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Journal of the Iranian Chemical Society

, Volume 17, Issue 2, pp 493–497 | Cite as

Practical synthesis of canthaxanthin

  • Shiqing Pi
  • Meiyang Xi
  • Liping Deng
  • Huiting Xu
  • Chengjie Feng
  • Runpu Shen
  • Chunlei WuEmail author
Original Paper

Abstract

In this study, a novel route for the total synthesis of canthaxanthin is described. The synthesis is firstly based on an epoxidation of α-ionone with metachloroperbenzoic acid to afford the epoxide, followed by conversion of the epoxide to 3-hydroxyl-β-ionone in the presence of sodium methoxide. Next, 3-hydroxyl-C14-aldehyde was obtained by a Darzens condensation with 4-hydroxyl-β-ionone and methyl chloroacetate, which can be converted to 3-hydroxyl-C15-phophonate via a Wittig–Horner condensation with tetraethyl methylenebisphosphonate. Then, a Wittig–Horner condensation with 3-hydroxyl-C15-phosphonate and C10-trienedial resulted in 4,4′-dihydroxyl-β-carotene, followed by an oxidation afforded the target product canthaxanthin. The overall yield of this route is 37% from α-ionone. The synthetic steps are easily operated and are practical for the large-scale production.

Keywords

Canthaxanthin Wittig–Horner condensation Total synthesis Phosphonate 

Notes

Acknowledgements

This study was supported by the Public Projects of Zhejiang Province of China (No. LGG19B020002).

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Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  • Shiqing Pi
    • 1
    • 2
  • Meiyang Xi
    • 1
  • Liping Deng
    • 1
  • Huiting Xu
    • 1
  • Chengjie Feng
    • 1
  • Runpu Shen
    • 1
    • 2
  • Chunlei Wu
    • 1
    Email author
  1. 1.Department of Chemistry and Chemical EngineeringShaoxing UniversityShaoxingPeople’s Republic of China
  2. 2.Zhejiang Medicine Co. Ltd, Xinchang Pharmaceutical FactoryXinchangPeople’s Republic of China

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