tetradecyl L-phenylalaninate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetradecyl L-phenylalaninate
• 英文别名: tetradecyl (2S)-2-amino-3-phenylpropanoate
• 化学式: C₂₃H₃₉NO₂
• 分子量: 361.568
• InChiKey: FVXQYYLHULJDTO-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetradecyl L-phenylalaninate 在 sodium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 60.0h， 生成 (S)-1-methyl-3-(2-((1-(tetradecyloxy)-1-oxo-3-phenylpropan-2-yl)amino)-2-oxoethyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  一系列L-苯丙氨酸衍生的表面活性离子液体的合成，自组装，细菌和真菌毒性以及初步的生物降解研究

  摘要：

  我们首次报告了对合成（由绿色化学指标支持），聚集性质，细菌/真菌毒性以及一系列24 L-苯丙氨酸衍生的表面活性离子液体（SAILs）的生物降解作用的初步数据的综合研究。各种阳离子头基包括吡啶鎓，咪唑鎓和胆鎓基团，能够全面分析烷基酯链的作用（从C 2到C 16）关于新型SAILs的合成，毒性，生物降解性和表面活性剂性能的研究。对SAIL的评估表明，各种特性严格取决于侧链长度，包括它们的细菌和真菌毒性（从低毒性到高毒性）以及聚集特性。L的加法将亲脂性侧链连接至阳离子头基的-苯基丙氨酸部分导致苯基基团基本上有助于自组装性能。与其他表面活性剂相比，苯环的分散相互作用和侧链疏水性之间的相互作用使我们能够对新型SAIL（从而鉴定出显着的SAIL）进行排名。这项研究中报道的SAILs的CMC值比具有相同侧链长度的常规表面活性剂报告的CMC值显着降低（最多10倍）。吸附和胶束化是影响所研究的SAILs毒性

  DOI：

  10.1039/c9gc00030e
• 作为产物：
  描述：

  tetradecyl (tert-butoxycarbonyl)-L-phenylalaninate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 tetradecyl L-phenylalaninate
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL IN HIV THERAPY
  [FR] COMPOSÉS UTILES DANS LA THÉRAPIE DU VIH

  摘要：

  这项发明涉及公式（I）的化合物，其盐，药物组合物，以及治疗或预防HIV的方法。

  公开号：

  WO2021194828A1

文献信息

• Synthesis, micellisation and interaction of novel quaternary ammonium compounds derived from l-Phenylalanine with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine as model membrane in relation to their antibacterial activity, and their selectivity over human red blood cells
  作者：Nausheen Joondan、Prakashanand Caumul、Matthew Akerman、Sabina Jhaumeer-Laulloo

  DOI：10.1016/j.bioorg.2015.01.001

  日期：2015.2

  l-Phenylalanine have been synthesized and their antibacterial efficiencies were determined against various strains of Gram-positive and Gram-negative bacteria. The antibacterial activity increased with increasing chain length, exhibiting a cut-off effect at C14 for Gram-positive and C12 for Gram-negative bacteria. The l-Phenylalanine QUATS displayed enhanced antibacterial properties with a higher cut-off point

  已经合成了一系列衍生自1-苯丙氨酸的季铵化合物（QUATS），并确定了它们对革兰氏阳性和革兰氏阴性细菌的各种菌株的抗菌效果。抗菌活性随链长的增加而增加，在革兰氏阳性菌的C 14和革兰氏阴性菌的C 12处表现出截断作用。的升-苯丙氨酸季铵化合物显示的增强相比于它们相应的更高的截止点的抗菌性能升-苯丙氨酸酯盐酸盐。CMC与MIC相关，推断胶束活性有助于抗菌活性的截止作用。溶血活性（HC还确定了针对人类红细胞的QUATS（50），以说明这些QUATS对细菌的选择性高于对哺乳动物细胞的选择性。通常，MIC低于HC 50，在TBS中作为一种常见介质对胶束对抗菌和溶血性评估的贡献进行评估，证实了这些QUATS在其单体浓度下可以起到抗菌但无毒的作用。QUATS与磷脂囊泡（1,2-dipalmitoyl- sn-甘油3-磷酸胆碱（DPPC）在1-苯胺基-8-萘磺酸盐（ANS）和1,6-二苯基-1,3,5-
• [EN] PRODUCTS AND METHODS FOR THE TREATMENT OF MIXTURES OF WATER AND HYDROPHOBIC LIQUIDS<br/>[FR] PRODUITS ET PROCÉDÉS POUR LE TRAITEMENT DE MÉLANGES D'EAU ET DE LIQUIDES HYDROPHOBES
  申请人：B C RES INC

  公开号：WO2019232629A1

  公开（公告）日：2019-12-12

  Chemical-based methods and products for mitigating the impact of an oil spill are disclosed. The products act by herding, thickening, gelling, and reducing adhesiveness. N-fatty acid amino acid (FA-AA) conjugates display oil-herding behavior when formulated as a free acid in water-miscible organic solvents. A water-miscible organic solvent is not required if the FA-AA conjugate is formulated as a salt. Various salts of FA-AA conjugates are water soluble and can herd oils and increase the thickness of the oil layer. Replacement of the acid group of fatty acid α-amino acid conjugates with other groups that act as hydrogen bond donors and acceptors results in potent phase selective organo-gellants. The oil spill herders can be prepared from bio-based feedstocks and are biodegradable. The oil thickeners or gellants, which are prepared from bio-based feedstocks, have low toxicity, high capacity for oil and reduce the need to use an organic solvent to apply the thickener or gellant to the oil and water mixture in order to gel the oil phase. Formulae (IB), (II), (III)

  本发明涉及化学方法和产品，用于减轻油污泄漏的影响。这些产品通过聚集、增稠、胶化和降低粘性来发挥作用。当N-脂肪酸氨基酸（FA-AA）共轭物被制成水溶性有机溶剂中的自由酸时，它们具有聚集油的行为。如果FA-AA共轭物被制成盐，则不需要水溶性有机溶剂。各种FA-AA共轭物的盐是水溶性的，可以聚集油并增加油层的厚度。将脂肪酸α-氨基酸共轭物的酸基替换为其他作为氢键供体和受体的基团，可以得到有效的相选择性有机胶凝剂。这些油污聚集剂可以从生物基原料制备，并且是可生物降解的。从生物基原料制备的油稠剂或胶凝剂具有低毒性，对油具有高容量，并且减少了使用有机溶剂将稠剂或胶凝剂应用于油水混合物以胶化油相的需要。公式（IB）、（II）、（III）。
• New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents
  作者：Krystyna Baczko、Chantal Larpent、Philippe Lesot

  DOI：10.1016/j.tetasy.2004.01.022

  日期：2004.3

  New amino acid-based anionic surfactants have been synthesized and their use as chiral oriented NMR solvents studied. A series of sulfonated amphiphilic L-Phe or L-Ala derivatives with pentyl to tetradecyl tails were prepared by reacting the corresponding amino acid esters with o-sulfobenzoic anhydride. Their critical micelle concentrations (CMCs) range from 1.6 x 10(-5) to 1.4 x 10(-2) mol/L and depend on the alkyl chain length as well as on the nature of the amino acid block. These values are comparatively lower than those of classical surfactants such as alkylbenzenesulfonates and N-acylamino-acid carboxylates. Their use as chiral liquid crystals (CLC) for analytical purposes is reported. In particular, it is shown that aqueous solutions of these chiral sulfonates in the presence of chlorinated solvents (CHCl3, CH2Cl2, C2H2Cl4, or CCl4) provide homogeneous oriented NMR solvents able to differentiate between enantiomers of D,L-alanine-2-d(1) using proton and deuterium NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.
• PRODUCTS AND METHODS FOR THE TREATMENT OF MIXTURES OF WATER AND HYDROPHOBIC LIQUIDS
  申请人：B.C. RESEARCH INC.

  公开号：US20210230466A1

  公开（公告）日：2021-07-29

  Chemical-based methods and products for mitigating the impact of an oil spill are disclosed. The products act by herding, thickening, gelling, and reducing adhesiveness. N-fatty acid amino acid (FA-AA) conjugates display oil-herding behavior when formulated as a free acid in water-miscible organic solvents. A water-miscible organic solvent is not required if the FA-AA conjugate is formulated as a salt. Various salts of FA-AA conjugates are water soluble and can herd oils and increase the thickness of the oil layer. Replacement of the acid group of fatty acid α-amino acid conjugates with other groups that act as hydrogen bond donors and acceptors results in potent phase selective organo-gellants. The oil spill herders can be prepared from bio-based feedstocks and are biodegradable. The oil thickeners or gellants, which are prepared from bio-based feedstocks, have low toxicity, high capacity for oil and reduce the need to use an organic solvent to apply the thickener or gellant to the oil and water mixture in order to gel the oil phase. Formulae (IB), (II), (III)