O-retinoyl-N-cyclohexyl-N'-cyclohexyl isourea | 1290540-12-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: O-retinoyl-N-cyclohexyl-N'-cyclohexyl isourea
• 英文别名: (N,N'-dicyclohexylcarbamimidoyl) (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• CAS: 1290540-12-3
• 化学式: C₃₃H₅₀N₂O₂
• 分子量: 506.772
• InChiKey: JFWVRMGJEUJMNS-PIWGTPRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  维A酸 、 N,N'-二环己基碳二亚胺 以 四氢呋喃 为溶剂， 以54%的产率得到O-retinoyl-N-cyclohexyl-N'-cyclohexyl isourea
  参考文献：
  名称：

  Carotenoids with two chromophores: carotenoid retinoates

  摘要：

  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-,-carotene-8,8'-dione and (3R,6R,3'R,6'R)-epsilon,epsilon-carotene-3,3'-diol (lactucaxanthin), as well as monoretinoates of (3R,3'RS,6'R)-3'-methoxy-,epsilon-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-,epsilon-caroten-3'-ol, (2R,6'RS)-,epsilon-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.

  DOI：

  10.1080/14786419.2010.488629

文献信息

• Carotenoids with two chromophores: carotenoid retinoates
  作者：Sissel Hertzberg、Bjart Frode Lutnaes、Synnøve Liaaen-Jensen

  DOI：10.1080/14786419.2010.488629

  日期：2011.3

  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-,-carotene-8,8'-dione and (3R,6R,3'R,6'R)-epsilon,epsilon-carotene-3,3'-diol (lactucaxanthin), as well as monoretinoates of (3R,3'RS,6'R)-3'-methoxy-,epsilon-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-,epsilon-caroten-3'-ol, (2R,6'RS)-,epsilon-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.