tetracosane-9,16-dicarboxylic acid

• 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: tetracosane-9,16-dicarboxylic acid
• 英文别名: 2,9-Dioctyldecanedioic acid
• 化学式: C₂₆H₅₀O₄
• 分子量: 426.681
• InChiKey: BRUKJMFVQPMUOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  30
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetracosane-9,16-dicarboxylic acid 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 以100%的产率得到sodium tetracosane-9,16-dicarboxylate
  参考文献：
  名称：

  Unusually Stable Aqueous Lyotropic Gyroid Phases from Gemini Dicarboxylate Surfactants

  摘要：

  Aqueous lyotropic liquid crystal (LLC) assemblies with bicontinuous cubic morphologies (Q-phases) have shown promise in applications ranging from selective chemical separations to ion transporting media, yet universal design criteria for amphiphiles that adopt these unique structures remain elusive. Recent reports have demonstrated that cationic gemini surfactants exhibit a tendency to form bicontinuous cubic LLCs as compared to single-tail amphiphiles; however, the universality of this surfactant design motif in stabilizing Q-phases remains untested. Herein, we report the modular synthesis of a new class of anionic gemini surfactants derived from aliphatic carboxylic acids and demonstrate their unexpectedly strong propensity to form gyroid LLC phases with unprecedented stability between 25 and 100 degrees C over amphiphile concentration windows up to 20 wt % wide. By systematically varying the alkyl spacer length and surfactant counterions (Na+, K+, and (CH3)(4)N+), we identify molecular motifs that favor formation of technologically useful bicontinuous cubic LLC morphologies.

  DOI：

  10.1021/ja2063555
• 作为产物：
  描述：

  1,6-二溴己烷 、 正癸酸 在 六甲基磷酰三胺 、 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 以68.2%的产率得到tetracosane-9,16-dicarboxylic acid
  参考文献：
  名称：

  Unusually Stable Aqueous Lyotropic Gyroid Phases from Gemini Dicarboxylate Surfactants

  摘要：

  Aqueous lyotropic liquid crystal (LLC) assemblies with bicontinuous cubic morphologies (Q-phases) have shown promise in applications ranging from selective chemical separations to ion transporting media, yet universal design criteria for amphiphiles that adopt these unique structures remain elusive. Recent reports have demonstrated that cationic gemini surfactants exhibit a tendency to form bicontinuous cubic LLCs as compared to single-tail amphiphiles; however, the universality of this surfactant design motif in stabilizing Q-phases remains untested. Herein, we report the modular synthesis of a new class of anionic gemini surfactants derived from aliphatic carboxylic acids and demonstrate their unexpectedly strong propensity to form gyroid LLC phases with unprecedented stability between 25 and 100 degrees C over amphiphile concentration windows up to 20 wt % wide. By systematically varying the alkyl spacer length and surfactant counterions (Na+, K+, and (CH3)(4)N+), we identify molecular motifs that favor formation of technologically useful bicontinuous cubic LLC morphologies.

  DOI：

  10.1021/ja2063555

文献信息

• DICARBOXYLATE GEMINI SURFACTANT THAT FORMS A LYOTROPIC LIQUID CRYSTAL
  申请人：Mahanthappa Mahesh Kalyana

  公开号：US20130306907A1

  公开（公告）日：2013-11-21

  Aliphatic dicarboxylate Gemini surfactants and lyotropic liquid crystal compositions formed thereby are disclosed. The Gemini surfactants are capable of robustly forming Q phase morphologies over broad ranges of temperature and concentration.

  公开了由脂肪族二羧酸盐Gemini表面活性剂形成的亲水液晶组合物。这些Gemini表面活性剂能够在广泛的温度和浓度范围内稳健地形成Q相形态。
• Platelet Aggregation Inhibiting and Anticoagulant Effects of Oligoamines, Part 33 From Tetradecane- to Octacosanediamines
  作者：Klaus Rehse、Rafaela Nolte-Driller

  DOI：10.1002/ardp.19963290404

  日期：——

  them inhibited the aggregation of human blood platelets in concentrations between 3–10 μmol/L halfmaximally (Born test, inducer collagen). With increasing m a decreasing n is necessary to achieve the optimum activity. In the most active compounds (7b, 7e, 7p) it is found that m + n = 9. When the nitrogen functions are hydroxyalkylated secondary amines with similar antiplatelet effects are obtained. The

  根据本系列前面部分的结构-活性关系设计并合成了 20 种烷二胺。它们的一般结构是 CH3-(CH2)n-CHNH2-(CH2)m-CHNH2-(CH2)n-CH3，(n = 2-10；m = 3-6)。其中 12 种在 3-10 μmol/L 的浓度范围内抑制人血小板的聚集，最大值为一半（Born test，诱导剂胶原蛋白）。随着 ma 的增加，n 的减少是达到最佳活性所必需的。在最活跃的化合物 (7b, 7e, 7p) 中，发现 m + n = 9。当氮官能团为羟烷基化仲胺时，可获得具有类似抗血小板作用的仲胺。氨基转化为sydnonimines伴随着活性的丧失。7f和7m的双乙氧基羰基衍生物(8f, 8m)口服后对大鼠表现出抗血栓形成作用。
• US8834743B2
  申请人：——

  公开号：US8834743B2

  公开（公告）日：2014-09-16
• Unusually Stable Aqueous Lyotropic Gyroid Phases from Gemini Dicarboxylate Surfactants
  作者：Gregory P. Sorenson、Keiva L. Coppage、Mahesh K. Mahanthappa

  DOI：10.1021/ja2063555

  日期：2011.9.28

  Aqueous lyotropic liquid crystal (LLC) assemblies with bicontinuous cubic morphologies (Q-phases) have shown promise in applications ranging from selective chemical separations to ion transporting media, yet universal design criteria for amphiphiles that adopt these unique structures remain elusive. Recent reports have demonstrated that cationic gemini surfactants exhibit a tendency to form bicontinuous cubic LLCs as compared to single-tail amphiphiles; however, the universality of this surfactant design motif in stabilizing Q-phases remains untested. Herein, we report the modular synthesis of a new class of anionic gemini surfactants derived from aliphatic carboxylic acids and demonstrate their unexpectedly strong propensity to form gyroid LLC phases with unprecedented stability between 25 and 100 degrees C over amphiphile concentration windows up to 20 wt % wide. By systematically varying the alkyl spacer length and surfactant counterions (Na+, K+, and (CH3)(4)N+), we identify molecular motifs that favor formation of technologically useful bicontinuous cubic LLC morphologies.