N-n-hexadecanoyl methyl (L)-valinate | 214706-35-1

• 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: N-n-hexadecanoyl methyl (L)-valinate
• 英文别名: methyl N-palmityl-L-valinate；methyl (2S)-2-(hexadecanoylamino)-3-methylbutanoate
• CAS: 214706-35-1
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: QTVZKWOGTDHNIX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-n-hexadecanoyl methyl (L)-valinate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 N-palmitoyl-L-valine
  参考文献：
  名称：

  新的N-酰基氨基酸和可再生脂肪酸的衍生物：烃的凝胶化和热学性质

  摘要：

  这项工作报告了从C16：0，C18：0，C18：1和C18：1（OH）脂肪酸家族合成新的脂肪N-酰基氨基酸和N-酰基氨基酯的过程，并证明了这些化合物作为有机凝胶的活性代理商。将化合物加热溶解在各种溶剂中（Ñ己烷，甲苯和汽油）。只有饱和C16：0和C18：从丙氨酸衍生0能够形成凝胶的甲苯溶液，和饱和的C16：从苯丙氨酸衍生的0表明胶凝Ñ正己烷。这是l的脂肪N-酰基氨基酯和N-酰基氨基酸衍生物的第一个证据-丝氨酸和脂肪酸C16：0，C18：0和C18：1能够与己烷形成凝胶。该观察证实了1-丝氨酸的片段衍生物中的羟基在形成良好凝胶中的重要性。

  DOI：

  10.1016/j.tetlet.2012.03.015
• 作为产物：
  描述：

  L-缬氨酸 在 氯化亚砜 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 11.0h， 生成 N-n-hexadecanoyl methyl (L)-valinate
  参考文献：
  名称：

  Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

  摘要：

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.028

文献信息

• <i>In situ</i> formation of AuNPs using fatty <i>N</i>-acylamino hydrazide organogelators as templates
  作者：Renata Ongaratto、Naiane Conte、Caroline R. Montes D’Oca、Rafael C. Brinkerhoff、Caroline Pires Ruas、Marcos Alexandre Gelesky、Marcelo G. Montes D’Oca

  DOI：10.1039/c8nj04127j

  日期：——

  N-acylamino hydrazides in various nonpolar and polar solvents (n-hexane, toluene, benzene, cyclohexane, and ethanol). Fatty N-acylamino hydrazide derived of the glycine and stearic acid (C18:0) did not form gels in any of the tested solvents. All other hydrazides did form gels in at least two of the organic solvents tested. The morphology of each gel was observed via scanning electron microscopy. The organogels

  这项工作首次报道了新的脂肪N-酰基氨基酰肼的合成，并证明了这些化合物作为低分子量有机胶凝剂和金纳米颗粒（AuNPs）制备模板的活性。最初，我们评估脂肪酸的凝胶化性能Ñ在各种非极性和极性溶剂-酰基酰肼（Ñ己烷，甲苯，苯，环己烷和乙醇）。由甘氨酸和硬脂酸（C18：0）衍生的脂肪N-酰氨基酰肼在任何测试的溶剂中均未形成凝胶。所有其他酰肼确实在至少两种测试的有机溶剂中形成了凝胶。通过观察每个凝胶的形态扫描电子显微镜。衍生自丙氨酸，缬氨酸和苯丙氨酸的有机凝胶具有半透明的特性，而丝氨酸有机凝胶则是不透明的。之后，实现了在有机胶凝剂的存在下使用微波辐射的AuNP的合成。有机胶凝剂还原HAuCl 4，显示530至543 nm之间的等离激元能带峰。另外，该方法不需要还原剂，还原剂通常是污染和毒性的潜在来源。因此，这项工作证实了新型脂肪N-酰基氨基酰肼中的酰肼基在凝胶形成中以及作为制备AuNPs的有机胶凝剂的重要性。
• The striking influence of SWNT–COOH on self-assembled gelation
  作者：Subhra Kanti Mandal、Tanmoy Kar、Dibyendu Das、Prasanta Kumar Das

  DOI：10.1039/c2cc16567h

  日期：——

  A miniscule amount of f-SWNTs remarkably improved (∼17-fold) the gelation efficiency of amphiphilic molecules by triggering the formation of interconnecting self-assembled fibrillar networks (SAFIN) in supramolecular gelation.

  极少量的 f-SWNT 通过触发超分子凝胶中互连自组装纤维网络 (SAFIN) 的形成，显着提高（±17 倍）两亲分子的凝胶效率。
• In situ synthesized Ag nanoparticle in self-assemblies of amino acid based amphiphilic hydrogelators: development of antibacterial soft nanocomposites
  作者：Anshupriya Shome、Sounak Dutta、Subhabrata Maiti、Prasanta Kumar Das

  DOI：10.1039/c0sm01087a

  日期：——

  synthesis and stabilization of AgNP and also in modulating the antibacterial activity of the nanocomposites. The antibacterial activities of soft nanocomposites comprising amphiphiles with cationic head group were found to be more efficient than the anionic soft nanocomposites. Interestingly, these nanocomposites have shown considerable biocompatibility to mammalian cell, NIH3T3. Furthermore, the well-known

  目前的工作报告了通过在基于氨基酸（色氨酸/酪氨酸）的两亲水凝胶的超分子自组装中原位合成银纳米颗粒（AgNP）来开发一类新型抗菌软纳米复合材料。有趣的是，纳米粒子合成不需要使用任何外部还原/稳定剂。通过紫外-可见光谱、透射电子显微镜 (TEM) 图像、X 射线衍射光谱 (XRD) 和热重分析 (TGA) 对纳米复合材料进行了表征。令人鼓舞的是，这些柔软的纳米复合材料对革兰氏阳性菌和革兰氏阴性菌均表现出优异的抗菌活性，而单独的两亲物仅对革兰氏阳性菌具有致命性。杀菌性 AgNP 在固有抗菌两亲凝胶剂的自组装中的明智组合导致开发出对这两种细菌均有效的软纳米复合材料。改变两亲物的头基电荷和结构，以研究它们在合成和稳定 AgNP 以及调节纳米复合材料的抗菌活性方面的重要作用。发现包含具有阳离子头基的两亲物的软纳米复合材料的抗菌活性比阴离子软纳米复合材料更有效。有趣的是，这些纳米复合材料已显示出与哺乳动物细胞
• Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids
  作者：Asish Pal、Yamuna K. Ghosh、Santanu Bhattacharya

  DOI：10.1016/j.tet.2007.05.028

  日期：2007.7

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.
• New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties
  作者：Rodrigo da Costa Duarte、Renata Ongaratto、Luciana Almeida Piovesan、Vânia Rodrigues de Lima、Valdir Soldi、Aloir Antônio Merlo、Marcelo G. Montes D’Oca

  DOI：10.1016/j.tetlet.2012.03.015

  日期：2012.5

  new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine

  这项工作报告了从C16：0，C18：0，C18：1和C18：1（OH）脂肪酸家族合成新的脂肪N-酰基氨基酸和N-酰基氨基酯的过程，并证明了这些化合物作为有机凝胶的活性代理商。将化合物加热溶解在各种溶剂中（Ñ己烷，甲苯和汽油）。只有饱和C16：0和C18：从丙氨酸衍生0能够形成凝胶的甲苯溶液，和饱和的C16：从苯丙氨酸衍生的0表明胶凝Ñ正己烷。这是l的脂肪N-酰基氨基酯和N-酰基氨基酸衍生物的第一个证据-丝氨酸和脂肪酸C16：0，C18：0和C18：1能够与己烷形成凝胶。该观察证实了1-丝氨酸的片段衍生物中的羟基在形成良好凝胶中的重要性。