Method for synthesizing 6''-O-palmitoyl-neohesperidin ester on line by using lipase as catalyst

A technology of hesperidin ester and neohesperidin is applied in the field of lipase catalyzed on-line controllable and selective synthesis of 6″-O-palmitoyl-neohesperidin ester, which can solve the problem of long reaction time, conversion rate and selection To solve the problem of low performance, it can achieve the effects of high reaction selectivity, shortened reaction time and high conversion rate.

Active Publication Date: 2014-03-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] At present, many domestic and foreign scholars have studied the enzymatic synthesis of neohesperidin esters in organic media, but this method often requires a long reaction time (24h), and the conversion rate and selectivity of the reaction are not high. , using microfluidic technology to explore new synthetic reactions to solve the technical bottlenecks of existing synthetic methods is a research hotspot at home and abroad today

Method used

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  • Method for synthesizing 6''-O-palmitoyl-neohesperidin ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-neohesperidin ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-neohesperidin ester on line by using lipase as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Synthesis of 6 "-O-palmitoyl-neohesperidin ester

[0033]

[0034] Device reference used figure 1 . Dissolve neohesperidin (0.49mmol) in 10mL of tert-amyl alcohol:DMSO=4:1 (v / v) mixed solvent, dissolve vinyl palmitate (3.92mmol) in 10mL of tert-amyl alcohol, and then pack Prepare in a 10mL syringe. 0.87g of lipase Lipozyme RMIM was evenly filled in the reaction channel of the microfluidic channel reactor, driven by the PHD2000 syringe pump, the two reaction solutions were divided into a total of 8.91 μL min -1 The flow rate of the flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 52°C through a water bath thermostat. The flow reaction was carried out for 35 minutes, and the reaction result was tracked and detected by thin-layer chromatography (TLC).

[0035] The reaction solution was collected online through the product collector, the solvent was distilled off under reduced ...

Embodiment 2-5

[0041] Change the temperature of the microfluidic channel reactor, others are the same as in Example 1, and the reaction results are as shown in Table 1:

[0042] Table 1: Effect of Temperature on Reaction

[0043]

[0044] The results in Table 1 show that when the flow rate is 8.91 μL min -1 , when the reaction time is 35min, the conversion rate increases obviously with the increase of the reaction temperature. When the reaction temperature reaches 52°C, the conversion rate and selectivity of the reaction are the best. The reduction of enzyme activity leads to a reduction in the conversion rate and selectivity of the reaction, so the optimal reaction temperature of neohesperidin palmitate in the microfluidic microchannel reactor of the present invention is 52°C.

Embodiment 6-10

[0046] Change the substrate molar ratio of vinyl palmitate and neohesperidin in the microfluidic microchannel reactor to 1:1 (Example 6), 4:1 (Example 7), 6:1 (Example 8) , 10:1 (Example 9), 12:1 (Example 10), the amount of neohesperidin was 0.49mmol unchanged, and the amount of vinyl palmitate was changed. Others are the same as Example 1, and the results are shown in Table 2.

[0047] Table 2: Effect of Neohesperidin and Vinyl Palmitate Substrate Ratio on Reaction

[0048]

[0049]

[0050] The result of table 2 shows, along with the increase of reactant vinyl palmitate, the conversion rate of reaction also increases, and when substrate ratio is 8:1, the conversion rate and selectivity of reaction are optimal, neohesperidin Quantitatively converted into neohesperidin-6 "-palmitate substantially. Now if continue to increase the consumption of reactant vinyl palmitate, will cause the conversion rate and the selectivity of reaction to reduce, thereby, the maximum of this...

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Abstract

The invention discloses a method for synthesizing a 6''-O-palmitoyl-neohesperidin ester on line by using lipase as a catalyst, which comprises the following steps: by using neohesperidin and vinyl palmitate in a mole ratio of 1:(1-12) as raw materials, 0.5-1.0g of lipase Lipozyme RMIM as a catalyst and a tertiary amyl alcohol-DMSO (dimethyl sulfoxide) mixed solvent as a reaction solvent, uniformly filling the lipase Lipozyme RMIM into a reaction channel of a microfluidic channel reactor, wherein the internal diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4mm, and the reaction channel is 0.5-1.0m long; continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction, wherein the acylation reaction temperature is controlled at 40-55 DEG C, and the acylation reaction time is 20-40 minutes; and collecting the reaction solution on line, and carrying out conventional after-treatment on the reaction solution to obtain the 6''-O-palmitoyl-neohesperidin ester. The method has the advantages of short reaction time, high selectivity and high yield.

Description

(1) Technical field [0001] The invention relates to a lipase-catalyzed online controllable selective synthesis method of 6"-O-palmitoyl-neohesperidin ester. (2) Background technology [0002] Neohesperidin (Neohesperidin), also called neohesperidin, is a dihydroflavonoid compound widely found in Citrus aurantium, citrus, lemon, bergamot and other plants, especially in the peel of Rutaceae plants. . It has good anti-cancer, antibacterial, anti-oxidation, lowering cholesterol, reducing capillary fragility, improving microcirculation and other biological activities, and is often used in medicine, cosmetics, food and other fields. [0003] According to research, various biological activities of flavonoids are based on antioxidant activity, which is related to anti-free radical or anti-lipid peroxidation. The special structure endows it with a series of unique chemical properties, such as complexation or electrostatic interaction with various metal ions, the characteristics of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60
Inventor 杜理华罗锡平凌慧敏何锋杨文俊
Owner ZHEJIANG UNIV OF TECH
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