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Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof

The technology of acid chitosan quaternary ammonium salt ester and chitosan trimethyl quaternary ammonium salt is applied in the field of gallic acid chitosan quaternary ammonium salt ester and its synthesis, and can solve the problem of low antioxidant efficiency and thermal stability of gallic acid. The problems of poor property and low molecular weight can achieve the effect of wide range of use, easy availability of equipment and raw materials, and enhanced biological activity.

Active Publication Date: 2013-09-18
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low molecular weight, gallic acid has poor thermal stability and low antioxidant efficiency, which limits the use of gallic acid as an antioxidant

Method used

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  • Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof
  • Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof
  • Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Chitosan gallic acid trimethyl quaternary ammonium salt ester is the compound shown in (formula 1)

[0020]

[0021] Synthesis of gallic acid chitosan trimethyl quaternary ammonium ester:

[0022] (1) Under the protection of nitrogen, 3.4g gallic acid and 2mL thionyl chloride were refluxed in tetrahydrofuran solvent for 2 hours, and the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain acylated gallic acid;

[0023] (2) Dissolve 2g chitosan trimethyl quaternary ammonium salt in 100mL N-methylpyrrolidone solvent.

[0024] (3) The acylated gallic acid in the step (1) was mixed with the chitosan trimethyl quaternary ammonium salt solution obtained in the step (2) in an ice bath, and the resulting reaction solution was reacted at room temperature for 8 h. After the reaction was finished, the reaction solution was poured into 600 mL of acetone, and a precipitate was precipitated. The precipitate was washed successively with acetone ...

Embodiment 2

[0030] The difference from Example 1 is:

[0031] (1) Under nitrogen protection, reflux 2 g of gallic acid and 2 mL of thionyl chloride in tetrahydrofuran solvent for three hours, then distill under reduced pressure to remove excess thionyl chloride and solvent to obtain acylated gallic acid.

[0032] (2) After mixing 2 g of chitosan trimethyl quaternary ammonium salt with acylated gallic acid obtained in the first step in 100 mL of N-methylpyrrolidone solvent, they were stirred and reacted at -3° C. for 10 hours.

[0033] (3) After the reaction, the obtained product is precipitated with acetone, washed with acetone and ethanol in sequence, and then freeze-dried under vacuum to obtain the product.

Embodiment 3

[0035] The difference from Example 1 is:

[0036] 1) Under the protection of nitrogen, reflux 1.7 g of gallic acid and 2 mL of thionyl chloride in tetrahydrofuran solvent for three hours, then distill under reduced pressure to remove excess thionyl chloride and solvent to obtain acylated gallic acid.

[0037] (2) After mixing 1 g of chitosan trimethyl quaternary ammonium salt with acylated gallic acid obtained in the first step in 100 mL of N-methylpyrrolidone solvent, they were stirred and reacted at 0° C. for 16 hours.

[0038] (3) After the reaction, the obtained product is precipitated with acetone, washed with acetone and ethanol in sequence, and then freeze-dried under vacuum to obtain the product.

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PUM

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Abstract

The invention relates to the daily chemical field and the medicinal industry, and concretely relates to a chitosan quaternary amine salt gallate, a synthetic method thereof and an application thereof. A chitosan trimethyl quaternary amine salt is reacted with acylated gallic acid to obtain the chitosan quaternary amine salt gallate which has a structure represented by formula (1). The chitosan quaternary amine salt gallate obtained in the invention, which can be dissolved in water, has a synergic effect and allows the chitosan application to be enlarged, can be widely applied to the daily chemical field of medicines and the like.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a gallic acid chitosan quaternary ammonium salt ester and a synthesis method and application thereof. Background technique [0002] Chitosan (Chitosan) is a renewable, non-toxic, side-effect, biocompatibility and degradable natural amino polysaccharide widely present in nature. It itself and its derivatives have many unique physiological and pharmacological functional properties. , are widely used in various industries such as medicine, food, agriculture, daily chemicals, and environmental protection. Chitosan itself has a special structure and properties, has bactericidal, antibacterial activity, and non-toxic, non-polluting characteristics, it can be used as the object of modification in order to develop secondary lead compounds. Compared with chitosan, chitosan trimethyl quaternary ammonium salt also has very good water solubility except that it ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K8/73A61Q19/08A23L1/30
Inventor 郭占勇任剑明董方彭德金朱慧贤冯艳
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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