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Preparation method of acetylated hyaluronic acid

A technology of hyaluronic acid and acetylation, which is applied in the field of preparation of acetylated hyaluronic acid, can solve the problems of increasing difficulty of hyaluronic acid, increasing production efficiency, and the risk of raw materials, and achieves easy scale-up production, easy reaction, and reaction short time effect

Active Publication Date: 2021-06-29
杭州华玮生物科技有限公司
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Problems solved by technology

[0009] It can be seen that in the process of acetylation modification of hyaluronic acid, there are widely used raw materials that are dangerous and often subject to government control. It is difficult to obtain raw materials, which actually increases the difficulty of acetylation modification of hyaluronic acid. Not conducive to increasing production efficiency and expanding production

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  • Preparation method of acetylated hyaluronic acid

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preparation example Construction

[0035] A preparation method of acetylated hyaluronic acid,

[0036] Activation treatment of hyaluronic acid with organic base, and then acetylation of activated hyaluronic acid with acetyl chloride;

[0037] Specifically include,

[0038] a) mixing hyaluronic acid with methylene chloride and an organic base,

[0039] b) adding acetyl chloride to the above mixture in an ice-water bath, and stirring at room temperature after the addition is completed, to obtain acetylated hyaluronic acid.

[0040] Preferably, the organic base is at least one of triethylamine, N,N-diisopropylethylamine or pyridine.

[0041] Preferably, the molar ratio of the hyaluronic acid, the organic base and the acetyl chloride is 1:(4-8):(3-7), more preferably, the hyaluronic acid, the organic The molar ratio of the base to the acetyl chloride is 1:(5-7):(4-6), most preferably, the molar ratio of the hyaluronic acid, the organic base to the acetyl chloride is 1:6 :5;

[0042] Preferably, in the step b),...

Embodiment 1

[0046] A preparation method of acetylated hyaluronic acid,

[0047] Activation treatment of hyaluronic acid with N,N-diisopropylethylamine, and then acetylation of the activated hyaluronic acid with acetyl chloride; molar ratio of hyaluronic acid, N,N-diisopropylethylamine and acetyl chloride 1:4:3, hyaluronic acid is hyaluronic acid with a molecular weight of 10,000;

[0048] Specifically include,

[0049] a) mixing hyaluronic acid with dichloromethane and N,N-diisopropylethylamine,

[0050] b) Add acetyl chloride to the above mixture in an ice-water bath, and stir at room temperature for 1 hour after the addition is completed. After the reaction is completed with stirring at room temperature, the solid is obtained by suction filtration, washed with water for several times, and then dried to obtain acetylated hyaluronic acid.

Embodiment 2

[0052] A preparation method of acetylated hyaluronic acid,

[0053] Activation treatment of hyaluronic acid with N,N-diisopropylethylamine, and then acetylation of the activated hyaluronic acid with acetyl chloride; molar ratio of hyaluronic acid, N,N-diisopropylethylamine and acetyl chloride 1:5:4, hyaluronic acid is hyaluronic acid with a molecular weight of 50,000;

[0054] Specifically include,

[0055] a) mixing hyaluronic acid with dichloromethane and N,N-diisopropylethylamine,

[0056]b) Add acetyl chloride to the above mixture in an ice-water bath, and stir at room temperature for 1.5 hours after the addition is completed. After the reaction is completed with stirring at room temperature, the solid is obtained by suction filtration, washed with water for several times, and then dried to obtain acetylated hyaluronic acid.

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Abstract

The invention belongs to the technical field of cosmetics. The invention discloses a preparation method of acetylated hyaluronic acid. The method comprises the following steps: activating hyaluronic acid by using organic alkali, and then acetylating the activated hyaluronic acid by using acetyl chloride. The preparation method specifically comprises the following steps: a) mixing hyaluronic acid with dichloromethane and organic alkali, and b) adding acetyl chloride into the mixture in an ice-water bath, and stirring at room temperature after the addition is completed to prepare acetylated hyaluronic acid. According to the invention, controlled raw materials such as concentrated sulfuric acid, acetic anhydride and the like are not used, so that the reaction is easier to carry out, and expanded production is easier; the reaction is carried out at room temperature, the reaction time is short, the reaction environment is mild, and the synthesis efficiency is high; and the preparation method has a relatively high reaction substitution rate, and the substitution rate of hyaluronic acid with the molecular weight of less than 1.5 million is 50% or more.

Description

technical field [0001] The invention relates to the technical field of cosmetics, in particular to a preparation method of acetylated hyaluronic acid. Background technique [0002] Hyaluronic acid, also known as hyaluronic acid, hyaluronic acid, molecular formula is (C 14 h 21 NO 11 ) n , is a disaccharide unit glycosaminoglycan composed of D-glucuronic acid and N-acetylglucosamine. [0003] Hyaluronic acid is an acidic mucopolysaccharide. In 1934, Meyer, a professor of ophthalmology at Columbia University in the United States, first isolated the substance from the bovine vitreous. With its unique molecular structure and physical and chemical properties, hyaluronic acid shows a variety of important physiological functions in the body, such as lubricating joints, regulating the permeability of blood vessel walls, regulating protein, water and electrolyte diffusion and operation, and promoting wound healing. Biochemical drugs with high clinical value are widely used in va...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC08B37/0072
Inventor 郑振华
Owner 杭州华玮生物科技有限公司