(3R,3'R)-3,3'-dihydroxy-7,7',8,8'-tetrahydro-β,β-carotene-8,8'-dione | 143932-64-3

• 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: (3R,3'R)-3,3'-dihydroxy-7,7',8,8'-tetrahydro-β,β-carotene-8,8'-dione
• 英文别名: (3R,3R')-(All-E)-7,8,7',8'-Tetrahydrozeaxanthin-8,8'-dione；(3R,3'R)-3,3'-dihydroxy-7,8,7',8'-tetrahydro-β,β-carotene-8,8'-dione；(3E,5E,7E,9E,11E,13E,15E)-1,18-bis[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaene-2,17-dione
• CAS: 143932-64-3
• 化学式: C₄₀H₅₆O₄
• 分子量: 600.882
• InChiKey: HWESJFUZKHLTQV-XVRQVXECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(Vitamin-A-oyl)imidazol 、 (3R,3'R)-3,3'-dihydroxy-7,7',8,8'-tetrahydro-β,β-carotene-8,8'-dione 在 吡啶 、 sodium hydride 作用下， 反应 3.0h， 以35%的产率得到(3R,3'R)-3,3'-dihydroxy-7,8,7',8'-tetrahydro-β,β-carotene-8,8'-dione monoretinoate
  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

• Haugan, Jarle Andre; Englert, Gerhard; Liaaen-Jensen, Synnoeve, Acta Chemica Scandinavica, 1992, vol. 46, # 7, p. 614 - 624
  作者：Haugan, Jarle Andre、Englert, Gerhard、Liaaen-Jensen, Synnoeve

  DOI：——

  日期：——
• 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.