L-3-O-benzoylmethylascorbic acid | 26633-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-3-O-benzoylmethylascorbic acid
• 英文别名: (2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-phenacyloxy-2H-furan-5-one
• CAS: 26633-25-0
• 化学式: C₁₄H₁₄O₇
• 分子量: 294.261
• InChiKey: XFLYVKFIYYXLAL-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 盐酸 、 碳酸氢钠 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 L-3-O-benzoylmethylascorbic 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

文献信息

• Ascorbic acid derivative
  申请人：NIPPON HYPOX LABORATORIES INCORPORATED

  公开号：EP0411184B1

  公开（公告）日：1993-12-29
• US5061812A
  申请人：——

  公开号：US5061812A

  公开（公告）日：1991-10-29
• US5143648A
  申请人：——

  公开号：US5143648A

  公开（公告）日：1992-09-01
• 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.