34026-74-9Relevant articles and documents
Carotenoids with two chromophores: Carotenoid retinoates
Hertzberg, Sissel,Lutnaes, Bjart Frode,Liaaen-Jensen, Synnove
experimental part, p. 511 - 525 (2011/05/12)
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 (1H-NMR mass spectrometry, visible and circular dichroism spectra) are discussed. Studies on other carotenoid derivatives with two chromophores are referred to here.
Animal carotenoids. 12. Chirality of asterinic acid.
Berger,Borch,Liaaen-Jensen
, p. 243 - 247 (2007/10/12)
The chirality of monoacetylenic asterinic acid [(3S,3'S)-7,8-didehydroastaxanthin, 1a] has been established by NaBH4-reduction and hydrolysis of the corresponding diesters 1b and 1c providing the tetrol 9 and CD-correlation with diatoxanthin [3R,3'R)-7,8-didehydro-beta, beta-carotene-3,3'-diol, 10]. Diacetylenic asterinic acid [3S,3'S)-7,8,7',8'-tetradehydro-beta, beta-carotene-3,3'-diol, 2a] was assigned the some absolute configuration by similar conversion to the diacetylenic tetrol 11 and CD-correlation with alloxanthin [3R,3'R)-7,8,7',8'-tetradehydro-beta, beta-carotene-3,3'-diol, 12]. IR and CD properties of the diacetates 1C and 2C of the naturally occurring alpha-ketols are reported.
