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Practical synthesis of canthaxanthin

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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.

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Acknowledgements

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

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, 312000, Zhejiang, People’s Republic of China

    Shiqing Pi, Meiyang Xi, Liping Deng, Huiting Xu, Chengjie Feng, Runpu Shen & Chunlei Wu

  2. Zhejiang Medicine Co. Ltd, Xinchang Pharmaceutical Factory, Xinchang, 312500, Zhejiang, People’s Republic of China

    Shiqing Pi & Runpu Shen

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  1. Shiqing Pi
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  2. Meiyang Xi
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  7. Chunlei Wu
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Correspondence to Chunlei Wu.

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Pi, S., Xi, M., Deng, L. et al. Practical synthesis of canthaxanthin. J IRAN CHEM SOC 17, 493–497 (2020). https://doi.org/10.1007/s13738-019-01784-2

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