34026-74-9Relevant academic research and scientific papers
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.
Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. V. Synthese von Astacin
Widmer, Erich,Lukac, Teodor,Bernhard, Kurt,Zell, Reinhard
, p. 671 - 683 (2007/10/02)
Starting from optically inactive astaxanthin intermediates, the highly oxygenated carotenoid astacene was synthesized in seven steps (55percent overall yield from 6-oxo-isophorone).Key features of the new approach are base- and acid-catalyzed rearrangements of acetylenic intermediates such as those described in Schemes 2, 7 and 8.
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.
