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Issue 21, 1975
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Carotenoids and related compounds. Part XXXII. Synthesis of astaxanthin, phoenicoxanthin, hydroxyechinenone, and the corresponding diosphenols

Abstract

Autoxidation of 4-oxo-carotenoids in the presence of potassium t-butoxide gives the corresponding diosphenols (3,4-didehydro-3-hydroxy-4-ones). These on reduction with potassium borohydride give the 3,4-dihydroxycompounds which, on carefully controlled oxidation, yield the 3-hydroxy-4-ones.

Astaxanthin (3,3′-dihydroxy-ββ-carotene-4,4′-dione), phoenicoxanthin (3-hydroxy-β,β-carotene-4,4′-dione), and hydroxyechinenone (3-hydroxy-β,β-caroten-4-one) have been synthesised in this way from canthaxanthin (β,β-carotene-4,4′-dione), echinenone (β,β-caroten-4-one), and their 15,15′-acetylenic analogues.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1975, 2195-2204
Article type
Paper

Carotenoids and related compounds. Part XXXII. Synthesis of astaxanthin, phoenicoxanthin, hydroxyechinenone, and the corresponding diosphenols

R. D. G. Cooper, J. B. Davis, A. P. Leftwick, C. Price and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 1975, 2195
DOI: 10.1039/P19750002195

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