trans-10-hydroperoxyoctadec-8-enoic acid | 96963-17-6

• 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: trans-10-hydroperoxyoctadec-8-enoic acid
• 英文别名: 10R,S-hydroperoxy-8E-octadecenoic acid；10-hydroperoxy-8E-octadecenoic acid；(E)-10-hydroperoxyoctadec-8-enoic acid
• CAS: 96963-17-6
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: HTIQDCPWTUODDW-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-10-hydroperoxyoctadec-8-enoic acid 在 sodium tetrahydroborate 作用下， 生成 methyl ester of (E)-10-hydroxy-8-octadecenoic acid
  参考文献：
  名称：

  A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids

  摘要：

  A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenyl methyl ester (IAP) derivatives. The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.

  DOI：

  10.1016/0009-3084(94)90056-6
• 作为产物：
  描述：

  油酸 生成 trans-10-hydroperoxyoctadec-8-enoic acid
  参考文献：
  名称：

  PORTER, NED A.;WUJEK, JACQUELINE SULLIVAN, J. ORG. CHEM., 52,(1987) N 23, 5085-5089

  摘要：

  DOI：

文献信息

• Allylic hydroperoxide rearrangement. .beta.-Scission or concerted pathway?
  作者：Ned A. Porter、Jacqueline Sullivan Wujek

  DOI：10.1021/jo00232a004

  日期：1987.11
• PORTER, NED A.;WUJEK, JACQUELINE SULLIVAN, J. ORG. CHEM., 52,(1987) N 23, 5085-5089
  作者：PORTER, NED A.、WUJEK, JACQUELINE SULLIVAN

  DOI：——

  日期：——
• LABEQUE R.; MARNETT L. J., J. AMER. CHEM. SOC., 109,(1987) N 9, 2828-2829
  作者：LABEQUE R.、 MARNETT L. J.

  DOI：——

  日期：——
• A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids
  作者：Lian-Ying Zhang、Mats Hamberg

  DOI：10.1016/0009-3084(94)90056-6

  日期：1994.12

  A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenyl methyl ester (IAP) derivatives. The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.