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

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

Active Publication Date: 2014-05-07
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] Embodiment 1: the preparation of O-linoleic acid acylated chitosan oligosaccharide

[0031] Get 1.62g of chitosan oligosaccharide with a degree of polymerization of 2-8 and dissolve it in 30mL of N,N-dimethylformamide, add 1.63g of p-methoxybenzaldehyde, stir at room temperature for 4 hours, add 5 Doubling the volume of ethanol, a large amount of light yellow precipitates were produced, suction filtered, the filter cake was washed 3 times with anhydrous acetone, and vacuum-dried to obtain 2.5 g of light yellow powder, which was amino schiff base protected chitosan oligosaccharide.

[0032] Get 2.8g amino-protected oligochitosan and dissolve in N, N-dimethylformamide, N, N-dimethylformamide; Add 0.1g dimethylaminopyridine; Add 3.0g linoleic acid N , N-dimethylformamide, react the above solution at 60°C for 6 hours, add ethanol 4 times its volume to the reaction solution to produce a large amount of light yellow precipitate, filter it with suction, and wash the filter cak...

Embodiment 2

[0036] Embodiment 2: the preparation of O-linolenic acid acylated chitosan oligosaccharide

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

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

Embodiment 3

[0042] Example 3: myristoleic acid, palmitoleic acid, oleic acid, octadecatrienoic 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 embodiment 1 and 2, unsaturated fatty acid raw material is selected from myristoleic acid, palmitoleic acid, oleic acid, octadecatrienoic acid, eicosapentaenoic acid, docosahexaenoic acid, eicosapentaenoic acid, Octadecadienoic acid, octadecatrienoic acid, eicosatetraenoic acid, O-myristoleic acid acylated chitosan oligosaccharide, O-palmitoleic acid acylated chitosan oligosaccharide, O-oleic acid can be prepared Acylated oligochitosan, O-octadecatrienoic acid acylated oligochitosan, O-eicosapentaenoic acid acylated oligochitosan, O-docosahexaenoic acid acylated oligochitosan, O - Octadecadienoic acid acylated oligochitosan, O-octadecadienoic acid acylated oligochitosan, O-eicosatetr...

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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 an O-unsaturated fatty acid acylated chitosan oligosaccharide, in particular to an O-unsaturated fatty acid acylated chitosan oligosaccharide and a preparation method and application thereof. Background technique [0002] Chitooligosaccharide, its structure is β-(1,4)-2-deoxy-2-glucosamine oligosaccharide. It is a rare alkaline oligosaccharide with special physical and chemical properties and excellent biological activity. Oligochitosan has the effects of lowering blood sugar, blood lipid, cholesterol, enhancing immune function, inhibiting tumors, anti-fatigue, delaying aging, antibacterial, antiviral, etc. It has 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 with one double bond in the carbon chain. Polyunsa...

Claims

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Application Information

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Patent Type & Authority Patents(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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