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Method for preparing hydroxytyrosol docosahexenoate from lipase

A technology of carbasexaenoate and hydroxytyrosol, which is applied in the field of preparation of hydroxytyrosol derivatives, can solve the problems of low bioavailability, achieve high purity, lower blood lipids, and mild reaction conditions

Inactive Publication Date: 2017-05-31
DALIAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although hydroxytyrosol has many health benefits and is well absorbed in the intestinal tract, its bioavailability is actually low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] S1, take 0.1mol hydroxytyrosol, slowly add methyl tert-butyl ether, the ratio of hydroxytyrosol: methyl tert-butyl ether is 1:25 (mol / L), and mix well by ultrasonic;

[0021] S2, taking 0.6mol DHA and adding it to the solution obtained in S1, and then thoroughly mixing by ultrasonic;

[0022] S3. Add lipase (Novozyme-435, from Candida antarctica, EC 3.1.1.3) into the solution obtained in S2. Enzyme: hydroxytyrosol is controlled at 30:1 (g / mol), and then the glass container is filled with nitrogen and sealed ;

[0023] S4. The glass container was placed in a constant temperature oscillator for reaction, the reaction temperature was 40° C., the oscillation speed was 100 rpm, and the reaction time was 48 hours. After the reaction is complete, take it out and place it in an ice-water bath to cool;

[0024] S5. Filtrate the solution obtained in S4 to remove lipase, and then rotary evaporate at a temperature of 35°C and a relative vacuum of -0.08Mpa to remove methyl tert-bu...

Embodiment 2

[0029] S1, take 0.1mol hydroxytyrosol in a sealable glass container, slowly add methyl tert-butyl ether, hydroxytyrosol: methyl tert-butyl ether is controlled at 1:50 (mol / L), and then fully mix;

[0030] S2. Take 1.2mol DHA and add it to the solution obtained in S1, and then mix thoroughly by ultrasound;

[0031] S3. Add lipase (Novozyme-435, from Candida antarctica, EC 3.1.1.3) into the solution obtained in S2. Enzyme: hydroxytyrosol is controlled at 50:1 (g / mol), and then the glass container is filled with nitrogen and sealed ;

[0032] S4. The glass container was placed in a constant temperature oscillator for reaction, the reaction temperature was 45° C., the oscillation speed was 150 rpm, and the reaction time was 48 hours. After the reaction is complete, take it out and place it in an ice-water bath to cool;

[0033] S5. Filtrate the solution obtained in S4 to remove lipase, and then rotary evaporate at a temperature of 40°C and a relative vacuum of -0.06Mpa to remov...

Embodiment 3

[0038] S1, take 0.1mol hydroxytyrosol in a sealable glass container, slowly add methyl tert-butyl ether, hydroxytyrosol: methyl tert-butyl ether is controlled at 1:30 (mol / L), and then fully mix;

[0039] S2, taking 0.8mol DHA and adding it to the solution obtained in S1, and then thoroughly mixing by ultrasonic;

[0040] S3, get lipase (Novozyme-435, from Candida Antarctica, EC 3.1.1.3) and add in the solution of S2 gained, the quality of enzyme: the molar number of hydroxytyrosol is controlled at 40:1 (g / mol), then to The glass container is filled with nitrogen and sealed;

[0041] S4. The glass container was placed in a constant temperature oscillator for reaction, the reaction temperature was 40° C., the oscillation speed was 150 rpm, and the reaction time was 48 hours. After the reaction is complete, take it out and place it in an ice-water bath to cool;

[0042] S5. Filtrate the solution obtained in S4 to remove lipase, and then rotary evaporate at a temperature of 40...

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Abstract

A method for preparing hydroxytyrosol docosahexenoate from lipase comprises the following steps: adding methyl tert-butyl ether to hydroxytyrosol, adding docosahexenoic acid to the obtained hydroxytyrosol solution, adding the lipase to the above obtained alcohol and acid mixed solution, sealing the solution, introducing nitrogen, carrying out an oscillation reaction, carrying out ice water cooling, filtering the obtained solution to remove the lipase, and carrying out rotary evaporation to remove the methyl tert-butyl ether in order to obtain a crude product; and dissolving the crude product in ethanol, adding sodium carbonate and water, carrying out reflux saponification under the protection of nitrogen, extracting the obtained saponification solution with n-hexane, and carrying out rotary evaporation to obtain the hydroxytyrosol docosahexenoate. The hydroxytyrosol reacts with the docosahexenoic acid under the catalysis of enzyme to prepare the hydroxytyrosol ester, so the hydroxytyrosol docosahexenoate can enhance the ability of the hydroxytyrosol entering cells and tissues, so the half life is prolonged; and DHA has inflammation inhibiting, blood fat lowering and memory and thinking ability enhancing functions.

Description

technical field [0001] The present invention relates to the preparation of hydroxytyrosol derivatives, more specifically, to a method for preparing hydroxytyrosol-docosahexaenoate by using lipase. Background technique [0002] Hydroxytyrosol (3,4-dihydroxyphenylethyl alcohol) is a natural polyphenolic compound mainly derived from olive oil and wastewater from olive oil processing. Relevant studies have shown that hydroxytyrosol is an important bioactive substance that has many beneficial effects on human health, such as increasing human high-density lipoprotein cholesterol (HDL-C), reducing human lipid oxidation damage, inhibiting inflammation, and enhancing endothelial Function, lower systolic blood pressure, inhibit tumor growth and metastasis, protect central nervous system, etc. [0003] Although hydroxytyrosol has many beneficial effects on human health and is well absorbed in the intestinal tract, its bioavailability is actually low. Hydroxytyrosol is rapidly metabol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/64
CPCC12P7/6436
Inventor 周大勇阴法文朱蓓薇刘玉欣宋亮吴梓宣
Owner DALIAN POLYTECHNIC UNIVERSITY
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