CN102030733B - The preparation method of a kind of high purity costuslactone and dehydro-α-curcumene - Google Patents
The preparation method of a kind of high purity costuslactone and dehydro-α-curcumene Download PDFInfo
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- CN102030733B CN102030733B CN201010614200.8A CN201010614200A CN102030733B CN 102030733 B CN102030733 B CN 102030733B CN 201010614200 A CN201010614200 A CN 201010614200A CN 102030733 B CN102030733 B CN 102030733B
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Abstract
The present invention relates to one high-speed countercurrent chromatography and prepare highly purified costuslactone and dehydro-α-curcumene method, comprising: (1) prepares suitable solvent system, must go up after stratification and descend phase mutually; (2) selection is mutually stationary phase, lower is moving phase mutually, is first full of counter current chromatograph pillar with stationary phase, adjustment engine speed is 600-1000rpm, moving phase is pumped in post with the flow velocity of 0.5-5.0ml/min, after whole Establishing running balance, by sampling valve sample introduction; (3) according to detector uv-spectrogram receiving target composition, concentrated, crystallization, to obtain final product.Present method is suitable for various model high-speed counter-current chromatograph and the costuslactone of various content and the preparation of dehydro-α-curcumene, and have fractional dose large, the rate of recovery is high, feature easy and simple to handle.
Description
Technical field
The invention belongs to the preparation field of lactone contained by the banksia rose, particularly the preparation method of a kind of high purity costuslactone and dehydro-α-curcumene.
Background technology
The banksia rose is the dry root of the composite family Saussurea lappa Clarke platymiscium banksia rose (Auckland ia lappaDecne), and effect of tool promoting the circulation of QI to relieve pain, strengthening the spleen to promote digestion, is mainly used in the treatment of the diseases such as Peptic Ulcers, biliary colic, bronchial asthma clinically.The banksia rose is mainly containing volatile oil, and its main component is Costunolide and dehydro-α-curcumene, and the two has relaxing smooth muscle and spasmolysis, is the main active ingredient of the banksia rose, is also the important indicator of banksia rose quality control.The Ginkgolide Components such as costuslactone and the bronchoconstriction effect of going lactone volatile oil all can cause antihistamine, vagusstoff and bariumchloride, wherein stronger with dihydrocostulactone effect.
The structural formula of costuslactone is as follows:
The structural formula of Costunolide is as follows:
High-speed countercurrent chromatography (High-SpeedCountercurrent Chromatography, HSCCC) be efficient without the need to any solid support of a kind of continuous print grown up for nearly 30 years, liquid liquid distribution chromatography isolation technique fast, its principle is the centrifugal force utilizing borded pile to produce when planetary motion, immiscible two-phase is constantly mixed, retain a phase (stationary phase) wherein simultaneously, constant flow pump is utilized to input another phase (moving phase) continuously, the solute entering borded pile with moving phase distributes between the two phases repeatedly, by the order of partition ratio, by wash-out successively.In moving phase allocation proportion large first by wash-out, otherwise, large rear by wash-out of allocation proportion in stationary phase.When the traditional liquid chromatography technology amount of being prepared is separated, allocative efficiency is low, and solvent-oil ratio is large, and the problem such as solid state adhesion body or carrier can bring that sample is adsorbed, loss and sex change.And HSCCC can ensure higher peak type resolving power, have easy and simple to handle, fractional dose is large, sample nondestructive consumes, separation efficiency is high, theoretical recovery is 100%, the advantages such as favorable reproducibility and isolating environment mitigation, has now been widely used in preparative separation and the purifying of the field chemical substances such as biology, medicine, environmental protection.
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation method of a kind of high purity costuslactone and dehydro-α-curcumene.The method overcomes the defect of conventional separation techniques, and adopt high-speed countercurrent chromatography (HSCCC) to prepare the method for high purity banksia rose ester and dehydro-α-curcumene, the method is easy and simple to handle, and the rate of recovery is high, and fractional dose is large.
The preparation method of a kind of high purity costuslactone of the present invention and dehydro-α-curcumene, comprising:
(1) 1-5: 0.5-1: 1-5: the 5-10 mixing by volume of component A, B component, component C and D component is placed in separating funnel, shakes up stratification, after ready to balance 20-40 minute, upper and lower phase is separated, obtain this solvent system; Wherein component A is methyl acetate, ethyl acetate or butylacetate; B component is n-propyl alcohol or propyl carbinol; Component C is ethanol or methyl alcohol; D component is water;
(2) selection is mutually stationary phase, lower is moving phase mutually, is first full of counter current chromatograph pillar with stationary phase, adjustment engine speed is 600-1000rpm, moving phase is pumped in post with the flow velocity of 0.5-5.0ml/min, after whole Establishing running balance, by sampling valve sample introduction;
(3) according to detector uv-spectrogram receiving target composition, flow point is carried out concentrate, crystallization, obtain costuslactone and dehydro-α-curcumene.
Above-mentioned solvent system is preferably ethyl acetate-propyl carbinol-ethanol-water system.
The preparation method of the sample entered in described step (2) is: be dissolved in upper and lower phase by Radix Aucklandiae extract.
Solvent system in described step (1) is ethyl acetate-n-propyl alcohol-methanol-water, and the volume ratio of this Four composition is followed successively by: 1: 1: 1: 7; Engine speed 850rpm in described step (2), the moving phase flow velocity pumped in post is 5.0ml/min.
Solvent system in described step (1) is methyl acetate-n-propyl alcohol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 4: 0.8: 2: 6; Engine speed 950rpm in described step (2), the moving phase flow velocity pumped in post is 0.5ml/min.
Solvent system in described step (1) is ethyl acetate-propyl carbinol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 3: 0.5: 1: 8; Engine speed 650rpm in described step (2), the moving phase flow velocity pumped in post is 3.0ml/min.
Solvent system in described step (1) is ethyl acetate-propyl carbinol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 1: 0.7: 2: 9; Engine speed 600rpm in described step (2), the moving phase flow velocity pumped in post is 1.0ml/min.
Solvent system in described step (1) is ethyl acetate-propyl carbinol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 2: 0.8: 3: 1; Engine speed 700rpm in described step (2), the moving phase flow velocity pumped in post is 2.0ml/min.
Solvent system in described step (1) is ethyl acetate-propyl carbinol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 5: 0.5: 4: 7; Engine speed 800rpm in described step (2), the moving phase flow velocity pumped in post is 3.0ml/min.Solvent system in described step (1) is ethyl acetate-propyl carbinol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 4: 1: 4: 5; Engine speed 1000rpm in described step (2), the moving phase flow velocity pumped in post is 4.0ml/min.
Solvent system in described step (1) is butylacetate-n-propyl alcohol-alcohol-water, and the volume ratio of this Four composition is followed successively by: 4: 1: 1: 6; Engine speed 750rpm in described step (2), the moving phase flow velocity pumped in post is 4.0ml/min.
According to solubility constant, when not destroying system balance, regulate the volume ratio of A, B, C, D Four composition.
Experiment condition is applicable to temperature 20-40 DEG C, and within the scope of said temperature, when temperature is higher, appearance time slightly shifts to an earlier date, and separating effect change is little, on peak shape without much impacts.
Engine speed and flow velocity need control within the specific limits, by volume solvent system are placed in separating funnel, shake up stratification.After ready to balance certain hour, upper and lower phase separated, adopt TBE-300B high-speed counter-current chromatograph, this type column volume is 300ml, and sample introduction circle is 20ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 600-1000rpm, moving phase is pumped in post with the flow velocity of 0.5-5.0ml/min.
High purity refers to purity >=98%; The target component being separated and collecting, will carry out crystallization again after being concentrated to certain purity and obtain monomer.
Present invention employs high speed adverse current chromatogram isolation technique and overcome solid support or carrier irreversible adsorption, loss and sex change, the separated object rate of recovery high theory is made to reach 100%, the present invention is actual reaches more than 95%, again because adopt preferred solvent system, the processing condition of Control release Conditions Temperature, adjustment engine speed and flow velocity, high efficiencyly can be separated, obtain highly purified costuslactone and dehydro-α-curcumene (reaching more than 98%).
beneficial effect
1, present invention employs high speed adverse current chromatogram isolation technique, ensure higher peak shape resolution, fractional dose is large, the rate of recovery is high, isolating environment relaxes, save solvent, easy and simple to handle.
2, the Radix Aucklandiae extract that the present invention is applicable to preparing from various process routes obtains highly purified costuslactone and dehydro-α-curcumene (reaching more than 98%).
Embodiment
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims limited range equally after the content of having read the present invention's instruction.
Embodiment 1
Choose methyl acetate-n-propyl alcohol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 25 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 4: 0.8: 2: 6 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 100mg banksia rose study to be dissolved on 10ml mutually and stand-by in the solution of phase solution composition under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 950rpm, pumps in post with the flow velocity of 0.5ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, carries out crystallization after concentrated freeze-dried, and its HPLC purity reaches 98.8%.
Embodiment 2
Choose ethyl acetate-propyl carbinol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 30 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 3: 0.5: 1: 8 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 650rpm, pumps in post with the flow velocity of 3.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches 98.5%.
Embodiment 3
Choose butylacetate-n-propyl alcohol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 22 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 4: 1: 1: 6 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 750rpm, pumps in post with the flow velocity of 4.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, carries out crystallization after concentrated freeze-dried, and its HPLC purity reaches 98.9%.
Embodiment 4
Choose ethyl acetate-n-propyl alcohol-methanol-water solution separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 40 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 1: 1: 1: 7 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 100mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 850rpm, pumps in post with the flow velocity of 5.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches 98.2%.
Embodiment 5
Choose ethyl acetate-propyl carbinol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 25 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 1: 0.7: 2: 9 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 600rpm, pumps in post with the flow velocity of 1.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches more than 98%.
Embodiment 6
Choose ethyl acetate-propyl carbinol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 28 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 2: 0.8: 3: 10 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 700rpm, pumps in post with the flow velocity of 2.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches more than 98%.
Embodiment 7
Choose ethyl acetate-propyl carbinol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 35 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 5: 0.5: 4: 7 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 800rpm, pumps in post with the flow velocity of 3.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches more than 98%.
Embodiment 8
Choose ethyl acetate-propyl carbinol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph.It is 38 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 4: 1: 4: 5 volume ratios and is configured in separating funnel, stratification after jolting.After ready to balance for some time, upper and lower phase is separated.Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station.Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml.Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 1000rpm, pumps in post with the flow velocity of 4.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, and carry out crystallization after concentrated, its HPLC purity reaches more than 98%.
Claims (1)
1. a preparation method for high purity costuslactone and dehydro-α-curcumene, comprising:
Choose butylacetate-n-propyl alcohol-ethanol-water system separation and purification costuslactone constituents on semi-preparative counter current chromatograph; It is 22 DEG C that experiment condition is applicable to temperature, first to be divided by above-mentioned solvent composition by 4: 1: 1: 6 volume ratios and is configured in separating funnel, stratification after jolting; After ready to balance for some time, upper and lower phase is separated; Adopt semi-preparative counter current chromatograph, be furnished with tetrafluoroethylene post, 20ml sampling valve, column volume is 300ml, is furnished with TBP-50A pump, TBD-23 detector and N2000 chromatographic working station; Take 150mg banksia rose study to be dissolved on 10ml mutually and stand-by in phase solution under 10ml; Before sample introduction, be first full of whole pillar with stationary phase, adjustment engine speed is 750rpm, pumps in post with the flow velocity of 4.0ml/min by moving phase; After whole Establishing running balance, by sampling valve sample introduction, then according to detector uv-spectrogram, receiving target composition, obtains costuslactone and dehydro-α-curcumene flow point, carries out crystallization after concentrated freeze-dried, and its HPLC purity reaches 98.9%.
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| CN104327026B (en) * | 2014-10-15 | 2016-06-15 | 西南民族大学 | A kind of method extracting separation costunolide and Decahydro-3,6,9-tris(methylene)azuleno[4,5-b |
| CN105315246A (en) * | 2015-04-16 | 2016-02-10 | 霍秀菊 | Method for separating and purifying costunolide and dehydrocostus lactone from costustoot |
| CN104876900A (en) * | 2015-05-18 | 2015-09-02 | 徐州医学院 | Method for extracting, separating and purifying costunolide and dehydrocostus lactone from elecampane |
| CN106138060A (en) * | 2016-08-14 | 2016-11-23 | 武晓丹 | The pharmaceutical composition of a kind of moclobemide and medical usage thereof |
| CN106317003A (en) * | 2016-08-14 | 2017-01-11 | 武晓丹 | Furazolidone pharmaceutical composition and biological and medicinal applications thereof |
| CN106279087A (en) * | 2016-08-14 | 2017-01-04 | 武晓丹 | A kind of compound and preparation method thereof, medical applications |
| CN106317002A (en) * | 2016-08-14 | 2017-01-11 | 武晓丹 | Natural compound separated from sargentgloryvine stem, preparation method and application thereof |
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| 李躬行,等,.高速逆流色谱法分离木香中的木香烃内酯和去氢木香内酯.《华西药学杂志》.2009,第24卷(第5期),第526-528页. * |
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