 30 minutes, react at a reaction temperature of 60°C, a stirring speed of 20r / min, and normal pressure. The reaction hydraulic pressure after the reaction is put into the hydrolysis tank, add 1500Kg water, adjust pH=5, stir and hydrolyze at room temperature for 12h, discharge and centrifuge; after centrifugation, the curcumin crude product is obtained, and the curcumin fine product 136.7Kg is obtained after drying, with a yield of 90%. 99% pure. The product is packaged in th...

Embodiment 2

[0028] Firstly, the calcium acetylacetonate was dried in a vacuum at 60°C; the water content was measured by the Fischer reagent method, and the source of acetylacetonate-calcium acetylacetonate was obtained after passing the test.

[0029] Put 49.1Kg of calcium acetylacetonate, 166Kg of isovanillin, 1500Kg of dimethylformamide, and 460Kg of tri-n-butyl borate into the reactor, raise the temperature to 88°C, and stir to dissolve. Heat 15Kg of n-butylamine to 40°C with a heater, drop it into the reactor within 30 minutes, react at a reaction temperature of 60°C, a stirring speed of 20r / min, and normal pressure. After the reaction, the reaction pressure is put into the hydrolysis tank, 3000Kg of water is added, the pH is adjusted to 5, the hydrolysis is stirred at room temperature for 12 hours, and the material is discharged and centrifuged; after centrifugation, the crude product of isovanillin-curcumin is obtained, and after drying, the refined product of isovanillin-curcumin 1...

Embodiment 3

[0032] Firstly, the calcium acetylacetonate was dried in a vacuum at 60°C; the water content was measured by the Fischer reagent method, and the source of acetylacetonate-calcium acetylacetonate was obtained after passing the test.

[0033] Put 49.1Kg of calcium acetylacetonate, 168Kg of p-hydroxybenzaldehyde, 1500Kg of dimethylformamide, and 460Kg of tri-n-butyl borate into the reactor, raise the temperature to 68°C, and stir to dissolve. Heat 15Kg of n-butylamine to 40°C with a heater, drop it into the reactor within 30 minutes, react at a reaction temperature of 60°C, a stirring speed of 20r / min, and normal pressure. After the reaction, the reaction pressure is put into the hydrolysis tank, 3500Kg of water is added, the pH is adjusted to 5, stirred and hydrolyzed at room temperature for 12 hours, and the material is discharged and centrifuged; after centrifugation, the crude product of bisdemethoxycurcumin is obtained, and bisdemethoxycurcumin is obtained after drying The f...

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Abstract

The invention discloses a method for artificially synthesizing curcumin and a derivative thereof. The method comprises the steps of adopting calcium acetylacetonate as a acetylacetone supply source, carrying out claisen-schmidt ester condensation reaction on the calcium acetylacetonate and a corresponding benzaldehyde derivative, and dehydrating under the catalysis of a dehydrating agent which is tributyl borate to obtain a product intermediate (I) which is curcumin calcium salt; then hydrolyzing the intermediate (I) through a one-pot method to obtain a crude product, and purifying the crude product so as to obtain the final product curcumin and the derivative thereof. Compared with a acetylacetone boric acid complex method, according to the method provided by the invention, the calcium acetylacetonate is used, so that active sites of acetylacetonate during a reaction process are more accurate and activated, the generation of by-products is reduced, and the yield of the curcumin and the derivative thereof is improved.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a method for artificially synthesizing curcumin and its derivatives. Background technique [0002] Curcumin is the main component of turmeric. Turmeric is the rhizome of Zingiberaceae. It is a blood-activating drug in traditional Chinese medicine. It was first recorded in "Xinxiu Materia Medica". Anti-inflammatory, antibacterial and other treatments. Curcumin is also the main yellow pigment in curry and mustard. It is a natural phenolic antioxidant. It is a commonly used seasoning and food coloring. Blood pressure, anti-cholesterol, anti-coagulant, analgesic, etc. Curcumin has a wide range of pharmacological effects, and its main properties are anti-cancer, anti-oxidation and anti-inflammation. American VITY Vitamin Magazine reported: "The main pharmacological effects of curcumin include anti-oxidation, anti-inflammation, anti-coagulation, lipid-lowering, anti-atherosclerosis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/248C07C45/42C07C49/255
CPCC07C45/42C07C45/77C07C49/248C07C49/92C07C49/255
Inventor 贺李文斐陈亮胡杨群何国栋方涛李小玲
Owner GREAT FOREST BIOMEDICAL LTD
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