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One kind of L -vitamin C hyaluronate derivatives and their preparation methods and applications

A technology of hyaluronic acid ester and hyaluronic acid, applied in the fields of medicine and daily necessities, can solve the problems of strong irritation, unstable L-vitamin C structure, and reduced activity of vitamin C derivatives, and achieve the effect of ensuring stability

Active Publication Date: 2022-04-08
润辉生物技术(威海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The L-vitamin C hyaluronate derivatives of the present invention have good stability, good sustained-release transdermal effect, excellent moisturizing, wrinkle-removing and whitening functions, and solve the problem of the L-vitamin C structure in the prior art. Defects such as instability, poor permeability, strong irritation, and easy to turn yellow, this type of product also has the effect of hyaluronic acid, and also solves the problem that hyaluronic acid ester and vitamin C in functional cosmetics need to be added separately and are easily affected by the environment However, there are technical problems such as inactivation, short action time, and reduced activity of some vitamin C derivatives.

Method used

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  • One kind of L -vitamin C hyaluronate derivatives and their preparation methods and applications
  • One kind of L -vitamin C hyaluronate derivatives and their preparation methods and applications
  • One kind of L -vitamin C hyaluronate derivatives and their preparation methods and applications

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Experimental program
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Effect test

Embodiment 1

[0084] The preparation of embodiment 1 hyaluronic acid-CTA salt

[0085] Dissolve 300 g of sodium hyaluronate with a molecular weight of 10 kDa to 100 kDa in 10 L of deionized water and set aside. 300g of cetyltrimethylammonium chloride was dissolved in 6L of deionized water, and then sodium hyaluronate solution was added dropwise. After reacting at 40°C for 16 hours, a white solid precipitated out. Filter and dry the solid at 50-55°C under reduced pressure to obtain the product (yield: 486g).

Embodiment 2

[0086] Embodiment 2 L-vitamin C and bromopropanol etherification reaction

[0087] Under the protection of nitrogen, 211g of triphenylphosphine was added into 500mL of tetrahydrofuran, stirred until it was completely dissolved, and cooled to about 0°C in a brine ice bath. 212 g of 1,2-diiodoethane was dissolved in 200 mL of tetrahydrofuran, and added dropwise to the triphenylphosphine solution. After stirring for 30 minutes, a solid precipitated out. Under nitrogen protection, 50 g of L-vitamin C and 50 g of 3-bromo-1-propanol were dissolved in 300 mL of tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition, the temperature was raised to 20-30°C and stirred for 16 hours. Next, the reaction temperature was increased to 40° C. and stirred for 3 hours, and the reaction was detected by thin layer chromatography (ethyl acetate:ethanol:water=20:10:1) to complete. The reaction system was concentrated until no solvent dripped out to obtain a white...

Embodiment 3

[0088] Embodiment 3 L-vitamin C and bromobutanol etherification reaction

[0089] Under the protection of nitrogen, 230 g of triphenylphosphine was added into 540 mL of tetrahydrofuran, stirred until it was completely dissolved, and cooled to about 0° C. in a brine ice bath. 230 g of 1,2-diiodoethane was dissolved in 250 mL of tetrahydrofuran, and added dropwise to the triphenylphosphine solution. After stirring for 30 minutes, a solid precipitated out. Under nitrogen protection, 55g of L-vitamin C and 60g of 4-bromo-1-butanol were dissolved in 300mL of tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition, the temperature was raised to 20-30°C and stirred for 16 hours. Next, the reaction temperature was raised to 40°C and stirred for another 3 hours. Thin layer chromatography (ethyl acetate:ethanol:water=20:9:1) detected that the reaction was complete. The reaction system was concentrated until no solvent dripped out to obtain a white sol...

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Abstract

The present invention provides a L-vitamin C hyaluronate derivative and its preparation method and application. It is a L-vitamin C hyaluronate derivative, which is characterized in that it is covalently composed of a vitamin C structure and a hyaluronic acid structure. A bonded structure, the vitamin C structure is shown in formula II, wherein formula II is bonded to the hyaluronic acid structure through the position, wherein k is selected from 2-4. The derivative of the present invention combines the functional activities of hyaluronic acid and L-vitamin C. It has excellent moisturizing, anti-wrinkle and whitening effects, and has a prolonged effect at the same time. It has a wide range of applications and can be applied to cosmetics, medicines and food field.

Description

technical field [0001] The invention relates to the fields of medicine and daily necessities, in particular to a L-vitamin C hyaluronate derivative and a preparation method and application thereof. Background technique [0002] The information disclosed in the Background of the Invention is intended to enhance the understanding of the general background of the invention, and the disclosure should not necessarily be construed as an acknowledgment or any form of suggestion that the information has become the prior art that is already known to those skilled in the art. [0003] The development of functional cosmetics has become the subject of development in the cosmetics industry today, and the added bioactive ingredients play an important role in regulating the growth and metabolism of cells. The molecular structure of hyaluronic acid is a repeating structure of disaccharide units composed of D-glucuronic acid and N-acetylglucosamine. It has a variety of important physiologica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K8/67A61K8/73A61K31/375A61K31/728A61K47/55A61K47/61A61P17/00A61P37/04A61Q19/00A61Q19/02A61Q19/08
CPCC08B37/0072A61K8/676A61K8/735A61Q19/02A61Q19/00A61Q19/08A61K31/375A61K47/61A61K47/55A61K31/728A61P17/00A61P37/04
Inventor 姬胜利郭凯殷金岗王盈盈
Owner 润辉生物技术(威海)有限公司
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