choline bis(2-ethylhexyl) phosphate | 1241963-01-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: choline bis(2-ethylhexyl) phosphate
• 英文别名: choline bis(2-ethylhexyl)phosphate；Bis(2-ethylhexyl) phosphate;2-hydroxyethyl(trimethyl)azanium；bis(2-ethylhexyl) phosphate;2-hydroxyethyl(trimethyl)azanium
• CAS: 1241963-01-8
• 化学式: C₅H₁₄NO*C₁₆H₃₄O₄P
• 分子量: 425.59
• InChiKey: SLWDUIZLNWNBIQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二(2-乙基己基)磷酸酯 、 胆碱 以 甲醇 、 乙醇 为溶剂， 生成 choline bis(2-ethylhexyl) phosphate
  参考文献：
  名称：

  Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications

  摘要：

  最近，离子液体（IL）磷酸胆碱（choline dihydrogen phosphate）被证明可改善几种模型蛋白质的热稳定性和保质期，因此具有作为蛋白质治疗的稳定赋形剂或溶剂的潜力。在新型 IL 用于生物医学应用之前，需要全面的数据来确定其生物相容性，包括细胞毒性效应和溶液行为。本研究分析了五种基于磷酸盐的阴离子分子：H2PO4-（DHP）、磷酸二丁酯（DBP）、双（2-乙基己基）磷酸酯（BEH）、双（2,4,4-三甲基戊基）膦酸酯（TMP）和 O,O′-二乙基二硫代磷酸酯（DEP），它们都与阳离子胆碱（C）配对。利用 J774 鼠巨噬细胞系确定了这些 IL 以及一种常见糖类和盐类的毒性水平。糖类三卤糖和单盐氯化钠及氯化胆碱的 EC50 值分别大于 100、63 和 34 mM。CDHP（20）、CDBP（9.1）和 CDEP（8.2）的 EC50 值（毫摩尔）低于单盐氯化钠（62.8）和氯化胆碱（33.7），但在其范围之内。CTMP 和 CBEH 的 EC50 值要低得多，分别为 0.25 和 0.30 毫摩尔。CDHP 和 CBEH 显示出激素反应。渗透压测量结果表明，CDHP、CDBP 和 CDEP 在水溶液中几乎完全解离，渗透系数分别为 1.0、0.9 和 0.8，而 CTMP 和 CBEH 的渗透系数分别为 0.5 和 0.3，更具有分子特征。EC50 值与阴离子质量分数之间的高度相关性表明，阴离子的大小以及是否存在中等长度和/或支化的烷基链可能会影响存活率。

  DOI：

  10.1039/b918726j

文献信息

• METHODS AND COMPOSITIONS FOR THE STABILIZATION OF BIOLOGIC MATERIAL
  申请人：Elliott Gloria

  公开号：US20130089912A1

  公开（公告）日：2013-04-11

  A method of screening an organic salt for potential toxicity if used as a stabilizing agent for live cells or viruses, the method comprising: (a) providing a composition of unilamellar vesicles; then (b) contacting an organic salt to the unilamellar vesicles; and then (c) detecting a change in at least one thermal parameter of the unilamellar vesicles caused by the organic salt at said known concentration. A change in the at least one thermal parameter indicates the organic salt is potentially toxic for use as a stabilizing agent for live cells or viruses. Compositions of organic salts identified by such methods, along with methods of using the same in stabilizing live cells or viruses, are also described.
• SYNERGISTIC MIXTURES OF IONIC LIQUIDS WITH OTHER IONIC LIQUIDS AND/OR WITH ASHLESS THIOPHOSPHATES FOR ANTIWEAR AND/OR FRICTION REDUCTION APPLICATIONS
  申请人：Aswath Pranesh

  公开号：US20130331305A1

  公开（公告）日：2013-12-12

  Anti-wear and/or friction reducing formulations that include a mixture of at least one first ionic liquid and at least one ashless antiwear compound. The ashless antiwear compound can be a second ionic liquid or an ashless thiophosphate compound. The formulation desirably provides synergistic anti-wear and/or friction reducing properties. The first IL can be a monocationie ionic liquid or a dicationic ionic liquid. The second IL is a dicationic ionic liquid. The ashless thiophosphate is desirably a thiophosphate, such as a fluorothiophosphate (FTP), an alkylphosphorofluoridothiolate, or an alkylthioperoxydithiophosphate. Antiwear and/or friction reduction formulations comprising the above mixtures diluted up to 25% by weight in a base oil.
• US9725669B2
  申请人：——

  公开号：US9725669B2

  公开（公告）日：2017-08-08
• [EN] SYNERGISTIC MIXTURES OF IONIC LIQUIDS WITH OTHER IONIC LIQUIDS AND/OR WITH ASHLESS THIOPHOSPHATES FOR ANTIWEAR AND/OR FRICTION REDUCTION APPLICATIONS<br/>[FR] MÉLANGES SYNERGIQUES DE LIQUIDES IONIQUES AVEC D'AUTRES LIQUIDES IONIQUES ET/OU AVEC DES THIOPHOSPHATES SANS CENDRES POUR DES APPLICATIONS ANTI-USURE ET/OU DE RÉDUCTION DU FROTTEMENT
  申请人：UNIV TEXAS

  公开号：WO2013169779A1

  公开（公告）日：2013-11-14

  Anti-wear and/or friction reducing formulations that include a mixture of at least one first ionic liquid and at least one ashless antiwear compound. The ashless antiwear compound can be a second ionic liquid or an ashless thiophosphate compound. The formulation desirably provides synergistic anti-wear and/or friction reducing properties. The first IL can be a monocationic ionic liquid or a dicationic ionic liquid. The second IL is a dicationic ionic liquid. The ashless thiophosphate is desirably a thiophosphate, such as a fluorothiophosphate (FTP), an alkylphosphorofluoridothiolate, or an alkylthioperoxydithiophosphate. Antiwear and/or friction reduction formulations comprising the above mixtures diluted up to 25% by weight in a base oil.
• Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications
  作者：Katherine D. Weaver、Hye Jin Kim、Jiazeng Sun、Douglas R. MacFarlane、Gloria D. Elliott

  DOI：10.1039/b918726j

  日期：——

  Recently, the ionic liquid (IL) choline dihydrogen phosphate was demonstrated to improve the thermostability and shelf life of several model proteins, thus exhibiting potential as a stabilizing excipient or solvent for protein therapeutics. Before novel ILs can be used for biomedical applications, comprehensive data is required to establish biocompatibility, including cytotoxicity effects and solution behavior. In this study five phosphate-based anion moieties were analyzed: H2PO4− (DHP), dibutyl phosphate (DBP), bis(2-ethylhexyl) phosphate (BEH), bis(2,4,4-trimethylpentyl) phosphinate (TMP), and O,O′-diethyl dithiophosphate (DEP), all paired with the cation choline (C). Toxicity levels for these ILs, and a common sugar and salts, were established using a J774 murine macrophage cell line. The sugar trehalose, and the simple salts sodium chloride and choline chloride yielded EC50 values of >100, 63 and 34 mM, respectively. The EC50 values (mM) of CDHP (20), CDBP (9.1), and CDEP (8.2) were lower than, but within the range of simple salts NaCl (62.8) and choline Cl (33.7). The EC50 values of CTMP and CBEH were considerably lower, 0.25 and 0.30 mM, respectively. CDHP and CBEH displayed a hormetic response. Osmolality measurements indicated that CDHP, CDBP, and CDEP exhibit nearly complete dissociation in aqueous solution, with osmotic coefficients of 1.0, 0.9, and 0.8, whereas CTMP and CBEH have coefficients of 0.5 and 0.3, and are more molecular in character. A high correlation between the EC50 value and the anion mass fraction indicated that anion size and the presence of moderately long and/or branched alkyl chains may affect viability.

  最近，离子液体（IL）磷酸胆碱（choline dihydrogen phosphate）被证明可改善几种模型蛋白质的热稳定性和保质期，因此具有作为蛋白质治疗的稳定赋形剂或溶剂的潜力。在新型 IL 用于生物医学应用之前，需要全面的数据来确定其生物相容性，包括细胞毒性效应和溶液行为。本研究分析了五种基于磷酸盐的阴离子分子：H2PO4-（DHP）、磷酸二丁酯（DBP）、双（2-乙基己基）磷酸酯（BEH）、双（2,4,4-三甲基戊基）膦酸酯（TMP）和 O,O′-二乙基二硫代磷酸酯（DEP），它们都与阳离子胆碱（C）配对。利用 J774 鼠巨噬细胞系确定了这些 IL 以及一种常见糖类和盐类的毒性水平。糖类三卤糖和单盐氯化钠及氯化胆碱的 EC50 值分别大于 100、63 和 34 mM。CDHP（20）、CDBP（9.1）和 CDEP（8.2）的 EC50 值（毫摩尔）低于单盐氯化钠（62.8）和氯化胆碱（33.7），但在其范围之内。CTMP 和 CBEH 的 EC50 值要低得多，分别为 0.25 和 0.30 毫摩尔。CDHP 和 CBEH 显示出激素反应。渗透压测量结果表明，CDHP、CDBP 和 CDEP 在水溶液中几乎完全解离，渗透系数分别为 1.0、0.9 和 0.8，而 CTMP 和 CBEH 的渗透系数分别为 0.5 和 0.3，更具有分子特征。EC50 值与阴离子质量分数之间的高度相关性表明，阴离子的大小以及是否存在中等长度和/或支化的烷基链可能会影响存活率。