5,8-epidioxy-5,8-dihydroretinoic acid | 129454-96-2

• 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: 5,8-epidioxy-5,8-dihydroretinoic acid
• 英文别名: (2E,4E,6E)-7-(5,5,8a-trimethyl-3,6,7,8-tetrahydro-1,2-benzodioxin-3-yl)-3-methylocta-2,4,6-trienoic acid
• CAS: 129454-96-2
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: QCBHAKOQLSSZNZ-JUPVTLSTSA-N

物化性质

• 沸点：
  461.3±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  维A酸 在 air 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 all-trans-5,6-Epoxyretinoic acid 、 5,8-Monoepoxy-vitamin-A-saeure 、 5,8-epidioxy-5,8-dihydroretinoic acid 、 5-hydroxy-8-oxo-6,7-dihydroretinoic acid
  参考文献：
  名称：

  Superoxidation of Retinoic Acid†

  摘要：

  Atmospheric pressure chemical ionization mass spectroscopy (APCI-MS) was used to examine the light-induced oxidation products of retinoic acid under conditions that favor and preclude its aggregation. We observed that in conditions that favor aggregation, i.e. in aqueous solutions, retinoic acid undergoes superoxidation to yield highly oxidized species. Oxidation is limited, however, in the absence of such communication, i.e. when the polyene is fully solvated. From a comparison of the measured MS with that obtained from chemical oxidation of retinoic acid under conditions that promote radical oxidation and singlet oxygen-mediated oxidation, we conclude that superoxidation is mediated by reactive oxygen species other than singlet oxygen.

  DOI：

  10.1562/2006-02-28-ra-828

文献信息

• Characterizationf of autoxidation products of retinoic acid
  作者：A.R. Oyler、M.G. Motto、R.E. Naldi、K.L. Facchine、P.F. Hamburg、D.J. Burinsky、R. Dunphy、M.L. Cotter

  DOI：10.1016/s0040-4020(01)85785-9

  日期：——

  Retinoic acid underwent autoxidation in 90% ethanol at 25–85.5 °C to give epoxides, dioxetanes, an endoperoxide, and double-bond cleavage products. The majority of these products appear to have resulted from the initial direct oxidation of the olefinic carbons rather than from the expected allylic α oxidation process.

  视黄酸在25％至85.5°C的90％乙醇中进行自氧化，得到环氧化物，二氧环乙烷，内过氧化物和双键裂解产物。这些产物中的大多数似乎是由于烯烃碳的直接直接氧化而不是预期的烯丙基α氧化过程而产生的。
• Retinoic Acid Oxidation at High Oxygen Pressures:  Evidence for Spin-Forbidden Direct Addition of Triplet Molecular Oxygen¹
  作者：K. Brady Clark、J. A. Howard、Alan R. Oyler

  DOI：10.1021/ja970774o

  日期：1997.10.1
• Superoxidation of Retinoic Acid†
  作者：Ilyas Washington、Nicholas J. Turro、Koji Nakanishi

  DOI：10.1562/2006-02-28-ra-828

  日期：——

  Atmospheric pressure chemical ionization mass spectroscopy (APCI-MS) was used to examine the light-induced oxidation products of retinoic acid under conditions that favor and preclude its aggregation. We observed that in conditions that favor aggregation, i.e. in aqueous solutions, retinoic acid undergoes superoxidation to yield highly oxidized species. Oxidation is limited, however, in the absence of such communication, i.e. when the polyene is fully solvated. From a comparison of the measured MS with that obtained from chemical oxidation of retinoic acid under conditions that promote radical oxidation and singlet oxygen-mediated oxidation, we conclude that superoxidation is mediated by reactive oxygen species other than singlet oxygen.