WO2005056507A3 - Method for producing astaxanthin and canthaxanthin intermediate products - Google Patents

Method for producing astaxanthin and canthaxanthin intermediate products Download PDF

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Publication number
WO2005056507A3
WO2005056507A3 PCT/EP2004/014119 EP2004014119W WO2005056507A3 WO 2005056507 A3 WO2005056507 A3 WO 2005056507A3 EP 2004014119 W EP2004014119 W EP 2004014119W WO 2005056507 A3 WO2005056507 A3 WO 2005056507A3
Authority
WO
WIPO (PCT)
Prior art keywords
canthaxanthin
intermediate products
protective group
producing astaxanthin
represents hydrogen
Prior art date
Application number
PCT/EP2004/014119
Other languages
German (de)
French (fr)
Other versions
WO2005056507A2 (en
Inventor
Bernd Rumpf
Petra Deckert
Thomas Mueller
Johannes Grimmer
Original Assignee
Basf Ag
Bernd Rumpf
Petra Deckert
Thomas Mueller
Johannes Grimmer
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 Basf Ag, Bernd Rumpf, Petra Deckert, Thomas Mueller, Johannes Grimmer filed Critical Basf Ag
Priority to EP04803760A priority Critical patent/EP1718589A2/en
Publication of WO2005056507A2 publication Critical patent/WO2005056507A2/en
Publication of WO2005056507A3 publication Critical patent/WO2005056507A3/en

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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a method for producing cyclohexenone derivatives of general formula (I), wherein R1 represents hydrogen or OH; R2 represents (Ia), comprising the following steps: (a) hydrolyzing a cyclohexenol compound of formula (II), wherein R3 represents hydrogen and R4 represents C1-C6-alkoxy or R3 and R4 represent vicinal hydroxy groups, which carry a common acetal protective group or a ketone protective group, R5 represents (IIa), and R6 represents a protected hydroxy group, in the absence of an organic solvent and in the presence of an acid catalyst; and; (b) extracting the reaction mixture by using a polar extracting agent.
PCT/EP2004/014119 2003-12-11 2004-12-10 Method for producing astaxanthin and canthaxanthin intermediate products WO2005056507A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04803760A EP1718589A2 (en) 2003-12-11 2004-12-10 Method for producing astaxanthin and canthaxanthin intermediate products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10358003.4 2003-12-11
DE10358003A DE10358003A1 (en) 2003-12-11 2003-12-11 Process for the preparation of astaxanthin and canthaxanthin precursors

Publications (2)

Publication Number Publication Date
WO2005056507A2 WO2005056507A2 (en) 2005-06-23
WO2005056507A3 true WO2005056507A3 (en) 2006-12-21

Family

ID=34672598

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/014119 WO2005056507A2 (en) 2003-12-11 2004-12-10 Method for producing astaxanthin and canthaxanthin intermediate products

Country Status (3)

Country Link
EP (1) EP1718589A2 (en)
DE (1) DE10358003A1 (en)
WO (1) WO2005056507A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060167319A1 (en) 2004-10-01 2006-07-27 Lockwood Samuel F Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
WO2018015525A1 (en) * 2016-07-22 2018-01-25 Basf Se 6-hydroxy-3-[3-hydroxy-3-methyl-penta-1,4-dienyl]-2,4,4-trimethyl-cyclohexa-2,5-dien-1-one

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0633258A1 (en) * 1993-07-05 1995-01-11 BASF Aktiengesellschaft Improved process for the production of astaxanthin, new intermediates therefor and a process for their production

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0633258A1 (en) * 1993-07-05 1995-01-11 BASF Aktiengesellschaft Improved process for the production of astaxanthin, new intermediates therefor and a process for their production

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
A. ESCHENMOSER ET AL.: "Über eine Synthese des .delta. 8,14,12, 13-8,11-Dimethyl-1,7-dioxo-decahydro-phenanthrens", HELVETICA CHIMICA ACTA, vol. 36, 1953, pages 482 - 488, XP009047289 *
YUMIKO YAMANO ET AL.: "Carontenoids and related polyenes. Part 6. Stereoselective synthesis of astaxanthin analogues and their antioxidant activities", J. CHEM. SOC., PERKIN TRANS. 1, 2001, pages 1862 - 69, XP002328746 *

Also Published As

Publication number Publication date
DE10358003A1 (en) 2005-07-14
WO2005056507A2 (en) 2005-06-23
EP1718589A2 (en) 2006-11-08

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