WO2007072529A3 - Process for the synthesis of intermediates for the preparation of astaxanthin - Google Patents

Process for the synthesis of intermediates for the preparation of astaxanthin Download PDF

Info

Publication number
WO2007072529A3
WO2007072529A3 PCT/IT2006/000835 IT2006000835W WO2007072529A3 WO 2007072529 A3 WO2007072529 A3 WO 2007072529A3 IT 2006000835 W IT2006000835 W IT 2006000835W WO 2007072529 A3 WO2007072529 A3 WO 2007072529A3
Authority
WO
WIPO (PCT)
Prior art keywords
oxo
astaxanthin
ionone
synthesis
preparation
Prior art date
Application number
PCT/IT2006/000835
Other languages
French (fr)
Other versions
WO2007072529A2 (en
Inventor
Negra Federico Della
Gabriella Santoni
Mariano Stivanello
Milan Soukup
Marco Fachini
Original Assignee
Italiana Sint Spa
Negra Federico Della
Gabriella Santoni
Mariano Stivanello
Milan Soukup
Marco Fachini
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 Italiana Sint Spa, Negra Federico Della, Gabriella Santoni, Mariano Stivanello, Milan Soukup, Marco Fachini filed Critical Italiana Sint Spa
Publication of WO2007072529A2 publication Critical patent/WO2007072529A2/en
Publication of WO2007072529A3 publication Critical patent/WO2007072529A3/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
    • C07C403/24—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
    • C07C403/04—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 halogen 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
    • C07C403/06—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
    • C07C403/14—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
    • 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 Table
    • 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
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a process for the preparation of intermediates useful in the synthesis of Astaxanthin, in particular C15-Wittig salts, but also 4-oxo-β-ionones, 3-hydroxy-4-oxo-β-ionones and the aryl esters thereof. 4-oxo-β-ionone is prepared by starting from a β-ionone by oxidation with bromates in the presence of iodine or iodide. 3-hydroxy-4-oxo-β-ionone is prepared in 4 steps, starting from 4 -oxo- β-ionone by oxidation with peracids; the aryl esters thereof are solids that are easily isolated and purified by crystallisation, and may be converted in 5 steps to C15-Wittig salts and finally, by the Wittig reaction, to Astaxanthin.
PCT/IT2006/000835 2005-12-23 2006-12-04 Process for the synthesis of intermediates for the preparation of astaxanthin WO2007072529A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI2005A002486 2005-12-23
IT002486A ITMI20052486A1 (en) 2005-12-23 2005-12-23 INTERMEDIATE SYNTHESIS PROCEDURE FOR THE PREPARATION OF ASTAXANTIN

Publications (2)

Publication Number Publication Date
WO2007072529A2 WO2007072529A2 (en) 2007-06-28
WO2007072529A3 true WO2007072529A3 (en) 2007-11-22

Family

ID=38006882

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IT2006/000835 WO2007072529A2 (en) 2005-12-23 2006-12-04 Process for the synthesis of intermediates for the preparation of astaxanthin

Country Status (3)

Country Link
AR (1) AR058750A1 (en)
IT (1) ITMI20052486A1 (en)
WO (1) WO2007072529A2 (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7759506B2 (en) 2002-02-25 2010-07-20 Diffusion Pharmaceuticals Llc Bipolar trans carotenoid salts and their uses
JP2005518453A (en) 2002-02-25 2005-06-23 ディフュージョン・ファーマシューティカルズ・エルエルシー Bipolar trans carotenoid salts and their use
EP2540696B1 (en) 2005-02-24 2020-01-01 Diffusion Pharmaceuticals LLC Trans carotenoids, formulation and uses
CA2703946A1 (en) 2007-10-31 2009-05-07 Diffusion Pharmaceuticals Llc A new class of therapeutics that enhance small molecule diffusion
CA2720243A1 (en) * 2008-05-30 2009-12-03 Dsm Ip Assets B.V. Crystal forms of astaxanthin
ES2401555T3 (en) * 2008-06-18 2013-04-22 Lexicon Pharmaceuticals, Inc. Solid forms of (1R, 2S, 3R) -1- (2- (isoxazol-3-yl) -1H-imidazol-4-yl) butane-1,2,3,4-tetraol and methods of use thereof
KR101875843B1 (en) 2009-06-22 2018-07-06 디퓨젼 파마슈티컬즈 엘엘씨 Diffusion enhancing compounds and their use alone or with thrombolytics
CN101805249B (en) * 2010-04-07 2012-12-19 湖南中烟工业有限责任公司 Method for synthesizing oxo-alpha-ionone or oxo-beta-ionone
AU2011262361A1 (en) 2010-06-02 2013-01-10 Diffusion Pharmaceuticals Llc Oral formulations of bipolar trans carotenoids
EP2776447B2 (en) 2011-11-09 2022-01-05 Basf Se Method for producing oxo-vinyl-ionol and o-protected derivatives thereof
US9061982B2 (en) 2011-11-09 2015-06-23 Basf Se Process for the preparation of oxovinylionol and its O-protected derivatives
US20130273619A1 (en) 2012-04-16 2013-10-17 Basf Se Process for the Preparation of (3E, 7E)-Homofarnesol
CN103245658B (en) * 2013-04-23 2015-07-29 山西省食品质量安全监督检验研究院 The method for quick of bromate in a kind of bread
WO2015067705A1 (en) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Process for the purification of astaxanthin
CN105705039B (en) * 2013-11-07 2019-11-19 帝斯曼知识产权资产管理有限公司 The method for purifying astaxanthin
EP3065566B1 (en) * 2013-11-07 2019-10-02 DSM IP Assets B.V. Process for the purification of astaxanthin
WO2015067706A1 (en) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Process for the purification of astaxanthin
WO2015067707A1 (en) * 2013-11-07 2015-05-14 Dsm Ip Assets B.V. Process for the purification of astaxanthin
US11185523B2 (en) 2016-03-24 2021-11-30 Diffusion Pharmaceuticals Llc Use of bipolar trans carotenoids with chemotherapy and radiotherapy for treatment of cancer
CN107739390B (en) * 2017-09-29 2019-08-20 上虞新和成生物化工有限公司 A kind of synthetic method of astaxanthin intermediate
CN109503545B (en) * 2018-11-30 2020-10-23 彩客化学(沧州)有限公司 Preparation method of 1, 4-cyclohexanedione monoethylene glycol ketal
CN111302925B (en) * 2020-03-16 2023-05-30 万华化学集团股份有限公司 Method for preparing cyclic alpha, beta-unsaturated ketone
CN112409155A (en) * 2020-10-28 2021-02-26 肇庆巨元生化有限公司 Preparation method of 4-oxo-beta-ionone
CN114940644B (en) * 2022-06-20 2024-04-09 万华化学集团股份有限公司 Crystallization method of 2, 7-dimethyl-2, 4, 6-octatriene-1, 8-dialdehyde

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BECHER E ET AL: "SYNTHESE VON ASTAXANTHIN AUS BETA-JONON. I. ERSCHLIESSUNG DER ENANTIOMEREN C15-WITTIGSALZE DURCH CHEMISCHE UND MIKROBIOLOGISCHE RACEMATSPALTUNG VON (PLUS OR MINUS)-3-ACETOXY-4-OXO-BETA-JONON SYNTHESIS OF ASTAXANTHIN FROM BETA-IONONE. I. A ROUTE TO THE E", HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 64, no. 7, 1981, pages 2419 - 2435, XP008052045, ISSN: 0018-019X *
KIM, TONG HEI ET AL: "Selective oxidation reaction at 3-position of .alpha.- and .beta.-ionones", CHEMISTRY EXPRESS , 6(2), 125-8 CODEN: CHEXEU; ISSN: 0911-9566, 1991, XP009084325 *

Also Published As

Publication number Publication date
AR058750A1 (en) 2008-02-20
ITMI20052486A1 (en) 2007-06-24
WO2007072529A2 (en) 2007-06-28

Similar Documents

Publication Publication Date Title
WO2007072529A3 (en) Process for the synthesis of intermediates for the preparation of astaxanthin
WO2009076142A3 (en) Processes for producing cycloalkylcarboxiamido-pyridine benzoic acids
WO2014089385A3 (en) Methods of synthesizing a prostacyclin analog
IL185493A0 (en) Methods for production of peptide derivatives
WO2008089984A3 (en) Process for the preparation of ezetimibe and derivatives thereof
WO2006127893A3 (en) Processes for production of 4-(biphenylyl)azetidin-2-one phosphonic acids
SG170729A1 (en) Processes and intermediates for preparing steric compounds
WO2010036329A3 (en) Process for making quinolone compounds
WO2009095933A3 (en) Improved and novel process for the preparation of bosentan
WO2007117591A3 (en) Total synthesis of salinosporamide a and analogs thereof
WO2009120774A8 (en) Method of preparing huperzine a and derivatives thereof
CY1111690T1 (en) METHOD FOR PREPARING DRPSPIRENONE
WO2009134531A3 (en) Total synthesis of salinosporamide a and analogs thereof
WO2007003200A3 (en) High yield synthesis methods for producing organic salts of strontium
NO20075829L (en) synthesis
EA201201666A1 (en) INTERMEDIATE COMPOUNDS AGOMELATIN AND METHOD OF THEIR OBTAINING
WO2006122020A3 (en) Process for production of 4-biphenylyazetidin-2-ones
WO2007013043A3 (en) Processes for the preparation of 7-amino-3-vinyl cephalosporanic acid
WO2011157388A8 (en) Process for the preparation of pteridine derivatives
WO2008090819A1 (en) Process for production of bicyclic proline compound
WO2005063731A3 (en) Production of dihydronepetalactone by reduction of nepetalic acid
DK1770082T3 (en) Process for the preparation of sorbitan fatty acid esters
WO2007070238A3 (en) Processes for the preparation of modafinil and analogs thereof
WO2007041273A3 (en) Process for the production of intermediates for making prostaglandin derivatives such as latanoprost, travaprost, and bimatoprost
WO2014133291A9 (en) Method for preparing (2rs)-amino-(3s)-hydroxy-butyric acid or derivative thereof

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06832350

Country of ref document: EP

Kind code of ref document: A2