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GB1076306A - A process for the manufacture of isocryptoxanthin and echinenone - Google Patents

A process for the manufacture of isocryptoxanthin and echinenone

Info

Publication number
GB1076306A
GB1076306A GB17635/66A GB1763566A GB1076306A GB 1076306 A GB1076306 A GB 1076306A GB 17635/66 A GB17635/66 A GB 17635/66A GB 1763566 A GB1763566 A GB 1763566A GB 1076306 A GB1076306 A GB 1076306A
Authority
GB
United Kingdom
Prior art keywords
echinenone
isocryptoxanthin
retinene
isomerized
trans
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
GB17635/66A
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 GB1076306A publication Critical patent/GB1076306A/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
    • C07C403/14—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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds of the formula <FORM:1076306/C2/1> <FORM:1076306/C2/2> where either X or Y is hydrogen and the other is alkanoyloxy of 1-7 carbon atoms or arylcarboxy, R1, R2 and R3 are aryl, aralkyl or alkyl and A is the anion of a mineral acid, are reacted in the presence of a strong base to give isocryptoxanthin which may be oxidized and isomerized to give echinenone. The oxidation of isocryptoxanthin may be achieved with an aluminium alkoxide or electrolytically. The mixture of cis- and trans-echinenone formed may be isomerized to all trans-echinenone by heating in a hydrocarbon solvent, e.g. heptane. The preparation of the intermediate 4-acetoxy retinene from retinene, acetic acid and N-bromo succinimide is described.
GB17635/66A 1965-04-28 1966-04-22 A process for the manufacture of isocryptoxanthin and echinenone Expired GB1076306A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US45163065A 1965-04-28 1965-04-28

Publications (1)

Publication Number Publication Date
GB1076306A true GB1076306A (en) 1967-07-19

Family

ID=23793020

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17635/66A Expired GB1076306A (en) 1965-04-28 1966-04-22 A process for the manufacture of isocryptoxanthin and echinenone

Country Status (4)

Country Link
BE (1) BE680076A (en)
ES (1) ES326062A1 (en)
GB (1) GB1076306A (en)
NL (1) NL6605422A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008122988A1 (en) * 2007-04-05 2008-10-16 Cadila Healthcare Limited Process for preparation of atovaquone and the conversion of cis-isomer to trans- isomer
CN113817299A (en) * 2021-08-18 2021-12-21 安徽建筑大学 A kind of PLA-based blended composite material with ionic and chemical double cross-linked structure and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008122988A1 (en) * 2007-04-05 2008-10-16 Cadila Healthcare Limited Process for preparation of atovaquone and the conversion of cis-isomer to trans- isomer
CN113817299A (en) * 2021-08-18 2021-12-21 安徽建筑大学 A kind of PLA-based blended composite material with ionic and chemical double cross-linked structure and preparation method thereof
CN113817299B (en) * 2021-08-18 2022-12-13 安徽建筑大学 PLA-based blended composite material with ion and chemical double-crosslinking structure and preparation method thereof

Also Published As

Publication number Publication date
NL6605422A (en) 1966-10-31
BE680076A (en) 1966-10-26
ES326062A1 (en) 1967-03-01

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