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Carotenoids with two chromophores: carotenoid retinoates.
Nat Prod Res. 2011 Mar; 25(5):511-25.NP

Abstract

In this study, carotenoid retinoates are described for the first time. The preparation was achieved by the azolide method. Various sec carotenols reacted with N-retinoylimidazol in the presence of catalytic amounts of sodium hydride. Mono- and diretinoates of (3R,3'R)-zeaxanthin and its (3S,3'S)-enantiomer, (9Z,9'Z; 3R,3'R)-alloxanthin, (3R,3'R)-7,8,7',8'-tetrahydro-3,3'-dihydroxy-β,β-carotene-8,8'-dione and (3R,6R,3'R,6'R)-ε,ε-carotene-3,3'-diol (lactucaxanthin), as well as monoretinoates of (3R,3'RS,6'R)-3'-methoxy-β,ε-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-β,ε-caroten-3'-ol, (2R,6'RS)-β,ε-caroten-2-ol, (3R,3'S; meso)-astaxanthin and (2'R)-aleuriaxanthin are reported in this study. Spectroscopic properties ((1)H-NMR mass spectrometry, visible and circular dichroism spectra) are discussed. Studies on other carotenoid derivatives with two chromophores are referred to here.

Authors+Show Affiliations

Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491, Trondheim, Norway.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21391114

Citation

Hertzberg, Sissel, et al. "Carotenoids With Two Chromophores: Carotenoid Retinoates." Natural Product Research, vol. 25, no. 5, 2011, pp. 511-25.
Hertzberg S, Lutnaes BF, Liaaen-Jensen S. Carotenoids with two chromophores: carotenoid retinoates. Nat Prod Res. 2011;25(5):511-25.
Hertzberg, S., Lutnaes, B. F., & Liaaen-Jensen, S. (2011). Carotenoids with two chromophores: carotenoid retinoates. Natural Product Research, 25(5), 511-25. https://doi.org/10.1080/14786419.2010.488629
Hertzberg S, Lutnaes BF, Liaaen-Jensen S. Carotenoids With Two Chromophores: Carotenoid Retinoates. Nat Prod Res. 2011;25(5):511-25. PubMed PMID: 21391114.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Carotenoids with two chromophores: carotenoid retinoates. AU - Hertzberg,Sissel, AU - Lutnaes,Bjart Frode, AU - Liaaen-Jensen,Synnøve, PY - 2011/3/11/entrez PY - 2011/3/11/pubmed PY - 2011/7/8/medline SP - 511 EP - 25 JF - Natural product research JO - Nat. Prod. Res. VL - 25 IS - 5 N2 - In this study, carotenoid retinoates are described for the first time. The preparation was achieved by the azolide method. Various sec carotenols reacted with N-retinoylimidazol in the presence of catalytic amounts of sodium hydride. Mono- and diretinoates of (3R,3'R)-zeaxanthin and its (3S,3'S)-enantiomer, (9Z,9'Z; 3R,3'R)-alloxanthin, (3R,3'R)-7,8,7',8'-tetrahydro-3,3'-dihydroxy-β,β-carotene-8,8'-dione and (3R,6R,3'R,6'R)-ε,ε-carotene-3,3'-diol (lactucaxanthin), as well as monoretinoates of (3R,3'RS,6'R)-3'-methoxy-β,ε-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-β,ε-caroten-3'-ol, (2R,6'RS)-β,ε-caroten-2-ol, (3R,3'S; meso)-astaxanthin and (2'R)-aleuriaxanthin are reported in this study. Spectroscopic properties ((1)H-NMR mass spectrometry, visible and circular dichroism spectra) are discussed. Studies on other carotenoid derivatives with two chromophores are referred to here. SN - 1478-6427 UR - https://www.unboundmedicine.com/medline/citation/21391114/Carotenoids_with_two_chromophores:_carotenoid_retinoates_ L2 - http://www.tandfonline.com/doi/full/10.1080/14786419.2010.488629 DB - PRIME DP - Unbound Medicine ER -