(E)-(S)-19-Methyl-icos-10-en-8-ol | 160667-17-4

• 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: (E)-(S)-19-Methyl-icos-10-en-8-ol
• 英文别名: (E,8S)-19-methylicos-10-en-8-ol
• CAS: 160667-17-4
• 化学式: C₂₁H₄₂O
• 分子量: 310.564
• InChiKey: NOCOLTMBUBARCR-WMJZSHNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (E)-(S)-19-Methyl-icos-10-en-8-ol 在 吡啶 作用下， 反应 19.0h， 以0.5 mg的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(S)-1-heptyl-12-methyl-tridec-3-enyl ester
  参考文献：
  名称：

  Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation.

  摘要：

  Panclicins A-E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMR and FAB-MS experiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to β-lactone esterase inhibitors of microbial origin, lipstatin, valilactone, ebelactones and esterastin. Panclicins also contain a β-lactone structure with two alkyl chains, one of which has an N-formylalanyloxy or N-formylglycyloxy substituent.

  DOI：

  10.7164/antibiotics.47.1376
• 作为产物：
  描述：

  (S)-2-Formylamino-propionic acid (S)-1-[(2S,3S)-3-(8-methyl-nonyl)-4-oxo-oxetan-2-ylmethyl]-octyl ester 在 sodium hydroxide 作用下， 生成 (E)-(S)-19-Methyl-icos-10-en-8-ol
  参考文献：
  名称：

  Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation.

  摘要：

  Panclicins A-E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMR and FAB-MS experiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to β-lactone esterase inhibitors of microbial origin, lipstatin, valilactone, ebelactones and esterastin. Panclicins also contain a β-lactone structure with two alkyl chains, one of which has an N-formylalanyloxy or N-formylglycyloxy substituent.

  DOI：

  10.7164/antibiotics.47.1376