3-hydroxyheptadecanoic acid | 76622-31-6

• 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: 3-hydroxyheptadecanoic acid
• 英文别名: (3R)-3-hydroxyheptadecanoic acid
• CAS: 76622-31-6
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: FWZUXWSQLNHYIC-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-hydroxyheptadecanoic acid 以 乙醚 为溶剂， 生成 methyl 3-methoxyheptadecanoate
  参考文献：
  名称：

  Antifungal Lipopeptides from Bacillus amyloliquefaciens Strain BO7

  摘要：

  Three new lipopeptides (1-3) were isolated from the organic extract of Bacillus amyloliquefaciens strain (BO7). These compounds represented the major Constituents (>60%) of the total cell lipids extractable with CHCl3/MeOH (2:1). Elucidation of their chemical structure was carried out by spectroscopic analyses, including 1D and 2D NMR spectroscopy, mass spectrometry (MS), and secondary ion mass spectrometry (MS/MS), along with chemical degradation. The compounds are members of the surfactins family and are based on, the heptapeptide Glu-Leu-Leu-Ala-Asp-Leu-Leu, N-acylated to the N-terminal by an (R)-3-hydroxy fatty acid with linear alkyl chains from 16:0 to 18:0 (1-3, respectively). An ester bond between the 3-hydroxyl group of the fatty add and the carboxylic group of the C-terminal amino acid closes a 13, membered lactone ring. The bacterial lipopeptides, particularly compound 3, displayed strong and dose-dependent antifungal activity against the plant pathogenic fungus Fusarium oxysporum.

  DOI：

  10.1021/np100408y