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Nat Prod Res ; 25(5): 511-25, 2011 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-21391114

RESUMO

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-ß,ß-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-ß,ε-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-ß,ε-caroten-3'-ol, (2R,6'RS)-ß,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.


Assuntos
Carotenoides/química , Tretinoína/química , Antioxidantes/química , Dicroísmo Circular , Dicicloexilcarbodi-Imida , Esterificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Compostos de Sódio
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