GB1508196A - (3r,3'r)-15,15'-didehydrozeaxanthin - Google Patents

(3r,3'r)-15,15'-didehydrozeaxanthin

Info

Publication number
GB1508196A
GB1508196A GB47892/76A GB4789276A GB1508196A GB 1508196 A GB1508196 A GB 1508196A GB 47892/76 A GB47892/76 A GB 47892/76A GB 4789276 A GB4789276 A GB 4789276A GB 1508196 A GB1508196 A GB 1508196A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
ionol
give
yne
didehydrozeaxanthin
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
Application number
GB47892/76A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1508196A publication Critical patent/GB1508196A/en
Expired legal-status Critical Current

Links

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
    • C07C403/06—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
    • 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 System
    • 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
    • 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
    • C07C2601/14—The ring being saturated
    • 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

Abstract

1508196 Didehydrozeaxanthin F HOFFMANN-LA ROCHE & CO AG 20 Aug 1975 [1 Nov 1974] 47892/76 Divided out of 1508195 Heading C2C The invention comprises [3R,3<SP>1</SP>R]-15,15<SP>1</SP>- didehydro-zeaxanthin. The compound may be prepared by reacting [4R,6R]-4-hydroxy-2,2,6- trimethylcyclohexanone with but-3-yn-2-ol suitably after the free hydroxy group has been masked by treatment of the ketone with isopropenyl methyl ether to yield 2-hydroxy-4- {[4R,6R] - 1,4 - dihydroxy - 2,2,6 - trimethylcyclohex - 1 - yl} but - 3 - yne, acetylating this to give 2 - acetoxy - 4 - {[4R,6R] - 4 - acetoxy- 1 - hydroxy - 2,2,6 - trimethyl - cyclohex - 1 - yl} - but-3-yne, dehydrating this to give the cyclohexene derivative and hydrogenating to yield [3R]-3-hydroxy-#-ionol. The ionol may be converted to a 4-{[4R]-4-hydroxy-2,2,6-trimethyl - cyclohex - 1 - en - 1 - yl} but - 3 - ene- 2-triarylphosphonium halide which may be condensed with 4,9-dimethyl-dodeca-2,4,8,10-tetraen-6-yne-1,12-dial to give the required didehydro zeaxanthin. Alternatively the ionol may be oxidized to [3R]-3-hydroxy-#-ionone, which is then reacted with sodium acetylide to give [3R] - 3 - hydroxy - ethynyl - # - ionol, subsequently hydrogenated to [3R] - 3 - hydroxy - vinyl - # - ionol, converted to [3R]- 3-hydroxy-#-ionylidene ethyl triphenyl phosphonium chloride or bromide which is then condensed with 2,7-dimethyl octa-2,6-then-4- yne-1,8-dial to give the required didehydrozeaxanthin.
GB47892/76A 1974-11-01 1975-08-20 (3r,3'r)-15,15'-didehydrozeaxanthin Expired GB1508196A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1467474 1974-11-01

Publications (1)

Publication Number Publication Date
GB1508196A true GB1508196A (en) 1978-04-19

Family

ID=4402920

Family Applications (1)

Application Number Title Priority Date Filing Date
GB47892/76A Expired GB1508196A (en) 1974-11-01 1975-08-20 (3r,3'r)-15,15'-didehydrozeaxanthin

Country Status (1)

Country Link
GB (1) GB1508196A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1293493A2 (en) * 2001-09-13 2003-03-19 Basf Aktiengesellschaft Process for the preparation of meso-zeaxanthine

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1293493A2 (en) * 2001-09-13 2003-03-19 Basf Aktiengesellschaft Process for the preparation of meso-zeaxanthine
EP1293493A3 (en) * 2001-09-13 2003-07-09 Basf Aktiengesellschaft Process for the preparation of meso-zeaxanthine
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

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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