FI63423C - Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion - Google Patents
Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion Download PDFInfo
- Publication number
- FI63423C FI63423C FI810216A FI810216A FI63423C FI 63423 C FI63423 C FI 63423C FI 810216 A FI810216 A FI 810216A FI 810216 A FI810216 A FI 810216A FI 63423 C FI63423 C FI 63423C
- Authority
- FI
- Finland
- Prior art keywords
- sitosterol
- mixture
- beta
- solvent
- water
- Prior art date
Links
- 229950005143 sitosterol Drugs 0.000 title claims abstract description 52
- 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 title claims abstract description 15
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 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 title claims abstract description 15
- 229940076810 beta sitosterol Drugs 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 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 claims abstract description 15
- 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 claims abstract description 15
- 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 claims abstract description 15
- 235000000431 campesterol Nutrition 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 230000007935 neutral effect Effects 0.000 claims abstract description 7
- 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 abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 229930182558 Sterol Natural products 0.000 claims description 12
- 150000003432 sterols Chemical class 0.000 claims description 12
- 235000003702 sterols Nutrition 0.000 claims description 12
- 235000015500 sitosterol Nutrition 0.000 claims description 7
- 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 5
- 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 5
- 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 5
- 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 5
- 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 5
- 238000001816 cooling Methods 0.000 claims description 5
- 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 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LPZCCMIISIBREI-JXMPMKKESA-N (Z)-24-ethylidenelophenol Chemical compound C[C@@H]1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CC/C(=C/C)C(C)C)CC[C@H]33)C)C3=CC[C@H]21 LPZCCMIISIBREI-JXMPMKKESA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 6
- 239000012467 final product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 3
- 229940083492 sitosterols Drugs 0.000 description 3
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003613 toluenes Chemical class 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)
- Junction Field-Effect Transistors (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI810216A FI63423C (fi) | 1981-01-27 | 1981-01-27 | Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion |
| CA000391858A CA1183126A (en) | 1981-01-27 | 1981-12-09 | PROCESS FOR THE ISOLATION OF .beta.-SITOSTEROL FROM A STEROL MIXTURE SEPARATED FROM THE NEUTRAL FRACTION OF RAW-SOAP |
| AT82300240T ATE7790T1 (de) | 1981-01-27 | 1982-01-18 | Verfahren zur abtrennung von beta-sitosterol aus einer steroidmischung. |
| EP82300240A EP0057075B1 (de) | 1981-01-27 | 1982-01-18 | Verfahren zur Abtrennung von beta-Sitosterol aus einer Steroidmischung |
| DE8282300240T DE3260196D1 (en) | 1981-01-27 | 1982-01-18 | A process for the isolation of beta-sitosterol from a steroid mixture |
| FI823904A FI63948C (fi) | 1981-01-27 | 1982-11-15 | Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI810216A FI63423C (fi) | 1981-01-27 | 1981-01-27 | Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion |
| FI810216 | 1981-01-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810216L FI810216L (fi) | 1982-07-28 |
| FI63423B FI63423B (fi) | 1983-02-28 |
| FI63423C true FI63423C (fi) | 1983-06-10 |
Family
ID=8514077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810216A FI63423C (fi) | 1981-01-27 | 1981-01-27 | Foerfarande foer separering av beta-sitosterol fraon en sterolblandning utvunnen ur raosaopans neutralfraktion |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0057075B1 (de) |
| AT (1) | ATE7790T1 (de) |
| CA (1) | CA1183126A (de) |
| DE (1) | DE3260196D1 (de) |
| FI (1) | FI63423C (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963346A (en) * | 1988-05-31 | 1990-10-16 | Amer & Company, Inc. | Method and composition for treatment or prevention of dental plaque calculus and gingivitis |
| EP1148062A3 (de) * | 1994-09-29 | 2003-06-11 | The University of British Columbia | Sterin-Zusammensetzungen aus Holz-Seife |
| JPH11228593A (ja) * | 1998-02-17 | 1999-08-24 | Arakawa Chem Ind Co Ltd | トール油ステロールの精製方法 |
| US6110502A (en) * | 1998-02-19 | 2000-08-29 | Mcneil-Ppc, Inc. | Method for producing water dispersible sterol formulations |
| AU4958799A (en) * | 1998-07-14 | 2000-02-07 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by single decantation precipitation |
| WO2000004038A1 (en) * | 1998-07-14 | 2000-01-27 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by direct precipitation |
| WO2000009535A1 (en) * | 1998-08-17 | 2000-02-24 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by direct crystallization, single phase |
| WO2000012533A1 (en) * | 1998-08-27 | 2000-03-09 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by direct crystallization, dual phase |
| US6057462A (en) * | 1998-11-06 | 2000-05-02 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by single decantation crystallization |
| US6242001B1 (en) | 1998-11-30 | 2001-06-05 | Mcneil-Ppc, Inc. | Method for producing dispersible sterol and stanol compounds |
| WO2000034305A1 (en) * | 1998-12-07 | 2000-06-15 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by dual decantation crystallization |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI59416C (fi) * | 1979-11-19 | 1981-08-10 | Farmos Oy | Foerfarande foer utvinning av beta-sitosterol ur en sterolblandning utvunnen fraon raosaopans neutralfraktion |
-
1981
- 1981-01-27 FI FI810216A patent/FI63423C/fi not_active IP Right Cessation
- 1981-12-09 CA CA000391858A patent/CA1183126A/en not_active Expired
-
1982
- 1982-01-18 EP EP82300240A patent/EP0057075B1/de not_active Expired
- 1982-01-18 DE DE8282300240T patent/DE3260196D1/de not_active Expired
- 1982-01-18 AT AT82300240T patent/ATE7790T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI810216L (fi) | 1982-07-28 |
| DE3260196D1 (en) | 1984-07-12 |
| EP0057075A1 (de) | 1982-08-04 |
| ATE7790T1 (de) | 1984-06-15 |
| CA1183126A (en) | 1985-02-26 |
| EP0057075B1 (de) | 1984-06-06 |
| FI63423B (fi) | 1983-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: FARMOS-YHTYMAE OY |