FR2470135A1 - Procede de separation du b-sitosterol - Google Patents
Procede de separation du b-sitosterol Download PDFInfo
- Publication number
- FR2470135A1 FR2470135A1 FR8024013A FR8024013A FR2470135A1 FR 2470135 A1 FR2470135 A1 FR 2470135A1 FR 8024013 A FR8024013 A FR 8024013A FR 8024013 A FR8024013 A FR 8024013A FR 2470135 A1 FR2470135 A1 FR 2470135A1
- Authority
- FR
- France
- Prior art keywords
- sitosterol
- mixture
- starting material
- water
- product
- 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
- 229950005143 sitosterol Drugs 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 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 21
- 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 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 description 18
- 239000007858 starting material Substances 0.000 claims description 17
- 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 13
- 235000015500 sitosterol Nutrition 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- 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 12
- 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 12
- 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 12
- 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 12
- 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 12
- 239000012467 final product Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 229940076810 beta sitosterol Drugs 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- KZJWDPNRJALLNS-FBZNIEFRSA-N clionasterol 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-FBZNIEFRSA-N 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 229930182558 Sterol Natural products 0.000 abstract description 12
- 150000003432 sterols Chemical class 0.000 abstract description 12
- 235000003702 sterols Nutrition 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 150000003431 steroids Chemical class 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 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 description 12
- 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 description 12
- 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 description 12
- 235000000431 campesterol Nutrition 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000344 soap Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 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
- 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 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004997 alkyl benzene derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940083492 sitosterols Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI793612A FI59416C (fi) | 1979-11-19 | 1979-11-19 | Foerfarande foer utvinning av beta-sitosterol ur en sterolblandning utvunnen fraon raosaopans neutralfraktion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2470135A1 true FR2470135A1 (fr) | 1981-05-29 |
| FR2470135B1 FR2470135B1 (show.php) | 1983-02-11 |
Family
ID=8513052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024013A Granted FR2470135A1 (fr) | 1979-11-19 | 1980-11-12 | Procede de separation du b-sitosterol |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4298539A (show.php) |
| DE (1) | DE3043543A1 (show.php) |
| FI (1) | FI59416C (show.php) |
| FR (1) | FR2470135A1 (show.php) |
| SE (1) | SE8008082L (show.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057075A1 (en) * | 1981-01-27 | 1982-08-04 | Farmos-Yhtyma Oy | A process for the isolation of beta-sitosterol from a steroid mixture |
| FR2510118A1 (fr) * | 1981-07-21 | 1983-01-28 | Kaukas Ab Oy | Procede de purification de b-sitosterol isole des non-saponifiables d'un savon brut provenant du traitement de la cellulose par un sulfate |
| WO1996010033A1 (en) * | 1994-09-29 | 1996-04-04 | The University Of British Columbia | Sterol compositions from pulping soap |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI65440C (fi) * | 1981-07-21 | 1984-05-10 | Kaukas Ab Oy | Foerfarande foer separering av beta-sitosterol med en laog alfa-sitosterolhalt |
| CA2118122C (en) * | 1992-04-15 | 2002-09-03 | Masato Tanabe | Isolation of steroids containing a 5,7-diene functionality from a sterol mixture |
| 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 |
| 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 |
| AU4958699A (en) * | 1998-08-17 | 2000-03-06 | 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 |
| US6107456A (en) * | 1998-08-31 | 2000-08-22 | Arizona Chemical Corporation | Method for separating sterols from tall oil |
| 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 |
| AU4958599A (en) * | 1998-12-07 | 2000-06-26 | Westvaco Corporation | Isolation and purification of sterols from neutrals fraction of tall oil pitch by dual decantation crystallization |
| DE19906551C1 (de) * | 1999-02-13 | 2000-06-29 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Phytosterinen |
| US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| NZ506676A (en) * | 1999-09-03 | 2002-09-27 | Thomas Harting | Recovery of pure sterols from black liquor soap skimmings or tall oil pitch |
| CA2433246A1 (en) * | 2003-06-25 | 2004-12-25 | Telum Technologies Inc. | Process for recovering value-added products from pulping soap |
| US8318962B2 (en) * | 2006-12-29 | 2012-11-27 | Cognis Ip Management Gmbh | Process for recovering sterols from a crude source containing sterol esters |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3840570A (en) * | 1970-12-07 | 1974-10-08 | Procter & Gamble | Process for preparing sterols from tall oil pitch |
| US4044031A (en) * | 1976-07-02 | 1977-08-23 | Ake Allan Johansson | Process for the separation of sterols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2839544A (en) * | 1956-09-04 | 1958-06-17 | Upjohn Co | Countercurrent extraction of steroids |
| US3691211A (en) * | 1970-12-07 | 1972-09-12 | Procter & Gamble | Process for preparing sterols from tall oil pitch |
| FI57956C (fi) * | 1978-12-12 | 1980-11-10 | Farmos Oy | Foerfarande foer isolering av beta-sitosterol med laog alfa-sitosterolhalt |
-
1979
- 1979-11-19 FI FI793612A patent/FI59416C/fi not_active IP Right Cessation
-
1980
- 1980-10-30 US US06/202,068 patent/US4298539A/en not_active Expired - Lifetime
- 1980-11-12 FR FR8024013A patent/FR2470135A1/fr active Granted
- 1980-11-18 SE SE8008082A patent/SE8008082L/ not_active Application Discontinuation
- 1980-11-18 DE DE19803043543 patent/DE3043543A1/de not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3840570A (en) * | 1970-12-07 | 1974-10-08 | Procter & Gamble | Process for preparing sterols from tall oil pitch |
| US4044031A (en) * | 1976-07-02 | 1977-08-23 | Ake Allan Johansson | Process for the separation of sterols |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057075A1 (en) * | 1981-01-27 | 1982-08-04 | Farmos-Yhtyma Oy | A process for the isolation of beta-sitosterol from a steroid mixture |
| FR2510118A1 (fr) * | 1981-07-21 | 1983-01-28 | Kaukas Ab Oy | Procede de purification de b-sitosterol isole des non-saponifiables d'un savon brut provenant du traitement de la cellulose par un sulfate |
| WO1996010033A1 (en) * | 1994-09-29 | 1996-04-04 | The University Of British Columbia | Sterol compositions from pulping soap |
Also Published As
| Publication number | Publication date |
|---|---|
| FI59416C (fi) | 1981-08-10 |
| FI59416B (fi) | 1981-04-30 |
| DE3043543A1 (de) | 1981-05-27 |
| US4298539A (en) | 1981-11-03 |
| SE8008082L (sv) | 1981-05-20 |
| FR2470135B1 (show.php) | 1983-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |