GB1173063A - Novel Polyene Compounds and a process for the manufacture and conversion thereof - Google Patents
Novel Polyene Compounds and a process for the manufacture and conversion thereofInfo
- Publication number
- GB1173063A GB1173063A GB7095/67A GB709567A GB1173063A GB 1173063 A GB1173063 A GB 1173063A GB 7095/67 A GB7095/67 A GB 7095/67A GB 709567 A GB709567 A GB 709567A GB 1173063 A GB1173063 A GB 1173063A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethyl
- methyl
- hydroxy
- give
- cyclohex
- 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
- -1 Polyene Compounds Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- 239000001775 zeaxanthin Substances 0.000 abstract 5
- 229940043269 zeaxanthin Drugs 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- AYODHZHFDRRQEZ-UHFFFAOYSA-N 2,7-dimethylocta-2,4,6-trienedial Chemical compound O=CC(C)=CC=CC=C(C)C=O AYODHZHFDRRQEZ-UHFFFAOYSA-N 0.000 abstract 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 abstract 2
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 abstract 1
- AJDYPKBZJGFSDZ-UHFFFAOYSA-N 1-(5-hydroxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol Chemical compound CC1CC(O)CC(C)(C)C1(O)C#CC(C)=CCO AJDYPKBZJGFSDZ-UHFFFAOYSA-N 0.000 abstract 1
- LVGHTZYRRMARRH-UHFFFAOYSA-N 13-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-2,7,11-trimethyltrideca-2,4,6,8,10-pentaen-12-ynal Chemical compound OC1CC(C(=C(C1)C)C#CC(=CC=CC(=CC=CC=C(C=O)C)C)C)(C)C LVGHTZYRRMARRH-UHFFFAOYSA-N 0.000 abstract 1
- RHTHCPQRNHYJEZ-UHFFFAOYSA-N 2,7,11-trimethyl-13-(2,6,6-trimethylcyclohex-2-en-1-yl)trideca-2,4,6,8,10,12-hexaenal Chemical compound O=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1C(C)=CCCC1(C)C RHTHCPQRNHYJEZ-UHFFFAOYSA-N 0.000 abstract 1
- HWGSJCVVUSKUGJ-UHFFFAOYSA-N 3-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-4-yn-3-ol Chemical compound CC1=CCCC(C)(C)C1C=CC(C)(O)C#C HWGSJCVVUSKUGJ-UHFFFAOYSA-N 0.000 abstract 1
- ZQOIDFBZYYQRNE-UHFFFAOYSA-N 3-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-1,4-dien-3-ol Chemical compound CC1=CCCC(C)(C)C1C=CC(C)(O)C=C ZQOIDFBZYYQRNE-UHFFFAOYSA-N 0.000 abstract 1
- ZSJHASYJQIRSLE-UHFFFAOYSA-N 3-methylpent-2-en-4-yn-1-ol Chemical compound C#CC(C)=CCO ZSJHASYJQIRSLE-UHFFFAOYSA-N 0.000 abstract 1
- OHYZJEHEHYMLGM-UHFFFAOYSA-N 4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,5,5-trimethylcyclohex-3-en-1-ol Chemical compound OCC=C(C)C#CC1=C(C)CC(O)CC1(C)C OHYZJEHEHYMLGM-UHFFFAOYSA-N 0.000 abstract 1
- ZTUOQBOZIFOYMP-UHFFFAOYSA-N 7,7,9-trimethyl-1,4-dioxaspiro[4.5]decane Chemical compound C1C(C)(C)CC(C)CC21OCCO2 ZTUOQBOZIFOYMP-UHFFFAOYSA-N 0.000 abstract 1
- WBHHAKSGKFSCJG-UHFFFAOYSA-N 8-(5-hydroxy-3-methylpent-3-en-1-ynyl)-7,7,9-trimethyl-1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1OC2(CC(C(C(C2)C)(O)C#CC(=CCO)C)(C)C)OC1 WBHHAKSGKFSCJG-UHFFFAOYSA-N 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- 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 1
- 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 1
- KNYAUFVTZONRSZ-UHFFFAOYSA-M [3-methyl-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-2,4-dienyl]-triphenylphosphanium;bromide Chemical compound [Br-].CC1=CCCC(C)(C)C1C=CC(C)=CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KNYAUFVTZONRSZ-UHFFFAOYSA-M 0.000 abstract 1
- FRMDZBGMAFBBAR-UHFFFAOYSA-N [5-(1-hydroxy-2,2,6-trimethyl-4-oxocyclohexyl)-3-methylpent-2-en-4-ynyl] acetate Chemical compound OC1(C(CC(CC1C)=O)(C)C)C#CC(=CCOC(C)=O)C FRMDZBGMAFBBAR-UHFFFAOYSA-N 0.000 abstract 1
- VTWIPBUIGMOKBO-UHFFFAOYSA-N [5-(4-acetyloxy-2,6,6-trimethylcyclohexen-1-yl)-3-methylpent-2-en-4-ynyl] acetate Chemical compound CC(=O)OCC=C(C)C#CC1=C(C)CC(OC(C)=O)CC1(C)C VTWIPBUIGMOKBO-UHFFFAOYSA-N 0.000 abstract 1
- GIPJUVPCGKSCAE-UHFFFAOYSA-M [5-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3-methylpent-2-en-4-ynyl]-triphenylphosphanium;bromide Chemical compound [Br-].CC=1CC(O)CC(C)(C)C=1C#CC(C)=CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GIPJUVPCGKSCAE-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 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 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 abstract 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract 1
- 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 1
- 235000010930 zeaxanthin Nutrition 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
- C07C403/14—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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/47—Addition of dyes or pigments, e.g. in combination with optical brighteners using synthetic organic dyes or pigments not covered by groups A23L5/43 - A23L5/46
-
- 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
- C07C403/24—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
- 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
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,173,063. Polyene compounds. ROCHE PRODUCTS Ltd. and B. C. L. WEEDON. 15 March, 1968 [14 Feb., 1967], No. 7095/67. Heading C2C. The invention comprises compounds of formula wherein the broken line represents an optional bond and R is a group of formula The compounds are prepared by reacting a phosphonium salt of formula wherein R<SP>1</SP> is an aryl group and A<SP>-</SP> is the anion of a mineral acid, with an aldehyde of formula wherein R<SP>2</SP> is a formyl group or a group of formula in the presence of a proton acceptor and converting any acyloxy or oxo group in the resulting compound of the formula into an hydroxy group by reduction or hydrolysis. In Examples: (1) 7,8,7<SP>1</SP>,8<SP>1</SP>-bisdehydro-zeaxanthin is prepared by reacting together 3-methylpent-2-en-4-yn-1-ol and 4,4-ethylenedioxy-2,2,6- trimethyl-cyclohexane in a Grignard reaction to give 5 - (4,4 - ethylenedioxy - 1 - hydroxy - 2,2,6 - trimethyl - cyclohexyl) - 3 - methyl - pent - 2 - en - 4-yn-1-ol which is reacted with acetic acid to yield a mixture of 5-(1-hydroxy-4-oxo.2,2,6- trimethyl - cyclohexyl) - 3 - methyl - pent - 2 - en - 4- yn - 1 - ol and 5 - (1 - hydroxy - 4 - oxo - 2,2,6 - trimethyl - cyclohexyl) - 1 - acetoxy - 3- methyl - pent - 2 - en - 4 - yne, the latter compound is treated with LiAlH4 to give 5-(1,4- dihydroxy - 2,2,6 - trimethyl - cyclohexyl) - 3 - methyl - pent - 2 - en - 4 - yn - 1 - ol, which is refluxed with acetic acid/acetic anhydride to give 5 - (4 - acetoxy 2,2,6 - trimethyl - cyclohex - 6 - enyl) - 1 - acetoxy - 3 - methyl - -pent 2 - en - 4 - yne, which is treated with methanolic KOH to yield 5-(4-hydroxy-2,2,6-trimethyl-cyclohex-6- enyl) - 3 - methyl - pent - 2 - en - 4 - yn - 1- ol, which is reacted with triphenyl-phosphine hydrobromide to give [5-(4-hydroxy-2,2,6-trimethyl - cyclohex - 6 - enyl) - 3 - methyl - pent - 2 - en - 4 - yn - 1 - yl] - triphenyl phosphonium bromide (compound X) which is reacted with 2,7 - dimethyl - octa - 2,4,6 - triene - 1,8 - dial to yield 13-(4-hydroxy-2,2,6-trimethyl-cyclohex - 6 - enyl) - 2,7,11 - trimethyl trideca- 2,4,6,8,10 - pentaen - 12 - yn - 1 - al which is further reacted with compound X to give 7,8, 7<SP>1</SP>,8<SP>1</SP>-bisdehydro-zeaxanthin; catalytic hydrogenation of the bisdehydro-zeaxanthin gives zeaxanthin: (2) alphaionone is added to a mixture of Li, liq. NH 3 and ferric nitrate through which acetylene has been passed and 5 - (2,2,6 - trimethyl - cyclohex - 5 - enyl) - 3 - methyl - pent - 4 - en - 1 - yn - 3 - ol is isolated and catalytically hydrogenated to give 5- (2,2,6 - trimethyl - cyclohex - 5 - enyl) - 3 - methyl - penta-1,4-dien-3-ol, which is reacted with triphenyl-phosphine hydrobromide to give [5- (2,2,6 - trimethyl - cyclohex - 5 - enyl) - 3 - methyl - penta - 2,4 - dien - 1 - yl] - triphenyl - phosphonium bromide, which is reacted with 2,7- dimethyl - octa - 2,4,6 - triene - 1,8 - dial to give 13 - (2,2,6 - trimethyl - cyclohex - 5 - enyl) - 2,7,11 - trimethyl - trideca - 2,4,6,8,10,12 - hexaen - 1-al (α-apo-12<SP>1</SP>-carotenal), which is reacted with compound X to give 7,8-dehydro-3-hydroxy-α- carotene: 7,8-dehydro-zeaxanthin, 7,8-dehydrolutein and 7,8-dehydro-3-hydroxy-#-carotene may be similarly prepared.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7095/67A GB1173063A (en) | 1967-02-14 | 1967-02-14 | Novel Polyene Compounds and a process for the manufacture and conversion thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7095/67A GB1173063A (en) | 1967-02-14 | 1967-02-14 | Novel Polyene Compounds and a process for the manufacture and conversion thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1173063A true GB1173063A (en) | 1969-12-03 |
Family
ID=9826530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7095/67A Expired GB1173063A (en) | 1967-02-14 | 1967-02-14 | Novel Polyene Compounds and a process for the manufacture and conversion thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1173063A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2355819A1 (en) * | 1975-06-09 | 1978-01-20 | Hoffmann La Roche | PROCESS FOR THE PREPARATION OF OXOCYCLIC COMPOUNDS |
| EP0004621A2 (en) * | 1978-03-27 | 1979-10-17 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Process for the multi-step preparation of zeaxanthine and alloxanthine starting from derivatives of cyclohexanon and cyclohexanol; derivatives of cyclohexanon and cyclohexanol |
| US4532355A (en) * | 1973-03-30 | 1985-07-30 | Hoffmann-La Roche Inc. | Substituted triaryl phosphonium derivatives |
| EP0454002A2 (en) * | 1990-04-27 | 1991-10-30 | F. Hoffmann-La Roche Ag | Dehydration process |
| US6103940A (en) * | 1997-06-04 | 2000-08-15 | Basf Aktiengesellschaft | Preparation of zeaxanthin, intermediates for this preparation, and the preparation thereof |
-
1967
- 1967-02-14 GB GB7095/67A patent/GB1173063A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532355A (en) * | 1973-03-30 | 1985-07-30 | Hoffmann-La Roche Inc. | Substituted triaryl phosphonium derivatives |
| FR2355819A1 (en) * | 1975-06-09 | 1978-01-20 | Hoffmann La Roche | PROCESS FOR THE PREPARATION OF OXOCYCLIC COMPOUNDS |
| EP0004621A2 (en) * | 1978-03-27 | 1979-10-17 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Process for the multi-step preparation of zeaxanthine and alloxanthine starting from derivatives of cyclohexanon and cyclohexanol; derivatives of cyclohexanon and cyclohexanol |
| EP0004621A3 (en) * | 1978-03-27 | 1980-04-16 | F.Hoffmann-La Roche & Co. Aktiengesellschaft | Process for the multi-step preparation of zeaxanthine and alloxanthine starting from derivatives of cyclohexanon and cyclohexanol; derivatives of cyclohexanon and cyclohexanol |
| EP0454002A2 (en) * | 1990-04-27 | 1991-10-30 | F. Hoffmann-La Roche Ag | Dehydration process |
| EP0454002A3 (en) * | 1990-04-27 | 1992-05-06 | F. Hoffmann-La Roche Ag | Dehydration process |
| US6103940A (en) * | 1997-06-04 | 2000-08-15 | Basf Aktiengesellschaft | Preparation of zeaxanthin, intermediates for this preparation, and the preparation thereof |
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