(10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester | 167697-50-9

• 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: (10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester
• 英文别名: methyl (5Z,8Z,10S,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoate
• CAS: 167697-50-9
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: XPCFQAJJTWHWSW-VEMWUNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester 在 lithium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以43%的产率得到(10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid
  参考文献：
  名称：

  Synthesis of 10(S)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid

  摘要：

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.

  DOI：

  10.1021/jo951061w
• 作为产物：
  描述：

  (Z)[7-(methoxycarbonyl)-3-heptenyl]triphenylphosphonium bromide 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 生成 (10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 10(S)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid

  摘要：

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.

  DOI：

  10.1021/jo951061w

文献信息

• Synthesis of 10(<i>S</i>)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid
  作者：Suresh N. Yeola、Samir A. Saleh、Alan R. Brash、Chandra Prakash、Douglass F. Taber、Ian A. Blair

  DOI：10.1021/jo951061w

  日期：1996.1.1

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.