CN103342628A - Method for simultaneously extracting and separating solanesol and nicotine from tobacco - Google Patents
Method for simultaneously extracting and separating solanesol and nicotine from tobacco Download PDFInfo
- Publication number
- CN103342628A CN103342628A CN2013103180779A CN201310318077A CN103342628A CN 103342628 A CN103342628 A CN 103342628A CN 2013103180779 A CN2013103180779 A CN 2013103180779A CN 201310318077 A CN201310318077 A CN 201310318077A CN 103342628 A CN103342628 A CN 103342628A
- Authority
- CN
- China
- Prior art keywords
- nicotine
- buddhist nun
- eggplant buddhist
- extraction
- tobacco
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims abstract description 61
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 229960002715 nicotine Drugs 0.000 title claims abstract description 59
- 241000208125 Nicotiana Species 0.000 title claims abstract description 45
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 23
- 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 abstract description 6
- 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 abstract description 6
- 238000000605 extraction Methods 0.000 claims abstract description 39
- 239000007788 liquid Substances 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 78
- 244000061458 Solanum melongena Species 0.000 claims description 65
- 235000002597 Solanum melongena Nutrition 0.000 claims description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 53
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- 238000000926 separation method Methods 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000012043 crude product Substances 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 15
- 238000000746 purification Methods 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 238000002137 ultrasound extraction Methods 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 239000000469 ethanolic extract Substances 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000001291 vacuum drying Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 claims description 5
- 229960001866 silicon dioxide Drugs 0.000 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010298 pulverizing process Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 8
- 238000013094 purity test Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000017471 coenzyme Q10 Nutrition 0.000 description 3
- 229940110767 coenzyme Q10 Drugs 0.000 description 3
- 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 3
- 238000004451 qualitative analysis Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 230000005477 standard model Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 208000006770 Ascorbic Acid Deficiency Diseases 0.000 description 1
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940074393 chlorogenic acid Drugs 0.000 description 1
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 1
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 1
- 235000001368 chlorogenic acid Nutrition 0.000 description 1
- 230000002279 cholagogic effect Effects 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 208000010233 scurvy Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
Landscapes
- Extraction Or Liquid Replacement (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a method for simultaneously extracting and separating solanesol and nicotine from a tobacco. The method comprises the following steps of: (1) extracting the solanesol and the nicotine at the same time; (2) extracting and separating; (3) separating and purifying the solanesol; (4) separating and purifying the nicotine. Because the nicotine is separated and extracted and the solanesol is saponified and extracted at the same time, the extraction steps are simplified greatly, and the consumption of time and solvents is saved. Compared with the prior art, the method disclosed by the invention is efficient, ensures that more products are extracted and less waste liquid is discharged, is simple in step and is an environmentally-friendly production technology.
Description
Technical field
The present invention relates to tobacco deep process technology field, specifically refer to a kind of from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously.
Background technology
Tobacco is important cash crop, belongs to Solanaceae annual herb plant, and single leaf alternate originates in South America, and 16 middle of century tobaccos are imported China into.China is the country of tobacco production and consumption amount maximum in the world, accounts for more than 1/3rd of global total amount.Smoking is harmful to your health has become final conclusion, and along with the rise of world's Tobacco Control campaign, the purposes of tobacco aspect cigarette also will greatly weaken.Yet as a kind of natural plant resource of high yield, the wholesome potential use of tobacco is also very extensive.Except containing protein, carbohydrate, also contain important pharmaceutical use compositions such as eggplant Buddhist nun alcohol, nicotine in the tobacco, its exploitation prospect is wide.Eggplant Buddhist nun alcohol is the higher effective medicinal components of a kind of added value, has pharmacological actions such as antibiotic, anti-inflammatory and hemostasis, also is the necessary raw material of synthesise vitamins K2 and Coenzyme Q10 99.0 simultaneously.Coenzyme Q10 99.0 is having unique curative effect aspect the treatment cardiovascular disorder, aspect treatment vitamin C deficiency, duodenal ulcer and stomach ulcer, gangrenosum acne periodontitis, the viral hepatitis significant curative effect is being arranged, and is finding more that recently it has significant auxiliary curative effect to acquired immune deficiency syndrome (AIDS).Therefore as Coenzyme Q10 99.0 must synthesis material extraction, the purifying of eggplant Buddhist nun alcohol also more and more cause people's attention.Nicotine is a kind of alkaloid in the tobacco leaf, and is colourless, tasteless, and normal temperature is liquid, can be miscible arbitrarily with water when being lower than 60 ℃, very easily be dissolved in organic solvents such as alcohol, ether, chloroform, sherwood oil.Natural nicotine is used very extensive, and its purposes mainly comprises agricultural chemicals and medical two broad aspect.Nicotine series pesticide platymiscium sterilant, have steam smoke, the characteristics of stomach toxicity, the function of tagging and the noresidue of degrading rapidly, being widely used as the sterilant of farm crop such as grain, oil plant, vegetables, fruit, herbage, is desirable efficient green sterilant and biological agricultural chemicals.In addition, high purity nicotine is to develop the extraordinary raw material of the medicine of illness such as treatment is cardiovascular, skin, snake bite and insect sting on the medicine industry.Chlorogenic acid is a kind of important biological material, have antibiotic, antiviral, increase effects such as white cell, hepatic cholagogic, antitumor, hypotensive, reducing blood-fat, removing free radical and stimulating central nervous system system.
Have some documents and patent report at present effective constituent in the tobacco has been carried out the research of extraction and application, disclose the method for from the low order tobacco, extracting eggplant Buddhist nun alcohol such as patent CN1087076; Patent CN1810747 discloses a kind of method of solanesol extracting and preparing; Patent CN1064680 discloses a kind of production technique of nicotine products; Patent CN101050212A discloses a kind of method of extracting high pure natural nicotine and eggplant Buddhist nun alcohol from abandoned tobacco simultaneously; Document (Anhui agricultural sciences 2008,36(35): 15287-15288) reported eggplant Buddhist nun ethanol-extracted Study on Conditions in the abandoned tobacco; Document (University of Fuzhou's journal 2008,36(2): 308-312) reported the extraction and purification research of nicotine and eggplant Buddhist nun alcohol in the inferior tobacco.These disclosed patents and document or to extract kind single, as can only obtaining eggplant Buddhist nun alcohol or nicotine, or complex steps, must could all extract the pure and mild nicotine of eggplant Buddhist nun in two steps, and length consuming time, separation efficiency is low, and product purity is low, and the waste water generation is big.
Summary of the invention
The purpose of this invention is to provide a kind of from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously, it be a kind of usefulness by easy in the step extraction can be with tobacco two kinds of products of the pure and mild nicotine of (free state and combined) eggplant Buddhist nun extract then the method for in addition separation and purification simultaneously.
For achieving the above object, provided by the invention from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously, it comprises the steps:
(1) extract the pure and mild nicotine of eggplant Buddhist nun the time: tobacco material adds circulating ultrasonic extraction device after pulverizing through oven dry, adds the ethanolic soln of the alkali of 10～15 times of tobacco material quality then, and supersound extraction obtains ethanol extract;
(2) extracting and separating: ultrasonic extraction finishes, filter ethanol extract and remove the filtrate that the tobacco filter residue obtains containing ethanol, again filtrate being regulated pH by hydrochloric acid soln is 2～4, and the ethanol removed in the filtrate of vacuum concentration gets eggplant Buddhist nun alcohol nicotine crude mixture then; Eggplant Buddhist nun alcohol nicotine crude mixture is carried out liquid liquid two-phase extraction with sherwood oil/water or normal hexane/water separates, the petroleum ether layer that extracting and separating obtains or normal hexane layer enriched product are crude product eggplant Buddhist nun alcohol, and the water layer enriched product that extracting and separating obtains is crude product nicotine;
(3) separation and purification of eggplant Buddhist nun alcohol: after the crude product eggplant Buddhist nun alcohol that extracting and separating is obtained is concentrated in vacuo to 5～10mL, be that the eluent of sherwood oil: ethyl acetate=9:1 carries out wash-out with volume ratio; The elutriant that eggplant Buddhist nun determining alcohol is high merges, concentrates, and adds the alcohol crystal solvent again and carries out crystallization and filtration, and the crystal vacuum-drying that obtains namely gets refining eggplant Buddhist nun alcohol;
(4) separation and purification of nicotine: after the crude product nicotine of extracting and separating is concentrated in vacuo to 100～150mL, adds alkali lye and regulate pH value to 9～11, carry out wet distillation then; Be concentrated in vacuo to 1/4～1/5 of original volume with slipping out liquid, add alkali lye and regulate pH value to 9～11, what obtain concentrating slips out liquid, with slipping out the isopyknic chloroform extraction of liquid twice with concentrated, merge the extraction liquid behind this twice chloroform extraction and use anhydrous sodium sulfate drying, chloroform is removed in last underpressure distillation, namely gets high purity nicotine.
As a kind of preferred version, tobacco material is 20 orders after pulverizing through oven dry in the described step (1); The NaOH of 0.1～0.2mol/L of 10～15 times of tobacco material quality of adding or the ethanolic soln of KOH, supersound extraction under the condition of 50～60 ℃ of temperature obtains ethanol extract; The ultrasonic power of described circulating ultrasonic extraction device is 100～300W, and the supersound extraction time is 30～60min.
As another preferred version, evenly be added drop-wise to 100～200 orders behind the crude product eggplant Buddhist nun alcohol vacuum concentration in the described step (3) and carry out wash-out on the silicagel column again, the Tc that described adding alcohol crystal solvent carries out crystallization is-15 ℃, and filtering the vacuum drying temperature of crystal that obtains is 20 ℃.
As another preferred version, add alkali lye in the described step (4) and regulate pH value to 11 for NaOH solution, receive liquid pH less than 3 with diluted acid absorption condensation liquid and control when carrying out wet distillation, stop distillation when liquid produces with 1% silicotungstic acid detection sediment-free when slipping out.
The invention has the advantages that: method of the present invention being dissociated and extracting nicotine, and the saponification of eggplant Buddhist nun alcohol and the extraction all carry out simultaneously, simplified extraction step greatly, saved time and solvent consumption.This method is more efficient than prior art, and it is many to extract product, and step is few, and the discharging of waste liquid amount is few, is a kind of green production technology that is conducive to environment protection.
Description of drawings
Fig. 1 is process flow sheet of the present invention.
Fig. 2 is the high-efficient liquid phase chromatogram of eggplant Buddhist nun alcohol standard model of the present invention.
Fig. 3 prepares the high-efficient liquid phase chromatogram of sample for the present invention.
Fig. 4 is the high-efficient liquid phase chromatogram of nicotine standard model of the present invention.
Fig. 5 prepares the high-efficient liquid phase chromatogram of sample for the present invention.
Embodiment
Below in conjunction with accompanying drawing the specific embodiment of the present invention is described in further detail.
Utilize the purity of high effective liquid chromatography for measuring polishing eggplant Buddhist nun's alcohol and nicotine in the embodiment of the invention, condition determination is as follows:
The high performance liquid chromatography test parameter of eggplant Buddhist nun alcohol:
Chromatographic column: C18 reversed-phase column (250 mm x, 4.6 mm, 5 μ m)
Moving phase: Virahol: acetonitrile=50%:50% (volume ratio)
Flow velocity: 1mL/min
Ultraviolet detection wavelength: 210nm
Column temperature: 25 ℃
Sample size: 10 μ L
The high performance liquid chromatography test parameter of nicotine:
Chromatographic column: C18 reversed-phase column (250 mm x, 4.6 mm, 5 μ m)
Moving phase: methyl alcohol: phosphate buffer solution=60%:40% (volume ratio)
The phosphate buffer solution preparation: the 2.420g Sodium phosphate dibasic, 3.5mL phosphoric acid and 6.5mL triethylamine add water and are settled to 1000mL.
Flow velocity: 1mL/mim
Ultraviolet detection wavelength: 259nm
Column temperature: 30 ℃
Sample size: 10 μ L
Embodiment one:
(1) extracts the pure and mild nicotine of eggplant Buddhist nun the time: after the 50g tobacco material is pulverized (about 20 orders) through oven dry, add circulating ultrasonic extraction device, the NaOH ethanolic soln that adds 500g 0.1mol/L then, at ultrasonic power 100W, ultrasonic circulating is extracted 30min under the condition that temperature is 50 ℃.
(2) extracting and separating: ultrasonic extraction finishes, and emits ethanol extract, and removes by filter the tobacco filter residue, and it is 2 that filtrate is regulated pH by hydrochloric acid soln, and vacuum concentration is removed ethanol and got eggplant Buddhist nun alcohol nicotine crude mixture then.Crude mixture is carried out liquid liquid two-phase extraction with 300mL sherwood oil/300mL water separates.The petroleum ether layer enriched product is crude product eggplant Buddhist nun alcohol, and the water layer enriched product is crude product nicotine.
(3) separation and purification of eggplant Buddhist nun alcohol: after the sherwood oil of extracting and separating is concentrated in vacuo to 5mL mutually, evenly be added drop-wise on (100-200 order) silicagel column, with (sherwood oil: ethyl acetate=9:1) eluent carries out wash-out.And eggplant Buddhist nun alcohol content in the elutriant of collecting by each different time sections of thin layer chromatography (TLC) qualitative analysis, the part that mainly contains eggplant Buddhist nun alcohol is merged, concentrate, add (ethanol) recrystallisation solvent then,-15 ℃ of following crystallizations, the crystal that filtration obtains namely gets refining eggplant Buddhist nun alcohol 0.38g at room temperature vacuum-drying (20 ℃), purity testing is 91%, yield 70%.
(4) separation and purification of nicotine: after the water of extracting and separating is concentrated in vacuo to 100mL, adds NaOH and regulate pH value to 9, carry out wet distillation then.Receive liquid pH less than 3 with diluted acid absorption condensation liquid and control all the time, stop distillation when liquid detects the sediment-free generation with 1% silicotungstic acid when slipping out.To slip out liquid then and be concentrated in vacuo to 25mL, and add NaOH and regulate pH value to 9, use twice of chloroform extraction, each 25mL, combined chloroform is also used anhydrous sodium sulfate drying, and last underpressure distillation is removed chloroform and is namely got high purity nicotine 1.62g, purity testing is 98%, yield 80%.
Embodiment two:
(1) extracts the pure and mild nicotine of eggplant Buddhist nun the time: after the 100g tobacco material is pulverized (about 20 orders) through oven dry, add circulating ultrasonic extraction device, the NaOH ethanolic soln that adds 1200g 0.1mol/L then, at ultrasonic power 200W, ultrasonic circulating is extracted 50min under the condition that temperature is 60 ℃.
(2) extracting and separating: ultrasonic extraction finishes, and emits ethanol extract, and removes by filter the tobacco filter residue, and it is 3 that filtrate is regulated pH by hydrochloric acid soln, and vacuum concentration is removed ethanol and got eggplant Buddhist nun alcohol nicotine crude mixture then.Crude mixture is carried out liquid liquid two-phase extraction with 500mL sherwood oil/500mL water separates.The petroleum ether layer enriched product is crude product eggplant Buddhist nun alcohol, and the water layer enriched product is crude product nicotine.
(3) separation and purification of eggplant Buddhist nun alcohol: the sherwood oil of extracting and separating is concentrated in vacuo to 8mL mutually, evenly is added drop-wise on (100-200 order) silicagel column, with (sherwood oil: ethyl acetate=9:1) eluent carries out wash-out.And eggplant Buddhist nun alcohol content in the elutriant of collecting by each different time sections of thin layer chromatography (TLC) qualitative analysis, the part that mainly contains eggplant Buddhist nun alcohol is merged, concentrate, add (ethanol) recrystallisation solvent then,-15 ℃ of following crystallizations, the crystal that filtration obtains namely gets refining eggplant Buddhist nun alcohol 0.82g at room temperature vacuum-drying (20 ℃), purity testing is 92%, yield 78%.
(4) separation and purification of nicotine: the water of extracting and separating is concentrated in vacuo to 150mL, adds NaOH and regulate pH value to 10, carry out wet distillation then.Receive liquid pH less than 3 with diluted acid absorption condensation liquid and control all the time, stop distillation when liquid detects the sediment-free generation with 1% silicotungstic acid when slipping out.To slip out liquid then and be concentrated in vacuo to 30mL, and add NaOH and regulate pH value to 10, use twice of chloroform extraction, each 30mL, combined chloroform is also used anhydrous sodium sulfate drying, and last underpressure distillation is removed chloroform and is namely got high purity nicotine 1.70g, purity testing is 98%, yield 84%.
Embodiment three:
(1) extracts the pure and mild nicotine of eggplant Buddhist nun the time: after the 100g tobacco material is pulverized (about 20 orders) through oven dry, add circulating ultrasonic extraction device, the NaOH ethanolic soln that adds 1500g 0.1mol/L then, at ultrasonic power 300W, ultrasonic circulating is extracted 60min under the condition that temperature is 60 ℃.
(2) extracting and separating: ultrasonic extraction finishes, and emits ethanol extract, and removes by filter the tobacco filter residue, and it is 4 that filtrate is regulated pH by hydrochloric acid soln, and vacuum concentration is removed ethanol and got eggplant Buddhist nun alcohol nicotine crude mixture then.Crude mixture is carried out liquid liquid two-phase extraction with 500mL sherwood oil/500mL water separates.The petroleum ether layer enriched product is crude product eggplant Buddhist nun alcohol, and the water layer enriched product is crude product nicotine.
(3) separation and purification of eggplant Buddhist nun alcohol: the sherwood oil of extracting and separating is concentrated in vacuo to 10mL mutually, evenly is added drop-wise on (100-200 order) silicagel column, with (sherwood oil: ethyl acetate=9:1) eluent carries out wash-out.And eggplant Buddhist nun alcohol content in the elutriant of collecting by each different time sections of thin layer chromatography (TLC) qualitative analysis, the part that mainly contains eggplant Buddhist nun alcohol is merged, concentrate, add (ethanol) recrystallisation solvent then,-15 ℃ of following crystallizations, the crystal that filtration obtains namely gets refining eggplant Buddhist nun alcohol 0.87g at room temperature vacuum-drying (20 ℃), purity testing is 91%, yield 80%.
(4) separation and purification of nicotine: the water of extracting and separating is concentrated in vacuo to 150mL, adds NaOH and regulate pH value to 11, carry out wet distillation then.Receive liquid pH less than 3 with diluted acid absorption condensation liquid and control all the time, stop distillation when liquid detects the sediment-free generation with 1% silicotungstic acid when slipping out.To slip out liquid then and be concentrated in vacuo to 30mL, and add NaOH and regulate pH value to 11, use twice of chloroform extraction, each 30mL, combined chloroform is also used anhydrous sodium sulfate drying, and last underpressure distillation is removed chloroform and is namely got high purity nicotine 1.72g, purity testing is 98%, yield 85%.
The present invention is to be raw material with tobacco leaf (fragment), by the easy auxiliary alkaline extraction using alcohol of a step ultrasonic wave, two kinds of products of the pure and mild nicotine of eggplant Buddhist nun in the tobacco are extracted then simultaneously the method for in addition separation and purification: utilize the circulating ultrasonic extractive technique to strengthen the release of active substance in the tobacco cell, diffusion and dissolving, improved the utilization ratio of ultrasonic field simultaneously to greatest extent; As extracting solvent, not only can make the nicotine salt in the tobacco leaf be dissociated into nicotine with alkaline ethanol, strengthen its solubleness in ethanol, improve the nicotine extraction yield; Simultaneously can also make the eggplant Buddhist nun alcohol (ester) of combined in extraction process, discharge more free state eggplant Buddhist nun alcohol with regard to direct generation saponification reaction, and then strengthened the extraction yield of eggplant Buddhist nun alcohol, overcome the shortcoming that also will then handle with the alkali lye saponification after extracting in the traditional technology.
Claims (4)
1. method of the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously from tobacco, it comprises the steps:
(1) extract the pure and mild nicotine of eggplant Buddhist nun the time: tobacco material adds circulating ultrasonic extraction device after pulverizing through oven dry, adds the ethanolic soln of the alkali of 10～15 times of tobacco material quality then, and supersound extraction obtains ethanol extract;
(2) extracting and separating: ultrasonic extraction finishes, filter ethanol extract and remove the filtrate that the tobacco filter residue obtains containing ethanol, again filtrate being regulated pH by hydrochloric acid soln is 2～4, and the ethanol removed in the filtrate of vacuum concentration gets eggplant Buddhist nun alcohol nicotine crude mixture then; Eggplant Buddhist nun alcohol nicotine crude mixture is carried out liquid liquid two-phase extraction with sherwood oil/water or normal hexane/water separates, the petroleum ether layer that extracting and separating obtains or normal hexane layer enriched product are crude product eggplant Buddhist nun alcohol, and the water layer enriched product that extracting and separating obtains is crude product nicotine;
(3) separation and purification of eggplant Buddhist nun alcohol: after the crude product eggplant Buddhist nun alcohol that extracting and separating is obtained is concentrated in vacuo to 5～10mL, be that the eluent of sherwood oil: ethyl acetate=9:1 carries out wash-out with volume ratio; The elutriant that eggplant Buddhist nun determining alcohol is high merges, concentrates, and adds the alcohol crystal solvent again and carries out crystallization and filtration, and the crystal vacuum-drying that obtains namely gets refining eggplant Buddhist nun alcohol;
(4) separation and purification of nicotine: after the crude product nicotine of extracting and separating is concentrated in vacuo to 100～150mL, adds alkali lye and regulate pH value to 9～11, carry out wet distillation then; Be concentrated in vacuo to 1/4～1/5 of original volume with slipping out liquid, add alkali lye and regulate pH value to 9～11, what obtain concentrating slips out liquid, with slipping out the isopyknic chloroform extraction of liquid twice with concentrated, merge the extraction liquid behind this twice chloroform extraction and use anhydrous sodium sulfate drying, chloroform is removed in last underpressure distillation, namely gets high purity nicotine.
According to claim 1 from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously, it is characterized in that: tobacco material is 20 orders after pulverizing through oven dry in the described step (1); The NaOH of 0.1～0.2mol/L of 10～15 times of tobacco material quality of adding or the ethanolic soln of KOH, supersound extraction under the condition of 50～60 ℃ of temperature obtains ethanol extract; The ultrasonic power of described circulating ultrasonic extraction device is 100～300W, and the supersound extraction time is 30～60min.
According to claim 1 from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously, it is characterized in that: evenly be added drop-wise to 100～200 orders behind the crude product eggplant Buddhist nun alcohol vacuum concentration in the described step (3) and carry out wash-out on the silicagel column again, the Tc that described adding alcohol crystal solvent carries out crystallization is-15 ℃, and filtering the vacuum drying temperature of crystal that obtains is 20 ℃.
According to claim 1 from tobacco the method for the pure and mild nicotine of extraction separation eggplant Buddhist nun simultaneously, it is characterized in that: add alkali lye in the described step (4) and regulate pH value to 11 for NaOH solution, receive liquid pH less than 3 with diluted acid absorption condensation liquid and control when carrying out wet distillation, stop distillation when liquid produces with 1% silicotungstic acid detection sediment-free when slipping out.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310318077.9A CN103342628B (en) | 2013-07-26 | 2013-07-26 | Method for simultaneously extracting and separating solanesol and nicotine from tobacco |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310318077.9A CN103342628B (en) | 2013-07-26 | 2013-07-26 | Method for simultaneously extracting and separating solanesol and nicotine from tobacco |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103342628A true CN103342628A (en) | 2013-10-09 |
| CN103342628B CN103342628B (en) | 2015-04-08 |
Family
ID=49277470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310318077.9A Active CN103342628B (en) | 2013-07-26 | 2013-07-26 | Method for simultaneously extracting and separating solanesol and nicotine from tobacco |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103342628B (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151140A (en) * | 2014-07-11 | 2014-11-19 | 武汉工程大学 | Method for comprehensively extracting multiple effective components from tobacco leaves |
| CN104326912A (en) * | 2014-07-25 | 2015-02-04 | 湖北中烟工业有限责任公司 | Separation method of effective components from tobacco |
| CN105011354A (en) * | 2015-05-06 | 2015-11-04 | 济南九州富得香料有限责任公司 | Method for supercritical CO2 extraction of upper-tobacco leaves of tobaccos, extract and application |
| CN106220386A (en) * | 2016-07-05 | 2016-12-14 | 陕西兰迪生物技术有限公司 | A kind of prevent and treat the plant insecticide of Gryllotalpa, preparation method and applications |
| CN109516972A (en) * | 2017-09-18 | 2019-03-26 | 湖南中烟工业有限责任公司 | A kind of isolation and purification method of nicotine |
| CN110903277A (en) * | 2018-09-18 | 2020-03-24 | 河南元萃生物科技有限公司 | Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation |
| CN110903168A (en) * | 2018-09-18 | 2020-03-24 | 河南元萃生物科技有限公司 | Method for subcritical extraction of solanesol in waste tobacco leaves |
| CN111035057A (en) * | 2019-11-27 | 2020-04-21 | 内蒙古昆明卷烟有限责任公司 | Method for preparing tar extract from waste cigarette butts and application of tar extract in cigarettes |
| CN111337604A (en) * | 2020-05-07 | 2020-06-26 | 贵州中烟工业有限责任公司 | Method for measuring nicotine content in tobacco product |
| CN111589181A (en) * | 2019-12-31 | 2020-08-28 | 常德市正阳生物科技股份有限公司 | Eluent |
| CN111603804A (en) * | 2019-12-31 | 2020-09-01 | 常德市正阳生物科技股份有限公司 | Eluent |
| CN113376303A (en) * | 2021-05-14 | 2021-09-10 | 河北中烟工业有限责任公司 | Nicotine optical isomer separation determination method based on two-dimensional liquid chromatography |
| CN113406231A (en) * | 2021-06-18 | 2021-09-17 | 云南民族大学 | Nicotine with low content of secondary alkaloid and application thereof |
| CN114605382A (en) * | 2020-12-04 | 2022-06-10 | 上海烟草集团有限责任公司 | Nicotine and preparation method thereof |
| CN114835679A (en) * | 2022-04-26 | 2022-08-02 | 云南信达健康科技有限公司 | Method for extracting nicotine from waste tobacco leaves |
| CN114940672A (en) * | 2022-05-27 | 2022-08-26 | 云南中烟工业有限责任公司 | Preparation method of tobacco alkaloid component |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139711A (en) * | 1976-05-17 | 1977-11-21 | Nisshin Flour Milling Co Ltd | Extraction of solanesole |
| JP2006219438A (en) * | 2005-02-14 | 2006-08-24 | Hiroyuki Yamane | Method for collecting solanesol |
| CN1944425A (en) * | 2006-08-11 | 2007-04-11 | 三明华健生物工程有限公司 | High effective simultanuous clean extraction of high purity solanesol and nicotine |
-
2013
- 2013-07-26 CN CN201310318077.9A patent/CN103342628B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139711A (en) * | 1976-05-17 | 1977-11-21 | Nisshin Flour Milling Co Ltd | Extraction of solanesole |
| JP2006219438A (en) * | 2005-02-14 | 2006-08-24 | Hiroyuki Yamane | Method for collecting solanesol |
| CN1944425A (en) * | 2006-08-11 | 2007-04-11 | 三明华健生物工程有限公司 | High effective simultanuous clean extraction of high purity solanesol and nicotine |
Non-Patent Citations (3)
| Title |
|---|
| 王幼君等: "茄尼醇和尼古丁的提取与工艺研究", 《天津化工》, vol. 17, no. 3, May 2003 (2003-05-01), pages 37 - 40 * |
| 王艳等: "烟叶中制备高纯度茄尼醇的新工艺", 《中成药》, vol. 32, no. 7, July 2010 (2010-07-01), pages 1128 - 1131 * |
| 逄敏洁: "烟草废弃物中茄尼醇等有效成分的提取分离与含量分析", 《中国优秀硕士学位论文全文数据库(电子期刊)农业科技辑》, no. 8, 15 August 2008 (2008-08-15), pages 047 - 75 * |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151140B (en) * | 2014-07-11 | 2016-01-06 | 武汉工程大学 | A kind of method of comprehensive extraction plurality of active ingredients from tobacco leaf |
| CN104151140A (en) * | 2014-07-11 | 2014-11-19 | 武汉工程大学 | Method for comprehensively extracting multiple effective components from tobacco leaves |
| CN104326912A (en) * | 2014-07-25 | 2015-02-04 | 湖北中烟工业有限责任公司 | Separation method of effective components from tobacco |
| CN105011354A (en) * | 2015-05-06 | 2015-11-04 | 济南九州富得香料有限责任公司 | Method for supercritical CO2 extraction of upper-tobacco leaves of tobaccos, extract and application |
| CN106220386A (en) * | 2016-07-05 | 2016-12-14 | 陕西兰迪生物技术有限公司 | A kind of prevent and treat the plant insecticide of Gryllotalpa, preparation method and applications |
| CN109516972B (en) * | 2017-09-18 | 2022-04-05 | 湖南中烟工业有限责任公司 | Separation and purification method of nicotine |
| CN109516972A (en) * | 2017-09-18 | 2019-03-26 | 湖南中烟工业有限责任公司 | A kind of isolation and purification method of nicotine |
| CN110903277A (en) * | 2018-09-18 | 2020-03-24 | 河南元萃生物科技有限公司 | Method for saponifying and hydrolyzing tobacco leaves by ultrasonic alkaline water and extracting nicotine by reduced pressure distillation |
| CN110903168A (en) * | 2018-09-18 | 2020-03-24 | 河南元萃生物科技有限公司 | Method for subcritical extraction of solanesol in waste tobacco leaves |
| CN110903168B (en) * | 2018-09-18 | 2024-01-26 | 河南元萃生物科技有限公司 | Method for subcritical extraction of solanesol in waste tobacco leaves |
| CN111035057A (en) * | 2019-11-27 | 2020-04-21 | 内蒙古昆明卷烟有限责任公司 | Method for preparing tar extract from waste cigarette butts and application of tar extract in cigarettes |
| CN111589181A (en) * | 2019-12-31 | 2020-08-28 | 常德市正阳生物科技股份有限公司 | Eluent |
| CN111603804A (en) * | 2019-12-31 | 2020-09-01 | 常德市正阳生物科技股份有限公司 | Eluent |
| CN111337604A (en) * | 2020-05-07 | 2020-06-26 | 贵州中烟工业有限责任公司 | Method for measuring nicotine content in tobacco product |
| CN114605382A (en) * | 2020-12-04 | 2022-06-10 | 上海烟草集团有限责任公司 | Nicotine and preparation method thereof |
| CN113376303A (en) * | 2021-05-14 | 2021-09-10 | 河北中烟工业有限责任公司 | Nicotine optical isomer separation determination method based on two-dimensional liquid chromatography |
| CN113406231A (en) * | 2021-06-18 | 2021-09-17 | 云南民族大学 | Nicotine with low content of secondary alkaloid and application thereof |
| CN113406231B (en) * | 2021-06-18 | 2023-06-09 | 云南民族大学 | Nicotine with low secondary alkaloid content and application thereof |
| CN114835679A (en) * | 2022-04-26 | 2022-08-02 | 云南信达健康科技有限公司 | Method for extracting nicotine from waste tobacco leaves |
| CN114940672A (en) * | 2022-05-27 | 2022-08-26 | 云南中烟工业有限责任公司 | Preparation method of tobacco alkaloid component |
| CN114940672B (en) * | 2022-05-27 | 2023-11-17 | 云南中烟工业有限责任公司 | Preparation method of tobacco alkaloid component |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103342628B (en) | 2015-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103342628B (en) | Method for simultaneously extracting and separating solanesol and nicotine from tobacco | |
| CN104151140B (en) | A kind of method of comprehensive extraction plurality of active ingredients from tobacco leaf | |
| CN101323648B (en) | Extraction method and and purification method of Sanghuang mushroom polysaccharide | |
| CN105963328B (en) | A method of continuously extracting Chinese torreya flavones and essential oil from Chinese torreya aril | |
| CN104326912B (en) | A kind of separation method of tobacco leaf effective constituent | |
| CN104592323B (en) | A kind of method of phloridzin in aqueous two-phase extraction pomace | |
| CN103804507A (en) | Maryland tobacco polysaccharide, extracting and purifying method and application thereof as antioxidant | |
| CN106967137A (en) | A kind of method that macroreticular resin is combined preparative liquid chromatography separating high-purity oleuropein | |
| CN100439319C (en) | Method for preparing salviol acid A | |
| CN102746355B (en) | Method for extracting and separating cordycepin | |
| CN101392000A (en) | High efficiency separation purification method of ginkgolide A, B, C, J and bilobalide monomer | |
| CN102579516A (en) | Method for separating purified seabuckthorn flavonoid from large berry seabuckthorn marc | |
| CN101530193B (en) | Method for comprehensively extracting and purifying oxidation-resistant active ingredient in sugarcane shoots or slag | |
| CN103059086A (en) | Extraction and purification method of cordycepin from cordyceps militaris solid mediums | |
| CN105294793A (en) | Separation method for naringin in aizoon stonecrop herb | |
| CN102311466A (en) | Method for extracting phenylethanoid glycoside active components from semenplantaginis | |
| CN102250174A (en) | Method for extracting jasminin from winter jasmine leaves | |
| CN103709217A (en) | Method for preparing luteoloside from radix achyranthis bidentatae vine | |
| CN103113196B (en) | Glechoma longituba phenol, and preparation method and application thereof | |
| CN101974059A (en) | Preparation of oleanolic acid structure analogues and semisynthesis method of oleanolic acid | |
| CN101450962B (en) | Method for extracting oleanolic acid from Kandelia candel leaf | |
| CN102010457A (en) | Method for preparing raddeanin A | |
| CN104610209A (en) | Industrial method for improving purity of barbaloin | |
| CN104606297A (en) | Method for extracting active ingredients in cistanche tubulosa | |
| CN103694301A (en) | Method for extracting sieboldianoside A from nigella glandulifera freyn |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |