GB924255A - A process for the manufacture of carotenoid compounds and novel carotenoid compounds - Google Patents

A process for the manufacture of carotenoid compounds and novel carotenoid compounds

Info

Publication number
GB924255A
GB924255A GB40024/59A GB4002459A GB924255A GB 924255 A GB924255 A GB 924255A GB 40024/59 A GB40024/59 A GB 40024/59A GB 4002459 A GB4002459 A GB 4002459A GB 924255 A GB924255 A GB 924255A
Authority
GB
United Kingdom
Prior art keywords
keto
group
compounds
ketalisation
trimethyl
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
GB40024/59A
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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
Priority to NL258405D priority Critical patent/NL258405A/xx
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB40024/59A priority patent/GB924255A/en
Priority to CH1266160A priority patent/CH403746A/en
Priority to US70131A priority patent/US3180892A/en
Priority to BE597269A priority patent/BE597269A/en
Priority to FR844593A priority patent/FR1338854A/en
Priority to DK468260AA priority patent/DK103182C/en
Publication of GB924255A publication Critical patent/GB924255A/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
    • C07C403/14—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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S426/00—Food or edible material: processes, compositions, and products
    • Y10S426/807—Poultry or ruminant feed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises carotenoids (excepting capsorubin and capsanthin) and dehydrocarotenoids of formula (I) where R is a 1:2:2-trimethylcyclopentyl group which may contain a hydroxy or keto substituent in the 3- or 4-position and the broken line denotes optional bonds. A process for the manufacture of <FORM:0924255/IV(a)/1> <FORM:0924255/IV(a)/2> <FORM:0924255/IV(a)/3> compounds of formula (I) comprises condensing a polyen(yn)-al or -dial of formulae (II) or (III), in which any keto group in the cyclohexenyl radical may be protected by ketalisation, under alkaline conditions with 1-acetyl-1:2:2-trimethylcyclopentane or a 3-or 4-hydroxy or keto derivative thereof (in which the keto group may be protected by ketalisation); any triple bond in the product may be hydrogenated to a double bond (e.g. with Pd/Pb/CaCO3 catalyst) and any protecting group is then hydrolysed. The condensation may be carried out in presence of an alcoholic solution of alkali-metal hydroxide. In an example, 1-acetyl-1.2.2.-trimethyl-cyclopentane is condensed with crocetindial in an ethanolic solution of KOH to form 1.20-di-(11.21.21-trimethyl-cyclopentyl) 4.8.13.17- tetramethyleicosanonaene-(2.4.6. 8.10.12.14.16.18)-dione-(1.20). Other examples are given. These compounds are highly coloured and they may be used for colouring foodstuffs. Specification 924,257 is referred to.
GB40024/59A 1959-11-25 1959-11-25 A process for the manufacture of carotenoid compounds and novel carotenoid compounds Expired GB924255A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL258405D NL258405A (en) 1959-11-25
GB40024/59A GB924255A (en) 1959-11-25 1959-11-25 A process for the manufacture of carotenoid compounds and novel carotenoid compounds
CH1266160A CH403746A (en) 1959-11-25 1960-11-11 Process for the production of carotenoids
US70131A US3180892A (en) 1959-11-25 1960-11-18 Carotenoid compounds
BE597269A BE597269A (en) 1959-11-25 1960-11-21 Process for the preparation of carotenoid
FR844593A FR1338854A (en) 1959-11-25 1960-11-22 Process for the preparation of carotenoids
DK468260AA DK103182C (en) 1959-11-25 1960-11-24 Process for the production of carotenoids.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB40024/59A GB924255A (en) 1959-11-25 1959-11-25 A process for the manufacture of carotenoid compounds and novel carotenoid compounds

Publications (1)

Publication Number Publication Date
GB924255A true GB924255A (en) 1963-04-24

Family

ID=10412789

Family Applications (1)

Application Number Title Priority Date Filing Date
GB40024/59A Expired GB924255A (en) 1959-11-25 1959-11-25 A process for the manufacture of carotenoid compounds and novel carotenoid compounds

Country Status (6)

Country Link
US (1) US3180892A (en)
BE (1) BE597269A (en)
CH (1) CH403746A (en)
DK (1) DK103182C (en)
GB (1) GB924255A (en)
NL (1) NL258405A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9133082B2 (en) * 2011-06-14 2015-09-15 Bikam Pharmaceuticals, Inc. Opsin-binding ligands, compositions and methods of use

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676988A (en) * 1951-09-11 1954-04-27 Eastman Kodak Co Method of making vitamin a and intermediates formed thereby
US2815379A (en) * 1954-09-13 1957-12-03 Hoffmann La Roche Alicyclic ketone and intermediates for the preparation thereof

Also Published As

Publication number Publication date
BE597269A (en) 1961-05-23
US3180892A (en) 1965-04-27
CH403746A (en) 1965-12-15
DK103182C (en) 1965-11-29
NL258405A (en) 1900-01-01

Similar Documents

Publication Publication Date Title
GB723079A (en) 1,4-diamino-2, 3-anthraquinone-dicarboximides
Barton et al. 29. Photochemical transformations. Part II. The constitution of lumisantonin
GB1247370A (en) Glyoxals and production thereof
Berson et al. The Action of Acetic Anhydride on 4-Methylpyridine-N-oxide1
Harborne et al. Anthochlor pigments. XII. Maritimein and marein
GB924255A (en) A process for the manufacture of carotenoid compounds and novel carotenoid compounds
SU515450A3 (en) The method of producing pyrido (3,2-) pyrimidine derivatives
Abe Substituent effects on the ultraviolet absorption spectrum of 1, 3, 5-trinitrobenzene in some solvents
US2859222A (en) 7alpha-acylthio substitution products of 4-androsten-3-ones
GB733650A (en) Isophorone and its homologues
Berson et al. The Reaction of Ketene with Pyridine1
Abe 4-Phenyl-quinol and its Innermolecular Rearrangements
GB571340A (en) Improvements in or relating to dicyandiamide salts and methods of preparing same
US2369168A (en) Synthesis of vitamin a
Birch et al. 594. Anthelmintics: kousso. Part II. The structures of protokosin, α-kosin, and β-kosin
GRAY Reductive Alkylation of Indole with Pyridinecarboxaldehydes
Wechter et al. 11-Alkylated Steroids. IV. 1 Synthesis and Reactions of Olefins Derived from 11β-Hydroxy-11-methyl-5β-pregnane-3, 20-dione
US2731474A (en) Hydroxytetrahydrocarbazoles
Achmatowicz et al. Photochemical transformations. Part XXX. Photolysis of thiobenzoic acid O-esters. Part I. Photolysis of O-cholesteryl thiobenzoate
Bailey et al. The constitution of conessine. Part VII. Degradation of some reduced quinoline and indole bases
Tanaka et al. The Chemical Constitution of Rubrofusarin: Part II. Alkaline Degradation Studies
GB1421942A (en) 2-3-methyl-1-acetoxy-4-alkoxy-phenoxy-1,3-butadiens and their manufacture and use
GB1065716A (en) Tetracycline derivatives and process for their preparation
GB818724A (en) Hydantoin derivatives
US2431911A (en) Amido naphthol ethers