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3-O-catechin higher fatty acid ester and preparation method thereof

A technology of higher fatty acids and fatty acid esters, applied in the direction of fat production, preservation of fatty substances with additives, organic chemistry, etc., can solve the problems of low bioavailability, limited application, and reduced activity, so as to improve the antioxidant effect, Good reaction selectivity and increased compatibility

Inactive Publication Date: 2014-01-22
BIOCHEM ENG COLLEGE OF BEIJING UNION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since catechin was extracted and separated, great progress has been made in basic and applied research, but in terms of its practical application, there are still the following problems: (1) The polyhydric water solubility of catechin limits its The application in lipid products, especially as an oil antioxidant, is difficult to add to the effective antioxidant concentration threshold in oil; (2) in terms of human body efficacy, it is difficult to penetrate the double lipid layer cell membrane due to poor fat solubility. Reach the target point of action and greatly reduce its proper activity
In addition, it has poor stability and low effective concentration in physiological environment, resulting in low bioavailability in vivo

Method used

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  • 3-O-catechin higher fatty acid ester and preparation method thereof
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  • 3-O-catechin higher fatty acid ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: The effect of adding molecular sieve 4A on the conversion rate of catechins at different reaction times

[0026] Take 0.15g catechin, 0.75g stearic acid, 0.605g Novozym435 lipase, add 150ml n-butanol as a solvent into a 250ml Erlenmeyer flask, put the Erlenmeyer flask into an air bath shaker, and shake the shaker at a speed of 60rpm / min, the temperature is controlled at 55-60°C, and after reacting for 5, 11, 24, and 36 hours respectively, add 22.5g of dry molecular sieve 4A, which is activated at 150°C for 24 hours before continuing the reaction. After 96 hours, the reaction was stopped. Filtrate to remove enzyme and molecular sieve; Concentrate under reduced pressure to remove solvent to obtain product, utilize thin-layer chromatography to separate and purify the reaction product, thin-layer developer is ethyl acetate: petroleum ether: ethanol: water: formic acid=15:1:1:2: 0.5. When adding molecular sieves at different reaction times, the conversion rate ...

Embodiment 2

[0029] Example 2: Effects of Variations in the Ratio of Catechin and Stearic Acid on the Conversion Rate of Catechin

[0030] 0.15g catechin, 0.605g Novozym435 lipase, the solvent is 150ml n-butanol, respectively, and different amounts of stearic acid are added to a 250ml Erlenmeyer flask, and the Erlenmeyer flask is placed in an air-bath shaker. The temperature is 50rpm / min, the temperature is controlled at 55-60°C, after 11 hours of reaction, add dry molecular sieve 4A15g to continue the reaction; after 96 hours, stop the reaction; filter to remove enzyme and molecular sieve; decompress and concentrate to remove solvent to obtain the product, use The reaction product was separated and purified by thin layer chromatography. Table 2 shows the effect of the ratio of catechin and stearic acid on the conversion rate of catechin. It can be seen from Table 2 that when the mass ratio of catechin to stearic acid is 1:5, the conversion rate of catechin is higher.

[0031] Table 2 Th...

Embodiment 3

[0033] Embodiment 3: the influence of different reaction temperatures on the conversion rate of catechins

[0034] Get catechin 0.15g, stearic acid 0.75g, 0.605g enzyme, 150ml n-butanol as solvent, add in 250ml Erlenmeyer flask, put Erlenmeyer flask into air bath shaker, shaker speed is 70rpm / Add 30g of molecular sieve 4A at 11h, control the temperature at 20-60°C, finish the reaction after 96 hours, filter to remove the enzyme and molecular sieve; concentrate under reduced pressure to remove the solvent to obtain the product, and use thin-layer chromatography to separate and purify the reaction product. The effects of different reaction temperatures on the conversion rate of catechins are shown in Table 3. It can be seen from Table 3 that when the reaction temperature is 60°C, the conversion rate of catechin is higher.

[0035] Table 3 Effects of different reaction temperatures on the conversion rate of catechins

[0036]

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Abstract

The invention discloses 3-O-catechin higher fatty acid ester represented by a formula (I) and a preparation method thereof. The method comprises the steps as follows: lipase Novozym 435 is adopted as a catalyst; higher fatty acid is adopted as an acyl donator; a 4A molecular sieve is adopted as a water absorbing agent in an esterification reaction; and catechin long-chain fatty acid is prepared. A product has good lipid solubility and oxidation resistance, and the 3-O-catechin higher fatty acid ester has an important significance on structural modification of flavonoid compounds.

Description

technical field [0001] The invention relates to a 3-O-catechin higher fatty acid ester and a preparation method thereof. Background technique [0002] Catechin is a widely distributed flavonoid compound, which is a derivative of flavanols. As a precursor of tannins, it is widely distributed in roots, barks, seeds and leaves of some plants, especially in tea leaves. A large percentage (10-20% of a dry tea leaf). Catechin has significant anti-oxidation, anti-mutation, anti-radiation, antibacterial and anti-inflammatory effects; it can enhance the function of the immune system and other biological activities, and has great application prospects in the fields of health food, cosmetics and pharmaceutical preparations. Catechin is very polar, has certain hydrophilicity, has poor compatibility with fats and oils, and is difficult to exist stably in fat solvents. For non-aqueous systems, its antioxidant capacity is greatly limited. Just limit the application of flavonoids in many ...

Claims

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Application Information

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IPC IPC(8): C07D311/62C11B5/00
CPCC07D311/62C11B5/0028C12P17/06
Inventor 霍清杨晓芳缪刚
Owner BIOCHEM ENG COLLEGE OF BEIJING UNION UNIV
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