CN103667400B - A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester - Google Patents
A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester Download PDFInfo
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Abstract
The invention discloses a kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester; described method is: take mol ratio as naringin and the vinyl palmitate of 1:1 ~ 9 be raw material; with 0.5 ~ 1.0g Lipozyme? does is RMIM catalyzer; with the mixed solvent of tertiary amyl alcohol and DMSO for reaction solvent; by Lipozyme? RMIM is uniformly filled in the reaction channel of microfluidic channel reactor, the reaction channel internal diameter of described microfluidic channel reactor is 0.8 ~ 2.4mm, and reaction channel length is 0.5 ~ 1.0m; Raw material and reaction solvent are passed in reaction channel continuously and carries out acylation reaction, controlling acylation reaction temperature is 40 ~ 55 DEG C, the acylation reaction time is 15 ~ 35min, collects reaction solution online, and reaction solution obtains 6 through conventional aftertreatment "-O-palmityl-naringin ester.The present invention has the advantage that the reaction times is short, selectivity is high and productive rate is high.
Description
(1) technical field
The present invention relates to a kind of synthesis 6 " method of-O-palmityl-naringin ester.
(2) background technology
Naringin (Naringin) is also known as naringin, naringin, aurantiin, it is a kind of flavanone kind composition, in the pericarp being mainly present in Citrus paradisi Macfadyen fruit, natsudaidai, tangerine and orange and pulp, there is good anticancer, antibacterial, anti-oxidant, decreasing cholesterol, reduction capillary fragility, improve the multiple biological activitys such as microcirculation, be usually used in the fields such as medicine, makeup, food.
The various biological activitys of flavonoid compound are all based on anti-oxidant activity according to the study, relevant with Green Tea Extract or anti peroxidation of lipid.Special structure gives the chemical property of its a series of uniqueness, if with many kinds of metal ions generation complexing or electrostatic interaction, there is reduction and catch the characteristic of free radical and many derivative reactions active etc.Flavonoid compound suppresses low-density lipoprotein LDL oxidation and suppresses the research of carotenoid and unsaturated fatty acids acid oxidase to show, aglycon has more outstanding anti-oxidant activity than glucosides.This is because aglycon lipotropy is strong, can embed in the kernel of microbial film hydrophobic layer and play a role.The poly-hydroxy of flavonoid glycoside compound and glycosyl structure make it have certain wetting ability, and this will certainly affect anti-oxidant activity.Flavonoid compound is modified by esterification, and introducing long hydrocarbon chain in the molecule can increase the fat-soluble of it, thus increases with the consistency of fat and improve oxidation-resistance.So, naringin is as applying one of maximum flavonoid compound, and the naringin fatty acid ester researching and developing its physiologically active stronger will have a good application prospect.
At present, the route of synthesis of naringin fatty ester mainly carries out enzymatic reaction in organic medium, carries out acylations to the hydroxyl on glycosyl, specifically comprises acidylate, esterification and transesterification reaction three kinds of methods.The mild condition although enzymatic reaction responds, the advantage that selectivity is good, but enzymic catalytic reaction is having some limitations property also, restriction between the activity of such as enzyme and the polarity of organic solvent, restriction between the polarity of organic solvent and the solvability of reaction substrate, reaction times longer, transformation efficiency not high-technology bottleneck.Therefore, naringin enzymatic selective esterification new technology is found significant for the production of development naringin fatty acid ester.
Micro-fluidic (Microfluidics) manipulates to receive to rise to technology and the science that skin rises volume fluid in micron scale construction, is the new cross discipline emerged rapidly nearly ten years.Current, the development of micro-fluidic has surmounted the original object being mainly analytical chemistry service greatly, and is becoming the important technological platform of whole chemistry subject, life science, instrumental science and even information science new round innovation research.
After Harrison seminar in 1997 has delivered the document of first section synthetic compound in micro-fluidic chip microreactor, micro-fluidic chip reactor has been successfully used to multiple organic synthesis, and illustrates application prospect widely.Along with the development of microring array, micro-reacting tcchnology in micro-fluidic chip, carry out building-up reactions in the chips and become one of the study hotspot in micro-fluidic chip field.
Compare with conventional chemical reactor, micro passage reaction not only has makes the diffusion length between reactant greatly shorten, and mass transfer velocity is fast; The easy control of reaction conditions such as reactant ratio, temperature, reaction times and flow velocity, side reaction is less; Need reactant consumption very micro-, not only can reduce the consumption of costliness, poisonous, adverse reaction thing, the environmental pollutant produced in reaction process are also few, are the technology of a kind of environmental friendliness, study on the synthesis novel substance.
At present, more Chinese scholars is had to be studied the Enzyme catalyzed synthesis of naringin ester in organic medium, but the method often needs the longer reaction times (24h), and reaction transformation efficiency and selectivity not high, utilizing microflow control technique to explore new building-up reactions, is study hotspot international and domestic now in order to solve the technical bottleneck of existing synthetic method.Our research group has also carried out systematic study to the enzymatic selectivity synthesis of saccharide compound in micro-fluidic reactor early stage, finds that the enzymatic selectivity synthesis utilizing microflow control technique to carry out saccharide compound has certain feasibility.And naringin is the sugary flavonoid compound of a class, in the pericarp deriving from shaddock fruit, natsudaidai, tangerine and orange and pulp, there is good anticancer, antibacterial, anti-oxidant, decreasing cholesterol, reduction capillary fragility, improve the multiple biological activitys such as microcirculation.The regioselectivity esterification of naringin is modified and not only can improve bioavailability, its application in fields such as medicine, food can also be expanded.And be the sugary flavonoid compound of a class, we can utilize the enzymatic regioselectivity esterification of Research foundation to naringin in early stage to study.Therefore we have studied lipase-catalyzed selectivity synthesis 6 in microfluidic channel reactor " method of-O-palmityl-naringin ester; be intended to the online controlled method for selective synthesis of the naringin palmitinic acid monoesters finding a kind of high-efficiency environment friendly; the naringin monoesters that different chain length replaces; its solvability; cell permeability etc. have a great difference; the naringin monoester class compound thus utilizing microflow control technique to synthesize different chain length to replace, its bioavailability can be furtherd investigate, expand its application in medicine and the field such as food.
(3) summary of the invention
The technical problem to be solved in the present invention is to provide lipase-catalyzed selectivity synthesis 6 in a kind of microfluidic channel reactor " novel process of-O-palmityl-naringin ester, there is the advantage that the reaction times is short, selectivity is high and productive rate is high.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester, described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, be communicated with reaction channel entrance by first interface, described product collector passes through the second interface and reaction channel outlet, and described reaction channel internal diameter is 0.8 ~ 2.4mm, and reaction channel length is 0.5 ~ 1.0m, described method comprises: the naringin being 1:1 ~ 1:9 with the ratio of amount of substance and vinyl palmitate are for raw material, with 0.5 ~ 1.0g Lipozyme RMIM for catalyzer, with the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide (DMSO) for reaction solvent, Lipozyme RMIM is uniformly filled in reaction channel, raw material and reaction solvent are placed in syringe, raw material and reaction solvent pass into continuously in reaction channel and carry out acylation reaction by syringe under syringe pump promotes, controlling acylation reaction temperature is 40 ~ 55 DEG C, the acylation reaction time is 15 ~ 35min, reaction solution is collected online by product collector, reaction solution is through aftertreatment obtained 6 "-O-palmityl-naringin ester.
In the microfluidic channel reactor that the present invention adopts, described syringe number can be one or more, depending on concrete reaction requirement.Such as, when use two syringes, T-shaped or Y type interface can be adopted to be connected with the entrance of reaction channel, different reactants is introduced from two entrances, conflux and enter public reaction channel, increased with probability of collision by reactant molecule contact in microchannel, make two strands of reaction solution streams mix in public reaction channel and react.Multiple syringe synchronously promotes by syringe pump.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel is placed in thermostat container, and such as reaction channel is enclosed in case by thermostat container, effectively can control temperature of reaction with this.Described thermostat container can require to select voluntarily according to temperature of reaction, such as constant temperature water box etc.
The present invention does not limit for the material of reaction channel, and recommendation is green, the material of environmental protection, such as silicone tube; Shape for reaction channel is preferably curved shape, can ensure at the uniform velocity stable the passing through of reaction solution.
The present invention, in implementation process, first can dissolve naringin with the mixed solvent (tertiary amyl alcohol: DMSO=4:1) of tertiary amyl alcohol and DMSO, as long as its consumption ensures that naringin can fully dissolve, and is loaded in syringe for subsequent use; Only dissolve vinyl palmitate with nontoxic tertiary amyl alcohol, be loaded in another syringe for subsequent use; Then under the synchronous promotion of syringe pump (such as PHD2000 syringe pump), make raw material and reaction solvent pass in reaction channel react.Therefore, in the present invention, in reaction solvent, tertiary amyl alcohol and DMSO volume ratio are greater than 4:1, react compared to the shaking table of routine, can be down to minimum by the usage quantity of poisonous DMSO.
Comparatively preferred, method of the present invention comprises the following steps:
First dissolve naringin with the mixed solvent that volume ratio is the tertiary amyl alcohol of 4:1 and DMSO, be loaded in syringe for subsequent use; Dissolve vinyl palmitate with tertiary amyl alcohol, be loaded in another syringe for subsequent use; Two syringes are connected with the entrance of reaction channel by Y type interface, then raw material and reaction solvent are passed in reaction channel under the synchronous promotion of syringe pump and carry out acylation reaction.
When use two syringes respectively to reaction channel inject be dissolved with the tertiary amyl alcohol of naringin and the mixing solutions of DMSO and be dissolved with the tert-amyl alcohol solution of vinyl palmitate time, volumetric usage for dissolving the tertiary amyl alcohol of vinyl palmitate is preferably equal with the volumetric usage of dissolving the tertiary amyl alcohol of naringin and the mixed solvent of DMSO, so that the consistence of two kinds of material molar ratios when ensureing to enter reaction channel.
The volumetric usage of the mixed solvent of described tertiary amyl alcohol and DMSO for dissolving naringin counts 10 ~ 25mL/mmol with the amount of substance of naringin usually.
In the present invention, the commodity that described Lipozyme RMIM uses letter (novozymes) company of Novi to produce, it is a kind of lipase obtained from Rhizomucormiehei, is to produce through submerged fermentation with a kind of gene-modified aspergillus oryzae (Aspergillusoryzae) microorganism.。LipozymeRMIM is granular product, and granularity is 0.2-0.6mm.
Lipozyme RMIM is uniformly filled in reaction channel by the inventive method, is directly evenly fixed in reaction channel by granular catalyzer by mechanical means.
Further, described naringin is preferably 1:7 ~ 9 with the ratio of the amount of substance of vinyl palmitate, most preferably is 1:7.
Further, described acylation reaction temperature is preferably 52 ~ 55 DEG C, most preferably is 52 DEG C.
Further, the described acylation reaction time is preferably 25 ~ 35min, most preferably is 30min.Regulate the flow velocity of reaction channel inner fluid by regulating syringe pump and then regulate the residence time of raw material in reaction channel, i.e. the reaction times.
Reaction product of the present invention can be collected online, and gained reaction solution can obtain 6 by conventional post-treating method "-O-palmityl-naringin ester.Described conventional post-treating method can be: the underpressure distillation of gained reaction solution is except desolventizing, residuum is separated through silica gel column chromatography, with 200-300 order silica gel wet method dress post, elution reagent is ethyl acetate, methyl alcohol, water volume ratio are the mixed solvent of 25:2.5:0.6, wet method upper prop after residuum dissolves with a small amount of elution reagent, collect elutriant, TLC follows the tracks of wash-out process simultaneously, the elutriant containing single product obtained is merged evaporate to dryness, flaxen monoesters crystal can be obtained, be 6 "-O-palmityl-naringin ester.
The reaction channel internal diameter that the present invention uses is 2mm, and reaction channel is long is 1.0m.Reaction channel internal diameter and length can affect rate of flow of fluid in reaction channel and the residence time, but do not cause direct impact to reaction itself.
In the present invention, although there is the hydroxyl of 6 similar nature in naringin, but lipase-catalyzed selectivity synthesis 6 in micro-fluidic micro passage reaction "-O-palmityl-naringin ester has higher transformation efficiency and selectivity; and the transformation efficiency of diester is very low; almost do not have, the content 100% of the monoesters obtained by column chromatography for separation.The structure warp of product
1hNMR confirms.This shows that the enzymatic selectivity synthesis of naringin cetylate in micro-fluidic micro passage reaction has good reaction conversion ratio and selectivity, can realize high monoesters rate.
Compared with prior art, beneficial effect of the present invention is: selectivity synthesis naringin-6 in microfluidic channel reactor of the present invention "-O-cetylate, this method not only shortens the reaction times widely, and has high transformation efficiency and reaction preference; Reduce the usage quantity of DMSO simultaneously, there is environment-friendly advantage.
(4) accompanying drawing explanation
Fig. 1 is the structural representation of the microfluidic channel reactor that the embodiment of the present invention adopts.
(5) embodiment
With specific embodiment, protection scope of the present invention is described further below, but protection scope of the present invention is not limited thereto:
Structural reference Fig. 1 of microfluidic channel reactor that the embodiment of the present invention uses, comprises a syringe pump (not shown), two syringes 1, reaction channel 3, constant temperature water box 5 (only showing its floor map) and product collector 4; Two syringes 1 are installed in syringe pump, be communicated with reaction channel 3 entrance by a Y type interface, described reaction channel 3 is placed in constant temperature water box 5, temperature of reaction is controlled by constant temperature water box 5, the internal diameter 2.0mm of described reaction channel 3, pipe range 1m, the outlet of described reaction channel 3 is communicated with product collector 4 by the second interface.
Embodiment 1:6 " synthesis of-O-palmityl-naringin ester
Equipment therefor is with reference to figure 1.Naringin (0.49mmol) is dissolved in 10mL tertiary amyl alcohol: in the mixed solvent of DMSO=4:1 (v/v), vinyl palmitate (3.43mmol) is dissolved in 10mL tertiary amyl alcohol, is then loaded in 10mL syringe for subsequent use respectively.0.87g Lipozyme RMIM is uniformly filled in the reaction channel of microfluidic channel reactor, and under PHD2000 syringe pump promotes, two-way reaction solution is respectively with totally 10.4 μ Lmin
-1flow velocity entered in reaction channel by " Y " type joint and react, temperature of reactor is controlled at 52 DEG C by constant temperature water box, syringe pump showing reaction solution actual volume in reaction channel is 314 microlitres, reaction solution is continuous flow reaction 30min in reaction channel, and reaction result is by thin-layer chromatography TLC tracing detection.
Reaction solution is collected online by product collector, underpressure distillation is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is ethyl acetate: methyl alcohol: water volume ratio=25:2.5:0.6, post height 35cm, column diameter 4.5cm, wet method upper prop after sample dissolves with a small amount of elution reagent, flow velocity 2mLmin collected by elutriant
-1, TLC follows the tracks of wash-out process simultaneously, the elutriant containing single product obtained is merged evaporate to dryness, obtains flaxen monoesters crystal, obtain naringin-6 " and-cetylate, be 6 "-O-palmityl-naringin ester.HPLC detects naringin transformation efficiency 92%, naringin-6 " the selectivity of-cetylate naringin ester total content of content/generation of-cetylate (naringin-6 ") is 100%.
Nuclear-magnetism characterization result is as follows:
1h-NMR (DMSO-d6, δ, ppm): naringin-6 "-cetylate: 12.04 (s, H
5), 9.62 (s, H
4'), 7.33 (d, 2H, J=8.5Hz, H
2'andH
6'), 6.79 (d, 2H, J=8.5Hz, H
3'andH
5'), 6.11 (d, 2H, J=25.5Hz, H
6andH
8), 5.49 (m, 1H, H
2), 5.44 (m, 1H, H
1 "), 5.41 (m, 1H, 2 " '-OHofnaringin), 5.17 (m, 1H, H
1 " '), 5.10 (d, 1H, J=5.1Hz; 4 " '-OHofnaringin), 4.74 (d, 1H, J=4.8Hz; 4 "-OHofnaringin), 4.69 (d, 1H, J=4.4Hz; 3 "-OHofnaringin), 4.50 (d, 1H, J=5.8Hz, 3 " '-OHofnaringin), 4.26 (d; 1H, J=11.9Hz, H
6 "acylated), 4.04 (m, 1H, H
6 "acylated), 3.73-3.16 (8H, Hofrhamnoglucosyl), 3.22 (m, 1H, H
3), 2.73 (d, 1H, J=3.2Hz, H
3), 2.22 (m, 2H ,-CH
2-CO-), 1.49 (m, 3HofCH
3ofrhamnosyl), 1.24 (m, 26Hof (CH
2)
13ofpalmitoyl), 0.85 (t, 3H, J=7.0Hz, CH
3).
IR(KBr,cm
-1):3415(OH),1740(C＝O),1643(C＝C)；
ESI-MS(m/z):853(M
1+2H
2O-H)
-,M
1correspondingexactlytothemolecularweightof6”-O-palmitoyl-naringin.
Embodiment 2-5
Change the temperature of microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: temperature is on the impact of reaction
The result of table 1 shows, when flow velocity is 10.4 μ Lmin
-1reaction times is when being 30min, react the rising with temperature, transformation efficiency also obviously raises, and when temperature of reaction reaches 52 DEG C, the transformation efficiency of reaction and selectivity are all best, if now continue to heat up, the reduction of enzymic activity will be caused, thus result in the transformation efficiency of reaction and selectivity decreases, thus in the present invention in micro-fluidic micro passage reaction the optimal reaction temperature of naringin cetylate be 52 DEG C.
Embodiment 6-9
Changing vinyl palmitate and the ratio of the amount of the substrate materials of naringin in micro-fluidic micro passage reaction is 1:1 (embodiment 6), 3:1 (embodiment 7), 5:1 (embodiment 8), 9:1 (embodiment 9), the consumption of naringin is that 0.49mmol is constant, changes the consumption of vinyl palmitate.Other are with embodiment 1, and result is as shown in table 2.
Table 2: the impact that naringin and the comparison of vinyl palmitate substrate are reacted
The result of table 2 shows, along with the increase of reactant vinyl palmitate, the transformation efficiency of reaction is also along with increase, and when substrate is than during for 7:1, the transformation efficiency of reaction and selectivity are optimum, and naringin substantially quantitatively transforms in order to naringin-6 completely "-cetylate.If now continue the consumption increasing reactant vinyl palmitate, the transformation efficiency of reaction and selectivity will be caused to reduce, and thus, the best substrate of this reaction is than being 7:1, under the reaction conditions, naringin transforms substantially completely in order to naringin-6 "-cetylate.
Embodiment 10-13
Changing the reaction times in micro-fluidic micro passage reaction is 15min (embodiment 10), 20min (embodiment 11), 25min (embodiment 12), 35min (embodiment 13), other are with embodiment 1, and result is as shown in table 3.
Table 3: the reaction times is on reaction conversion ratio and optionally affect
| Embodiment | Reaction times [min] | Transformation efficiency [%] | Selectivity [%] |
| 10 | 15 | 58 | 100 |
| 11 | 20 | 75 | 100 |
| 12 | 25 | 88 | 100 |
| 1 | 30 | 92 | 100 |
| 13 | 35 | 86 | 99 |
The result of table 3 shows, the naringin-6 that 15min can obtain 58% is carried out in reaction "-palmitinic acid monoesters, selectivity is now 100%, and naringin is be converted into naringin-6 completely substantially "-palmitinic acid monoesters.Along with the increase in reaction times, the transformation efficiency of reaction increases gradually, and when 30min is carried out in reaction, the transformation efficiency of reaction and selectivity are optimum, naringin-6 "-palmitinic acid monoesters transformation efficiency can reach 92%, and reaction preference also can reach 100%.If now continue to extend the reaction times, reaction conversion ratio can be caused on the contrary and optionally reduce, thus, naringin-6 in microfluidic channel reactor " Best Times that synthesizes of-palmitinic acid monoesters is 30min.
Comparative example 1 ~ 3
Change the catalyzer in micro-fluidic micro passage reaction, change Lipozyme TLIM (comparative example 1), lipase Novozym435 (comparative example 2), bacillus alkaline protease (comparative example 3) respectively into, other are with embodiment 1, and result is as shown in table 4.
Table 4: different enzyme is on reaction conversion ratio and optionally affect
| Enzyme source | Transformation efficiency [%] | Selectivity [%] | |
| Comparative example 1 | Lipozyme TLIM | 58 | 100 |
| Comparative example 2 | Novozym 435 | 35 | 100 |
| Comparative example 3 | Bacillus alkaline protease | 10 | 100 |
| Embodiment 1 | Lipozyme RMIM | 92 | 100 |
The result of table 4 shows, for the regioselectivity esterification of enzymatic naringin in microfluidic channel reactor, different enzymes has fairly obvious impact to reaction.Utilizing Lipozyme TLIM catalyzed reaction, naringin-6 " transformation efficiency of-palmitinic acid monoesters is 58%.And utilize this reaction of bacillus alkaline protease catalysis, naringin-6 " transformation efficiency of-palmitinic acid monoesters is only 10%.From the result of table 4, for the regioselectivity esterification of enzymatic naringin in microfluidic channel reactor, the most effective catalyzer is Lipozyme RMIM, and the transformation efficiency of naringin is 90%, and selectivity is 100%.
Comparative example 4 ~ 5
Change different types of flavonoid compound in micro-fluidic micro passage reaction, the naringin (0.49mmol) of embodiment 1 is changed into respectively hesperidine 0.49mmol (comparative example 4), saligenin (comparative example 5), other with embodiment 1, result is as shown in table 3.
Table 5: different enzyme is on reaction conversion ratio and optionally affect
| Flavone derivative | Transformation efficiency [%] | Selectivity [%] | |
| Comparative example 4 | Hesperidine | 2 | 100 |
| Comparative example 5 | Saligenin | 10 | 100 |
| Embodiment 1 | Naringin | 92 | 100 |
The result of table 5 shows, for the regioselectivity esterification of enzymatic flavonoid compound in microfluidic channel reactor, different flavonoid compounds has different reaction results.Under the same reaction conditions, transformation efficiency is only 2% to hesperidine, and reaction and difficulty thereof, react hardly.The reaction result of saligenin is also undesirable, and transformation efficiency is only 10%.From the result of table 5, for the regioselectivity esterification of enzymatic flavonoid compound in microfluidic channel reactor, naringin can obtain more satisfactory reaction result, and the transformation efficiency of reaction can reach 92%, and selectivity is 100%.
Claims (6)
1. a lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester, it is characterized in that described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, be communicated with the entrance of reaction channel by first interface, described product collector passes through the outlet of the second interface and reaction channel, described reaction channel internal diameter is 0.8 ~ 2.4mm, and reaction channel length is 0.5 ~ 1.0m, described method comprises: the naringin being 1:7 ~ 9 with the ratio of amount of substance and vinyl palmitate are for raw material, with 0.5 ~ 1.0g Lipozyme RMIM for catalyzer, with the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide for reaction solvent, Lipozyme RMIM is uniformly filled in reaction channel, raw material and reaction solvent are placed in syringe, raw material and reaction solvent pass into continuously in reaction channel and carry out acylation reaction by syringe under the promotion of syringe pump, controlling acylation reaction temperature is 52 ~ 55 DEG C, the acylation reaction time is 25 ~ 35min, reaction solution is collected online by product collector, reaction solution is through aftertreatment obtained 6 "-O-palmityl-naringin ester.
2. lipase-catalyzed online synthesis 6 as claimed in claim 1 " method of-O-palmityl-naringin ester; it is characterized in that: described method comprises the following steps: to be first that the tertiary amyl alcohol of 4:1 and the mixed solvent of DMSO dissolve naringin by volume ratio, is loaded in syringe for subsequent use; Dissolve vinyl palmitate with tertiary amyl alcohol, be loaded in another syringe for subsequent use; Two syringes are connected with the entrance of reaction channel by Y type interface, then raw material and reaction solvent are passed in reaction channel under the synchronous promotion of syringe pump and carry out acylation reaction.
3. lipase-catalyzed online synthesis 6 as claimed in claim 1 " method of-O-palmityl-naringin ester, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
4. lipase-catalyzed online synthesis 6 as claimed in claim 2 " method of-O-palmityl-naringin ester, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
5. lipase-catalyzed online synthesis 6 as claimed in claim 1 " method of-O-palmityl-naringin ester, it is characterized in that: described naringin is 1:7 with the ratio of the amount of substance of vinyl palmitate.
6. lipase-catalyzed online synthesis 6 as claimed in claim 1 " method of-O-palmityl-naringin ester, it is characterized in that: described acylation reaction temperature is 52 DEG C, the described acylation reaction time is 30min.
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| CN107955824A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- chlorobenzyls）The method of laurate thioesters |
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