7-cis-retinal | 24315-14-8

• 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: 7-cis-retinal
• 英文别名: (2E,4E,6E,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
• CAS: 24315-14-8
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: NCYCYZXNIZJOKI-LYJDTWPQSA-N

物化性质

• 沸点：
  421.4±14.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-cis-retinal 生成 视黄醛
  参考文献：
  名称：

  三重态下视网膜的构型变化：7-顺式，11-顺式和13-顺式异构体的皮秒时间分辨吸收光谱和光致异构化的高效液相色谱分析

  摘要：

  DOI：

  10.1021/j100327a018
• 作为产物：
  描述：

  维生素A 在 manganese(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 7-cis-retinal
  参考文献：
  名称：

  Selective isomerization of retinal upon two-photon excitation

  摘要：

  The products of photo-isomerization when excited directly up to the two-photon-allowed (1)A(g)(-) excited state of alltrans and five cis isomers of retinal were determined. The composition of the isomers at the photo-stationary state was drastically changed as compared to one-photon excitation. The production of the 13-cis isomer was selectively increased, and the production of the dicis isomers was observed in the case of a direct excitation upon the 3(1)A(g)(-) state, although they were hard to be produced by one-photon excitation in n-hexane solution. These results clearly evidenced that there exist isomerization pathways via two-photon-allowed excited states. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0009-2614(02)02034-1

文献信息

• Photoisomerization of polyenes. 30. Quantum chain processes in photoisomerization of the all-trans, 7-cis, and 11-cis isomers of retinal.
  作者：Srinivasan Ganapathy、Robert S. H. Liu

  DOI：10.1021/ja00035a045

  日期：1992.4

  in the photoisomerization of retinal isomers (all-trans, 7-cis, and 11-cis) are reflected in the dependence of quantum yield of isomerization on concentration of retinal (to values exceeding unity), the presence of one-photon multiple-bond isomerization, and changes of product distribution on retinal concentration. The processes are believed to take place exclusively from the triplet states. Reaction

  视黄醛异构体（全反式、7-顺式和 11-顺式）光异构化中的量子链过程反映在异构化的量子产率对视黄醛浓度（超过统一的值）、单光子的存在的依赖性多键异构化，以及产物分布对视网膜浓度的变化。据信，这些过程仅从三重态发生。涉及参与量子链过程的 12-(S)-顺式构象异构体的反应方案已被改进以解释所有结果
• Photoisomerization of the C15-aldehyde and the C18-ketone in the vitamin a series. Solvent effect on photoisomerization of compounds related to retinal
  作者：V. Ramamurthy、M. Denny、R.S.H. Liu

  DOI：10.1016/s0040-4039(01)92933-8

  日期：1981.1

  The directions of photoisomerization of polyenals and polyenones are believed to be controlled by the relative ordering of the n,π* and π, πa* states.

  认为多烯和多烯的光异构化的方向受n，π *和π，πa *状态的相对顺序控制。
• Seven new hindered isomeric rhodopsins
  作者：Liu S.H. Robert、Hiroyuki Matsumoto、Aravinda Kini、Alfred E. Asato、Marlene Denny、Allen Kropf、Willem J. DeGrip

  DOI：10.1016/0040-4020(84)85052-8

  日期：1984.1

  11-dicis 7,9,11-tricis 7,9,13-tricis) with bovine opsin are reported. All of them form pigments with absorption maxima varying between 450 and 480 nm. The rates of pigment formation were generally considerably lower than those of 11-cis-retinal and the yields were less than quantitative. Implications of these results for the stereospecificity of the binding site of opsin are discussed.

  视网膜7新的几何异构体的相互作用的结果（7-顺，7,9- dicis ; 7,11- dicis，7,13- dicis ; 9,11- dicis 7,9,11- tricis 7,9,13 - tricis）与牛视报告。它们全部形成最大吸收在450至480nm之间变化的颜料。色素形成的速率通常大大低于11-顺-视网膜的速率，并且产率低于定量。讨论了这些结果对视蛋白结合位点的立体特异性的影响。
• Photoisomerization of 7-cis-retinal. The concentration effect
  作者：S. Ganapathy、A. Trehan、R. S. H. Liu

  DOI：10.1039/c39900000199

  日期：——

  A Triplet quantum chain process is believed to be responsible for the concentration dependent quantum yield of omerization of 7-cis-retinal.

  据信三重态量子链过程负责7-顺-视黄醛的聚合的浓度依赖性量子产率。
• A Model Study of Rhodopsin Regeneration in Visual Cell. Photoisomerization of all-trans Retinal in Phosphatidylcholine Vesicles
  作者：Hiroshi Tanie、Katsunori Ohba、Minoru Sakurai、Yoshio Inoue、Riichiro Chûjô

  DOI：10.1246/bcsj.62.2589

  日期：1989.8

  photochemical behavior has been investigated for all-trans retinal in egg york phosphatidylcholine(EPC) vesicles and dipalmitoylphosphatidylcholine (DPPC) vesicles. In EPC vesicles, 10% of all-trans isomer is isomerized to 11-cis one upon direct irradiation of 15 W-fluorescence light for 180 min. In organic solvents the photoisomerization of all-trans isomer is induced depending on the dielectric constant

  研究了全反式视黄醛在蛋黄磷脂酰胆碱 (EPC) 囊泡和二棕榈酰磷脂酰胆碱 (DPPC) 囊泡中的光化学行为。在 EPC 囊泡中，在 15 W 荧光灯直接照射 180 分钟后，10% 的全反式异构体异构化为 11-顺式异构体。在有机溶剂中，全反式异构体的光异构化取决于溶剂的介电常数。EPC 囊泡中视黄醛异构体的分布类似于在极性较小的溶剂（如乙醚）中获得的分布。在高于和低于 Tc 的 DPPC 囊泡中视网膜异构体的分布之间没有发现显着差异。