A method for preparing hydrophilic phytosterol dibasic acid sugar esters in an organic phase by enzymatic method

A technology of dibasic acid sugar ester and phytosterol, which is applied in the field of preparing hydrophilic phytosterol dibasic acid sugar ester by whole enzymatic method, can solve the problems of low food safety factor, large amount of catalyst used, complicated post-processing, etc. Good public acceptance, improved hydrophilicity, and simple operation

Active Publication Date: 2021-12-24
HENAN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
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Problems solved by technology

At the same time, the present invention also provides a method for synthesizing hydrophilic phytosterol dibasic acid sugar esters by one-pot two-step enzymatic method in the organic phase by catalyzing transesterification, without the need for functional group protection, simple operation, low energy consumption, and high yield High quality, stable quality, easy storage, can effectively solve the defects of high reaction temperature, high solvent toxicity, large amount of catalyst used, complicated post-processing, low food safety factor and other defects in the previous chemical synthesis method

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  • A method for preparing hydrophilic phytosterol dibasic acid sugar esters in an organic phase by enzymatic method
  • A method for preparing hydrophilic phytosterol dibasic acid sugar esters in an organic phase by enzymatic method
  • A method for preparing hydrophilic phytosterol dibasic acid sugar esters in an organic phase by enzymatic method

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Embodiment 1

[0041] Preparation of β-Sitosterol Vinyl Adipate

[0042] Preparation method: respectively add 3 g β-sitosterol, 3 ml divinyl adipate, 0.5 g Candida rugosa lipase Candida Rugosa, and 100 ml dehydrated isooctane into the reaction flask in turn, and place in a constant temperature shaking reactor , start the shaking speed at 250 rpm, adjust the temperature to 50 °C, and react for 14 h. The conversion rate of β-sitosterol vinyl adipate was detected by HPLC-ELSD up to 95.7%. figure 1 High performance liquid chromatogram for β-sitosterol vinyl adipate. The reaction solution was filtered to remove the enzyme, and the solvent was removed by rotary evaporation to obtain 3.7 g of β-sitosterol vinyl adipate.

[0043] Structural identification: HPLC-MS: The relative molecular mass of β-sitosterol is 414 respectively. The relative molecular mass of β-sitosterol vinyl adipate is 568. β-sitosterol vinyl adipate in ES + Under ionization, [M+Na] in the presence of β-sitosterol vinyl adip...

Embodiment 2

[0045] Preparation of campesterol sucrose adipate

[0046] Preparation method: (1) respectively add 3 g campesterol, 3 ml divinyl adipate, 1 g Novozymes immobilized lipase Novozyme 435, and 100 ml dehydrated petroleum ether into the reaction bottle in sequence, and place at constant temperature to shake In the reactor, start the shaking speed at 250 rpm, adjust the temperature to 55 °C, and react for 48 h. The conversion rate of campesterol vinyl adipate can reach 81.7% as detected by HPLC-ELSD. (2) After sampling, filter the reaction liquid in the first step to remove the enzyme, remove the solvent by rotary evaporation, add 6 g of hydrophilic modifier sucrose, 0.2 g of alkaline protease, and 30 ml of pyridine, place the reaction bottle in a constant temperature shaking reactor, and open The shaking speed was 250 rpm, the temperature was adjusted to 55 °C, and the reaction was carried out for 96 h. Sampling is carried out for HPLC-ELSD analysis, and the conversion rate of t...

Embodiment 3

[0049] Preparation of β-Sitosterol Succinate Sorbitan Ester

[0050] Preparation method: (1) Add 3 g of β-sitosterol, 3 ml of divinyl succinate, 1 g of immobilized lipase Lipozyme RM, and 80 ml of dehydrated n-heptane into the reaction bottle in sequence, and place it in a constant temperature shaking reaction Turn on the shaker at 250 rpm, adjust the temperature to 60 °C, and react for 48 h. The conversion rate of phytosterol vinyl adipate can reach 97.1% as detected by HPLC-ELSD. (2) After sampling, filter the reaction solution in the first step to remove the enzyme, remove the solvent by rotary evaporation, add 3 g of hydrophilic modifier sorbitol, 0.5 g of neutral protease, and 20 ml of binary mixed solvent of pyridine and acetone, and the reaction The bottle was placed in a constant temperature shaking reactor, the shaking speed was turned on at 250 rpm, the temperature was adjusted to 40 °C, and the reaction was carried out for 120 h. Sampling is carried out for HPLC-E...

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Abstract

The invention provides a method for preparing hydrophilic phytosterol dibasic acid sugar ester in an organic phase by enzymatic method. The preparation steps are as follows: S1: Preparation of phytosterol dibasic acid vinyl ester: Weigh phytosterol, dibasic acid divinyl ester, and lipase respectively in a reaction vessel, add the reaction solvent that has been dehydrated in advance, and place it in a constant temperature shaker Medium shock reaction; S2: Preparation of phytosterol dibasic acid sugar ester: filter the reaction solution to remove enzyme, remove solvent by rotary evaporation, add sugar / sugar alcohol, protease and pre-dehydrated solvent to continue the reaction, that is, synthesize hydrophilic Phytosterol dibasic acid sugar ester. The method of the present invention does not require functional group protection, simple operation, low energy consumption, high yield, stable quality, and easy storage, and can effectively solve the problems of high reaction temperature, high solvent toxicity, large catalyst usage, and post-processing problems that occurred in the previous chemical synthesis process. Dealing with defects such as complex processing and low food safety factor.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for preparing hydrophilic phytosterol dibasic acid sugar esters in an organic phase by enzymatic method. Background technique [0002] Phytosterols are a class of compounds with a chemical structure similar to cholesterol, with a hydrophobic steroid skeleton, a β-hydroxyl group at the C-3 position, and a side chain on the D ring. Common phytosterols mainly include β-sitosterol, stigmasterol, brassicasterol and campesterol. They are mainly found in plants and marine organisms and cannot be synthesized in the human body. In food processing, phytosterols are valuable by-products produced during oil refining. [0003] Since it was first discovered in the 1950s that phytosterols have the function of lowering blood lipid and cholesterol, researchers have conducted extensive research on phytosterols, and guidelines and consensus on phytosterol consumption have also...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P33/00
CPCC12P33/00
Inventor 马传国胡毓元陈小威白歌
Owner HENAN UNIVERSITY OF TECHNOLOGY
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