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

A technology of naringin dihydrochalcone ester and naringin dihydrochalcone ester, which is applied in the field of lipase-catalyzed online synthesis of 6″-O-lauroyl-naringin dihydrochalcone ester, capable of Solve the problems of no enzymatic modification of naringin dihydrochalcone, long reaction time, low conversion rate and selectivity, and achieve the effects of shortening reaction time, high reaction selectivity and high conversion rate

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

Problems solved by technology

[0008] At present, many scholars at home and abroad have studied the enzymatic regioselective esterification of flavonoids in organic media, but there is no research on the enzymatic modification of naringin dihydrochalcone.
Moreover, the reported enzymatic regioselective esterification methods of flavonoids in organic media often require a long reaction time (24h), and the conversion rate and selectivity of the reaction are not high. Using microfluidic technology to explore new synthetic methods Reaction, to solve the technical bottleneck of existing synthetic methods is a research hotspot at home and abroad

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 6″-O-lauroyl-naringin dihydrochalcone ester

[0033]

[0034] Device reference used figure 1 . Dissolve naringin dihydrochalcone (0.49 mmol) in 10 mL of tert-amyl alcohol: DMSO=4:1 (v / v) mixed solvent, and dissolve vinyl laurate (3.43 mmol) in 10 mL of tert-amyl alcohol , and then packed in 10mL syringes for use. 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 dis...

Embodiment 2-5

[0040] 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:

[0041] Table 1: Effect of Temperature on Reaction

[0042]

[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 of enzyme activity has caused the conversion rate and selectivity of the reaction to be reduced, so the optimal reaction temperature of naringin dihydrochalcone laurate in the microfluidic microchannel reactor of the present invention is 52 ° C .

Embodiment 6-9

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

[0047] Table 2: Effect of naringin dihydrochalcone and vinyl laurate substrate ratio on reaction

[0048]

[0049] The result of table 2 shows, along with the increase of reactant vinyl laurate, the conversion rate of reaction also increases thereupon, and when substrate ratio is 7:1, the conversion rate and selectivity of reaction are optimal, and naringin di Hydrochalcone has been quantitatively and completely converted into naringin dihydrochalcone-6 "-laurate. If continue to increase the consumption of reactant vinyl laurate at this moment, will cause the conversion rate and the selectivity of rea...

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Abstract

The invention discloses a method for synthesizing a 6''-O-lauroyl-aringin dihydrochalcone ester on line by using lipase as a catalyst, which comprises the following steps: by using naringin dihydrochalcone and vinyl laurate 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-lauroyl-aringin dihydrochalcone 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-lauroyl-naringin dihydrochalcone ester. (2) Background technology [0002] Naringin dihydrochalcone (Naringin dihydrochalcone) is a flavonoid derivative obtained by oxidizing naringin isolated from natural citrus plants. Its sweetness is 500-700 times that of sucrose. It has It has the characteristics of high sweetness, low calorie, non-toxic, safe, etc., and has various biological activities such as anti-cancer, anti-bacterial, anti-oxidant, and cholesterol-lowering, so it is used in food, medicine, and daily chemical industries. In addition, naringin dihydrochalcone has a refreshing taste, with a special fragrance, and has an excellent effect of shielding bitterness. Therefore, naringin dihydrochalcone is especially suitable for vegetable food processing, jam, chewing gum, Toothpaste and lozenges. [0003] According to research, various biological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/44
Inventor 杜理华罗锡平何锋凌慧敏杨文俊
Owner ZHEJIANG UNIV OF TECH
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