4-hydroxy-2-nonanal diethyl acetal | 161017-71-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-2-nonanal diethyl acetal
• 英文别名: 1,1-diethoxynonan-4-ol
• CAS: 161017-71-6
• 化学式: C₁₃H₂₈O₃
• 分子量: 232.364
• InChiKey: ONPVRKWVVWPMBF-UHFFFAOYSA-N

物化性质

• 沸点：
  305.742±32.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.914±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  16.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-nonanal diethyl acetal 在 磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 cis-2-ethoxy-5-pentyltetrahydrofuran 、 (2S,5R)-2-ethoxy-5-pentyltetrahydrofuran
  参考文献：
  名称：

  Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization

  摘要：

  The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.

  DOI：

  10.1021/ja108642s
• 作为产物：
  描述：

  4-hydroxy-trans-non-2-enal diethylacetal 在 platinum(II) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-hydroxy-2-nonanal diethyl acetal
  参考文献：
  名称：

  NADP+-dependent dehydrogenase activity of carbonyl reductase on glutathionylhydroxynonanal as a new pathway for hydroxynonenal detoxification

  摘要：

  An NADP(+) -dependent dehydrogenase activity on 3-glutathiony1-4-hydroxynonanal (GSHNE) was purified to electrophoretic homogeneity from a line of human astrocytoma cells (ADF). Proteomic analysis identified this enzymatic activity as associated with carbonyl reductase 1 (EC 1.1.1.184). The enzyme is highly efficient at catalyzing the oxidation of GSHNE (K-M 33 mu M, k(cat) 405 min(-1)), as it is practically inactive toward trans-4-hydroxy-2-nonenal (HNE) and other HNE-adducted thiol-containing amino acid derivatives. Combined mass spectrometry and nuclear magnetic resonance spectroscopy analysis of the reaction products revealed that carbonyl reductase oxidizes the hydroxyl group of GSHNE in its hemiacetal form, with the formation of the corresponding 3-glutathionylnonanoic-delta-lactone. The relevance of this new reaction catalyzed by carbonyl reductase 1 is discussed in terms of HNE detoxification and the recovery of reducing power. (C) 2015 Published by Elsevier Inc.

  DOI：

  10.1016/j.freeradbiomed.2015.02.001