GB1508195A - Process for the manufacture of optically active cyclohexane derivatives - Google Patents
Process for the manufacture of optically active cyclohexane derivativesInfo
- Publication number
- GB1508195A GB1508195A GB34605/75A GB3460575A GB1508195A GB 1508195 A GB1508195 A GB 1508195A GB 34605/75 A GB34605/75 A GB 34605/75A GB 3460575 A GB3460575 A GB 3460575A GB 1508195 A GB1508195 A GB 1508195A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- give
- retinyl
- converted
- halide
- 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
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000004820 halides Chemical class 0.000 abstract 15
- 239000001775 zeaxanthin Substances 0.000 abstract 10
- 229940043269 zeaxanthin Drugs 0.000 abstract 10
- 229960000342 retinol acetate Drugs 0.000 abstract 9
- 239000011770 retinyl acetate Substances 0.000 abstract 9
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 abstract 7
- 238000006317 isomerization reaction Methods 0.000 abstract 7
- QPRQNCDEPWLQRO-ZCEAMUHZSA-N (3R)-all-trans-3-hydroxyretinal Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C QPRQNCDEPWLQRO-ZCEAMUHZSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 5
- 239000011707 mineral Substances 0.000 abstract 5
- 239000004212 Cryptoxanthin Substances 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- OBODKGDXEIUEIH-ZCEAMUHZSA-N (1r)-4-[(1e,3e,5e,7e)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-3,5,5-trimethylcyclohex-3-en-1-ol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C OBODKGDXEIUEIH-ZCEAMUHZSA-N 0.000 abstract 3
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 230000002207 retinal effect Effects 0.000 abstract 3
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 abstract 2
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 abstract 2
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 abstract 2
- 235000002360 beta-cryptoxanthin Nutrition 0.000 abstract 2
- DMASLKHVQRHNES-ITUXNECMSA-N beta-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CCCC2(C)C DMASLKHVQRHNES-ITUXNECMSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 235000019244 cryptoxanthin Nutrition 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- -1 phosphonium halide Chemical class 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 abstract 2
- 235000010930 zeaxanthin Nutrition 0.000 abstract 2
- CSPVUHYZUZZRGF-RNFRBKRXSA-N (4R,6R)-hydroxy-2,2,6-trimethylcyclohexanone Chemical compound C[C@@H]1C[C@@H](O)CC(C)(C)C1=O CSPVUHYZUZZRGF-RNFRBKRXSA-N 0.000 abstract 1
- NNHZRFWALNMRKS-YLXHPXFOSA-N (4r,6r)-1-(3-hydroxybut-1-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol Chemical compound CC(O)C#CC1(O)[C@H](C)C[C@@H](O)CC1(C)C NNHZRFWALNMRKS-YLXHPXFOSA-N 0.000 abstract 1
- AYJXHIDNNLJQDT-UHFFFAOYSA-N 2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical compound CC1=CC(=O)CC(C)(C)C1=O AYJXHIDNNLJQDT-UHFFFAOYSA-N 0.000 abstract 1
- UBFBTMRIJJRZOA-UHFFFAOYSA-N 2,7-dimethylocta-2,4,6-triene Chemical compound CC(C)=CC=CC=C(C)C UBFBTMRIJJRZOA-UHFFFAOYSA-N 0.000 abstract 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 abstract 1
- QXJSYJRWEUENRT-PSAUJTBTSA-N 4,9-dimethyldodeca-2,4,6,8,10-pentaenedial Chemical compound O=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O QXJSYJRWEUENRT-PSAUJTBTSA-N 0.000 abstract 1
- WFLRJRATQLPRDT-UHFFFAOYSA-N 4,9-dimethyldodeca-2,4,8,10-tetraen-6-ynedial Chemical compound O=CC=CC(C)=CC#CC=C(C)C=CC=O WFLRJRATQLPRDT-UHFFFAOYSA-N 0.000 abstract 1
- PCYSRECLJVMEPX-UHFFFAOYSA-N 8,8-diethoxy-3,7-dimethylocta-2,4,6-trienal Chemical compound CCOC(OCC)C(C)=CC=CC(C)=CC=O PCYSRECLJVMEPX-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- SPBPMWXNKPPVSX-KXOLNMLNSA-N Citraurin Natural products CC(=C/C=C/C(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=CC(O)CC1(C)C)C)/C)C=O SPBPMWXNKPPVSX-KXOLNMLNSA-N 0.000 abstract 1
- TXHARUYWUGDGQT-WPZCJLIBSA-N [(1r)-4-(3-acetyloxybut-1-ynyl)-3,5,5-trimethylcyclohex-3-en-1-yl] acetate Chemical compound CC(=O)OC(C)C#CC1=C(C)C[C@@H](OC(C)=O)CC1(C)C TXHARUYWUGDGQT-WPZCJLIBSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- LQAJUQDHCUNJJY-OVWFGJEDSA-N all-trans-1,6-seco-1,2-didehydroretinal Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=O LQAJUQDHCUNJJY-OVWFGJEDSA-N 0.000 abstract 1
- GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001746 carotenes Chemical class 0.000 abstract 1
- 235000005473 carotenes Nutrition 0.000 abstract 1
- 235000021466 carotenoid Nutrition 0.000 abstract 1
- 150000001747 carotenoids Chemical class 0.000 abstract 1
- 150000001934 cyclohexanes Chemical class 0.000 abstract 1
- 229930002839 ionone Natural products 0.000 abstract 1
- 150000002499 ionone derivatives Chemical class 0.000 abstract 1
- HVHHZSFNAYSPSA-ZCFIWIBFSA-N levodione Chemical compound C[C@@H]1CC(=O)CC(C)(C)C1=O HVHHZSFNAYSPSA-ZCFIWIBFSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- ABTRFGSPYXCGMR-AXXBKCDFSA-N rubixanthin Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C ABTRFGSPYXCGMR-AXXBKCDFSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1143474A CH605533A5 (da) | 1974-08-21 | 1974-08-21 | |
| CH1467474 | 1974-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1508195A true GB1508195A (en) | 1978-04-19 |
Family
ID=25708324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34605/75A Expired GB1508195A (en) | 1974-08-21 | 1975-08-20 | Process for the manufacture of optically active cyclohexane derivatives |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS587277B2 (da) |
| AT (1) | AT347422B (da) |
| DE (1) | DE2537060C3 (da) |
| FR (3) | FR2303797A1 (da) |
| GB (1) | GB1508195A (da) |
| IT (1) | IT1041904B (da) |
| NL (1) | NL169195C (da) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1293493A2 (de) * | 2001-09-13 | 2003-03-19 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Meso-Zeaxanthin |
| EP2957565B1 (en) | 2014-06-18 | 2018-03-07 | Allied Biotech Corporation | Methods for preparation of lycopenes from C-15 Wittig salts and methods for purification of high all-E containing and high 6Z containing C15-Wittig salts |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000198A (en) * | 1975-06-09 | 1976-12-28 | Hoffmann-La Roche Inc. | Hydroxy-acetylene-substituted cyclohexenone |
| JPS61105975U (da) * | 1984-12-14 | 1986-07-05 | ||
| DE19543619A1 (de) | 1995-11-23 | 1997-05-28 | Basf Ag | Verfahren zur Reindarstellung von trans- und cis-4-Hydroxy-2,2,6-trimethyl-cyclohexan-l-on aus Isomerengemischen |
| DE19723480A1 (de) * | 1997-06-04 | 1998-12-10 | Basf Ag | Verfahren zur Herstellung von Zeaxanthin, Zwischenprodukte für dieses Verfahren und Verfahren zu deren Herstellung |
| EP0982406B1 (en) * | 1998-08-19 | 2006-03-01 | DSM IP Assets B.V. | Microbial production of actinol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1167712A (fr) * | 1955-07-22 | 1958-11-28 | Hoffmann La Roche | Procédé pour la préparation de caroténoïdes |
| FR1210619A (fr) * | 1955-08-31 | 1960-03-09 | Hoffmann La Roche | Procédé pour la préparation de caroténoïdes |
| FR1165058A (fr) * | 1955-10-11 | 1958-10-17 | Hoffmann La Roche | Procédé pour la préparation de cétones cycliques |
-
1975
- 1975-08-18 IT IT7526389A patent/IT1041904B/it active
- 1975-08-19 FR FR7525631A patent/FR2303797A1/fr active Granted
- 1975-08-19 JP JP50099888A patent/JPS587277B2/ja not_active Expired
- 1975-08-20 AT AT645575A patent/AT347422B/de not_active IP Right Cessation
- 1975-08-20 GB GB34605/75A patent/GB1508195A/en not_active Expired
- 1975-08-20 DE DE2537060A patent/DE2537060C3/de not_active Expired
- 1975-08-21 NL NLAANVRAGE7509925,A patent/NL169195C/xx not_active IP Right Cessation
-
1976
- 1976-06-03 FR FR7616821A patent/FR2303786A1/fr active Granted
- 1976-06-03 FR FR7616822A patent/FR2303798A1/fr active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1293493A2 (de) * | 2001-09-13 | 2003-03-19 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Meso-Zeaxanthin |
| EP1293493A3 (de) * | 2001-09-13 | 2003-07-09 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Meso-Zeaxanthin |
| US6743954B2 (en) | 2001-09-13 | 2004-06-01 | Basf Aktiengesellschaft | Process for the preparation of meso-zeaxanthin |
| US6747177B2 (en) | 2001-09-13 | 2004-06-08 | Basf Aktiengesellschaft | Process for the preparation of meso-zeaxanthin |
| EP2957565B1 (en) | 2014-06-18 | 2018-03-07 | Allied Biotech Corporation | Methods for preparation of lycopenes from C-15 Wittig salts and methods for purification of high all-E containing and high 6Z containing C15-Wittig salts |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2303797B1 (da) | 1980-07-25 |
| AT347422B (de) | 1978-12-27 |
| ATA645575A (de) | 1978-05-15 |
| DE2537060B2 (de) | 1979-05-23 |
| FR2303786A1 (fr) | 1976-10-08 |
| NL169195C (nl) | 1982-06-16 |
| DE2537060C3 (de) | 1980-01-17 |
| FR2303798B1 (da) | 1982-10-29 |
| FR2303798A1 (fr) | 1976-10-08 |
| NL169195B (nl) | 1982-01-18 |
| FR2303797A1 (fr) | 1976-10-08 |
| FR2303786B1 (da) | 1980-05-30 |
| JPS5182789A (da) | 1976-07-20 |
| NL7509925A (nl) | 1976-02-24 |
| IT1041904B (it) | 1980-01-10 |
| DE2537060A1 (de) | 1976-03-04 |
| JPS587277B2 (ja) | 1983-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Crawford et al. | Metalation of limonene. Novel method for the synthesis of bisabolane sesquiterpenes | |
| Corey et al. | Stereospecific total synthesis of prostaglandins E3 and F3. alpha. | |
| Casey et al. | Stereochemistry and mechanism of the reaction of LiCuMe2 with. beta.-cyclopropyl. alpha.,. beta.-unsaturated ketones | |
| Maruyama et al. | Synthesis of naturally occurring quinones. Part 3. Allylation of quinones with allyltin reagents. New synthesis of coenzyme Q1 and plastoquinone-1 | |
| GB1508195A (en) | Process for the manufacture of optically active cyclohexane derivatives | |
| Widmer et al. | Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6‐Oxo‐isophorone: Syntheses of (3R, 3′ R)‐Zeaxanthin. Part I | |
| Bentley | Total syntheses of prostanoids | |
| US4028385A (en) | Process for preparing stereospecific farnesylacetic acid and ester thereof | |
| Young et al. | Allylic Rearrangements. XXX. The Formation and Rearrangement of α, α-Dialkylallyl Acetates1 | |
| Rowland et al. | Macrocyclic Diterpenes Isolated from Tobacco. α-and β-3, 8, 13-Duvatriene-1, 5-diols | |
| Ege et al. | Synthesis of methyl 5, 8, 11, 14-eicosatetraenoate (methyl arachidonate) | |
| Whitmore et al. | Grignard Reductions. IX. 1, 2, 3 Further Studies on the Reduction of Acid Halides | |
| Eastman et al. | Replacement of Hydrogen at a Tertiary Carbon Atom with OH by Alkaline Permanganate1 | |
| Cambie et al. | 783. Chemistry of the higher fungi. Part XVI. Polyacetylenic metabolites from Aleurodiscus roseus | |
| Barrero et al. | Occurrence and chemical synthesis of apocarotenoids from Mucorales: A review | |
| Brunke et al. | Chemistry of sandalwood fragrance | |
| EP0114612B1 (de) | Racemisches und optisch aktives 3-Hydroxy-alpha-cyclocitral, deren Acetale und optisch aktive 3-Oxo-alpha-cyclocitralacetale sowie Herstellung und Verwendung dieser Verbindungen | |
| US2870197A (en) | 4, 4'-disubstituted-c40-carotenoids and their preparation | |
| Isler et al. | The synthesis and labeling of vitamin A and related compounds | |
| GB1199012A (en) | A process for the manufacture of Polyene Compounds | |
| Mayer et al. | [237] Synthesis of vitamins K | |
| Boeckman Jr et al. | Synthesis and reactivity of endocyclic α, β-epoxy-γ-butyrolactones | |
| US2760998A (en) | Preparation of hydrohalic acid esters of alcohols | |
| US2369162A (en) | Synthesis of vitamin a | |
| US2845440A (en) | Process and intermediates for the preparation of carotenoids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19920820 |