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N-phenylpropenoyl chitosan oligosaccharide and preparation thereof

A technology of phenylacryloyl chitosan and phenylacryloyl, which is applied in the field of chitosan and can solve problems such as poor water solubility

Active Publication Date: 2012-04-18
广州申晶雅农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But his poor water solubility limits his application

Method used

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  • N-phenylpropenoyl chitosan oligosaccharide and preparation thereof
  • N-phenylpropenoyl chitosan oligosaccharide and preparation thereof
  • N-phenylpropenoyl chitosan oligosaccharide and preparation thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of N-phenylacryloyl chitosan oligosaccharide (ammonolysis method):

[0026] Dissolve 1.48g of phenylacrylic acid in N,N-dimethylformamide (DMF), add 2.7g of p-nitrophenol, stir, add 0.1g of dimethylaminopyridine, dropwise add 2.06g of dicyclohexylcarbodiethylene Dissolve the amine in 5mL of DMF, react at 85°C for 6h after dripping, filter, pour the filtrate into ice water, precipitate crystals, filter with suction, and recrystallize with absolute ethanol to obtain p-nitrophenyl phenylacrylate 2.15 g

[0027] P-nitrophenyl ester can also be prepared as follows:

[0028] Add an appropriate amount of acetone to a dry reaction bottle containing 1.67g of phenylacryloyl chloride under ice bath, stir vigorously, add 10-40mL of anhydrous triethylamine and 2.7g of p-nitrophenol in 20mL of acetone solution dropwise, and react 1- 5h, filtered, the filtrate was poured into ice water, crystals were precipitated, filtered, washed with 5% Na 2 CO 3 Th...

Embodiment 2

[0031] Embodiment 2: 3, the preparation of 4-dihydroxyphenylacryloyl chitosan oligosaccharide (acyl chloride method)

[0032] The preparation of 3,4-dihydroxyphenylacryloyl chloride: 10mL SOCl 2 Put it into the reaction flask equipped with HCl gas absorption device, add 1.67g of 3,4-dihydroxyphenylacrylic acid to it under the protection of nitrogen at -10~5°C, stir, add a few drops of anhydrous DMF, and put it in an oil bath Slowly raise the temperature to 65-85°C, and after refluxing for 3 hours, evaporate the excess SOCl under reduced pressure 2 , to obtain 3,4-dihydroxyphenylacryloyl chloride as a yellow solid, which can be reacted without separation.

[0033] Take 1.98g (10mmol) 3,4-dihydroxyphenylacryloyl chloride and dissolve it in 50mLDMF; another K 2 CO 3Dissolve 2g in 20mL of water, add 1.4g of chitosan oligosaccharide and stir to fully dissolve it, slowly add its acid chloride solution to the chitosan oligosaccharide (COS) solution dropwise at low temperature (-10...

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Abstract

The invention relates to chito-oligosaccharide, in particular to an N-benzene acryloyl chito-oligosaccharide and the preparation thereof; wherein, the chito-oligosaccharide is provided with mixed components with the average molecular weight from 800 to 6000 and the degree of deacetylation from 80 to 100 percent; the degree of substitution of the benzene acryloyl is from 30 to 100 percent; the general structure formula of the components is provided as follows, wherein the R is or CH3 and nu=0-30, the chito-oligosaccharide has the effects of lowering the blood fat and blood glucose, enhancing the immune function, inhibiting the tumor and fighting against the fatigue and delaying the aging as well as alleviating the analgesia, diminishing the inflammation and the effects of anti liver virus, anti snake venom, etc., and can be served as the important raw material for certain medicines, health food and cosmetics.

Description

technical field [0001] The invention relates to chitosan oligosaccharide, specifically a kind of N-phenylacryloyl chitosan oligosaccharide and its preparation. Background technique [0002] Oligochitosan, the scientific name is β-(1,4)-2-deoxy-2-glucosamine oligosaccharide. It is a rare animal oligosaccharide with special physical and chemical properties and excellent biological activity. It has the effects of lowering blood sugar, lowering blood lipid, enhancing immune function, inhibiting tumors, anti-fatigue, delaying aging, and antibacterial, etc. It has been used in medicine, health food, cosmetics, agriculture, etc. Phenylacrylic acid substances are an important class of pharmaceutical intermediates, which have good antiviral, antibacterial, anti-inflammatory, analgesic, antitumor and hepatoprotective effects. Among them, 3,4-dihydroxyphenylacrylic acid, caffeic acid can also Neutralizes free radicals, delays aging, has the functions of anti-oxidation and shortening ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C08B37/08A61K31/702A61K31/722A61P3/06A61P3/10A61P35/00A61P37/04A61P29/00A61P31/12A61P39/02
Inventor 杜昱光郭振楚刘启顺白雪芳
Owner 广州申晶雅农业科技有限公司
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