CN102408311B - Method for purifying solanesol through urea adduction fractionation - Google Patents
Method for purifying solanesol through urea adduction fractionation Download PDFInfo
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- CN102408311B CN102408311B CN201110389902.5A CN201110389902A CN102408311B CN 102408311 B CN102408311 B CN 102408311B CN 201110389902 A CN201110389902 A CN 201110389902A CN 102408311 B CN102408311 B CN 102408311B
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- salanesol
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- 239000004202 carbamide Substances 0.000 title claims abstract description 56
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 31
- AFPLNGZPBSKHHQ-MEGGAXOGSA-N solanesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO AFPLNGZPBSKHHQ-MEGGAXOGSA-N 0.000 title claims abstract description 14
- AFPLNGZPBSKHHQ-UHFFFAOYSA-N Betulaprenol 9 Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO AFPLNGZPBSKHHQ-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000005194 fractionation Methods 0.000 title abstract 3
- 239000013078 crystal Substances 0.000 claims abstract description 37
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000000284 extract Substances 0.000 claims abstract description 5
- -1 waxiness Substances 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 88
- 239000000706 filtrate Substances 0.000 claims description 40
- 238000003756 stirring Methods 0.000 claims description 28
- 238000005406 washing Methods 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 238000001816 cooling Methods 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000006210 lotion Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 11
- 238000007127 saponification reaction Methods 0.000 claims description 11
- 238000005267 amalgamation Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000287 crude extract Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- 238000013517 stratification Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 3
- 238000004440 column chromatography Methods 0.000 abstract description 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 2
- 229930195729 fatty acid Natural products 0.000 abstract description 2
- 239000000194 fatty acid Substances 0.000 abstract description 2
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Abstract
The invention relates to a method for purifying solanesol through urea adduction fractionation from crude solanesol. The method comprises the following steps: dissolving a defined amount of crude solanesol, filtering, saponifying, extracting to obtain a saponified substance of which the solanesol content is 30-40%, concentrating the saponified substance, dissolving, crystallizing, and performing urea adduction fractionation to crystals three times to ensure that the solanesol purity is up to above 90% and the yield is up to about 70%. By adopting the method to purify solanesol from tobacco extract, column chromatography is not required, the process is simple, impurities such as waxiness, fatty acids and the like can be effectively removed and the yield of solanesol is high.
Description
Technical field
The invention belongs to Separation of Natural Products technical field, relate to specifically a kind of method of Salanesol purifying.
Background technology
Salanesol is four sesquiterpene alcoholses, and mainly the form with free state and chemical combination state exists in tobacco leaf, and the Salanesol of chemical combination state is mainly the form of fatty acid ester.Salanesol is important medicine, industrial chemicals, there is stronger antibiont activity and antibacterial and anti-inflammation functions, be the intermediate of the newtype drugs such as synthetic prevention and cure of cardiovascular disease, anticancer, antiulcer agent, can be used for synthesizing coenzyme Q 10, multiprenylmenaquinone, anticancer synergist SDB etc.
Complicated component in Salanesol crude product, had both contained free state and chemical combination state Salanesol, and chemical combination state Salanesol wherein need change into free state through saponification; Also contain the impurity such as the waxs such as straight or branched fatty compounds, lipid acid and pigment, wax and Salanesol are very close on solvability, molecular weight, adopt the methods such as general repeatedly extraction, chromatography, recrystallization to be difficult to separated with Salanesol, and solvent consumption is large, product yield is low.
Summary of the invention
The above-mentioned defect existing for solving prior art, the object of this invention is to provide and a kind ofly from Salanesol content, be about the method for purified solanesol 15% crude extract, to improve Salanesol product purity and productive rate, simplifies technique, reduces costs.
For achieving the above object, the technical solution used in the present invention: the method for this urea adduct method purified solanesol, is characterized in that operating in the steps below:
Salanesol crude product is joined in a certain amount of ethanol, and through stirring and dissolving, filtration, the pretreatment process of two-phase saponification, extraction, concentrated, crystallization, obtains Salanesol coarse crystal; By Salanesol coarse crystal, urea and stirring solvent heating for dissolving, low temperature inclusion; Separated inclusion compound, collects filtrate, and with petroleum ether extraction filtrate, inspissated oil ether phase, crystallization in ethanol, filtration, obtain product.
Described low temperature inclusion number of times is three times, is specially urea clathration condition and is: urea is 1-2 times of Salanesol coarse crystal, and 99% ethanol is 4-9 times (v/w) of Salanesol coarse crystal; Urea, Salanesol coarse crystallization are mixed with ethanol, and at 70-90 ℃ of return stirring 30-40min, mixed solution is cooling, and at 10-15 ℃, inclusion is 6 hours.
Described three low temperature inclusions, wherein inclusion for the first time: amount of urea is the 1-2 doubly (w/w) of Salanesol coarse crystal, 99% ethanol consumption is the 4-9 doubly (v/w) of Salanesol coarse crystal; Urea is dissolved in ethanol at 80 ℃ of abundant return stirrings, adds Salanesol coarse crystal, at 80 ℃ of return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours; Inclusion for the second time: inclusion compound is filtered, and collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, in filtrate and urea, be about 4:1 (v/w) ratio and add urea in amalgamation liquid, at 80 ℃ of abundant return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours; Inclusion for the third time: inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, in filtrate and urea, be about 5:1 (v/w) ratio again and add urea in amalgamation liquid, at 80 ℃ of abundant return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours.
Described pretreatment process is specially: by Salanesol dissolving crude product, in 99% ethanol of 9-12 times of volume (v/w), ultrasonic dissolution, by solution filter; By the 6-8%(w/w of Salanesol crude product weight) in filtrate, add potassium hydroxide, stirring and dissolving; The sherwood oil that adds again the 0.5-0.7 times of volume (v/v) of ethanol, is uniformly mixed, and saponification 2-3 hour refluxes at 55-65 ℃; After saponification mixture is cooling, by 0.5 times of volume (v/v) of ethanol consumption, add water, stratification, phase in collection; Separately get phase under the isopyknic petroleum ether extraction of ethanol consumption, extract and the upper merging mutually separating, be washed to neutrality, and vacuum concentration obtains Salanesol crude extract; Salanesol crude extract is dissolved in 98% ethanol of 8-10 times of volume (v/w), at 5-10 ℃, crystallization is 3 hours, filters, and obtains Salanesol coarse crystal.
Described inclusion compound separation method is: inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, and after amalgamation liquid vacuum concentration to 1/2 volume, add equal-volume water, with the isopyknic petroleum ether extraction of filtrate 2 times, merge sherwood oil phase, washing, vacuum concentration obtains product after inclusion; After inclusion, in product, add in 90% ethanol of 8-10 times of volume (v/w), at 5-10 ℃, crystallization is 3 hours, filters, and obtains product.
The present invention adopts a certain amount of Salanesol crude product is obtained saponified after dissolving, filtration, two-phase saponification, extracting and separating, saponifiable content reaches 30-40%, by saponified concentrated, dissolving, crystallization, three urea clathrations of crystallisate, urea clathration is removed wax, lipid acid, the crystallization that urea forms in organic solvent is six prismatic tubbiness crystal, can wrap in wherein by not double bond containing saturated fatty acid and containing low unsaturated fatty acids and other hydrocarbon polymer of one, two two keys, thereby remove these materials.Purity through three urea clathration Salanesols reaches more than 90%, and yield reaches 70% left and right.The method compares with chromatography that technological process is simple, equipment requirements is low, higher than product recovery rate with crystallization phases.
The present invention has the following advantages:
1, first by urea clathration application of principle in Salanesol purifying process.
The advantages such as 2, compare with repeatedly extraction process, recrystallization method, it is high that urea adduct method has impurity removal percentage, and product loss is few.
3, compare with column chromatography, urea adduct method has that technique is simple, solvent consumption is little, low cost and other advantages.
Accompanying drawing explanation
Fig. 1 process flow diagram of the present invention.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but it is not limitation of the invention.
embodiment 1:
The method of this urea adduct method purified solanesol, is characterized in that operating in the steps below:
By Salanesol dissolving crude product, in 99% ethanol of 9-12 times of volume (v/w), ultrasonic dissolution, by solution filter.By the 6-8%(w/w of Salanesol crude product weight) in filtrate, add potassium hydroxide, stirring and dissolving; The sherwood oil that adds again the 0.5-0.7 times of volume (v/v) of ethanol, is uniformly mixed, and saponification 2-3 hour refluxes at 55-65 ℃.After saponification mixture is cooling, by 0.5 times of volume (v/v) of ethanol consumption, add water, stratification, phase in collection; Separately get phase under the isopyknic petroleum ether extraction of ethanol consumption,
extract and the upper phase separatingmerge, be washed to neutrality, vacuum concentration obtains Salanesol crude extract.Salanesol crude extract is dissolved in 98% ethanol of 8-10 times of volume (v/w), at 5-10 ℃, crystallization is 3 hours, filters, and obtains Salanesol coarse crystal.Amount of urea is 1-2 times (w/w) of Salanesol coarse crystal, 99% ethanol consumption is 4-9 times (v/w) of Salanesol coarse crystal, urea is dissolved in ethanol at 80 ℃ of abundant return stirrings, add Salanesol coarse crystal, at 80 ℃ of return stirring 30min, then mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours.Inclusion compound is filtered, and collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, and be about 4:1 (v/w) ratio and add urea in amalgamation liquid, at 80 ℃ of abundant return stirring 30min in filtrate and urea, then mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours.Inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, then in filtrate and urea, are about 5:1 (v/w) ratio add urea in amalgamation liquid, at 80 ℃ of abundant return stirring 30min, then mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours.Inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, after amalgamation liquid vacuum concentration to 1/2 volume, add equal-volume water, with the isopyknic petroleum ether extraction of filtrate 2 times, merge sherwood oil phase, washing, vacuum concentration obtains product after inclusion.After inclusion, in product, add in 90% ethanol of 8-10 times of volume (v/w), at 5-10 ℃, crystallization is 3 hours, filters, and obtains product, and the purity of Salanesol reaches more than 90%, and yield reaches 70% left and right.
embodiment 2:
The method of this urea adduct method purified solanesol, is characterized in that operating in the steps below: get the Salanesol crude product 20g of Salanesol total content 15%, be placed in beaker, add 160ml ethanol, ultrasonic dissolution, filtration.To filtrate, add 1.5g potassium hydroxide, stirring and dissolving, is transferred in there-necked flask, then adds 100ml sherwood oil, stirring and refluxing 2.5h at 60 ℃.Saponification liquor is cooling, be transferred in separating funnel, add 80ml water, standing phase-splitting, phase in collection, use again phase under 160ml petroleum ether extraction once, by extract and upper merging mutually, to be washed to nearly neutrality, with anhydrous sodium sulfate dehydration, vacuum concentration, to paste, reclaims sherwood oil, the thick cream 8g of final Salanesol.The thick cream of Salanesol is added in 98% ethanol of 8 times (v/w), stirring and dissolving, be placed at 10 ℃ crystallization 3 hours, filter to obtain Salanesol coarse crystal 6.2g, by Salanesol coarse crystal: urea: ethanol=1:1:4(w/w/v), by urea at 80 ℃ stirring and dissolving in 25 ml ethanol, again Salanesol coarse crystal is dissolved in ethanol, at 80 ℃ of stirring and refluxing 30min, mixture is transferred in beaker, cooling after as for 15 ℃ of inclusion 6h.
take outfilter inclusion mixture, with 10ml washing with alcohol urea crystal, washing lotion and filtrate merge, and press
amount of filtrate1/4 (v/w) ratio add urea, for the second time at 80 ℃ of stirring and refluxing 30min, cooling after as for 15 ℃ of inclusion 6h.
take outfilter inclusion mixture, with 100ml washing with alcohol urea crystal, washing lotion and filtrate merge, and press
filtrateamount 1/5 add urea, for the third time at 80 ℃ of stirring and refluxing 30min, cooling after as for inclusion 6h at 15 ℃.
take outfilter inclusion mixture, with 10ml washing with alcohol urea crystal, washing lotion and filtrate merge, will
amalgamation liquidbe concentrated into half volume, add isopyknic water, use 100ml petroleum ether extraction 2 times, merge sherwood oil phase, washing, vacuum concentration, to paste, reclaims sherwood oil.Paste is dissolved in 8 times of volumes (v/w), 90% ethanol, and at 5-10 ℃, crystallization is 3 hours, filters, and obtains product, final Salanesol 2.4g, the product purity 93% of obtaining.The rate of recovery 74.4%.
Claims (1)
1. the method for a urea adduct method purified solanesol, it is characterized in that operating in the steps below: Salanesol crude product is joined in a certain amount of ethanol, through stirring and dissolving, filtration, the pretreatment process of two-phase saponification, extraction, concentrated, crystallization, obtains Salanesol coarse crystal; By Salanesol coarse crystal, urea and stirring solvent heating for dissolving, low temperature inclusion; Separated inclusion compound, collects filtrate, and with petroleum ether extraction filtrate, inspissated oil ether phase, crystallization in ethanol, filtration, obtain product;
Described low temperature inclusion number of times is three times, is specially urea clathration condition and is: urea is 1-2 times of Salanesol coarse crystal, and 99% ethanol volumetric usage is 4-9 times of Salanesol coarse crystal weight; Urea, Salanesol coarse crystallization are mixed with ethanol, and at 70-90 ℃ of return stirring 30-40min, mixed solution is cooling, and at 10-15 ℃, inclusion is 6 hours;
Described three low temperature inclusions, wherein inclusion for the first time: amount of urea be Salanesol coarse crystal weight 1-2 doubly, 99% ethanol volumetric usage be Salanesol coarse crystal weight 4-9 doubly; Urea is dissolved in ethanol at 80 ℃ of abundant return stirrings, adds Salanesol coarse crystal, at 80 ℃ of return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours; Inclusion for the second time: inclusion compound is filtered, and collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, by filtrate volume consumption and weight of urea usage ratio, be that 4:1 adds urea in amalgamation liquid, at 80 ℃ of abundant return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours; Inclusion for the third time: inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, in filtrate volume consumption and weight of urea consumption, be that 5:1 ratio adds urea in amalgamation liquid again, at 80 ℃ of abundant return stirring 30min, then that mixed solution is cooling, at 10-15 ℃, inclusion is 6 hours;
Described pretreatment process is specially: by Salanesol dissolving crude product, in 99% ethanol of 9-12 times of volume of its weight, ultrasonic dissolution, by solution filter; 6-8% by Salanesol crude product weight adds potassium hydroxide, stirring and dissolving in filtrate; The sherwood oil that adds again 0.5-0.7 times of volume of ethanol, is uniformly mixed, and saponification 2-3 hour refluxes at 55-65 ℃; After saponification mixture is cooling, by 0.5 times of volume of ethanol consumption, add water, stratification, phase in collection; Separately get phase under the isopyknic petroleum ether extraction of ethanol consumption, extract and the upper merging mutually separating, be washed to neutrality, and vacuum concentration obtains Salanesol crude extract; Salanesol crude extract is dissolved in 98% ethanol of 8-10 times of volume of its weight, at 5-10 ℃, crystallization is 3 hours, filters, and obtains Salanesol coarse crystal;
Described inclusion compound separation method is: inclusion compound is filtered, collect filtrate, with a small amount of washing with alcohol urea crystals, washing lotion and filtrate merge, and after amalgamation liquid vacuum concentration to 1/2 volume, add equal-volume water, with the isopyknic petroleum ether extraction of filtrate 2 times, merge sherwood oil phase, washing, vacuum concentration obtains product after inclusion; After inclusion, in product, add in 90% ethanol of 8-10 times of volume of its weight, at 5-10 ℃, crystallization is 3 hours, filters, and obtains product.
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| CN201110389902.5A CN102408311B (en) | 2011-11-30 | 2011-11-30 | Method for purifying solanesol through urea adduction fractionation |
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| CN201110389902.5A CN102408311B (en) | 2011-11-30 | 2011-11-30 | Method for purifying solanesol through urea adduction fractionation |
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| CN102408311B true CN102408311B (en) | 2014-04-09 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1821196A (en) * | 2006-02-13 | 2006-08-23 | 李祥庆 | Method for extracting high purity solanesol from low content solanesol extract |
| JP2006219438A (en) * | 2005-02-14 | 2006-08-24 | Hiroyuki Yamane | Method for collecting solanesol |
| CN101182284A (en) * | 2007-12-21 | 2008-05-21 | 中国科学院山西煤炭化学研究所 | Method for extracting high-purity solanesol from potato leaf, tobacco leaf and/or tobacco stem |
| CN101497557A (en) * | 2009-03-23 | 2009-08-05 | 西北师范大学 | Method for extracting purified solanesol from potato leaf |
| CN101973848A (en) * | 2010-09-20 | 2011-02-16 | 中国科学院山西煤炭化学研究所 | Method for separating and purifying solanesol by urea column chromatography |
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2011
- 2011-11-30 CN CN201110389902.5A patent/CN102408311B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006219438A (en) * | 2005-02-14 | 2006-08-24 | Hiroyuki Yamane | Method for collecting solanesol |
| CN1821196A (en) * | 2006-02-13 | 2006-08-23 | 李祥庆 | Method for extracting high purity solanesol from low content solanesol extract |
| CN101182284A (en) * | 2007-12-21 | 2008-05-21 | 中国科学院山西煤炭化学研究所 | Method for extracting high-purity solanesol from potato leaf, tobacco leaf and/or tobacco stem |
| CN101497557A (en) * | 2009-03-23 | 2009-08-05 | 西北师范大学 | Method for extracting purified solanesol from potato leaf |
| CN101973848A (en) * | 2010-09-20 | 2011-02-16 | 中国科学院山西煤炭化学研究所 | Method for separating and purifying solanesol by urea column chromatography |
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| 郑立辉.尿素包合法制取低熔点石蜡的研究.《精细石油化工》.2002,(第6期),第11-13页. |
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