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Beta-sitosterol type catechinic acid liposolubility antioxidant and preparation method thereof

A technology of catechin fat and sitosterol type, which is applied in the field of β-sitosterol type catechin molecule and its preparation, can solve the problems of limited practical use range and poor solubility of free phytosterol, and achieve good fat-soluble anti-oxidation Functional, cheap, good antioxidant effect

Active Publication Date: 2017-04-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the solubility of free phytosterols in oils is poor, which limits its practical application range

Method used

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  • Beta-sitosterol type catechinic acid liposolubility antioxidant and preparation method thereof
  • Beta-sitosterol type catechinic acid liposolubility antioxidant and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0029] β-sitosterol (414.7mg), succinic anhydride (100.1mg) and triethylamine (151.0mg) were stirred and reacted at room temperature in dimethylformamide for 1 hour, and extracted with ethyl acetate after the reaction was completed, to obtain The product was reacted with tetrapropionylcatechin (514.3mg) and N,N'-dicyclohexylcarbodiimide (412.0mg) at room temperature for 2 hours with stirring, and treated with hydrazine (300.0mg) after the reaction Then extracted with chloroform, and purified by chromatography to obtain 70% of β-sitosterol type catechin.

[0030] Structure determination data: NMR data show the characteristic peaks of 5-9ppm catechin and 1-4ppm β-sitosterol, IR 1731cm -1 The characteristic absorption peaks of ester groups are shown on the left and right, and the mass spectrum shows the molecular ion peak of 809.43 after adding sodium. These data demonstrate the correctness of the structure of the synthesized substance.

Embodiment 2

[0032] β-sitosterol (414.7mg), succinic anhydride (150.1mg) and potassium carbonate (210.0mg) were stirred and reacted at room temperature in dimethylformamide for 1 hour, and extracted with ethyl acetate after the reaction was completed, and the obtained The product reacted with tetrapropionyl catechin (600.3mg) and N,N'-dicyclohexylcarbodiimide (490.0mg) at room temperature for 2 hours with stirring. After the reaction was completed, it was treated with hydrazine (300.0mg) and then Chloroform extraction, chromatographic purification to obtain β-sitosterol type catechin 81%.

Embodiment 3

[0034] β-sitosterol (414.7mg), succinic anhydride (150.1mg) and sodium hydroxide (50.0mg) were stirred and reacted in dimethylformamide at room temperature for 1 hour, and extracted with ethyl acetate after the reaction was completed to obtain The product was reacted with tetrapropionylcatechin (640.3mg) and N,N'-dicyclohexylcarbodiimide (550.0mg) at room temperature for 2 hours with stirring, and treated with hydrazine (300.0mg) after the reaction Then extracted with chloroform and purified by chromatography to obtain 85% of β-sitosterol type catechin.

[0035] Antioxidant activity test: The fat-soluble antioxidant activity of β-sitosterol catechin was tested using the classic liposome model. The results showed that the antioxidant activity of β-sitosterol catechin was 5 times that of catechin. times, 20% higher than the commonly used strong fat-soluble antioxidant TBHQ.

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Abstract

The invention discloses a beta-sitosterol type catechinic acid liposolubility antioxidant and a preparation method thereof. The preparation method comprises the steps that butanedioic anhydride and beta-sitosterol react; under the action of a coupling reagent, intermediate products react with catechinic acid with hydroxyl on benzene rings being protected till the reaction is completed; and obtained products are subjected to deprotection, and the beta-sitosterol type catechinic acid liposolubility antioxidant is obtained through posttreatment. The beta-sitosterol type catechinic has a very good liposolubility antioxidant function. The beta-sitosterol type catechinic has a very good antioxygenic property in grease. The beta-sitosterol type catechinic is low in price and suitable for industrialized production and application. Meanwhile, the preparation method for the beta-sitosterol type catechinic is simple in process, simple, practical and suitable for industrialized mass production.

Description

technical field [0001] The invention belongs to the field of functional food and health food, and specifically relates to a β-sitosterol type catechin molecule and a preparation method thereof. Background technique [0002] β-Sitosterol is a class of natural components present in plants. A large number of animal experiments and human clinical trial data show that phytosterols have significant significance in reducing blood cholesterol levels and reducing the occurrence of cardiovascular diseases, and are an important health food ingredient. However, the solubility of free phytosterols in oils is poor, which limits its practical application range. Phytosterols are esterified with carboxylic acids to form phytosterol esters, which can significantly improve their solubility. The carbon chain length of fatty acids and the degree of saturation of fatty acids affect the melting point and fat solubility of phytosterol esters. By selecting the type and composition of fatty acids, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00C11B5/00
CPCC07J17/00C11B5/0035
Inventor 刘松柏吴珊珊
Owner ZHEJIANG UNIV
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