2-octyldodecyl 2-(trimethylammonio)ethyl phosphate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-octyldodecyl 2-(trimethylammonio)ethyl phosphate
• 英文别名: 2-Octyldodecyl 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₂₅H₅₄NO₄P
• 分子量: 463.682
• InChiKey: MEHHJCUAHJPBQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  31
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-辛基十二醇 在 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.0h， 生成 2-octyldodecyl 2-(trimethylammonio)ethyl phosphate
  参考文献：
  名称：

  Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain

  摘要：

  成功合成了具有一条直链和一条不对称支链烷基链的烷基膦酰胆碱两亲物，使用2-氯-2-氧代-1,3,2-二氧磷环在四氢呋喃或乙酸乙酯中进行合成。1H和31P核磁共振研究表明，直链烷基膦酰胆碱（Cn-PC）在D2O中提供水溶胶束，在CDCl3中提供反向胶束，而支链烷基膦酰胆碱（ISOFOLn-PC）在D2O中形成囊泡。通过荧光染料溶解方法测定了Cn-PC的临界胶束浓度（CMCs）：在25°C的水中，C12-PC、C14-PC、C16-PC和C18-PC的CMCs分别为1.6、0.38、0.16和0.11 mM。在25°C的水中，ISOFOL16-PC、ISOFOL20-PC和ISOFOL24-PC的临界缔合浓度（CACs）分别为0.068、0.005和0.077 mM。通过动态光散射方法测量了ISOFOLn-PC在水溶液中的囊泡大小。ISOFOLn-PC囊泡的平均直径约为30 nm，尺寸分布相对单一。ISOFOLn-PC囊泡在水溶液中形成，具有几周时间的胶体稳定性。

  DOI：

  10.1246/bcsj.78.1558

文献信息

• Relationship between aggregation properties and antimicrobial activities of alkylphosphocholines with branched alkyl chains
  作者：Miloš Lukáč、Mária Garajová、Martin Mrva、Marián Bukovský、František Ondriska、Eszter Máriássy、Ferdinand Devínsky、Ivan Lacko

  DOI：10.1016/j.ijpharm.2011.11.047

  日期：2012.2

  Synthesis of five alkylphosphocholines with branched alkyl chains (Isophol-PCs) with different length of alkyl chains was described. Isophol(8)-PC and Isophol(12)-PC represent new compounds. The physicochemical properties of Isophol-PCs were determined, critical micelle concentration and types of formed aggregates in aqueous solutions were investigated. The biological activities of Isophol-PCs have been studied for the first time in the present study. Antimicrobial activities of alkylphosphocholines were studied against bacteria (Staphylococcus aureus, Escherichia coli), yeast (Candida albicans) and pathogenic free-living amoebae (Acanthamoeba lugdunensis and Acanthamoeba quina). A. lugdunensis and A. quina are relatively insusceptible to action of miltefosine (standard compound of alkylphosphocholines) and therefore they are good models for studies of amoebicidal action of the investigated compounds. Relationship between structure, physico-chemical and biological activities of Isophol-PCs was discussed. S. aureus and C. albicans were sensitive to action of Isophol(16)-PC, Isophol(20)-PC. E. coli was not sensitive to action of all studied alkylphosphocholines in the concentrations equal to, or less than 10 mM. Among all the synthesized compounds, Isophol(16)-PC had the highest level of activity against both strains of Acanthamoeba. The minimum trophocidal concentrations of lsophol(16)-PC against A. lugdunensis and A. quina are about four times lower than the minimum trophocidal concentrations of miltefosine against booth strains. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain
  作者：Eui-Chul Kang、Shingo Kataoka、Kenji Kato

  DOI：10.1246/bcsj.78.1558

  日期：2005.8

  Alkyl phosphorylcholine amphiphiles bearing one linear chain and one asymmetrically branched alkyl chain were successfully synthesized using 2-chloro-2-oxo-1,3,2-dioxaphospholane in tetrahydrofuran or ethyl acetate. 1H and 31P NMR studies revealed that the linear alkyl phosphorylcholines (Cn-PC) provide aqueous micelles in D2O and reverse micelles in CDCl3, while the branched alkyl phosphorylcholines (ISOFOLn-PC) give vesicles in D2O. The critical micelle concentrations (CMCs) of Cn-PC were measured by fluorescence dye solubilization methods: the CMCs of C12-PC, C14-PC, C16-PC, and C18-PC were 1.6, 0.38, 0.16, and 0.11 mM, respectively, in water at 25 °C. The critical association concentrations (CACs) of ISOFOL16-PC, ISOFOL20-PC, and ISOFOL24-PC were 0.068, 0.005, and 0.077 mM, respectively, in water at 25 °C. The vesicle size of ISOFOLn-PC in aqueous solution was measured by the dynamic light scattering method. The mean diameter of ISOFOLn-PC vesicles was approximately 30 nm and the size distribution was relatively monodisperse. The ISOFOLn-PC vesicles formed were colloidally stable in water over the period of several weeks.

  成功合成了具有一条直链和一条不对称支链烷基链的烷基膦酰胆碱两亲物，使用2-氯-2-氧代-1,3,2-二氧磷环在四氢呋喃或乙酸乙酯中进行合成。1H和31P核磁共振研究表明，直链烷基膦酰胆碱（Cn-PC）在D2O中提供水溶胶束，在CDCl3中提供反向胶束，而支链烷基膦酰胆碱（ISOFOLn-PC）在D2O中形成囊泡。通过荧光染料溶解方法测定了Cn-PC的临界胶束浓度（CMCs）：在25°C的水中，C12-PC、C14-PC、C16-PC和C18-PC的CMCs分别为1.6、0.38、0.16和0.11 mM。在25°C的水中，ISOFOL16-PC、ISOFOL20-PC和ISOFOL24-PC的临界缔合浓度（CACs）分别为0.068、0.005和0.077 mM。通过动态光散射方法测量了ISOFOLn-PC在水溶液中的囊泡大小。ISOFOLn-PC囊泡的平均直径约为30 nm，尺寸分布相对单一。ISOFOLn-PC囊泡在水溶液中形成，具有几周时间的胶体稳定性。