Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491, Trondheim, Norway.
Nat Prod Res. 2011 Mar;25(5):511-25. doi: 10.1080/14786419.2010.488629.
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.
本文首次描述了类胡萝卜素视黄酸酯。该制备方法通过氮唑环法实现。各种 sec 类胡萝卜醇在催化量的氢化钠存在下与 N-视黄酰基咪唑反应。（3R,3'R）-玉米黄质及其（3S,3'S）-对映体、（9Z,9'Z; 3R,3'R）-全氧黄质、（3R,3'R）-7,8,7',8'-四氢-3,3'-二羟基-β,β-胡萝卜素-8,8'-二酮和（3R,6R,3'R,6'R）-ε,ε-胡萝卜素-3,3'-二醇（乳黄素）的单和二视黄酸酯，以及（3R,3'RS,6'R）-3'-甲氧基-β,ε-胡萝卜素-3-醇、（3R,3'RS,6'R）-3-甲氧基-β,ε-胡萝卜素-3'-醇、（2R,6'RS）-β,ε-胡萝卜醇、（3R,3'S; 内消旋）-虾青素和（2'R）-Aleuriaxanthin 的单视黄酸酯也在本研究中报道。讨论了光谱性质（1H-NMR 质谱、可见和圆二色谱）。这里还提到了其他具有两个生色团的类胡萝卜素衍生物的研究。
