(2R)-3,4-dihydroxy-2-[(4S)-2-undecyl-1,3-dioxolan-4-yl]-2H-furan-5-one | 69677-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2R)-3,4-dihydroxy-2-[(4S)-2-undecyl-1,3-dioxolan-4-yl]-2H-furan-5-one
• CAS: 69677-84-5
• 化学式: C₁₈H₃₀O₆
• 分子量: 342.433
• InChiKey: QKUPZRYITWPWAK-BHVXPOTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-3,4-dihydroxy-2-[(4S)-2-undecyl-1,3-dioxolan-4-yl]-2H-furan-5-one 、 一氯丙酮 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以25%的产率得到3-O-acetonyl-5,6-O-dodecylideneascorbic acid
  参考文献：
  名称：

  3-O-alkylascorbic acids as free radical quenchers. 3. Protective effect on coronary occlusion-reperfusion induced arrhythmias in anesthetized rats

  摘要：

  Structural modification of ascorbic acid by substitution of the 3-hydroxy group with lipophilic moieties has allowed the development of agents for treating reperfusion injury. These ascorbic acid derivatives inhibited lipid peroxidation, and some of them also reduced coronary reperfusion-induced arrhythmias in anesthetized rats. We found that 3-O-[(dodecylcarbonyl)methyl]ascorbic acid (8) was protective against reperfusion injury without directly influencing hemodynamics. 2-O-Octadecylascorbic acid (19) and 5,6-O-dodecylideneascorbic acid (15) also exhibited a marked effect on reperfusion injury, but significantly reduced the arterial blood pressure and heart rate in rats.

  DOI：

  10.1021/jm00087a017
• 作为产物：
  描述：

  十二醛 、 维生素 C 在 对甲苯磺酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以40%的产率得到(2R)-3,4-dihydroxy-2-[(4S)-2-undecyl-1,3-dioxolan-4-yl]-2H-furan-5-one
  参考文献：
  名称：

  3-O-alkylascorbic acids as free radical quenchers. 3. Protective effect on coronary occlusion-reperfusion induced arrhythmias in anesthetized rats

  摘要：

  Structural modification of ascorbic acid by substitution of the 3-hydroxy group with lipophilic moieties has allowed the development of agents for treating reperfusion injury. These ascorbic acid derivatives inhibited lipid peroxidation, and some of them also reduced coronary reperfusion-induced arrhythmias in anesthetized rats. We found that 3-O-[(dodecylcarbonyl)methyl]ascorbic acid (8) was protective against reperfusion injury without directly influencing hemodynamics. 2-O-Octadecylascorbic acid (19) and 5,6-O-dodecylideneascorbic acid (15) also exhibited a marked effect on reperfusion injury, but significantly reduced the arterial blood pressure and heart rate in rats.

  DOI：

  10.1021/jm00087a017

文献信息

• 3-O-alkylascorbic acids as free radical quenchers. 3. Protective effect on coronary occlusion-reperfusion induced arrhythmias in anesthetized rats
  作者：Yasunori Nihro、Satoshi Sogawa、Akihiro Izumi、Akihiro Sasamori、Tadamitsu Sudo、Tokutaro Miki、Hitoshi Matsumoto、Toshio Satoh

  DOI：10.1021/jm00087a017

  日期：1992.5

  Structural modification of ascorbic acid by substitution of the 3-hydroxy group with lipophilic moieties has allowed the development of agents for treating reperfusion injury. These ascorbic acid derivatives inhibited lipid peroxidation, and some of them also reduced coronary reperfusion-induced arrhythmias in anesthetized rats. We found that 3-O-[(dodecylcarbonyl)methyl]ascorbic acid (8) was protective against reperfusion injury without directly influencing hemodynamics. 2-O-Octadecylascorbic acid (19) and 5,6-O-dodecylideneascorbic acid (15) also exhibited a marked effect on reperfusion injury, but significantly reduced the arterial blood pressure and heart rate in rats.