(5Z,8Z,11Z,13E,15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt | 339046-14-9

• 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: (5Z,8Z,11Z,13E,15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt
• 英文别名: 15(S)-HETE Na salt；Icomucret sodium；sodium;(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoate
• CAS: 339046-14-9
• 化学式: C₂₀H₃₁O₃*Na
• 分子量: 342.454
• InChiKey: RQVLCLFGGVMPGP-OMIIFBLASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (15S,5Z,8Z,11Z,13E)-15-羟基二十碳四烯酸 在 水 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以98%的产率得到(5Z,8Z,11Z,13E,15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt
  参考文献：
  名称：

  Manufacture of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic Acid Sodium Salt for Clinical Trials

  摘要：

  A robust synthesis of (5Z,8Z,11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15(S)-HETE) sodium salt was established, utilising a biooxidalion process. Treatment of arachidonic acid with soybean lipoxidase in 0.1 M sodium tetraborate buffer under oxygen pressure resulted in formation of the hydroperoxide, 15(S)HPETE. Addition of sodium borohydride to the reaction mixture reduced the hydroperoxide to 15(S)-HETE, which was then purified by column chromatography. 15(S)-HETE sodium salt was prepared by treatment of an ethanol solution of HETE with aqueous sodium hydrogen carbonate. Multiple 10-g batches of 15(S)-HETE sodium salt with >98% enantiomeric excess and >98% chemical purity were prepared to support clinical trials.

  DOI：

  10.1021/op100244n

文献信息

• Manufacture of (5<i>Z</i>,8<i>Z</i>,11<i>Z</i>,13<i>E</i>)(15<i>S</i>)-15-Hydroxyeicosa-5,8,11,13-tetraenoic Acid Sodium Salt for Clinical Trials
  作者：Raymond E. Conrow、Paul Harrison、Mark Jackson、Shaun Jones、Christel Kronig、Ian C. Lennon、Shaun Simmonds

  DOI：10.1021/op100244n

  日期：2011.1.21

  A robust synthesis of (5Z,8Z,11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15(S)-HETE) sodium salt was established, utilising a biooxidalion process. Treatment of arachidonic acid with soybean lipoxidase in 0.1 M sodium tetraborate buffer under oxygen pressure resulted in formation of the hydroperoxide, 15(S)HPETE. Addition of sodium borohydride to the reaction mixture reduced the hydroperoxide to 15(S)-HETE, which was then purified by column chromatography. 15(S)-HETE sodium salt was prepared by treatment of an ethanol solution of HETE with aqueous sodium hydrogen carbonate. Multiple 10-g batches of 15(S)-HETE sodium salt with >98% enantiomeric excess and >98% chemical purity were prepared to support clinical trials.