Method for preparing phloretin from phlorizin through hydrolysis in biphase system

A technology of phloretin and phloretin, which is applied in the field of preparation of phloretin, can solve the problems of long production cycle, low product purity, environmental pollution, etc., and achieve reduction of by-product generation, reduction of reaction volume, and shortening of reaction time Effect

Inactive Publication Date: 2018-08-03
湖北尧一生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention overcomes technical problems such as long production period, low yield, low product purity and environmental pollution in the traditional preparation of phloretin, and is suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 4.00g of phlorizin, 20mL of 3% hydrochloric acid solution, and 20mL of n-butanol into a 50mL two-necked bottle, stir to dissolve; heat up to 80°C, keep warm for 3h, TLC (chloroform:methanol:acetic acid=7:1:0.1) Detection of complete hydrolysis of phlorizin. Cool to room temperature and let stand to separate layers. The acidic water layer was recovered and used mechanically, and the n-butanol layer was washed successively with 20 mL of distilled water (combined with the acidic water layer), 20 mL of 1% sodium bicarbonate solution, and 20 mL of saturated brine. The n-butanol was recovered by vacuum distillation, and the crude phloretin was recrystallized with ethanol:water (volume ratio 1:2) to obtain 2.34 g of light pink phloretin with a yield of 93.08%.

Embodiment 2

[0028] Add 4.00g of phlorizin, 20mL of 2% sulfuric acid aqueous solution, and 20mL of n-butanol into a 50mL two-necked bottle, stir and dissolve; heat up to 100°C, keep warm for 1.5h, TLC (chloroform:methanol:acetic acid=7:1:0.1 ) to detect the complete hydrolysis of phlorizin. Cool to room temperature and let stand to separate layers. The acidic aqueous layer was recovered and applied mechanically, and the n-butanol layer was washed successively with 20 mL of distilled water (combined with the acidic aqueous layer), 20 mL of 1% sodium bicarbonate solution, and 20 mL of saturated brine. The n-butanol was recovered by vacuum distillation, and the crude phloretin was recrystallized with ethanol:water (volume ratio 1:2) to obtain 2.38 g of light pink phloretin with a yield of 94.67%.

Embodiment 3

[0030] Add 4.00g of phlorizin, 20mL of 3% hydrochloric acid solution, and 20mL of n-amyl alcohol into a 50mL two-necked bottle, stir to dissolve, heat up to 100°C, keep warm for 1h, TLC (chloroform:methanol:acetic acid=7:1:0.1) Detection of complete hydrolysis of phlorizin. Naturally cool to room temperature, let stand and separate layers. The acidic water layer was recovered and used mechanically, and the n-pentanol layer was washed successively with 20 mL of distilled water, 20 mL of 0.5% sodium carbonate solution, and 20 mL of saturated brine. N-pentanol was recovered by distillation under reduced pressure, and the crude phloretin was recrystallized with ethanol:water (volume ratio 1:1) to obtain 2.03 g of light pink phloretin with a yield of 80.75%.

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Abstract

The invention discloses a preparation method of phloretin. The phloretin is used as raw materials; through two-phase acid hydrolysis, the phloretin pure product with the yield being 95 percent is obtained. Compared with the existing phlorizin semi-preparation production method, the problems of low phloretin conversion rate, many byproducts and low product purity are solved. The whole reaction andseparation purification operation is simple; the conditions are mild; the catalyst can be cyclically used in a water phase; the organic solvents can be recovered and used; green and environment-friendly effects are achieved. The method is suitable for industrial production.

Description

technical field [0001] The invention provides a method for preparing phloretin, in particular to a method for preparing phloretin by acid hydrolyzing phloridzin in a two-phase system, and belongs to the field of chemical synthesis. Background technique [0002] Phloretin is named 3-(4'-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone, and its molecular formula is C 15 h 14 o 5 , the molecular weight is 274.27. Its pure product is light pink, easily soluble in methanol, ethanol, acetone, dimethyl sulfoxide and other organic solvents, soluble in alkali solution, slightly soluble in chloroform, insoluble in petroleum ether, benzene, water, melting point is 230 ~231°C. In the form of its glycoside-phloridzin, it is widely present in the rhizomes or root barks of apples, pears and other fruits and various vegetables. [0003] Phloretin belongs to dihydrochalcone compounds and has 4 phenolic hydroxyl groups, among which the ortho hydroxyl group of the benzene ring and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/83C07C45/42C07C45/81
CPCC07C45/42C07C45/81C07C49/83
Inventor 但飞君唐倩伍杨杨进
Owner 湖北尧一生物科技有限公司
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