(+)-(R)-all-trans-4-hydroxyretinal | 160397-99-9

• 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: (+)-(R)-all-trans-4-hydroxyretinal
• 英文别名: (all-E)-(4R)-4-Hydroxyretinal；(2E,4E,6E,8E)-9-[(3R)-3-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal
• CAS: 160397-99-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: CYVVUYORRQQAQE-WQKURRJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  all-trans-4-acetoxyretinol 在 吡啶 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (+)-(R)-all-trans-4-hydroxyretinal
  参考文献：
  名称：

  Synthesis of enantiopure C₃- and C₄-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

  摘要：

  (R)-全反式-3-羟基视黄醛 1、(S)-全反式-4-羟基视黄醛 3 和(R)-全反式-4-羟基视黄醛 5 是通过 Horner-Wadsworth-Emmons 和 Stille 交叉偶联作为成键反应立体选择性合成的。在对映体分离步骤中采用了 CBS 酮还原法，为 4-羟基视黄醛对映体的合成提供了前体。已测定了爪蟾 ADH8 与这些视黄酸的动力学常数。

  DOI：

  10.1039/b514273c

文献信息

• Retinoids and Related Compounds. Part 16. Synthesis of (+)-(4S)- and (-)-(4R)-(11Z)-4-Hydroxyretinals and Determination of the Absolute Stereochemistry of a Visual Pigment Chromophore in the Firefly Squid, Watasenia scintillans
  作者：Yuko Katsuta、Masayoshi Ito、Kazuo Yoshihara、Koji Nakanishi、Takahiro Kikkawa、Takaji Fujiwara

  DOI：10.1021/jo00102a014

  日期：1994.11

  First syntheses of(+)-(4S)- and (-)-(4R)-(11Z)-4-hydroxyretinals (4-OH-RALs) (4a and 4b) were accomplished from (4S)- and (4R)-4-hydroxy-beta-ionones, respectively, to determine the absolute configuration of a visual pigment chromophore in Watasenia scintillans, which has been isolated as a new chromophore in the animal kingdom. The CD spectra of the native chromophore and its anti-oxime agreed with those of synthetic (4R)-compounds. Application of the CD exciton chirality method to the p-(dimethylamino)cinnamate of (4R)-4-OH-RAL also established the absolute configuration of the native chromophore as 4b.