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Chitosan oligosaccharide-M-cinnamyl alcohol derivative, and preparation method and application thereof

A technology of chitosan oligosaccharide and cinnamyl alcohol, applied in the field of food additives, can solve the problems of low antibacterial activity and the like, and achieve the effects of enhanced antibacterial activity, strong inhibitory effect and simple reaction steps

Pending Publication Date: 2020-10-02
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, since oligochitosan is a natural macromolecular product, when used as a food antiseptic and antibacterial agent, it still has disadvantages such as low antibacterial activity compared with traditional commonly used chemical preservatives, so there is an urgent need for a high antibacterial activity in this area. Chitosan oligosaccharide derivatives make it more valuable in industry

Method used

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  • Chitosan oligosaccharide-M-cinnamyl alcohol derivative, and preparation method and application thereof
  • Chitosan oligosaccharide-M-cinnamyl alcohol derivative, and preparation method and application thereof
  • Chitosan oligosaccharide-M-cinnamyl alcohol derivative, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation method of chitosan oligosaccharide-M-cinnamyl alcohol derivative of the present invention comprises the following steps:

[0041] (1) Preparation of Cinnamyl Bromide

[0042] Add 1 mol of cinnamyl alcohol to 30 mL of anhydrous ether, add dropwise 0.25 mL of pyridine, and stir at room temperature until clear and transparent to obtain a mixture of cinnamyl alcohol; under stirring in an ice bath, add 0.4 mol of phosphorus tribromide and 20 mL of diethyl ether to tribromide Phosphorus mixed solution, added dropwise to the cinnamyl alcohol mixed solution within 15 minutes; after the dropwise addition, the temperature was raised to 50°C, and after heating and stirring for 2 hours, the upper organic layer was separated into water, sodium bicarbonate solution and saturated sodium chloride solution using a separatory funnel. After washing, dry over anhydrous sodium sulfate, overnight, rotary evaporation to obtain a yellow syrupy product, that is, cinnamyl bromide...

Embodiment 2

[0054] The preparation method of chitosan oligosaccharide-M-cinnamyl alcohol derivative of the present invention comprises the following steps:

[0055] (1) Preparation of Cinnamyl Bromide

[0056] Add 1 mol of cinnamyl alcohol to 30 mL of anhydrous ether, add dropwise 0.15 to 0.25 mL of pyridine, and stir at room temperature until clear and transparent to obtain a cinnamon alcohol mixture; Phosphorus bromide mixed solution, added dropwise to the cinnamyl alcohol mixed solution within 15 minutes; after the dropwise addition, the temperature was raised to 40-50°C, and after heating and stirring for 2 hours, the upper organic layer was separated with water, sodium bicarbonate solution, and saturated After washing with sodium chloride solution, drying with anhydrous sodium sulfate, overnight, rotary evaporation to obtain a yellow syrupy product, that is, cinnamyl bromide.

[0057] (2) Preparation of oligochitosan-M-cinnamyl alcohol derivatives

[0058] Select chitosan oligosacc...

Embodiment 3

[0063] The preparation method of chitosan oligosaccharide-M-cinnamyl alcohol derivative of the present invention comprises the following steps:

[0064] (1) Preparation of Cinnamyl Bromide

[0065] Add 1 mol of cinnamyl alcohol to 30 mL of anhydrous ether, add dropwise 0.15 to 0.25 mL of pyridine, and stir at room temperature until clear and transparent to obtain a cinnamon alcohol mixture; Phosphorus bromide mixed solution, added dropwise to the cinnamyl alcohol mixed solution within 15 minutes; after the dropwise addition, the temperature was raised to 40-50°C, and after heating and stirring for 2 hours, the upper organic layer was separated with water, sodium bicarbonate solution, and saturated After washing with sodium chloride solution, drying with anhydrous sodium sulfate, overnight, rotary evaporation to obtain a yellow syrupy product, that is, cinnamyl bromide.

[0066] (2) Preparation of oligochitosan-M-cinnamyl alcohol derivatives

[0067] Select oligochitosacchari...

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Abstract

The invention discloses a chitosan oligosaccharide-M-cinnamyl alcohol derivative, and a preparation method and application thereof. The preparation method comprises the following steps: chitosan oligosaccharide and cinnamyl bromide are dissolved in an organic solvent and then are mixed, a catalyst is added, stirring is performed, a water bath reaction is conducted for 6 h, dialysis is conducted with water for 48 h after the reaction is completed, and vacuum freeze drying is conducted to obtain the chitosan oligosaccharide-M-cinnamyl alcohol derivative, wherein the molar ratio of the chitosan oligosaccharide to the cinnamyl bromide is 1: (1-3). A cinnamyl group is grafted on an active amino group and a hydroxyl group of the chitosan oligosaccharide through bromine atoms in the cinnamyl group, so that the antibacterial activity of the chitosan oligosaccharide is enhanced, the chitosan oligosaccharide derivative with good solubility and mutual synergy is obtained, and the chitosan oligosaccharide derivative has a good application prospect in the fields of medicines, foods, cosmetics and agriculture.

Description

technical field [0001] The invention belongs to the technical field of food additives, and specifically relates to a chitosan oligosaccharide-M-cinnamyl alcohol derivative, a preparation method and an application thereof. Background technique [0002] With the development of the food industry, in order to prolong the shelf life of food and inhibit microbial contamination, traditional physical antiseptic methods no longer meet the needs. The method of adding preservatives has been quickly applied because of its simplicity, durability and lower cost. Due to the potential cumulative toxicity of chemical preservatives, misuse or excessive use will cause food safety problems. With the improvement of people's living standards and the enhancement of safety awareness, some safe, non-toxic, green natural preservatives are more popular. [0003] Oligochitosan is a natural preservative extracted from animal-related substances. It has the characteristics of biological non-toxicity, nat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A01N43/16A01P1/00
CPCA01N43/16C08B37/003
Inventor 乐琳孙丹王斌姜启兴于沛沛王周平夏文水
Owner JIANGNAN UNIV
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