Selective deacylation method for polyphenol esters

A deacylation and selective technology, applied in the field of functional food and medicine, can solve the problems of inability to achieve directional regulation and potential environmental harm, and achieve the effects of avoiding toxic and corrosive reagents, strong selectivity, and mild reaction conditions.

Active Publication Date: 2019-06-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this technical scheme, hydrazine or p-methylbenzylamine is used for deprotection, and the reagents used are potentially harmful to the environment; more importantly, this deprotection process can only convert all ester groups into hydroxyl groups, but cannot achieve orientation control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Weigh phloroglucinol triacetate (CAS number: 2999-40-8, 252.0mg / 1mmoL) in a round bottom flask, add alanine (100.0mg / 1.12mmoL) and N,N-dimethyl formamide / water (2mL / 2mL), and stir on a magnetic stirrer to dissolve the sample. Slowly add NaHCO with stirring 3 (113.0 mg / 1.35 mmoL). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated and removed under reduced pressure with a rotary evaporator to obtain a yield of phloroglucinol mono-deesterification product of 82%.

[0032] Phloroglucinol mono-deesterification product structure determination data: 1 H NMR (400MHz, CDCl 3 ) δ6.84 (d, J=0.9Hz, 1H), 6.45(s, 2H), 2.28 (d, J=0.7Hz, 6H). The results of...

Embodiment 2

[0038] Weigh resorcinol diacetate (CAS number: 108-58-7, 194.0mg / 1mmoL) in a round bottom flask, add alanine (115.0mg / 1.29mmoL) and N,N-dimethyl Acetamide / water (2mL / 2mL), and stir on a magnetic stirrer to dissolve the sample. Slowly add Na with stirring 2 CO 3 (140.0 mg / 1.32 mmoL). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated under reduced pressure with a rotary evaporator to obtain a yield of resorcinol mono-deesterification product of 85%.

[0039] Structural determination data of resorcinol mono-deesterification product: 1 H NMR (400MHz, CDCl 3 )δ7.22 (m, 1H), 6.73 (m, 3H), 2.29 (s, 3H). The results of mass spectrometry showed that its mo...

Embodiment 3

[0041] Weigh phloroglucinol triacetate (252.0mg) into a round bottom flask, add glycine (95.0mg) and N,N-dimethylformamide / water (2mL / 2mL), and place on a magnetic stirrer Stir to dissolve the sample. Slowly add NaHCO with stirring 3(104.0 mg). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated under reduced pressure with a rotary evaporator to obtain a phloroglucinol mono-deesterified product with a yield of 90%.

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Abstract

The invention discloses a selective deacylation method for polyphenol esters. The method comprises the steps that the polyphenol esters, a deacylation reagent and a water-based solvent are mixed, andsingle acyl is removed through an ammonolysis reaction, wherein the deacylation reagent is selected from amino acid, the water-based solvent is a homogeneous mixture of water and an organic solvent, and the organic solvent is selected from amine substances. According to the selective deacylation method for the polyphenol esters, directional adjustment and control over the polyphenol esters are achieved, and the method has the advantages of being high in selectivity and yield, mild in reaction condition, environmentally friendly and the like.

Description

technical field [0001] The invention belongs to the field of functional food and medicine, and in particular relates to a method for selective deacylation of polyphenol esters. Background technique [0002] Polyphenols are the general term for plant components with multiple hydroxyphenols in their molecules. They are secondary metabolites of plants and mainly exist in the bark, roots, stems, leaves, and fruits of plants, and their content is second only to cellulose, semi- Cellulose and lignin. Polyphenols come from a wide range of sources and are abundant in nature, such as green tea, oolong tea, soybeans, apples, grapes, cranberries, basil, and cocoa beans. Plant polyphenols have biologically active functions such as scavenging free radicals in the body, anti-oxidation, delaying the aging of the body, anti-tumor, slowing down osteoporosis, preventing cardiovascular diseases, preventing cancer, and anti-radiation. and other fields are widely used. Therefore, plant polyph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/29C07C69/18C07C69/16
Inventor 刘松柏周佳慧许璐靖
Owner ZHEJIANG UNIV
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