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

A technology of hesperidin dihydrochalcone ester and neohesperidin dihydrochalcone ester, which is applied in the field of online synthesis of 6″-O-palmitoyl-neohesperidin dihydrochalcone ester by lipase catalysis , can solve the problems of low conversion rate and selectivity, long reaction time, no enzymatic modification of neohesperidin dihydrochalcone, etc., and achieve the effects 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
  • 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 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-palmitoyl-neohesperidin dihydrochalcone ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-neohesperidin dihydrochalcone ester on line by using lipase as catalyst
  • Method for synthesizing 6''-O-palmitoyl-neohesperidin dihydrochalcone ester on line by using lipase as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of 6''-O-palmitoyl-neohesperidin dihydrochalcone ester

[0032]

[0033] Device reference used figure 1 . Dissolve neohesperidin dihydrochalcone (0.49mmol) in 10mL of tert-amyl alcohol:DMSO=4:1 (v / v) mixed solvent, and dissolve vinyl palmitate (3.92mmol) in 10mL of tert-amyl alcohol , and then filled 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 8.91 μL min -1 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 actual volume of the reaction liquid in the reaction channel is displayed on the syringe pump as 314 microliters, and the reaction liquid flows continuously in the reaction channel. The reaction was carried out for 35 minutes, and the reacti...

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] 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, thereby caused the conversion rate of reaction and selectivity to reduce to some extent, so the optimal reaction temperature of neohesperidin dihydrochalcone palmitate in the microfluidic microchannel reactor among the present invention is 52 ℃.

Embodiment 6-10

[0045] Change the substrate molar ratio of vinyl palmitate and neohesperidin dihydrochalcone 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 dihydrochalcone was 0.49 mmol unchanged, and the amount of vinyl palmitate was changed. Others are the same as Example 1, and the results are shown in Table 2.

[0046] Table 2: Effect of Neohesperidin Dihydrochalcone and Vinyl Palmitate Substrate Ratio on Reaction

[0047]

[0048]

[0049] 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 Dihydrochalcone has been almost completely converted to neohesperidin dihydrochalcone-6''-palmitate. Now if continue to increase the consumption of reactant vinyl palmitate, will cause the conversion...

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Abstract

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

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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