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

A technology of lipase and palmitoyl is applied in the field of lipase-catalyzed online controllable selective synthesis of 6″-O-palmitoyl-naringin ester, which can solve the problems of long reaction time, conversion rate and low selectivity, etc. Achieve high reaction selectivity, shorten reaction time, and high conversion

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 enzyme-catalyzed synthesis of naringin 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-naringin ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-naringin ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-naringin ester on line by using lipase as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of 6 "-O-palmitoyl-naringin ester

[0033]

[0034] Device reference used figure 1 . Dissolve naringin (0.49mmol) in 10mL of tert-amyl alcohol: DMSO=4:1 (v / v) mixed solvent, dissolve vinyl palmitate (3.43mmol) in 10mL of tert-amyl alcohol, and then pack them in Ready-to-use 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 10.4 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 30 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 ...

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 10.4 μL min -1 , when the reaction time is 30min, 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 in enzyme activity leads to a reduction in the conversion rate and selectivity of the reaction, so the optimal reaction temperature of naringin palmitate in the microfluidic microchannel reactor of the present invention is 52°C.

Embodiment 6-9

[0046] Change the ratio of the amount of the substrate substance of vinyl palmitate and naringin in the microfluidic microchannel reactor to 1:1 (Example 6), 3:1 (Example 7), 5:1 (Example 7). 8), 9:1 (Example 9), the dosage of naringin is 0.49mmol unchanged, and the dosage of vinyl palmitate is changed. Others are the same as Example 1, and the results are shown in Table 2.

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

[0048]

[0049] The result of table 2 shows, along with the increase of reactant vinyl palmitate, the conversion rate of reaction also increases thereupon, and when substrate ratio is 7:1, the conversion rate of reaction and selectivity are optimal, and naringin basically Quantitatively converted completely into naringin-6 "-palmitate. If continue to increase the consumption of reactant vinyl palmitate at this moment, will cause the conversion rate of reaction and selectivity to reduce, thereby, the optimal bottom of ...

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Abstract

The invention discloses a method for synthesizing a 6''-O-palmitoyl-naringin ester on line by using lipase as a catalyst, which comprises the following steps: by using naringin and vinyl palmitate in a mole ratio of 1:(1-9) 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 15-35 minutes; and collecting the reaction solution on line, and carrying out conventional after-treatment on the reaction solution to obtain the 6''-O-palmitoyl-naringin 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-naringin ester. (2) Background technology [0002] Naringin (Naringin), also known as naringin, citrusin, isohesperidin, is a dihydroflavonoid compound, mainly found in the peel and pulp of pomelo fruit, grapefruit, tangerine and orange of the Rutaceae plant. 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 reducin...

Claims

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Application Information

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