CN102167693B - Method for separating and preparing alpha-terthienyl, thianthrene and p-terphenyl - Google Patents
Method for separating and preparing alpha-terthienyl, thianthrene and p-terphenyl Download PDFInfo
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- CN102167693B CN102167693B CN 201110046654 CN201110046654A CN102167693B CN 102167693 B CN102167693 B CN 102167693B CN 201110046654 CN201110046654 CN 201110046654 CN 201110046654 A CN201110046654 A CN 201110046654A CN 102167693 B CN102167693 B CN 102167693B
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- terthienyl
- thianthrene
- terphenyl
- purity
- petroleum ether
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- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical group C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 title claims abstract description 52
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229930184652 p-Terphenyl Natural products 0.000 title claims abstract description 22
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000004185 countercurrent chromatography Methods 0.000 claims abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 22
- 238000000605 extraction Methods 0.000 claims description 19
- 241001479588 Packera glabella Species 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 36
- 239000003208 petroleum Substances 0.000 abstract description 18
- 238000000926 separation method Methods 0.000 abstract description 15
- 239000000284 extract Substances 0.000 abstract description 11
- 239000000178 monomer Substances 0.000 abstract description 6
- 238000010262 high-speed countercurrent chromatography Methods 0.000 abstract description 5
- 241000208812 Flaveria bidentis Species 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 abstract description 3
- 150000002191 fatty alcohols Chemical class 0.000 abstract description 2
- 241000723353 Chrysanthemum Species 0.000 description 21
- 230000005526 G1 to G0 transition Effects 0.000 description 16
- 238000005070 sampling Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002186 photoactivation Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 1
- 241000208811 Flaveria Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001472925 Helenieae Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- KTHDTJVBEPMMGL-VKHMYHEASA-N N-acetyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(C)=O KTHDTJVBEPMMGL-VKHMYHEASA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- LCAFHCBIBRIVQJ-UHFFFAOYSA-N acetonitrile;dichloromethane;heptane Chemical compound CC#N.ClCCl.CCCCCCC LCAFHCBIBRIVQJ-UHFFFAOYSA-N 0.000 description 1
- MYBBMMORFOKMMQ-UHFFFAOYSA-N acetonitrile;hexane Chemical compound CC#N.CCCCCC MYBBMMORFOKMMQ-UHFFFAOYSA-N 0.000 description 1
- 230000036531 allelopathy Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- -1 biology Substances 0.000 description 1
- VRNIDUBKKMCRPB-UHFFFAOYSA-N butan-1-ol;2-methoxy-2-methylpropane Chemical compound CCCCO.COC(C)(C)C VRNIDUBKKMCRPB-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229950001390 sudismase Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for separating and preparing high-purity monomers of alpha-terthienyl, thianthrene and p-terphenyl from plant flaveria bidentis extracts, obtained by petroleum ether refluxing, with high-speed countercurrent chromatography. In the method, the countercurrent chromatography is adopted to separate and prepare the high-purity alpha-terthienyl, thianthrene and p-terphenyl from the plant flaveria bidentis extracts, obtained by petroleum ether refluxing, a solvent comprises three components including petroleum ether or n-alkane, dichloromethane and acetonitrile or fatty alcohol in the volume ratio of 10:(0-3):(12-7); and the method is suitable for separation and preparation of the monomers of alpha-terthienyl, thianthrene and p-terphenyl through various models of countercurrent chromatographs, so that a large amount of crude products or synthetic mixtures can be directly fed, the purity of separated alpha-terthienyl is over 99%, and the purity of thianthrene and p-terphenyl can reach more than 90%.
Description
Technical field
The present invention relates to a kind of preparation separation method that adopts high-speed countercurrent chromatography from the Alien Invasive Plants yellowtop extract, to separate preparation high-purity monomer α-terthienyl, thianthrene and p-terphenyl.
Background technology
Huang Dingju [
Flaveria bidentis(L.) Kuntze] be the yellow top of composite family helenieae Chrysanthemum (
Flaveria) the annual herb plant, originate from South America.Yellow top chrysanthemum plant is tall and big intensive, and seed production is surprising, and fecundity and adaptability are extremely strong, can invade the habitats such as farmland, roadside, wasteland, and can suppress by allelopathy the growth of other plant, thereby capture rapidly ecological niche.Except the country of origin, Huang Dingju all shows invasion in other countries and area, and ecotope and agriculture production are had great threat, is the high Alien Invasive Plants of a kind of danger.From calendar year 2001 since lakeside, China Hengshui is found first, Huang Dingju is at ground rapid spreads such as Hebei, Tianjin.From present experience of prevention and treatment, only rely on traditional manually root out and simple chemical control is difficult to the control effect that reaches desirable, therefore, illustrate the chemical fundamentals of species interaction from the angle of chemical ecology, its invasion mechanism of profound announcement reaches the impact on the ecosystem and species diversity, must also be urgent for setting up yellow integrated campaign and the hierarchy of control of pushing up the chrysanthemum Sustainable development.On the other hand, in the research control measures, if can further investigate, further develop active secondary substance and corresponding medicine and agricultural functional, just can turn waste into wealth, become and do harm to be beneficial, for the comprehensive regulation of Huang Dingju searches out a new outlet.Contain flavonoid in the chrysanthemum of the yellow top of bibliographical information; thiophene-based isoreactivity material; the existing investigator Flavonoid substances of from Huang Dingju, purifying out; this paper mainly extracts in the chrysanthemum of yellow top the apolar substances such as thiophene-based; wherein α-terthienyl is a kind of light-sensitive compound; it is to mosquito larvae; fly larva and other insect have strong photoactivation toxic action; α-terthienyl is also to phytopathogen; Plant nematode has photoactivation poisoning synergism; and α-terthienyl also can improve intracellular oxyradical by inducing; the activity that suppresses sudismase; destroy the anti-oxidation protection system of cell, finally suppress the plant materials growth.
Existing bibliographical information adopts the Grignard reagent cross-coupling reaction to prepare α-terthienyl, but can not obtain the monomer of extreme high purity, and the adverse current chromatogram method for separating and preparing can obtain high-purity monomer.Because high speed adverse current chromatogram (High-speed Countercurrent Chromatography, HSCCC) be grew up in recent years a kind of continuous need not any solid support efficiently, liquid liquid distribution chromatography isolation technique fast, the variety of issue that it has avoided solid state adhesion body or carrier to bring---sample easily is adsorbed, loss and sex change, HSCCC guarantees higher peak type resolution, fractional dose is large, sample nondestructive loses, the rate of recovery is high, isolating environment relaxes, and saves solvent.Counter current chromatograph can directly advance slightly get sample in a large number product or synthetic mixture, and separating resulting can reach quite high purity, even can directly connect the instruments such as mass spectrograph, has been widely used in preparation separation and the purifying of the field chemical substances such as biology, medicine, environmental protection.
Summary of the invention
The objective of the invention is take the Huang of Petroleum ether extraction top chrysanthemum crude product as raw material from content only α-the terthienyl as 2.2% obtain the α-terthienyl of purity more than 99% through the method for high speed adverse current chromatogram, in the separation and Extraction process, can obtain thianthrene and the p-terphenyl of purity more than 90% simultaneously.
The solution of the present invention is: the Huang top chrysanthemum crude product raw material of sherwood oil refluxing extraction separates preparation high-purity alpha-terthienyl, thianthrene and p-terphenyl by counter current chromatography.Select the two-phase non-aqueous solvent system, be made of three components, the A component is sherwood oil, normal paraffin, and the B component is methylene dichloride, and the C component is acetonitrile, Fatty Alcohol(C12-C14 and C12-C18).
Adopt non-aqueous solvent system, below be stationary phase mutually, lower is moving phase mutually, under guaranteeing that phase volume ratio is less than 1 prerequisite up and down, according to solubility constant, in the situation of not destroying the system balance, regulate the volume ratio of A:B:C three components: 10:0-3:12-7 obtains α-terthienyl, thianthrene and p-terphenyl through a counter-current separation.
Experiment condition is fit to room temperature 10-25 ° C, and room temperature is larger on the separation efficiency impact, and the optimal separation temperature is 15 ℃, if temperature is too much, solvent system keeps very poor, can't reach separation requirement.
At first by volume above-mentioned solvent system is disposed in the separating funnel, shakes up rear standing demix.Ready to balance after for some time separates upper and lower phase.Adopt analysis mode or half countercurrent chromatography instrument, be furnished with the NS-1007 pump, 2mL or 20mL sampling valve, tetrafluoroethylene post, column volume are 40mL, 230 or 240mL, 500mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.Huang is pushed up the chrysanthemum crude extract to be dissolved in the moving phase stand-by.Before the sample introduction, be filled with whole pillar with stationary phase first, adjusting engine speed is 500-1800 rpm, with the flow velocity of 0.5-3.0mL/min moving phase is pumped in the post, after whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition.
More than its purity to 99% of α-terthienyl with present method extraction, thianthrene and p-terphenyl purity reach more than 90%.Be applicable to adopt the counter current chromatograph of various models to separate preparation α-terthienyl, thianthrene and p-terphenyl monomer, can directly advance slightly get sample in a large number product or synthetic mixture, separating resulting can reach high purity.
Embodiment
Embodiment 1
Choose normal hexane-acetonitrile and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph GS10AB, at first by the 1:1 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shake up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 200mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 1.5mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, receiving target composition, HPLC detect α-terthienyl purity and reach more than 99%, and the purity of thianthrene and p-terphenyl reaches more than 90%.
Embodiment 2
Choose normal heptane-methylene dichloride-acetonitrile and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph GS10A, at first by the 10:2:8 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shakes up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 230mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 129.4mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, receiving target composition, HPLC detect α-terthienyl purity and reach more than 99%, and the purity of thianthrene and p-terphenyl reaches more than 90%.
Embodiment 3
Choose Skellysolve A-methylene dichloride-acetonitrile and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph EMC-500A, at first by the 10:3:7 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shakes up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 500mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 400.1mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, receiving target composition, HPLC detect α-terthienyl purity and reach more than 99%, and the purity of thianthrene and p-terphenyl reaches more than 90%.
Embodiment 4
Choose normal hexane-ethanol and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph GS10AB, at first by the 5:6 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shake up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 134.6mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, receiving target composition, HPLC detect α-terthienyl purity and reach more than 99%, and the purity of thianthrene and p-terphenyl reaches more than 90%.
Embodiment 5
Choose normal hexane-methyl alcohol and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph GS10AB, at first by the 1:1 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shake up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 299.7mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, the purity that HPLC detects α-terthienyl, thianthrene and p-terphenyl reaches more than 90%.
Embodiment 6
Choose sherwood oil-propyl carbinol and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at half preparation type counter current chromatograph GS10AB, at first by the 1:1 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shake up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 150.7mg Petroleum ether extraction in 5mL upper with 5mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 800rpm, with the flow velocity of 3.0mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, the purity that HPLC detects α-terthienyl, thianthrene and p-terphenyl reaches more than 90%.
Embodiment 7
Choose methyl tertiary butyl ether-propyl carbinol and come separation and purification yellowtop extract (the Huang top chrysanthemum raw material of Petroleum ether extraction) at analysis mode counter current chromatograph GS20, at first by the 1:1 volume ratio above-mentioned solvent composition is disposed in the separating funnel, shake up rear standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is upper as moving phase.Adopt the analysis mode counter current chromatograph, be furnished with the NS-1007 pump, the 2mL sampling valve, tetrafluoroethylene post, column volume are 40mL, 8823A-UV UV-detector, Yokogawa 3057 Portable type recorders.The Huang top chrysanthemum material dissolution that takes by weighing the 30.1mg Petroleum ether extraction in 1mL upper with 1mL under stand-by in the phase mixing solutions.Before the sample introduction, be filled with whole pillar with stationary phase first, the adjustment engine speed is 1800rpm, with the flow velocity of 0.5mL/min moving phase is pumped in the post; After whole Establishing running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, the purity that HPLC detects α-terthienyl, thianthrene and p-terphenyl reaches more than 90%.
Claims (1)
1. the method for separating and preparing of a α-terthienyl, thianthrene and p-terphenyl, it is characterized in that: it is to adopt counter current chromatography to separate preparation α-terthienyl, thianthrene and p-terphenyl from the chrysanthemum sherwood oil refluxing extraction thing of the yellow top of plant, wherein, α-terthienyl purity is more than 99%, thianthrene and p-terphenyl purity are more than 90%, and its solvent composition is made of three components:
Be made of sherwood oil or normal hexane or normal heptane or Skellysolve A, methylene dichloride and acetonitrile or methyl alcohol or ethanol or propyl carbinol, volume ratio is followed successively by: 10:0-3:7-12.
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| CN108558983A (en) * | 2018-05-14 | 2018-09-21 | 北京化工大学 | A kind of method that separation prepares four kinds of active materials of cycloartenyl ferulate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101565437A (en) * | 2009-05-27 | 2009-10-28 | 北京化工大学 | Separation and preparation method of patuletin-3-O-glucoside and astragalin |
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| CN101565437A (en) * | 2009-05-27 | 2009-10-28 | 北京化工大学 | Separation and preparation method of patuletin-3-O-glucoside and astragalin |
Non-Patent Citations (8)
| Title |
|---|
| Alicia Mariel Agnese, et al..Chemotaxonomic features in Argentinian species of Flaveria (Compositae).《Biochemical Systematics and Ecology》.1999,第27卷第739-742页. |
| Anticoagulant effect and action mechanism of sulphated flavonoids from Flaveria bidentis;Hugo A. Guglielmone, et al.;《Thrombosis Research》;20021231;第105卷;第183–188页 * |
| Chemotaxonomic features in Argentinian species of Flaveria (Compositae);Alicia Mariel Agnese, et al.;《Biochemical Systematics and Ecology》;19991231;第27卷;第739-742页 * |
| Hugo A. Guglielmone, et al..Anticoagulant effect and action mechanism of sulphated flavonoids from Flaveria bidentis.《Thrombosis Research》.2002,第105卷第183–188页. |
| Isolation of Chlorogenic Acid from Flaveria bidentis (L.) Kuntze by CCC and Synthesis of Chlorogenic Acid-Intercalated Layered Double Hydroxide;Yun Wei, et al.;《Chromatographia》;20110111;第73卷(第Suppl.1期);第S97–S102页 * |
| Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography;Yun Wei,et al.;《Journal of Chromatography A》;20110128;第1218卷;第6206–6211页 * |
| Yun Wei, et al..Isolation of Chlorogenic Acid from Flaveria bidentis (L.) Kuntze by CCC and Synthesis of Chlorogenic Acid-Intercalated Layered Double Hydroxide.《Chromatographia》.2011,第73卷(第Suppl.1期),第S97–S102页. |
| YunWei et al..Separation of patuletin-3-O-glucoside |
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