Skip to content

Research at St Andrews

Identification of products from canthaxanthin oxidation

Research output: Contribution to journalArticle

DOI

Open Access permissions

Open

Author(s)

Raphael C. Mordi, John Christopher Walton

School/Research organisations

Abstract

Canthaxanthin is a carotenoid that lacks pro-vitamin A activity but is known to have antioxidant activity. The products of its oxidation in oxygen were found to be mainly substituted apo-carotenals and apo-carotenones. The product profile resembles that obtained in the oxidation of β-carotene, except that with canthaxanthin these products are the 4-oxo-β-apo-carotenals and 4-oxo-β-apo-carotenones. Epoxides and diepoxides were clearly identified from β-carotene oxidation but in contrast, with canthaxanthin, apart from 5,6-epoxy-canthaxanthin, which was detected at the early stage of oxidation and minor quantities of 5,6-epoxy-β-ionone and 5,6-epoxy-4-oxo-β-apo-11-carotenal, no other epoxides were detected. The identities of these products lead us to suggest that the mechanism of canthaxanthin oxidation bears significant similarity to that of β-carotene.
Close

Details

Original languageEnglish
Pages (from-to)836-840
Number of pages5
JournalFood Chemistry
Volume197
Issue numberPart A
Early online date12 Nov 2015
DOIs
StatePublished - 15 Apr 2016

    Research areas

  • Canthaxanthin, β-Carotene, Carotenoids, Oxidation, Antioxidant, Apo-Carotenoids

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study

    Yeh, P-P., Taylor, J. E., Stark, D. G., Daniels, D. S. B., Fallan, C., Walton, J. C. & Smith, A. D. 16 Oct 2017 In : Organic & Biomolecular Chemistry. In press

    Research output: Contribution to journalArticle

  2. A valuable upgrade to the portfolio of cycloaddition reactions

    Walton, J. C. 9 Jun 2016 In : Angewandte Chemie International Edition. 55, 25, p. 7034-7036 3 p.

    Research output: Contribution to journalArticle

  3. Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals

    Walton, J. C. 18 May 2016 In : Molecules. 21, 5

    Research output: Contribution to journalReview article

  4. Functionalised oximes: emergent precursors for carbon-, nitrogen- and oxygen-centred radicals

    Walton, J. C. 7 Jan 2016 In : Molecules. 21, 1, 23 p., 63

    Research output: Contribution to journalReview article

  5. Bicarbonate and alkyl carbonate radicals: structural integrity and reactions with lipid components

    Buehl, M., DaBell, P., Manley, D., McCaughan, R. & Walton, J. C. 30 Dec 2015 In : Journal of the American Chemical Society. 137, 51, p. 16153–16162

    Research output: Contribution to journalArticle

Related by journal

  1. Structural elucidation of olive pomace fed sea bass (Dicentrarchus labrax) polar lipids with cardioprotective activities

    Nasopoulou, C., Smith, T., Detopoulou, M., Tsikrika, C., Papaharisis, L., Barkas, D. & Zabetakis, I. 15 Feb 2014 In : Food Chemistry. 145, p. 1097-1105 9 p.

    Research output: Contribution to journalArticle

  2. Hemocyanin-derived phenoloxidase activity: A contributing factor to hyperpigmentation in Nephrops norvegicus

    Coates, C. J. & Nairn, J. 15 Sep 2013 In : Food Chemistry. 140, 1-2, p. 361-369 9 p.

    Research output: Contribution to journalArticle

ID: 230675566