N-nicotinoyl chitosan oligosaccharide and preparation method thereof

A kind of nicotinyl chitosan oligosaccharide and nicotinyl oligosaccharide technology, applied in the field of chitosan oligosaccharide

Active Publication Date: 2007-10-17
DALIAN GLYCOBIO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nicotinic acid, cyclohexanol nicotinate and tocopheryl nicotinate are drugs used to treat hypertension and arteriosclerosis, but they have the disadvantage of causing side effects of digestive tract disorders, which limits their clinical application

Method used

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  • N-nicotinoyl chitosan oligosaccharide and preparation method thereof
  • N-nicotinoyl chitosan oligosaccharide and preparation method thereof
  • N-nicotinoyl chitosan oligosaccharide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of N-nicotinoyl chitosan oligosaccharide (ammonolysis method):

[0028] Take 1.23g of nicotinic acid and dissolve it in N,N-dimethylformamide (DMF) (the solvent can also be pyridine, dimethyl sulfoxide, dichloromethane, etc.), add 2.7g of p-nitrophenol, stir, and add 0.1 g dimethylaminopyridine, add dropwise a solution of 2.06g dicyclohexylcarbodiimide dissolved in 5mL DMF, react under heating conditions at 60-70°C for 2-6h after dropping, filter, pour the filtrate into ice water, and precipitate White crystals, filtered, and recrystallized with absolute ethanol to obtain 1.0 g of p-nitrophenyl nicotinate,

[0029] Nicotinic acid p-nitrophenyl ester can also be prepared according to the following method:

[0030] Add an appropriate amount of anhydrous acetone to a dry reaction flask containing 0.8 g of nicotinic acid chloride under ice bath, stir vigorously, add 10 mL of anhydrous triethylamine and 1.0 g of p-nitrophenol in 20 mL of aceton...

Embodiment 2

[0034] Embodiment 2: the preparation of N-nicotinoyl chitosan oligosaccharide (acyl chloride method)

[0035] The preparation of nicotinoyl chloride: 10mLSOCl 2 Put it into a reaction flask equipped with an HCl gas absorption device, add 1.67g of nicotinic acid to it under the protection of nitrogen at -10~5°C, stir, drop a few drops of anhydrous DMF, and slowly raise the temperature to 90°C in an oil bath, After reflux for 3 h, excess SOCl was distilled off under reduced pressure 2 , to obtain nicotinoyl chloride as a yellow solid with a yield of 80%, which can be reacted without separation.

[0036] Take 3.0g of nicotinyl chloride prepared from nicotinic acid and dissolve it in 50mL of DMF; 2 CO 3 Dissolve 2g in 20mL of water, add 1.6g of chitosan oligosaccharide (COS) and stir to make it fully dissolved, slowly add its acid chloride solution dropwise to the chitosan oligosaccharide (COS) solution under nitrogen protection and low temperature (-10°C ~ 5°C) In, after dri...

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Abstract

The invention discloses a N-nicotinoyl chitosan. It is characterized in that : it is a mixture, the average molecular weight is 800-6000, and the deacetylation degree of the mixture is 50%-100%, N-nicotinoyl substitution is 30%-100%. The inventive product possesses functions for reducing blood fat, blood sugar, cholesterol, building up immune function, suppressing cancer and resisting fatigue, delaying aging, suppressing bacteria and virus so its can be important material of medicine ,health product, cosmetics and biological pesticide.

Description

technical field [0001] The invention relates to chitosan oligosaccharide, specifically a kind of N-nicotinoyl 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 lipids, lowering cholesterol, enhancing immune function, inhibiting tumors, anti-fatigue, delaying aging, inhibiting bacteria, and anti-virus. It has been applied in medicine, health food, cosmetics, agriculture, etc. Nicotinic acid, cyclohexanol nicotinate and tocopheryl nicotinate are drugs used to treat hypertension and arteriosclerosis, but they have the disadvantage of causing side effects of digestive tract disorders, which limits their clinical application. Some people attach nicotinoyl to the N atom in the glucosamine molecule...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/06C08B37/08
Inventor 杜昱光刘启顺郭振楚白雪芳
Owner DALIAN GLYCOBIO
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