hexadec-8-ynoic acid | 90284-25-6

• 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: hexadec-8-ynoic acid
• 英文别名: 8-hexadecynoic acid；8-Hexadecynoic acid
• CAS: 90284-25-6
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: OGXDPOIXMXFWHX-UHFFFAOYSA-N

物化性质

• 熔点：
  59.1°C (estimate)
• 沸点：
  409.64°C (rough estimate)
• 密度：
  0.9310 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  hexadec-8-ynoic acid 在 硫酸 、 氢气 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 、 乙二胺 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 生成 1-(8Z-hexadecenoyl)-rac-glycerol
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912
• 作为产物：
  描述：

  2-[(7-溴庚基)氧基]四氢-2H-吡喃 在 Jones reagent 、 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 丙酮 为溶剂， 反应 0.5h， 生成 hexadec-8-ynoic acid
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912

文献信息

• Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug‐Resistant <scp> <i>Staphylococcus aureus</i> </scp>
  作者：David J. Sanabria‐Ríos、Christian Morales‐Guzmán、Joseph Mooney、Solymar Medina、Tomás Pereles‐De‐León、Ashley Rivera‐Román、Carlimar Ocasio‐Malavé、Damarith Díaz、Nataliya Chorna、Néstor M. Carballeira

  DOI：10.1002/lipd.12213

  日期：2020.3

  In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C‐3, C‐6, C‐8, C‐9, C‐10, and C‐12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C‐4 or C‐5 were also

  在本研究中，进一步研究了赋予C 16炔属脂肪酸（aFA）抗菌活性的结构特征。四个步骤进行了在C-3，C-6，C-8，C-9，C-10和C-12处含有三键的十六碳烯酸（HDA）的合成，总产率为34- 78％。此外，还分别制备了C-4或C-5含硫原子的HDA类似物，总产率分别为69-77％。这项研究的结果表明，C-2处的三键对于2-HDA所显示的抗菌活性至关重要，而三键距羰基的位置越远，其对革兰氏阳性细菌的杀菌活性就越低，包括耐甲氧西林金黄色葡萄球菌的临床分离株（CIMRSA）菌株。还对五种对环丙沙星（Cipro）耐药的CIMRSA菌株评估了2-HDA作为抗菌剂的潜力，证明与单独使用Cipro或等摩尔组合Cipro相比，2-HDA是抑制其生长的最有效方法。和2‐HDA。此外，已证明金黄色葡萄球菌DNA促旋酶的抑制作用可能与2-HDA表现出的抗菌活性有关。最后，确定了HDA类似物形成胶束的能力可
• Preparation and Cancer Cell Invasion Inhibitory Effects of C16-Alkynic Fatty Acids.
  作者：Kazuyoshi Ohashi、Hendig Winarno、Mutsuko Mukai、Hirotaka Shibuya

  DOI：10.1248/cpb.51.463

  日期：——

  Five C16-alkynic fatty acids (2—6) were prepared and examined their inhibitory effects on cancer cell invasion. It has been found that hexadeca-6,8,10-triynoic acid (5) and hexadeca-8,10,12-triynoic acid (6) exhibit similar potent inhibitory activities with that of octadeca-8,10,12-triynoic acid (1) which was isolated from Scurrula atropurpurea (Loranthaceae).

  五种C16-炔基脂肪酸（2-6）被制备并研究了它们对癌细胞侵袭的抑制作用。研究发现，六烯-6,8,10-三炔酸（5）和六烯-8,10,12-三炔酸（6）与从黑紫埂（Loranthaceae）中分离的八烯-8,10,12-三炔酸（1）表现出相似的强效抑制活性。
• ——
  作者：Walter Soares Leal、Shigefumi Kuwahara、Xiongwei Shi、Hiroya Higuchi、Claudia E. B. Marino、Mikio Ono、Jerrold Meinwald

  DOI：10.1023/a:1022307600446

  日期：——

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.