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Synthesis method of dihydroquercetin

A technology of dihydroquercetin and a synthesis method, which is applied in the field of synthesis of dihydroquercetin, can solve the problems of high production cost of dihydroquercetin, unsuitability for large-scale industrial production, etc., and achieve shortened production time, easy Effect of industrialized production and reduction of production cost

Active Publication Date: 2013-06-05
SHAANXI JIAHE PHYTOCHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The invention provides a method for synthesizing dihydroquercetin, which mainly solves the problems that the existing method for preparing dihydroquercetin has high cost and is not suitable for large-scale industrial production

Method used

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  • Synthesis method of dihydroquercetin
  • Synthesis method of dihydroquercetin
  • Synthesis method of dihydroquercetin

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preparation example Construction

[0037] The synthetic method of this dihydroquercetin comprises the following steps:

[0038] 1] Preparation of 2,4,6-trihydroxyacetophenone pyryl ether

[0039] 1.1] Preparation of 2,4,6-trihydroxyacetophenone

[0040] Take anhydrous phloroglucinol and acetonitrile, and prepare 2,4,6-trihydroxyacetophenone through Hoesch reaction according to the dosage of 1 mol: 0.5~2.0 mol;

[0041] 1.2] Preparation of 2,4,6-trihydroxyacetophenone tripyranyl ether

[0042] Dissolve the 2,4,6-trihydroxyacetophenone prepared in step 1.1 into a solvent for reaction, add 3,4-dihydropyran and a catalyst during the reaction, and the reaction temperature is 20-80°C. After the reaction is completed Generate 2,4,6-trihydroxyacetophenone dipyranyl ether; the feed ratio of the 2,4,6-trihydroxyacetophenone, 3,4-dihydropyran and catalyst is 1 mol:2.0 ~6.0mol: 0.2~0.6mol; the volume of the solvent is 5~50 times the mass of 2,4,6-trihydroxyacetophenone; the end point of the reaction is detected by TLC; 2,...

Embodiment 1

[0053] 1] Preparation of 2,4,6-trihydroxyacetophenone pyryl ether

[0054] 1.1] Preparation of 2,4,6-trihydroxyacetophenone

[0055] In a 500ml three-necked reaction flask, add 150ml of isopropyl ether, anhydrous ZnCl 2 16g, stir and disperse, then add 25.2g of anhydrous phloroglucinol and 12.3g of acetonitrile, and continue stirring; the low temperature reactor controls the temperature at 0-2°C. Infuse saturated HCl gas (produced by adding concentrated hydrochloric acid to concentrated sulfuric acid dropwise), continuously ventilate for 2 days, then place at room temperature for 3 days, the reaction stops; pour out isopropyl ether (it can be used as a solvent next time), and in the Add 200ml of water and reflux for 2h, cool to obtain 32.3g of yellow solid with a yield of 87%;

[0056] 1.2] Preparation of 2,4,6-trihydroxyacetophenone tripyranyl ether

[0057] Add 18.6g of 2,4,6-trihydroxyacetophenone and 7.5gmol of pyridinium p-toluenesulfonate into a 500ml three-necked rea...

Embodiment 2

[0067] 1] Preparation of 2,4,6-trihydroxyacetophenone pyryl ether

[0068] 1.1] Preparation of 2,4,6-trihydroxyacetophenone

[0069] In a 500ml three-necked reaction flask, add 150ml of isopropyl ether, anhydrous ZnCl 2 20.4g, stirred and dispersed, then added 25.2g of anhydrous phloroglucinol and 12.3g of acetonitrile, and continued to stir. The temperature of the low temperature reactor is controlled at 0-2°C; saturated HCl gas (generated by adding concentrated hydrochloric acid to concentrated sulfuric acid) is passed through, continuously ventilated for 2 days, and then left at room temperature for 3 days, the reaction is stopped; pour out isopropyl ether ( It can be used as a solvent next time), add 200ml of water to the residue, reflux for 2h, cool down, and obtain 31.6g of yellow solid with a yield of 85%;

[0070] 1.2] Preparation of 2,4,6-trihydroxyacetophenone pyryl ether

[0071] Add 18.6g of 2,4,6-trihydroxyacetophenone and 7.5g of pyridinium p-toluenesulfonate ...

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Abstract

The invention provides a synthesis method of dihydroquercetin, which mainly solves the problems of high preparation cost and unsuitability for large-scale industrial production of dihydroquercetin by the conventional method. The synthesis method of the dihydroquercetin comprises the following steps of: 1, preparing 2,4,6- trihydroxyacetophenone pyran ether; 2, preparing 3,4-protocatechualdehyde dipyran ether; 3, preparing chalcone; 4, preparing epoxy chalcone; and 5, removing a protective group and closing a loop so as to obtain a dihydroquercetin product, wherein a reaction end point is detected by thin layer chromatography. Raw materials and reagents used in a synthesis process are cheap and readily available, the entire route has high yield and low production cost; and the synthesis method has the characteristics of simple process, mature reaction steps, small using amounts of solvents, little environmental pollution, low requirement on production equipment and suitability for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of dihydroquercetin, which belongs to the field of drug synthesis Background technique [0002] [0003] Dihydroquercetin, English name: taxifolin, chemical name: 3,3',4',5,7-pentahydroxydihydroflavonol, aliases: Taxifolin; Taxifolin; Taxifolin; (2R,3R)-Dihydroquercetin. It comes from larch and Douglas fir of the Pinaceae plant, the mother tree of the willowberry plant, the wild black cherry of the Rosaceae plant, the wood, the root of the dragon's tooth, the heartwood of the Pistacia chinensis plant of the Anacardaceae plant, and the Coleus amber leaves of the Lamiaceae plant. Dihydroquercetin was first extracted from the bark of Douglas fir by American scholar Kurth and Ervin F. It is an important bioflavonoid, a strong antioxidant, and can also be used as a food preservative. It is used in medicine to increase the activity of red blood cells to delay the aging of the human body. In addition, dihydroq...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/32
CPCY02P20/55
Inventor 王春德肖金霞郭文华王晓莹肖红
Owner SHAANXI JIAHE PHYTOCHEM
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