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
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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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