GB1452012A - Isomerising vitamin a compounds - Google Patents

Isomerising vitamin a compounds

Info

Publication number
GB1452012A
GB1452012A GB3656874A GB3656874A GB1452012A GB 1452012 A GB1452012 A GB 1452012A GB 3656874 A GB3656874 A GB 3656874A GB 3656874 A GB3656874 A GB 3656874A GB 1452012 A GB1452012 A GB 1452012A
Authority
GB
United Kingdom
Prior art keywords
vitamin
compounds
palladium
group
isomerized
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
GB3656874A
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 GB1452012A publication Critical patent/GB1452012A/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
    • C07C403/06—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • C07C403/10—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 etherified 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
    • C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • 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
    • C07B2200/09—Geometrical 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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1452012 Isomerizing vitamin A compounds F HOFFMANN-LA ROCHE & CO AG 20 Aug 1974 [21 Aug 1973] 36568/74 Heading C2V Vitamin A compounds and derivatives are isomerized by contact with palladium compounds other than palladium phthalocyanin and palladium compounds containing cyanide groups. The vitamin A compounds are those of formula where X is -CHO, -CH 2 OH, -COOH, -CH(R) 2 , -CH 2 OR<SP>1</SP>, -COOR<SP>2</SP>, -CONHR<SP>3</SP> or -CON(R<SP>3</SP>) 2 , R being an alkoxy group or two R's together are an alkylenedioxy group, R<SP>1</SP> being an alkanoyl or aroyl group, R<SP>2</SP> being an alkyl, aryl or aralkyl group and R<SP>3</SP> a hydrogen atom or an alkyl, aryl or aralkyl group. The isomerization may be carried out by heating in a solvent a mixture of the vitamin A compound and the palladium compound. In examples 9- cis, 11-cis and all-trans isomers of vitamin A acetate and aldehyde are isomerized with various palladium compounds.
GB3656874A 1973-08-21 1974-08-20 Isomerising vitamin a compounds Expired GB1452012A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1199473A CH590222A5 (en) 1973-08-21 1973-08-21

Publications (1)

Publication Number Publication Date
GB1452012A true GB1452012A (en) 1976-10-06

Family

ID=4378834

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3656874A Expired GB1452012A (en) 1973-08-21 1974-08-20 Isomerising vitamin a compounds

Country Status (13)

Country Link
JP (1) JPS5613712B2 (en)
AT (1) AT355231B (en)
BE (1) BE819012A (en)
CH (1) CH590222A5 (en)
CS (1) CS181769B2 (en)
DD (1) DD114803A5 (en)
DE (1) DE2439860C3 (en)
FR (1) FR2245626B1 (en)
GB (1) GB1452012A (en)
IL (1) IL45366A (en)
NL (1) NL176259C (en)
SU (1) SU731894A3 (en)
ZA (1) ZA744737B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011132084A2 (en) 2010-04-19 2011-10-27 Qlt Inc. Therapeutic regimen and method for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
WO2013134867A1 (en) 2012-03-01 2013-09-19 Qlt Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency
US10130606B2 (en) 2009-09-15 2018-11-20 Novelion Therapeutics Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
CN111233726A (en) * 2020-03-26 2020-06-05 万华化学集团股份有限公司 Method for preparing all-trans vitamin A acetate
CN112358429A (en) * 2020-11-06 2021-02-12 万华化学集团股份有限公司 Heterogeneous catalyst, preparation method thereof and preparation method of all-trans vitamin A acetate
CN113321604A (en) * 2021-06-23 2021-08-31 万华化学集团股份有限公司 Preparation method of beta-carotene with high all-trans content
WO2023099792A1 (en) * 2021-12-03 2023-06-08 Dsm Ip Assets B.V. Novel compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5908957A (en) * 1997-02-14 1999-06-01 Roche Vitamins Inc. Isomerization process

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10130606B2 (en) 2009-09-15 2018-11-20 Novelion Therapeutics Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
US10736865B2 (en) 2009-09-15 2020-08-11 Retinagenix Therapeutics, Inc. Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle
US9987245B2 (en) 2010-04-19 2018-06-05 Novelion Therapeutics Inc. Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
WO2011132084A2 (en) 2010-04-19 2011-10-27 Qlt Inc. Therapeutic regimen and method for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
US9173856B2 (en) 2010-04-19 2015-11-03 Qlt Inc. Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency
WO2013134867A1 (en) 2012-03-01 2013-09-19 Qlt Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency
US10828267B2 (en) 2012-03-01 2020-11-10 Retinagenix Therapeutics, Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency
CN111233726A (en) * 2020-03-26 2020-06-05 万华化学集团股份有限公司 Method for preparing all-trans vitamin A acetate
CN112358429A (en) * 2020-11-06 2021-02-12 万华化学集团股份有限公司 Heterogeneous catalyst, preparation method thereof and preparation method of all-trans vitamin A acetate
CN112358429B (en) * 2020-11-06 2023-05-02 万华化学集团股份有限公司 Heterogeneous catalyst and preparation method thereof, and preparation method of all-trans vitamin A acetate
CN113321604A (en) * 2021-06-23 2021-08-31 万华化学集团股份有限公司 Preparation method of beta-carotene with high all-trans content
CN113321604B (en) * 2021-06-23 2023-01-13 万华化学集团股份有限公司 Preparation method of beta-carotene
WO2023099792A1 (en) * 2021-12-03 2023-06-08 Dsm Ip Assets B.V. Novel compositions

Also Published As

Publication number Publication date
JPS5613712B2 (en) 1981-03-30
NL7411171A (en) 1975-02-25
ZA744737B (en) 1975-08-27
DE2439860C3 (en) 1980-01-17
NL176259B (en) 1984-10-16
AT355231B (en) 1980-02-25
FR2245626A1 (en) 1975-04-25
DE2439860B2 (en) 1979-05-23
ATA678474A (en) 1979-07-15
FR2245626B1 (en) 1978-11-10
CH590222A5 (en) 1977-07-29
NL176259C (en) 1985-03-18
BE819012A (en) 1975-02-20
IL45366A (en) 1979-05-31
SU731894A3 (en) 1980-04-30
JPS5049256A (en) 1975-05-01
DD114803A5 (en) 1975-08-20
IL45366A0 (en) 1974-10-22
DE2439860A1 (en) 1975-03-06
CS181769B2 (en) 1978-03-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee