2,9-HDA

• 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: 2,9-HDA
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: JXTKSBGEKCPFTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  溴己烷 、 1,8-壬二炔 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,9-HDA
  参考文献：
  名称：

  Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria

  摘要：

  The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogs in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 mu g/mL), Staphylococcus saprophyticus (MIC = 15.5 mu g/mL), and Bacillus cereus (MIC = 31.3 mu g/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 mu g/mL) and Pseudomonas aeruginosa (MIC = 125 mu g/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 mu g/mL) and clinical isolates of MRSA (MIC = 3.9 mu g/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 and the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.12.006

文献信息

• Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria
  作者：David J. Sanabria-Ríos、Yaritza Rivera-Torres、Gamalier Maldonado-Domínguez、Idializ Domínguez、Camille Ríos、Damarith Díaz、José W. Rodríguez、Joanne S. Altieri-Rivera、Eddy Ríos-Olivares、Gabriel Cintrón、Nashbly Montano、Néstor M. Carballeira

  DOI：10.1016/j.chemphyslip.2013.12.006

  日期：2014.2

  The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogs in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 mu g/mL), Staphylococcus saprophyticus (MIC = 15.5 mu g/mL), and Bacillus cereus (MIC = 31.3 mu g/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 mu g/mL) and Pseudomonas aeruginosa (MIC = 125 mu g/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 mu g/mL) and clinical isolates of MRSA (MIC = 3.9 mu g/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 and the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations. (C) 2013 Elsevier Ireland Ltd. All rights reserved.