6-methyl-9-heptadecynoic acid | 276881-70-0

• 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: 6-methyl-9-heptadecynoic acid
• 英文别名: 6-methylheptadec-9-ynoic acid
• CAS: 276881-70-0
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: LERJRSUHUYDOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-9-heptadecynoic acid 在 镍 氢气 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 15.0h， 以91%的产率得到(Z)-6-methyl-9-heptadecenoic acid
  参考文献：
  名称：

  摘要：

  Difficulties in isolating and purifying antibiotic fatty acids from culture filtrates of Pseudozyma flocculosa, a biocontrol agent against powdery mildew, have been limiting factors in studying the properties and understanding the mode of action of the biocontrol agent. We report a new protocol for synthesizing (Z)-9-heptadecenoic and for the first time synthesis of (Z)-6-methyl-9-heptadecenoic acids, two antibiotic fatty acids produced by P. flocculosa. This allowed reproducible and quantifiable means of assaying biological activity of the molecules. In these bioassays, both molecules exhibited antifungal activity corresponding to their expected potency. These new developments should facilitate further studies aimed at deciphering the ecological properties of P. flocculosa.

  DOI：

  10.1023/a:1005464326573
• 作为产物：
  描述：

  3-甲基-1,5-戊二醇 在 sodium hydroxide 、 三溴化磷 、 magnesium 、 三苯基膦 、 sodium iodide 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 51.5h， 生成 6-methyl-9-heptadecynoic acid
  参考文献：
  名称：

  摘要：

  Difficulties in isolating and purifying antibiotic fatty acids from culture filtrates of Pseudozyma flocculosa, a biocontrol agent against powdery mildew, have been limiting factors in studying the properties and understanding the mode of action of the biocontrol agent. We report a new protocol for synthesizing (Z)-9-heptadecenoic and for the first time synthesis of (Z)-6-methyl-9-heptadecenoic acids, two antibiotic fatty acids produced by P. flocculosa. This allowed reproducible and quantifiable means of assaying biological activity of the molecules. In these bioassays, both molecules exhibited antifungal activity corresponding to their expected potency. These new developments should facilitate further studies aimed at deciphering the ecological properties of P. flocculosa.

  DOI：

  10.1023/a:1005464326573