N,N-di-[O-lauroyl-2-hydroxyethyl]-N-hydroxyethyl-N-methylammonium chloride | 263889-53-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-di-[O-lauroyl-2-hydroxyethyl]-N-hydroxyethyl-N-methylammonium chloride
• 英文别名: N,N-di-[O-dodecanoyl-2-hydroxyethyl]-N-(2-hydroxyethyl)-N-methylammonium chloride；bis(2-dodecanoyloxyethyl)-(2-hydroxyethyl)-methylazanium;chloride
• CAS: 263889-53-8
• 化学式: C₃₁H₆₂NO₅*Cl
• 分子量: 564.29
• InChiKey: ZBEQXQHQWOHAOZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  38
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  月桂酰氯 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 18.0h， 生成 N,N-di-[O-lauroyl-2-hydroxyethyl]-N-hydroxyethyl-N-methylammonium chloride
  参考文献：
  名称：

  Cationic Amphiphiles with Fatty Acyl Chain Asymmetry of Coconut Oil Deliver Genes Selectively to Mouse Lung

  摘要：

  Recent structure activity studies have revealed a dramatic influence of hydrophobic chain asymmetry in enhancing gene delivery efficacies of synthetic cationic amphiphiles (Nantz, M. H. et al. Mol. Pharmaceutics 2010, 7, 786-794; Koynova, R et al. Mol. Pharmaceutics 2009, 6, 951-958). The present findings demonstrate for the first time that such a transfection enhancing influence of asymmetric hydrocarbon chains observed in pure synthetic cationic amphiphiles also works for cationic amphiphiles designed with natural, asymmetric fatty acyl chains of a food-grade oil. Herein, we demonstrate that cationic amphiphiles designed with the natural fatty acyl chain asymmetry of food-grade coconut oil are less cytotoxic and deliver genes selectively to mouse lung. Despite lauroyl chains being the major fatty acyl chains of coconut oil, both the in vitro and In vivo gene transfer efficiencies of such cationic amphiphiles were found to be remarkably superior (> 4-fold) to those of their pure dilauroyl analogue. Mechanistic studies involving the technique of fluorescence resonance energy transfer (FRET) revealed higher biomembrane fusibility of the cationic liposomes of the coconut amphiphiles than that of the symmetric dilauroyl analogue. AFM study revealed pronounced fusogenic nonlamellar structures of the liposomes of coconut amphiphiles. Findings in the FRET and cellular uptake study, taken together, support the notion that the higher cellular uptake resulting from the more fusogenic nature of the liposomes of coconut amphiphiles 1 are likely to play a dominant role in making the coconut amphiphiles transfection competent.

  DOI：

  10.1021/bc100537r

文献信息

• アミノ酸系農薬用効力増強剤組成物
  申请人：花王株式会社

  公开号：JP2015205869A

  公开（公告）日：2015-11-19

  【課題】生分解性、水生生物毒性（魚毒性）に優れ、アミノ酸系農薬と相溶性に優れ、安定で、アミノ酸系農薬の効力、なかでも耐雨性を効果的に増強できるアミノ酸系農薬用効力増強剤を提供する。【解決手段】エステル基を有する３種の特定の第４級アンモニウム塩を、特定の質量比で含有するアミノ酸系農薬用効力増強剤組成物。【選択図】なし

  这段文本描述了一种提供用于氨基酸类农药的增效剂，具有优越的生物降解性、水生生物毒性（鱼毒性），与氨基酸类农药相容性好，稳定性强，能有效增强氨基酸类农药的功效，特别是增强其耐雨性。解决方案是包含三种具有酯基的特定第四级铵盐，在特定质量比下的氨基酸类农药用增效剂组合物。
• Synthesis and Properties of Di-Chain Esterquat Surfactants
  作者：Bing Han、Tao Geng、Yajie Jiang、Hongbin Ju

  DOI：10.1007/s11743-014-1597-y

  日期：2015.1

  series of cationic surfactants, di‐chain esterquat surfactants (EQs), were synthesized from N‐methyl diethanolamine, hydrochloric acid, ethylene oxide, and caprylic acid, decylic acid, or lauric acid by a three‐step process. The synthesized surfactants were characterized by IR, MS, and 1HNMR. Surface properties, antibacterial activity, and biodegradability of the synthesized surfactants were investigated

  由N-甲基二乙醇胺，盐酸，环氧乙烷，辛酸，癸酸或月桂酸经三步法合成了一系列阳离子表面活性剂二链酯季铵盐表面活性剂（EQs）。合成的表面活性剂通过IR，MS和1 HNMR表征。研究了合成表面活性剂的表面性质，抗菌活性和生物降解性。结果表明，合成的EQs具有较高的表面活性和良好的生物降解性。此外，合成的表面活性剂N，N-二[[ O-癸酰基-2-羟乙基] -N-羟乙基-N-甲基氯化铵对大肠杆菌和金黄色葡萄球菌具有出色的抗菌活性。
• Anthraquinone hair dyes having a quaternary ammonium side chain
  申请人：Bristol-Myers Company

  公开号：EP0758547A1

  公开（公告）日：1997-02-19

  Anthraquinone compounds of formula I wherein R1 and R2 are methyl and R3 is propyl, or R1 and R2 are ethyl and R3 is methyl and A- is a cosmetically acceptable anion, are useful for the dyeing of hair. Compounds of formula I may advantageously be employed with direct dyes. Compositions and a method of use employing same are disclosed.

  式 I 的蒽醌化合物 其中 R1 和 R2 为甲基，R3 为丙基，或 R1 和 R2 为乙基，R3 为甲基，A- 为化妆品可接受的阴离子，可用于染发。式 I 的化合物可与直接染料一起使用。本发明公开了组合物及其使用方法。
• Quaternized blue anthraquinone hair dyes in an isatin/amine dye system
  申请人：Bristol-Myers Squibb Company

  公开号：EP0818193A2

  公开（公告）日：1998-01-14

  Quaternized blue anthraquinone compounds of Formula I wherein R1 and R2 are methyl and R3 is propyl, or R1 and R2 are ethyl and R3 is methyl and A- is a cosmetically acceptable anion, when employed in an isatin/amine dye system for the dyeing of hair enable the hair colorist to develop a full range of shades for the isatin/amine dye system. The compound of Formula I wherein R1 and R2 are methyl and R3 is propyl is preferred. Compositions and a method of use employing same are disclosed.

  式 I 的季铵化蓝色蒽醌化合物 其中 R1 和 R2 为甲基，R3 为丙基，或 R1 和 R2 为乙基，R3 为甲基，A- 为美容上可接受的阴离子，当用于染发的异靛蓝/胺染料体系中时，可使染发师为异靛蓝/胺染料体系调配出各种色调。首选式 I 的化合物，其中 R1 和 R2 为甲基，R3 为丙基。本发明公开了使用该化合物的组合物和使用方法。
• US5474578A
  申请人：——

  公开号：US5474578A

  公开（公告）日：1995-12-12