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

A technology for hesperidin dihydrochalcone ester and neohesperidin dihydrochalcone ester, which is applied in the field of lipase-catalyzed online synthesis of 6″-O-lauroyl-neohesperidin dihydrochalcone ester , can solve the problems of no enzymatic modification of neohesperidin dihydrochalcone, long reaction time, low conversion rate and selectivity, etc., and achieve the effect of shortening reaction time, high reaction selectivity and high conversion rate

Active Publication Date: 2014-03-26
ZHEJIANG FORESTRY UNIVERSITY
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  • Abstract
  • Description
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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 neohesperidin 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-neohesperidin dihydrochalcone ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-lauroyl-neohesperidin dihydrochalcone ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-lauroyl-neohesperidin 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-neohesperidin dihydrochalcone ester

[0033]

[0034] Reference of the device used figure 1 . Dissolve neohesperidin dihydrochalcone (0.49mmol) in 10mL tert-amyl alcohol: DMSO=4∶1 (v / v) mixed solvent, and dissolve vinyl laurate (3.92mmol) in 10mL tert-amyl alcohol Then put them into 10mL syringes for use. 0.87g lipase Lipozyme RMIM is evenly filled in the reaction channel of the microfluidic channel reactor. Driven by the PHD2000 syringe pump, the two reaction solutions are respectively 8.91μL·min -1 The flow rate of the reactor enters the reaction channel through the "Y" connector for reaction. The actual volume of the reaction liquid in the reaction channel is 314 microliters displayed on the syringe pump. The temperature of the reactor is controlled at 52℃ through the water bath thermostat, and the reaction liquid is continuous in the reaction channel. The flow reaction was conducted for 35 minutes, and the reaction results were tra...

Embodiment 2-5

[0041] The temperature of the microfluidic channel reactor was changed, and the others were the same as in Example 1. The reaction results are shown in Table 1:

[0042] Table 1: The influence of temperature on the reaction

[0043]

[0044] The results in Table 1 show that when the flow rate is 8.91μL·min -1 When the reaction time is 35min, the conversion rate of the reaction increases obviously with the increase of temperature. When the reaction temperature reaches 52℃, the conversion rate and selectivity of the reaction are both the best. At this time, if the temperature continues to rise, it will cause The decrease of enzyme activity leads to a decrease in the conversion rate and selectivity of the reaction. Therefore, the optimal reaction temperature of neohesperidin dihydrochalcone laurate in the microfluidic microchannel reactor of the present invention is 52 ℃.

Embodiment 6-10

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

[0047] Table 2: The effect of the ratio of neohesperidin dihydrochalcone and vinyl laurate on the reaction

[0048]

[0049]

[0050] The results in Table 2 show that as the reactant vinyl laurate increases, the conversion rate of the reaction also increases. When the substrate ratio is 8:1, the conversion rate and selectivity of the reaction are optimal, and neohesperidin Dihydrochalcone has basically been completely converted into neohesperidin dihydrochalcone-6″-laurate. At this time, if the amount of reactant vinyl laurate is increased, the conversion rate and selecti...

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Abstract

The invention discloses a method for synthesizing a 6''-O-lauroyl-neohesperidin dihydrochalcone ester on line by using lipase as a catalyst, which comprises the following steps: by using neohesperidin dihydrochalcone and vinyl laurate 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-lauroyl-neohesperidin 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 method for lipase-catalyzed online controllable and selective synthesis of 6"-O-lauroyl-neohesperidin dihydrochalcone ester. (2) Background technology [0002] Neohesperidin dihydrochalcone (Neohesperidin dihydrochalcone) is a flavonoid derivative derived from the oxidation of neohesperidin extracted from natural citrus plants. Its sweetness is 500-700 times that of sucrose. It has the characteristics of high sweetness, low calorie, non-toxicity, safety, etc., and has various biological activities such as anti-cancer, antibacterial, antioxidant, and cholesterol-lowering, so it is used in food, medicine and daily chemical industries. In addition, neohesperidin dihydrochalcone has a refreshing taste with a special fragrance and has an excellent effect of shielding bitterness. Therefore, neohesperidin dihydrochalcone is especially suitable for vegetable food processing, jam, Chewing gum, toothpaste and oral tablets. [0003] Acco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/44
Inventor 罗锡平杜理华何锋凌慧敏杨文俊
Owner ZHEJIANG FORESTRY UNIVERSITY
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