CN103667400A - Method for synthesizing 6''-O-palmitoyl-naringin ester on line by using lipase as catalyst - Google Patents
Method for synthesizing 6''-O-palmitoyl-naringin ester on line by using lipase as catalyst Download PDFInfo
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Abstract
The invention discloses a method for synthesizing a 6''-O-palmitoyl-naringin ester on line by using lipase as a catalyst, which comprises the following steps: by using naringin and vinyl palmitate 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-palmitoyl-naringin ester. The method has the advantages of short reaction time, high selectivity and high yield.
Description
(1) technical field
The present invention relates to a kind of synthetic 6 " methods of O-palmityl-naringin ester of lipase-catalyzed online controlled selectivity.
(2) background technology
Naringin (Naringin) claim again naringin, naringin, aurantiin, it is a kind of flavanone kind composition, mainly be present in the pericarp and pulp of Citrus paradisi Macfadyen fruit, natsudaidai, tangerine and orange, 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 all be take anti-oxidant activity as basis according to the study, relevant with Green Tea Extract or anti peroxidation of lipid.Special structure is given 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 reaction activity etc.Flavonoid compound inhibition low-density lipoprotein LDL is oxidized and the research of inhibition carotenoid and unsaturated fatty acids acid oxidase shows, 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 in molecule, introducing long hydrocarbon chain can increase the fat-soluble of it, thereby increases and fatty consistency and raising oxidation-resistance.So, naringin is as one of maximum flavonoid compound of application, and researching and developing the naringin fatty acid ester that its physiologically active is stronger will have a good application prospect.
At present, the route of synthesis of naringin fatty ester is mainly in organic medium, to carry out enzymatic reaction, and the hydroxyl on glycosyl is carried out to acylations, specifically comprises acidylate, esterification and three kinds of methods of transesterification reaction.The mild condition although enzymatic reaction responds, the advantage that selectivity is good, but enzymic catalytic reaction is having some limitations property also, such as the restriction between the activity of enzyme and the polarity of organic solvent, restriction between the polarity of organic solvent and the solvability of reaction substrate, long, transformation efficiency of reaction times is high-technology bottleneck not.Therefore, searching naringin enzymatic selective esterification new technology is significant for the production of development naringin fatty acid ester.
Micro-fluidic (Microfluidics) is in micron order structure, to control to receive to rise to technology and the science that skin rises volume fluid, is the new cross discipline emerging rapidly nearly ten years.Current, the development of micro-fluidic has surmounted the original object that is 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.
From Harrison seminar in 1997, delivered after the document of first piece of writing synthetic compound in micro-fluidic chip microreactor, micro-fluidic chip reactor has been successfully used to multiple organic synthesis, and has shown application prospect widely.Along with the development of micro-mixing, micro-reaction technology in micro-fluidic chip, in chip, carry out building-up reactions and become one of the study hotspot in micro-fluidic chip field.
With conventional chemical reactor, compare, micro passage reaction not only has the diffusion length making between reactant to be shortened greatly, 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 that produce in reaction process are also few, are the technology of a kind of environmental friendliness, study on the synthesis novel substance.
At present, there is more Chinese scholars to be studied the enzyme catalysis of naringin ester in organic medium is synthetic, but the method often needs the reaction times (24h) of growing, and transformation efficiency and the selectivity of reaction are not high, utilizing microflow control technique to explore new building-up reactions, is current international and domestic study hotspot in order to solve the technical bottleneck of existing synthetic method.Our research group early stage has also been carried out systematic study to the enzymatic selectivity of saccharide compound in micro-fluidic reactor is synthetic, finds to utilize microflow control technique to carry out that the enzymatic selectivity of saccharide compound is synthetic has certain feasibility.And naringin is the sugary flavonoid compound of a class, derive from the pericarp and pulp of shaddock fruit, natsudaidai, tangerine and orange, there is good anticancer, antibacterial, anti-oxidant, decreasing cholesterol, reduction capillary fragility, the multiple biological activitys such as microcirculation of improving.The regioselectivity esterification of naringin is modified and not only can be improved bioavailability, can also expand it in the application in the fields such as medicine, food.And be the sugary flavonoid compound of a class, we can utilize the Research foundation in early stage to study the enzymatic regioselectivity esterification of naringin.Therefore we have studied lipase-catalyzed selectivity synthetic 6 in microfluidic channel reactor " a kind of method of O-palmityl-naringin ester; be intended to find online controlled method for selective synthesis of naringin palmitinic acid monoesters of high-efficiency environment friendly; the naringin monoesters that different chain length replaces; its solvability; cell permeability etc. have a great difference; thereby the naringin monoester class compound that utilizes the synthetic different chain length of microflow control technique to replace, can further investigate its bioavailability, expand it in the application in the fields such as medicine and food.
(3) summary of the invention
The technical problem to be solved in the present invention is to provide in a kind of microfluidic channel reactor lipase-catalyzed selectivity synthetic 6, and " novel process of O-palmityl-naringin ester has advantages of 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 synthetic 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 is communicated with reaction channel outlet by the second interface, and described reaction channel internal diameter is 0.8～2.4mm, and reaction channel length is 0.5～1.0m, described method comprises: naringin and palmitinic acid vinyl acetate that the ratio of amount of substance of take is 1:1～1:9 are raw material, 0.5～1.0g Lipozyme RMIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide (DMSO) of take is reaction solvent, by Lipozyme RMIM uniform filling in reaction channel, raw material and reaction solvent are placed in to syringe, syringe carries out acylation reaction in raw material and reaction solvent being passed into reaction channel continuously under syringe pump promotes, controlling acylation reaction temperature is 40～55 ℃, the acylation reaction time is 15～35min, by product collector, collect online reaction solution, reaction solution makes 6 through aftertreatment " 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 using two syringes, can adopt T-shaped or Y type interface to be connected with the entrance of reaction channel, different reactants is introduced from two entrances, conflux and enter public reaction channel, middle reactant molecule contact by microchannel increases with probability of collision, makes two strands of reaction solution streams in public reaction channel, mix and react.Syringe pump synchronously promotes a plurality of syringes.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel is placed in thermostat container, and for example thermostat container is enclosed in reaction channel in case, with this, can effectively control temperature of reaction.Described thermostat container can require to select voluntarily according to temperature of reaction, such as constant temperature water bath case etc.
The present invention does not limit for the material of reaction channel, and recommendation is green, the material of environmental protection, for example silicone tube; Shape for reaction channel is preferably curved shape, can guarantee at the uniform velocity stable the passing through of reaction solution.
The present invention, in implementation process, can first use the mixed solvent (tertiary amyl alcohol: DMSO=4:1) dissolve naringin, its consumption needs only and guarantees that naringin can fully dissolve, and is loaded in syringe standby of tertiary amyl alcohol and DMSO; Only with nontoxic tertiary amyl alcohol, dissolve palmitinic acid vinyl acetate, be loaded in another syringe standby; Then for example, under the synchronous promotion of syringe pump (PHD2000 syringe pump), make raw material and reaction solvent react in passing into reaction channel.Therefore, in the present invention, in reaction solvent, tertiary amyl alcohol and DMSO volume ratio are greater than 4:1, than conventional shaking table reaction, can the usage quantity of poisonous DMSO are down to minimum.
Comparatively preferred, method of the present invention comprises the following steps:
The tertiary amyl alcohol that is first 4:1 by volume ratio and the mixed solvent of DMSO dissolve naringin, are loaded in syringe standby; With tertiary amyl alcohol, dissolve palmitinic acid vinyl acetate, be loaded in another syringe standby; Two syringes are connected with the entrance of reaction channel by Y type interface, carry out acylation reaction in then raw material and reaction solvent being passed into reaction channel under the synchronous promotion of syringe pump.
When using two syringes be dissolved with the tertiary amyl alcohol of naringin and the mixing solutions of DMSO and be dissolved with the tertiary amyl alcohol solution of palmitinic acid vinyl acetate to reaction channel injection respectively, for dissolving, the volumetric usage of the tertiary amyl alcohol of palmitinic acid vinyl acetate preferably equates with the volumetric usage of dissolving the tertiary amyl alcohol of naringin and the mixed solvent of DMSO, so that the consistence of assurance two kinds of material molar ratios while entering reaction channel.
Describedly for dissolving the volumetric usage of the tertiary amyl alcohol of naringin and the mixed solvent of DMSO, conventionally with the amount of substance of naringin, count 10～25mL/mmol.
In the present invention, the commodity that described Lipozyme RMIM is used letter (novozymes) company of Novi to produce, it is a kind of lipase obtaining from Rhizomucor miehei, is that aspergillus oryzae (Aspergillus oryzae) microorganism with a kind of gene modification produces through submerged fermentation.。Lipozyme RM IM is granular product, and granularity is 0.2-0.6mm.
The inventive method at reaction channel, is directly evenly fixed on granular catalyzer Lipozyme RMIM uniform filling in reaction channel by mechanical means.
Further, described naringin is preferably 1:7～9 with the ratio of the amount of substance of palmitinic acid vinyl acetate, most preferably is 1:7.
Further, described acylation reaction temperature is preferably 52～55 ℃, most preferably is 52 ℃.
Further, the described acylation reaction time is preferably 25～35min, most preferably is 30min.Can be by regulating syringe pump to regulate the flow velocity of reaction channel inner fluid and then regulating the residence time of raw material in reaction channel, i.e. 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 the mixed solvent that ethyl acetate, methyl alcohol, water volume ratio are 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 that contains single product obtaining is merged to evaporate to dryness, can obtain flaxen monoesters crystal, 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 and the residence time in reaction channel, but do not cause direct impact to reacting itself.
In the present invention, although there are 6 hydroxyls that performance is close in naringin, but " O-palmityl-naringin ester has higher transformation efficiency and selectivity to lipase-catalyzed selectivity synthetic 6; transformation efficiency of diester is very low; almost do not have, the content 100% of the monoesters obtaining by column chromatography for separation in micro-fluidic micro passage reaction.The structure warp of product
1h NMR confirmation.This shows that the enzymatic selectivity of naringin cetylate in micro-fluidic micro passage reaction is synthetic and has good reaction conversion ratio and selectivity, can realize high monoesters rate.
Compared with prior art, beneficial effect of the present invention is: synthetic naringin-6 of selectivity in microfluidic channel reactor of the present invention " O-cetylate, this method has not only shortened the reaction times widely, and has high transformation efficiency and reaction preference; The usage quantity that has simultaneously reduced DMSO, has environment-friendly advantage.
(4) accompanying drawing explanation
Fig. 1 is the structural representation of the microfluidic channel reactor of embodiment of the present invention employing.
(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 to this:
The structure of the microfluidic channel reactor that the embodiment of the present invention is used, with reference to figure 1, comprises a syringe pump (not shown), two syringes 1, reaction channel 3, constant temperature water bath case (5, only show its floor map) and product collector 4; Two syringes 1 are installed in syringe pump, by a Y type interface, be communicated with reaction channel 3 entrances, described reaction channel 3 is placed in constant temperature water bath case 5, by constant temperature water bath case 5, control temperature of reaction, 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 " synthesizing of O-palmityl-naringin ester
Equipment therefor is with reference to figure 1.Naringin (0.49mmol) is dissolved in the mixed solvent of 10mL tertiary amyl alcohol: DMSO=4:1 (v/v), and palmitinic acid vinyl acetate (3.43mmol) is dissolved in 10mL tertiary amyl alcohol, is then loaded on respectively in 10mL syringe standby.0.87g Lipozyme RMIM uniform filling is 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 by " Y " type joint, enter in reaction channel and react, by constant temperature water bath case, control temperature of reactor at 52 ℃, on syringe pump, show that in reaction channel, reaction solution actual volume is 314 microlitres, reaction solution is continuous flow reaction 30min in reaction channel, and reaction result is followed the tracks of and detected by thin-layer chromatography TLC.
By product collector, collect online reaction solution, 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, the high 35cm of post, column diameter 4.5cm, wet method upper prop after sample dissolves with a small amount of elution reagent, elutriant is collected flow velocity 2mLmin
-1, TLC follows the tracks of wash-out process simultaneously, and the elutriant that contains single product obtaining is merged to evaporate to dryness, obtains flaxen monoesters crystal, obtains naringin-6 " cetylate is 6 " O-palmityl-naringin ester.HPLC detects naringin transformation efficiency 92%, the naringin ester total content of the content/generation of naringin-6 " selectivity of cetylate (naringin-6 "-cetylate) be 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 'and H
6 '), 6.79 (d, 2H, J=8.5Hz, H
3 'and H
5 '), 6.11 (d, 2H, J=25.5Hz, H
6and H
8), 5.49 (m, 1H, H
2), 5.44 (m, 1H, H
1 "), 5.41 (m, 1H, 2 " '-OH of naringin), 5.17 (m, 1H, H
1 " '), 5.10 (d, 1H, J=5.1Hz, 4 " '-OH of naringin), 4.74 (d, 1H, J=4.8Hz; 4 "-OH of naringin), 4.69 (d, 1H, J=4.4Hz, 3 " OH of naringin), 4.50 (d, 1H; J=5.8Hz, 3 " '-OH of naringin), 4.26 (d, 1H, J=11.9Hz, H
6 "acylated), 4.04 (m, 1H, H
6 "acylated), 3.73-3.16 (8H, H of rhamnoglucosyl), 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, 3H of CH
3of rhamnosyl), 1.24 (m, 26H of (CH
2)
13of palmitoyl), 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
1corresponding?exactly?to?the?molecular?weight?of6″-O-palmitoyl-naringin.
Embodiment 2-5
The temperature that changes microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: the impact of temperature on reaction
The result of table 1 shows, when flow velocity is 10.4 μ Lmin
-1reaction times is while being 30min, reaction is with the rising of temperature, transformation efficiency also obviously raises, and when temperature of reaction reaches 52 ℃, the transformation efficiency of reaction and selectivity are all best, if now continued, heat up, will cause the reduction of enzymic activity, thereby cause transformation efficiency and the selectivity of reaction to decrease, thus in the present invention in micro-fluidic micro passage reaction the optimal reaction temperature of naringin cetylate be 52 ℃.
Embodiment 6-9
Changing palmitinic acid vinyl acetate in micro-fluidic micro passage reaction is 1:1(embodiment 6 with the ratio of the substrate amount of substance of naringin), 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 palmitinic acid vinyl acetate.Other are with embodiment 1, and result is as shown in table 2.
Table 2: naringin is compared the impact of reacting with palmitinic acid vinyl acetate substrate
The result of table 2 shows, along with the increase of reactant palmitinic acid vinyl acetate, the transformation efficiency of reaction is also along with increase, and when substrate is when for 7:1, the transformation efficiency of reaction and selectivity are optimum, and naringin substantially quantitatively transforms for naringin-6 " cetylate completely.If now continue to increase the consumption of reactant palmitinic acid vinyl acetate, transformation efficiency and the elective reduction that will cause reaction, thereby the best substrate of this reaction is than being 7:1, under this reaction conditions, naringin transforms substantially completely for 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, result is as shown in table 3.
Table 3: the reaction times is on reaction conversion ratio and optionally impact
| 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, reaction is carried out 15min and can be obtained 58% naringin-6 " palmitinic acid monoesters, selectivity is now 100%, naringin is " the palmitinic acid monoesters that is converted into naringin-6 completely substantially.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, and " palmitinic acid monoesters transformation efficiency can reach 92%, and reaction preference also can reach 100% in naringin-6.If now continue to extend the reaction times, can cause on the contrary reaction conversion ratio and optionally reduce, thereby " the synthetic Best Times of palmitinic acid monoesters is 30min in naringin-6 in microfluidic channel reactor.
Comparative example 1～3
Change the catalyzer in micro-fluidic micro passage reaction, change respectively Lipozyme TLIM(comparative example 1 into), lipase Novozym435(comparative example 2), bacillus alkaline protease (comparative example 3), other are with embodiment 1, and result is as shown in table 4.
Table 4: different enzymes are on reaction conversion ratio and optionally impact
| ? | Enzyme source | Transformation efficiency [%] | Selectivity [%] |
| Comparative example 1 | Lipozyme?TLIM | 58 | 100 |
| Comparative example 2 | Novozym435 | 35 | 100 |
| Comparative example 3 | Bacillus alkaline protease | 10 | 100 |
| |
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." transformation efficiency of palmitinic acid monoesters is 58% to utilize Lipozyme TLIM catalyzed reaction, naringin-6.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, change respectively the naringin of embodiment 1 (0.49mmol) into hesperidine 0.49mmol(comparative example 4), saligenin (comparative example 5), other are with embodiment 1, result is as shown in table 3.
Table 5: different enzymes are on reaction conversion ratio and optionally impact
| ? | Flavone derivative | Transformation efficiency [%] | Selectivity [%] |
| Comparative example 4 | Hesperidine | 2 | 100 |
| Comparative example 5 | Saligenin | 10 | 100 |
| |
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.Hesperidine is under same reaction conditions, and transformation efficiency is only 2%, 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 be obtained more satisfactory reaction result, and the transformation efficiency of reaction can reach 92%, and selectivity is 100%.
Claims (8)
1. the one kind lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, it is characterized in that described method employing 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 is communicated with the outlet of reaction channel by the second interface, described reaction channel internal diameter is 0.8～2.4mm, and reaction channel length is 0.5～1.0m, described method comprises: naringin and palmitinic acid vinyl acetate that the ratio of amount of substance of take is 1:1～9 are raw material, 0.5～1.0g Lipozyme RMIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide of take is reaction solvent, by Lipozyme RMIM uniform filling in reaction channel, raw material and reaction solvent are placed in to syringe, syringe carries out acylation reaction in raw material and reaction solvent being passed into reaction channel continuously under the promotion of syringe pump, controlling acylation reaction temperature is 40～55 ℃, the acylation reaction time is 15～35min, by product collector, collect online reaction solution, reaction solution makes 6 through aftertreatment " O-palmityl-naringin ester.
2. the as claimed in claim 1 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester; it is characterized in that: the tertiary amyl alcohol that it is first 4:1 with volume ratio that described method comprises the following steps: and the mixed solvent of DMSO dissolving naringin, be loaded in syringe standby; With tertiary amyl alcohol, dissolve palmitinic acid vinyl acetate, be loaded in another syringe standby; Two syringes are connected with the entrance of reaction channel by Y type interface, carry out acylation reaction in then raw material and reaction solvent being passed into reaction channel under the synchronous promotion of syringe pump.
3. as claimed in claim 1 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
4. as claimed in claim 2 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
As described in one of claim 1～4 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described naringin is 1:7～9 with the ratio of the amount of substance of palmitinic acid vinyl acetate.
As described in one of claim 1～4 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described acylation reaction temperature is 52～55 ℃, and the described acylation reaction time is 25～35min.
7. as claimed in claim 5 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described naringin is 1:7 with the ratio of the amount of substance of palmitinic acid vinyl acetate.
8. as claimed in claim 6 lipase-catalyzed online synthetic 6 " method of O-palmityl-naringin ester, is characterized in that: described acylation reaction temperature is 52 ℃, and the described acylation reaction time is 30min.
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| CN107988278A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl laurate thioesters |
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| CN107988277A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl palmitic acid thioesters |
| CN107988278A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl laurate thioesters |
| CN107988278B (en) * | 2017-12-21 | 2021-06-04 | 浙江农林大学 | Method for synthesizing S-benzyl lauric acid thioester on line by lipase catalysis |
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