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O-unsaturated fatty acid acylated chitosan oligosaccharides as well as preparation and application thereof

A technique for fatty acid acylation of chitooligosaccharides and unsaturated fatty acids, which is applied in the field of O-unsaturated fatty acid acylation of chitooligosaccharides and its preparation, and can solve problems such as insufficient activity, insufficient stability of unsaturated fatty acids, troublesome use and storage, etc. , to achieve the effect of high selectivity, clear structure and simple operation

Active Publication Date: 2012-07-04
DALIAN GLYCOBIO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are many foods and health products about unsaturated fatty acids, but there are still some problems, such as the activity is not high enough; in addition, unsaturated fatty acids are generally not stable enough, and it is troublesome to use and store

Method used

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  • O-unsaturated fatty acid acylated chitosan oligosaccharides as well as preparation and application thereof
  • O-unsaturated fatty acid acylated chitosan oligosaccharides as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of O-linoleic acid acylated chitooligosaccharide

[0031] Take 1.62g of chitosan oligosaccharides with a degree of polymerization of 2-8 and dissolve in 30mL of N,N-dimethylformamide, add 1.63g of p-methoxybenzaldehyde, stir at room temperature for 4 hours, and add 5 to the reaction solution. A double volume of ethanol produces a large amount of light yellow precipitate, which is suction filtered. The filter cake is washed 3 times with anhydrous acetone and dried under vacuum to obtain 2.5 g of light yellow powder, which is an amino schiff base protected chitosan oligosaccharide.

[0032] Take 2.8g amino-protected chitosan oligosaccharide and dissolve it in N,N-dimethylformamide and N,N-dimethylformamide; then add 0.1g dimethylaminopyridine; add 3.0g linoleic acid N , N-dimethylformamide, react the above solution at 60°C for 6 hours, add 4 times the volume of ethanol to the reaction solution to produce a large amount of light yellow precipitate, suctio...

Embodiment 2

[0036] Example 2: Preparation of O-linolenic acid acylated chitosan oligosaccharide

[0037] Take 1.62g of chitosan with a degree of polymerization of 2-15 and dissolve in 30mL of N,N-dimethylformamide, add 1.63g of benzaldehyde, stir at room temperature for 4 hours, and add 5 times its volume of ethanol to the reaction solution , A large amount of light yellow precipitate is produced, filtered by suction, the filter cake is washed 3 times with anhydrous acetone, and dried in vacuum to obtain 2.5 g of light yellow powder, which is an amino schiff base protected chitosan oligosaccharide.

[0038] Dissolve 2.8g amino-protected chitosan oligosaccharide in N,N-dimethylformamide and N,N-dimethylformamide; add 0.1g dimethylaminopyridine; add 4.1g linolenic acid N, N-Dimethylformamide, react the above solution at 60°C for 8 hours, add 4 times its volume of ethanol to the reaction solution to produce a large amount of light yellow precipitate, filter with suction, and wash the filter cake ...

Embodiment 3

[0042] Example 3: Myristic acid, palmitoleic acid, oleic acid, stearidonic acid, eicosapentaenoic acid, docosahexaenoic acid, octadecadienoic acid, octadecatriene Preparation of O-acylated chitosan oligosaccharides such as acid and eicosatetraenoic acid

[0043] According to the method of Examples 1 and 2, the unsaturated fatty acid raw materials are selected from myristic acid, palmitoleic acid, oleic acid, stearidonic acid, eicosapentaenoic acid, docosahexaenoic acid, and ten Octadienoic acid, octadecadienoic acid, and eicosatetraenoic acid can be prepared to obtain O-myristoleic acid acylated chitooligosaccharides, O-palmitoleic acid acylated chitosan oligosaccharides, and O-oleic acid Acylated chito-oligosaccharides, O-octadecosatrienoic acid acylated chito-oligosaccharides, O-eicosapentaenoic acid acylated chito-oligosaccharides, O-docosahexaenoic acid acylated chito-oligosaccharides, O -Octadecadienoic acid acylated chitosan oligosaccharide, O-octadecadienoic acid acylated...

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Abstract

The invention relates to O-unsaturated fatty acid acylated chitosan oligosaccharides, which are characterized in that the O-unsaturated fatty acid acylated chitosan oligosaccharides are a mixed component and have a molecular weight of 800-25000 Da; the deacelation degree of the mixed component is 50-100%; the substitution degree of O-unsaturated fatty acid is 30-200%; and the components of the O-unsaturated fatty acid acylated chitosan oligosaccharides have a structure shown in the specification, wherein R1 is H or CH3CO-, R2 is C12-22 unsaturated fatty acid acyl or H, and n is 0-30. The O-unsaturated fatty acid acylated chitosan oligosaccharides have activities of resisting oxidation, delaying aging, inhibiting tumor, resisting inflammation, lowering blood pressure, preventing thrombosis, improving diabetes mellitus, lowering blood sugar, resisting atherosclerosis and the like, and can be used as important raw materials for medicines, health-care food and cosmetics.

Description

Technical field [0001] The invention relates to O-unsaturated fatty acid acylated chitosan oligosaccharides, in particular to O-unsaturated fatty acid acylated chitosan oligosaccharides, and a preparation method and application thereof. Background technique [0002] Chitooligosaccharides have a structure of β-(1,4)-2-deoxy-2-aminoglucose oligosaccharides. It is a rare basic oligosaccharide with special physical and chemical properties and excellent biological activity. Chitooligosaccharides have the functions of lowering blood sugar, lowering blood lipids, lowering cholesterol, enhancing immune function, inhibiting tumors, anti-fatigue, anti-aging, antibacterial, anti-virus, etc., and have been used in medicine, health food, cosmetics, agriculture, etc. . [0003] Unsaturated fatty acids are divided into monounsaturated fatty acids and polyunsaturated fatty acids according to the number of double bonds. Monounsaturated fatty acids refer to fatty acids that contain one double bond...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C07H13/06C07H1/00A61P9/12A61P39/00A61P3/10A61P35/00A61P29/00A61P9/10A61P39/06A23L1/09
CPCY02P20/55
Inventor 杜昱光刘启顺乔莹白雪芳赵静玫崔刚
Owner DALIAN GLYCOBIO
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