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Semi-synthesis method of phenolic hydroxyl flavonoid compounds and iodine recycling method

A technology of phenolic hydroxyflavonoids and phenolic hydroxy dihydroflavonoids is applied in the fields of medicine and chemistry, and can solve the problems of large amount of pyridine, low product yield, cumbersome post-processing and the like

Inactive Publication Date: 2014-05-07
迁西县板栗产业研究发展中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A and B are two ways to better solve the problems of large pyridine consumption, cumbersome post-treatment and low product yield in the dehydrogenation of phenolic hydroxyl dihydroflavonoids
Therefore, the production cost of the product is low

Method used

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  • Semi-synthesis method of phenolic hydroxyl flavonoid compounds and iodine recycling method
  • Semi-synthesis method of phenolic hydroxyl flavonoid compounds and iodine recycling method
  • Semi-synthesis method of phenolic hydroxyl flavonoid compounds and iodine recycling method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take 5g of 95% hesperetin in a 250ml iodine measuring bottle, add 6ml of pyridine, 20ml of ethylene glycol and 4.2g of iodine, stir well, and react in a sealed water bath at 80°C (or a drying tube with calcium chloride added to the upper end of the condenser tube). Stir once every 1 hour, after 2 hours, it becomes a homogeneous liquid, and continue to seal the reaction for 6 hours. Add 0.5g of sodium hydrosulfite, stir evenly, quickly pour into 300ml of 1.5% NaOH solution, stir to dissolve, add hydrochloric acid to make it acidic, place it in a closed place for 30min, and then filter with suction to obtain acid water solution 1 (stored in a separate container) and filter cake . Wash the filter cake with water until there is no acidity, dissolve the filter cake with 50% ethanol alkaline water, adjust the pH to 3-5 with hydrochloric acid, and filter after standing for 3 hours, wash the filter cake with a small amount of 50% ethanol, and dry it at 60°C, that is Obtain 4.6...

Embodiment 2

[0038] Take 5g of 95% hesperetin in a 250ml iodine measuring bottle, add 6ml of 2-methylpyridine, 20ml of glycerol and 4.2g of iodine, stir well, and react in a closed water bath at 85°C (or add calcium chloride to the upper end of the condenser tube to dry tube), stir once, after 1 hour it becomes a homogeneous liquid, continue the closed reaction for 7 hours, add 0.5g of sodium hydrosulfite, stir evenly, quickly pour into 300ml of 1.5% NaOH solution, stir to dissolve, quickly add phosphoric acid to adjust to acidity, stir, After airtight for 30 minutes, filter with suction to obtain acid water solution 2 (stored in a separate container) and filter cake. Wash the filter cake with water until it is acid-free, wash the filter cake with a small amount of 50% ethanol, and dry it at 60°C to obtain 4.68g of diosmin with a purity of 96.5%.

Embodiment 3

[0040] Take 10g of 98% naringin in a 250ml iodine measuring bottle, add 5ml of 2-methylpyridine, 20ml of glycerin and 4.3g of iodine, stir well, and react in a water bath at 80°C (or add calcium chloride to the upper end of the condenser tube for drying). tube), stir once every 2 hours, after 8 hours it becomes a homogeneous liquid, add 0.5g of sodium hydrosulfite, stir evenly, quickly pour into 500ml aqueous solution, stir to dissolve, add phosphoric acid to make it acidic, seal it for 5 hours, and suction filter to get Acid water 3 (storage in another container) and filter cake. Wash the filter cake with water until it is acid-free, soak the filter cake with a small amount of 50% ethanol to wash the filter cake, and dry it at 60°C to obtain 8.89 g of Rhodoglucoside with a purity of 98.9%.

[0041]

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Abstract

The invention discloses a semi-synthesis method of phenolic hydroxyl flavonoid compounds and an iodine recycling method, relating to two ways A and B and iodine recycling, wherein in the way A, flavone is easily dissolved in a pyridine solvent of ethylene glycol or glycerin, and with iodine as a dehydrogenating agent, flavone is generated by heating and dehydration; in the way B, flavanone or flavone is not dissolved in pyridine of alcohol, the complexing of trivalent aluminum and flavanone is adopted, the solubility of the complexing and dehydrogenation products is high in alcohol, flavone is separated from the aluminum complex by use of phosphoric acid and the like, and flavone insoluble in water is separated out and obtained by filtering. The method disclosed by the invention is a universal method for preparing flavonoid compounds through dehydrogenation of phenolic hydroxyl dihydro flavonoids, the dosage of the reagents such as pyridine and the like is very small, and the treatment is simple, so that the method is suitable for industrial production. Take the diosmin preparation using hesperidin as an example, compared with the existing documents and patents, in the method disclosed by the invention, the dosage of organic solvents such as pyridine and the like is the least, the treatment is the simplest, the yield is the highest, and the method is environment-friendly (iodides can be oxidized by hydrogen peroxide, the recycling process is simple, and the yield is relatively high), and industrial production is easy to realize.

Description

technical field [0001] The invention relates to a semi-synthetic method for dehydrogenating phenolic hydroxyl dihydroflavonoids to generate phenolic hydroxyl flavonoids and an iodine recovery method, and belongs to the fields of chemistry and medicine. Background technique [0002] Dihydroflavonoids containing phenolic hydroxyl groups: As natural dihydroflavonoids are secondary metabolites of plants, the molecules are usually labeled with enzymes, contain more phenolic hydroxyl groups, and are widely found in nature. The extraction process is simple and the price is low. For example, the market price of 90% hesperidin is about 150 yuan per kilogram, and the market price of 98% naringin is about 260 yuan per kilogram. However, the pharmacological effects of dihydroflavonoids are not as obvious as those of flavonoids. The reason is that the conjugated structure of flavonoids is stronger than that of dihydroflavonoids. The former is worse than the latter in anti-inflammatory, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07H17/07C07H1/00C01B7/14
CPCC01B7/14C07D311/30C07H1/00C07H17/07
Inventor 闻永举申秀丽粱爱军
Owner 迁西县板栗产业研究发展中心
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