CA1184897A - Process for the separation of sterols or mixtures of sterols - Google Patents
Process for the separation of sterols or mixtures of sterolsInfo
- Publication number
- CA1184897A CA1184897A CA000407609A CA407609A CA1184897A CA 1184897 A CA1184897 A CA 1184897A CA 000407609 A CA000407609 A CA 000407609A CA 407609 A CA407609 A CA 407609A CA 1184897 A CA1184897 A CA 1184897A
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- mixture
- sterol
- methanol
- sitosterol
- 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
Links
- 229930182558 Sterol Natural products 0.000 title claims abstract description 49
- 235000003702 sterols Nutrition 0.000 title claims abstract description 49
- 150000003432 sterols Chemical class 0.000 title claims abstract description 47
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000000926 separation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000002904 solvent Substances 0.000 claims abstract description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229950005143 sitosterol Drugs 0.000 claims abstract description 27
- 229910001868 water Inorganic materials 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims abstract description 18
- 239000002244 precipitate Substances 0.000 claims abstract description 14
- 230000007935 neutral effect Effects 0.000 claims abstract description 13
- 239000000344 soap Substances 0.000 claims abstract description 9
- 235000013311 vegetables Nutrition 0.000 claims abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 18
- 235000015500 sitosterol Nutrition 0.000 claims description 17
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims description 16
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims description 16
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims description 16
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 claims description 16
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims description 16
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims description 16
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 16
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 16
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000003784 tall oil Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 210000003918 fraction a Anatomy 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 9
- 239000000047 product Substances 0.000 abstract description 5
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 abstract description 4
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 abstract description 4
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 abstract description 4
- 235000000431 campesterol Nutrition 0.000 abstract description 4
- 238000002955 isolation Methods 0.000 abstract description 3
- 235000018185 Betula X alpestris Nutrition 0.000 abstract description 2
- 235000018212 Betula X uliginosa Nutrition 0.000 abstract description 2
- 229920002678 cellulose Polymers 0.000 abstract description 2
- 239000001913 cellulose Substances 0.000 abstract description 2
- 239000002023 wood Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 3
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229940031439 squalene Drugs 0.000 description 3
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 3
- JYDNKGUBLIKNAM-UHFFFAOYSA-N Oxyallobutulin Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C JYDNKGUBLIKNAM-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- LGJMUZUPVCAVPU-ANOYILKDSA-N (3s,8r,9s,10s,13r,14s,17r)-17-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical class C1CC2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@H](CC)C(C)C)[C@@]1(C)CC2 LGJMUZUPVCAVPU-ANOYILKDSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 235000003932 Betula Nutrition 0.000 description 1
- 241000219429 Betula Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940083492 sitosterols Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 sterol esters Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI812278A FI65440C (fi) | 1981-07-21 | 1981-07-21 | Foerfarande foer separering av beta-sitosterol med en laog alfa-sitosterolhalt |
| FI812278 | 1981-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1184897A true CA1184897A (en) | 1985-04-02 |
Family
ID=8514586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000407609A Expired CA1184897A (en) | 1981-07-21 | 1982-07-20 | Process for the separation of sterols or mixtures of sterols |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4420427A (https=) |
| JP (1) | JPS5824598A (https=) |
| CA (1) | CA1184897A (https=) |
| DD (1) | DD202581A5 (https=) |
| DE (1) | DE3226224A1 (https=) |
| FI (1) | FI65440C (https=) |
| FR (1) | FR2510119A1 (https=) |
| SE (1) | SE456088B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE461793B (sv) * | 1986-09-12 | 1990-03-26 | Triple Crown Ab | Foerfarande foer frigoerande av steroler ur organiskt material |
| US5244887A (en) * | 1992-02-14 | 1993-09-14 | Straub Carl D | Stanols to reduce cholesterol absorption from foods and methods of preparation and use thereof |
| ES2464465T3 (es) * | 1994-09-29 | 2014-06-02 | Pharmachem Laboratories, Inc. | Composiciones de esteroles a partir de jabón de pulpa |
| CA2230373A1 (en) * | 1998-02-20 | 1999-08-20 | Forbes Medi-Tech Inc. | Method for the preparation of phytosterols from tall oil pitch |
| US20050107582A1 (en) * | 2003-07-30 | 2005-05-19 | Alfred Wong | Method for the preparation of phytosterols from tall oil pitch |
| DE19916034C1 (de) * | 1999-04-09 | 2000-08-03 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Phytosterinen |
| WO2000064922A1 (en) * | 1999-04-27 | 2000-11-02 | Sterol Technologies Ltd. | Alkanol, methyl ethyl ketone water solvent system for the separation of sterols |
| US6677327B1 (en) | 1999-11-24 | 2004-01-13 | Archer-Daniels-Midland Company | Phytosterol and phytostanol compositions |
| JP2002080493A (ja) * | 2000-09-06 | 2002-03-19 | Kanegafuchi Chem Ind Co Ltd | ステロール類の精製方法 |
| US20020107232A1 (en) * | 2001-01-12 | 2002-08-08 | Flickinger Brent D. | Methods for producing sterol ester-rich compositions |
| US7368138B2 (en) * | 2002-03-21 | 2008-05-06 | Archer-Daniels-Midland Company | Extraction of phytosterols from corn fiber using green solvents |
| US7514107B2 (en) | 2002-03-21 | 2009-04-07 | Mars, Incorporated | Treatment of diseases involving defective gap junctional communication |
| CA2433246A1 (en) * | 2003-06-25 | 2004-12-25 | Telum Technologies Inc. | Process for recovering value-added products from pulping soap |
| WO2006045008A2 (en) * | 2004-10-19 | 2006-04-27 | Cargill, Incorporated | Meat having increased level of hdl |
| WO2006092449A2 (en) | 2005-03-02 | 2006-09-08 | Metanomics Gmbh | Process for the production of fine chemicals |
| CN101247869B (zh) * | 2005-07-26 | 2011-06-08 | 苏舍化学技术有限公司 | 通过从溶剂混合物分级层状结晶提纯高熔点有机粗产品或化合物混合物的方法和装置 |
| US8309156B2 (en) * | 2005-12-20 | 2012-11-13 | Pharmachem Laboratories, Inc. | Compositions comprising one or more phytosterols and/or phytostanols, or derivatives thereof, and high HLB emulsifiers |
| WO2007071036A1 (en) * | 2005-12-20 | 2007-06-28 | Forbes Medi-Tech Inc. | Emulsions comprising non-esterified phytosterols in the aqueous phase |
| EP2020874A4 (en) * | 2006-05-01 | 2015-07-15 | Pharmachem Lab Inc | COMPOSITION COMPRISING ONE OR MORE EXTRACTED PHYTOSTEROLS AND / OR PHYTOSTANOLES IN WHICH ONE OR MORE NON-SELECTED PHYTOSTEROLS AND / OR PHYTOSTANOLES ARE SOLUBILIZED TO OBTAIN THERAPEUTIC ADVANTAGES AND FORMULATION BENEFITS |
| US20070254026A1 (en) * | 2006-05-01 | 2007-11-01 | Forbes Medi-Tech Inc. | Softgel capsules |
| EP2252626B1 (en) * | 2008-03-10 | 2014-07-23 | SunPine AB | Recovery of phytosterols from residual vegetable oil streams |
| CA3146266A1 (en) * | 2019-09-27 | 2021-04-01 | Basf Se | Process for the purification of phytosterol |
| WO2021058646A1 (en) * | 2019-09-27 | 2021-04-01 | Basf Se | Process for the production and purification of sterols |
| CA3145091A1 (en) * | 2019-09-27 | 2021-04-01 | Basf Se | Process for the production of sterols and/or tocopherols with recovery of by-products |
| CN111171099A (zh) * | 2020-01-17 | 2020-05-19 | 杭州益品新五丰药业有限公司 | 一种双溶剂结晶提取谷甾醇的方法及利用其提取的谷甾醇 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866797A (en) * | 1954-11-01 | 1958-12-30 | Gen Mills Inc | Improved process of isolating sterols |
| US2839544A (en) * | 1956-09-04 | 1958-06-17 | Upjohn Co | Countercurrent extraction of steroids |
| US2843610A (en) * | 1957-08-28 | 1958-07-15 | Eastman Kodak Co | Separation of sterols from deodorizer sludges |
| US4044031A (en) * | 1976-07-02 | 1977-08-23 | Ake Allan Johansson | Process for the separation of sterols |
| US4153622A (en) * | 1978-05-18 | 1979-05-08 | Medipolar Oy | Process for the recovery of β-sitosterol |
| FI58333C (fi) * | 1978-10-27 | 1981-01-12 | Kaukas Ab Oy | Foerfarande foer framstaellning av under 5 vikt-% alfa2-sitosterol innehaollande beta-sitosterolkoncentrat |
| FI59416C (fi) * | 1979-11-19 | 1981-08-10 | Farmos Oy | Foerfarande foer utvinning av beta-sitosterol ur en sterolblandning utvunnen fraon raosaopans neutralfraktion |
-
1981
- 1981-07-21 FI FI812278A patent/FI65440C/fi not_active IP Right Cessation
-
1982
- 1982-07-08 US US06/396,336 patent/US4420427A/en not_active Expired - Lifetime
- 1982-07-12 SE SE8204272A patent/SE456088B/sv not_active IP Right Cessation
- 1982-07-14 DE DE19823226224 patent/DE3226224A1/de active Granted
- 1982-07-19 DD DD82241765A patent/DD202581A5/de not_active IP Right Cessation
- 1982-07-20 CA CA000407609A patent/CA1184897A/en not_active Expired
- 1982-07-20 JP JP57126631A patent/JPS5824598A/ja active Granted
- 1982-07-21 FR FR8212729A patent/FR2510119A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI65440B (fi) | 1984-01-31 |
| FI812278L (fi) | 1983-01-22 |
| SE456088B (sv) | 1988-09-05 |
| JPS5824598A (ja) | 1983-02-14 |
| JPH0153679B2 (https=) | 1989-11-15 |
| SE8204272D0 (sv) | 1982-07-12 |
| US4420427A (en) | 1983-12-13 |
| FR2510119A1 (fr) | 1983-01-28 |
| DE3226224A1 (de) | 1983-02-10 |
| DD202581A5 (de) | 1983-09-21 |
| FR2510119B1 (https=) | 1985-03-01 |
| FI65440C (fi) | 1984-05-10 |
| SE8204272L (sv) | 1983-01-22 |
| DE3226224C2 (https=) | 1993-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1184897A (en) | Process for the separation of sterols or mixtures of sterols | |
| CA1065303A (en) | Process for the separation of sterols | |
| US6465665B1 (en) | High efficiency process for the recovery of the high pure sterols | |
| US4298539A (en) | Process for the isolation of β-sitosterol | |
| US2715638A (en) | Production of sterols from tall oil pitch | |
| US4265824A (en) | Process for the isolation of β-sitosterol containing a low percentage of α-sitosterol | |
| US4153622A (en) | Process for the recovery of β-sitosterol | |
| US4422974A (en) | Process for the purification of β-sitosterol isolated from the unsaponifiables in crude soap from the sulphate cellulose process | |
| US6762312B1 (en) | Process for purification of phytosterol from fatty acids and their esters | |
| EP4025676B1 (en) | Production of an extract of phytosterols and stanols from tall oil pitch | |
| US4279827A (en) | Process for the preparation of a β-sitosterol concentrate containing less than 5% by weight of α-sitosterol | |
| US7173144B1 (en) | Process for producing phytosterols by saponification in an alcohol/water solvent | |
| RU2139293C1 (ru) | Способ получения ситостерина | |
| US6770767B1 (en) | Method for the extraction and isolation of neutral substances from a soap | |
| WO2000012533A1 (en) | Isolation and purification of sterols from neutrals fraction of tall oil pitch by direct crystallization, dual phase | |
| JPS6314797A (ja) | ２４−メチレンシクロアルタノ−ルフエルラ酸エステルの分離方法 | |
| EP1190025B1 (en) | Extraction and isolation method | |
| WO2000009535A1 (en) | Isolation and purification of sterols from neutrals fraction of tall oil pitch by direct crystallization, single phase | |
| WO2000064922A1 (en) | Alkanol, methyl ethyl ketone water solvent system for the separation of sterols | |
| CH561229A5 (en) | Substd. tetra-enes and trienes - oestrogenic and antilipaemic |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |