2-O-benzyl-3-O-acetonylascorbic acid | 139870-22-7

• 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: 2-O-benzyl-3-O-acetonylascorbic acid
• 英文别名: (2R)-2-[(1S)-1,2-dihydroxyethyl]-3-(2-oxopropoxy)-4-phenylmethoxy-2H-furan-5-one
• CAS: 139870-22-7
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: DFHHMJIKXFLIMY-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-O-benzyl-3-O-acetonylascorbic acid 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 4.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 3-O-acetonyl-6-O-palmitoylascorbic 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：

  3-O-acetonyl-5,6-O-isopropylideneascorbic acid 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 2-O-benzyl-3-O-acetonylascorbic 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