Chitooligosaccharide-N-geraniol derivatives, methods for preparing and application thereof

Patent metadata

Field	Value
Publication number	US-11084841-B1
Application number	US-202017020858-A
Country	US
Kind code	B1
Filing date	Sep 15, 2020
Priority date	Mar 24, 2020
Publication date	Aug 10, 2021
Grant date	Aug 10, 2021

Abstract

The present invention provides a chitooligosaccharide-N-geraniol derivative and a preparation method and application thereof. The degree of substitution of a chitooligosaccharide-N-geraniol derivative is from 0.26 to 0.283. The method includes dissolving oligosaccharide in dimethyl sulfoxide, dissolving geranyl bromide in dimethylformamide, and then mixing, performing a water bath reaction and adding acetone in after the water bath reaction, performing a centrifugation and collecting precipitates, performing Soxhlet extraction and vacuum drying to obtain the chitooligosaccharide-N-geraniol derivative. The present invention has the advantages of easy preparation method, low cost, simple purification method and stable properties. The chitooligosaccharide derivative has good water solubility, antibacterial activity against Staphylococcus aureus, Escherichia coli and other bacteria, and has good application prospect in the fields of medicine, food, cosmetics, agriculture, etc.

First claim

The invention claimed is:

1. A chitooligosaccharide-N-geraniol derivative having chitooligosaccharide unit represented by chemical formula (I):

wherein R is independently selected from geraniol or hydrogen; wherein n is an integer from 6 to 20; wherein a degree of substitution is from 0.26 to 0.283.

2. The chitooligosaccharide-N-geraniol derivative of claim 1 , wherein the molecular weight of the chitooligosaccharide is approximately 1000 Da and the deacetylation degree of the chitooligosaccharide is approximately 90%.

3. A method for preparing the chitooligosaccharide-N-geraniol derivative of claim 1 , comprising:
dissolving chitooligosaccharide in dimethyl sulfoxide to obtain a first solution;
dissolving geranyl bromide in dimethylformamide to obtain a second solution;
mixing the first solution and second solution, adding at least one catalyst in and stirring to obtain a third solution;
performing a water bath reaction to the third solution and adding acetone in after the water bath reaction to obtain a fourth solution;
performing a centrifugation to the fourth solution and collecting precipitates;
performing Soxhlet extraction and vacuum drying to the precipitates so as to obtain the chitooligosaccharide-N-geraniol derivative.

4. A method for preparing the chitooligosaccharide-N-geraniol derivative of claim 2 , comprising:
dissolving chitooligosaccharide in dimethyl sulfoxide to obtain a first solution;
dissolving geranyl bromide in dimethylformamide to obtain a second solution;
mixing the first solution and second solution, adding at least one catalyst in and stirring to obtain a third solution;
performing a water bath reaction to the third solution and adding acetone in after the water bath reaction to obtain a fourth solution;
performing a centrifugation to the fourth solution and collecting precipitates;
performing Soxhlet extraction and vacuum drying to the precipitates so as to obtain the chitooligosaccharide-N-geraniol derivative.

5. The method of claim 3 , wherein the mass ratio of the chitooligosaccharide and the geranyl bromide is approximately 2:1 to 2:3.

6. The method of claim 4 , wherein the mass ratio of the chitooligosaccharide and the geranyl bromide is approximately 2:1 to 2:3.

7. The method of claim 3 , wherein the temperature of the water bath reaction is approximately 50° C. and the reaction time of the water bath reaction is approximately 6 hours.

8. The method of claim 4 , wherein the temperature of the water bath reaction is approximately 50° C. and the reaction time of the water bath reaction is approximately 6 hours.

9. The method of claim 3 , wherein the at least one catalyst is triethylamine.

10. The method of claim 4 , wherein the at least one catalyst is triethylamine.

11. The method of claim 3 , wherein the molecular weight of the chitooligosaccharide is approximately 1000 Da and the degree of polymerization is approximately from 4 to 100.

12. The method of claim 4 , wherein the molecular weight of the chitooligosaccharide is approximately 1000 Da and the degree of polymerization is approximately from 4 to 100.

13. The method of claim 3 , further comprising performing a purification reaction comprising dialyzing chitooligosaccharide-N-geraniol derivative in water for 24 hours after said vacuum drying and performing freeze drying to obtain a purified chitooligosaccharide-N-geraniol derivative.

14. The method of claim 4 , further comprising performing a purification reaction, comprising dialyzing chitooligosaccharide-N-geraniol derivative in water for 24 hours after said vacuum drying and performing freeze drying to obtain a purified chitooligosaccharide-N-geraniol derivative.

15. The method of claim 3 , wherein the geranyl bromide is prepared by dissolving geraniol in anhydrous ether, adding a catalyst including pyridine, and stirring to obtain a clear solution; stirring the clear solution in an ice bath, adding a mixture including phosphorus tribromide and ether to obtain a reaction solution within 15 minutes; washing, drying, and rotating evaporation to obtain the geranyl bromide.

16. The method of claim 4 , wherein the geranyl bromide is prepared by dissolving geraniol in anhydrous ether, adding a catalyst including pyridine, and stirring to obtain a clear solution; stirring the clear solution in an ice bath, adding a mixture including phosphorus tribromide and ether to obtain a reaction solution within 15 minutes; washing, drying, and rotating evaporation to obtain the geranyl bromide.

Assignees

• Univ Jiangnan

Inventors

• Yue Lin
• Bi Ran
• Sun Dan
• Jiang Qixing
• Wang Bin
• Liu Xiaoli
• Yu Peipei
• Wang Zhouping
• Xia Wenshui

Classifications

• C08B37/003 Primary

  Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/736

  Chitin; Chitosan; Derivatives thereof · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23L29/30

  containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin (products from apiculture A23L21/20; artificial sweetening agents A23L27/30) · CPC title