CA2218444C - A process for the simultaneous production of artemisinin and essential oil from the plant artemisia annua - Google Patents
A process for the simultaneous production of artemisinin and essential oil from the plant artemisia annua Download PDFInfo
- Publication number
- CA2218444C CA2218444C CA002218444A CA2218444A CA2218444C CA 2218444 C CA2218444 C CA 2218444C CA 002218444 A CA002218444 A CA 002218444A CA 2218444 A CA2218444 A CA 2218444A CA 2218444 C CA2218444 C CA 2218444C
- Authority
- CA
- Canada
- Prior art keywords
- hexane
- artemisinin
- artemisinic acid
- essential oil
- acetonitrile
- 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.)
- Expired - Fee Related
Links
- 229960004191 artemisinin Drugs 0.000 title claims abstract description 72
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 title claims abstract description 71
- 229930101531 artemisinin Natural products 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000000341 volatile oil Substances 0.000 title claims abstract description 38
- 240000000011 Artemisia annua Species 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 135
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 84
- PLQMEXSCSAIXGB-SAXRGWBVSA-N (+)-artemisinic acid Chemical compound C1=C(C)CC[C@H]2[C@H](C)CC[C@@H](C(=C)C(O)=O)[C@H]21 PLQMEXSCSAIXGB-SAXRGWBVSA-N 0.000 claims abstract description 62
- LZMOBPWDHUQTKL-RWMBFGLXSA-N artemisinic acid Natural products CC1=C[C@@H]2[C@@H](CCC[C@H]2C(=C)C(=O)O)CC1 LZMOBPWDHUQTKL-RWMBFGLXSA-N 0.000 claims abstract description 31
- PLQMEXSCSAIXGB-UHFFFAOYSA-N artemisininic acid Natural products C1=C(C)CCC2C(C)CCC(C(=C)C(O)=O)C21 PLQMEXSCSAIXGB-UHFFFAOYSA-N 0.000 claims abstract description 31
- 241000196324 Embryophyta Species 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 21
- JYGAZEJXUVDYHI-DGTMBMJNSA-N dihydroartemisinic acid Chemical compound C1CC(C)=C[C@@H]2[C@H]([C@@H](C)C(O)=O)CC[C@@H](C)[C@@H]21 JYGAZEJXUVDYHI-DGTMBMJNSA-N 0.000 claims abstract description 20
- 238000000638 solvent extraction Methods 0.000 claims abstract description 19
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002035 hexane extract Substances 0.000 claims abstract description 11
- JYGAZEJXUVDYHI-UHFFFAOYSA-N dihydroartemisininic acid Natural products C1CC(C)=CC2C(C(C)C(O)=O)CCC(C)C21 JYGAZEJXUVDYHI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000005194 fractionation Methods 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 239000000741 silica gel Substances 0.000 claims description 14
- 229910002027 silica gel Inorganic materials 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 230000008020 evaporation Effects 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 239000003463 adsorbent Substances 0.000 claims description 7
- 238000007539 photo-oxidation reaction Methods 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 4
- 238000011210 chromatographic step Methods 0.000 claims description 4
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 4
- 235000001405 Artemisia annua Nutrition 0.000 claims description 3
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims 1
- 229910052906 cristobalite Inorganic materials 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 229910052682 stishovite Inorganic materials 0.000 claims 1
- 229910052905 tridymite Inorganic materials 0.000 claims 1
- 230000009977 dual effect Effects 0.000 abstract description 2
- 239000006260 foam Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 31
- 239000002253 acid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QWQSMEDUZQDVLA-KPHNHPKPSA-N arteannuin b Chemical compound C([C@@]1(C)O[C@H]11)C[C@H]2[C@H](C)CC[C@@H]3[C@@]12OC(=O)C3=C QWQSMEDUZQDVLA-KPHNHPKPSA-N 0.000 description 3
- DMAQAYJMMDODRC-UHFFFAOYSA-N arteannuin-B Natural products CC1CCC2C(=C)COC23C1CCC4(C)OC34 DMAQAYJMMDODRC-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000061 acid fraction Substances 0.000 description 2
- 239000003430 antimalarial agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229930004725 sesquiterpene Natural products 0.000 description 2
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000000222 aromatherapy Methods 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229930009674 sesquiterpene lactone Natural products 0.000 description 1
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
- A61K36/282—Artemisia, e.g. wormwood or sagebrush
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/022—Refining
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/025—Recovery by solvent extraction
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN652DE1997 IN188174B (en]) | 1997-03-17 | 1997-03-17 | |
| IN652/DEL/97 | 1997-03-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2218444A1 CA2218444A1 (en) | 1998-09-17 |
| CA2218444C true CA2218444C (en) | 2006-09-26 |
Family
ID=11090697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002218444A Expired - Fee Related CA2218444C (en) | 1997-03-17 | 1997-10-16 | A process for the simultaneous production of artemisinin and essential oil from the plant artemisia annua |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5955084A (en]) |
| AU (1) | AU728188C (en]) |
| CA (1) | CA2218444C (en]) |
| IN (1) | IN188174B (en]) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN191696B (en]) | 1999-02-12 | 2003-12-20 | Council Scient Ind Res | |
| DE10016449B4 (de) * | 2000-03-29 | 2005-03-17 | Council Of Scientific And Industrial Research (C.S.I.R.) | Verbessertes Verfahren zur Isolierung des hepatoprotektiven Mittels Silymarin aus den Samen der Pflanze Silybum marianum |
| WO2002072743A1 (en) * | 2001-03-13 | 2002-09-19 | Council Of Scientific And Industrial Research | A simple portable mini distillation apparatus for the production of essential oils and hydrosols |
| US20060247477A1 (en) * | 2002-03-25 | 2006-11-02 | Council Of Scientific And Industrial Research | Essential oil with citronellol and rose oxides from Dracocephalum heterophyllum benth and a process thereof |
| US6685972B2 (en) * | 2002-03-25 | 2004-02-03 | Council Of Scientific And Industrial Research | Process for isolating artemisinin from Artemisia annua |
| FR2882255B1 (fr) * | 2005-02-24 | 2008-05-16 | Apis Spheromont | Spheroides prepares a partir d'un principe actif isole d'origine vegetale et d'une solution d'origine vegetale contenant le principe actif ou un precurseur de celui-ci |
| CN101421275A (zh) * | 2006-03-10 | 2009-04-29 | 科学与工业研究委员会 | 青蒿素一锅转变成蒿酸的方法 |
| EP2289897A1 (en) | 2009-09-01 | 2011-03-02 | Sanofi-Aventis | Photochemical process for producing artemisinin |
| AU2010293907B2 (en) | 2009-09-11 | 2016-03-03 | Huvepharma Italia S.R.L | Process for the production of artemisinin intermediates |
| CN101731284B (zh) * | 2009-12-03 | 2013-06-05 | 河海大学 | 从黄花蒿中提取抑藻活性成分的方法及抑藻方法 |
| CN102190665B (zh) * | 2011-03-07 | 2013-05-08 | 中国药科大学 | 利用非水系统的活性炭柱色谱法分离纯化青蒿素的方法 |
| CN103524525B (zh) * | 2013-09-25 | 2016-04-06 | 湘西华方制药有限公司 | 从青蒿素生产废弃物中提取青蒿酸及其衍生物的方法 |
| CN103570739A (zh) * | 2013-11-01 | 2014-02-12 | 湖南科源生物制品有限公司 | 一种从青蒿精油中分离青蒿酸的方法 |
| CN109053759A (zh) * | 2018-09-19 | 2018-12-21 | 中国科学院过程工程研究所 | 一种生产青蒿素的系统及方法 |
| CN112940003B (zh) * | 2021-02-09 | 2023-03-31 | 威胜生物医药(苏州)股份有限公司 | 一种连续提取青蒿精油、青蒿素的方法 |
| CN113105947A (zh) * | 2021-04-21 | 2021-07-13 | 禹州市天源生物科技有限公司 | 一种青蒿精油的制备方法 |
| CN114181226A (zh) * | 2021-11-04 | 2022-03-15 | 河南天源药物研究有限公司 | 一种青蒿精油的提纯制备工艺 |
| CN118638004B (zh) * | 2024-08-12 | 2024-12-20 | 威胜生物医药(苏州)股份有限公司 | 一种从青蒿副产物中提取分离青蒿酸的方法 |
-
1997
- 1997-03-17 IN IN652DE1997 patent/IN188174B/en unknown
- 1997-10-06 US US08/944,865 patent/US5955084A/en not_active Expired - Lifetime
- 1997-10-10 AU AU40964/97A patent/AU728188C/en not_active Ceased
- 1997-10-16 CA CA002218444A patent/CA2218444C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IN188174B (en]) | 2002-08-31 |
| AU4096497A (en) | 1998-09-17 |
| CA2218444A1 (en) | 1998-09-17 |
| US5955084A (en) | 1999-09-21 |
| AU728188C (en) | 2001-10-18 |
| AU728188B2 (en) | 2001-01-04 |
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