2-(ethoxycarbonyl)octadecanoic acid | 41433-82-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(ethoxycarbonyl)octadecanoic acid
• 英文别名: hexadecyl malonic acid monoethyl ester；Hexadecyl-malonsaeure-monoaethylester；2-Ethoxycarbonyloctadecanoic acid；2-ethoxycarbonyloctadecanoic acid
• CAS: 41433-82-3
• 化学式: C₂₁H₄₀O₄
• 分子量: 356.546
• InChiKey: ZXDIXFNRWBPPCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethoxycarbonyl)octadecanoic acid 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-{[(9Z)-octadec-9-enylamino]carbonyl}octadecanoic acid
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022
• 作为产物：
  描述：

  十六烷基丙二酸二乙酯 在 乙醇 、 potassium hydroxide 作用下， 以75%的产率得到2-(ethoxycarbonyl)octadecanoic acid
  参考文献：
  名称：

  长链β-内酯的合成及其对致病性分枝杆菌的抗菌活性。

  摘要：

  为了寻求新的抗菌剂，开发了一系列新颖的长链和中链单和双取代β-内酯。它们针对三种致病性分枝杆菌-M的活性。通过刃天青素微量滴定分析（REMA）评估脓肿，海藻分枝杆菌和结核分枝杆菌。在合成的16种β-内酯中，只有3-十六烷基氧杂环丁烷-2-酮（VM005）表现出对脓肿分支杆菌的有希望的活性，而大多数β-内酯表现出了有趣的抗海藻分支杆菌的活性，类似于经典抗生素，异烟肼。关于结核分枝杆菌，发现有六种化合物对这种分枝杆菌有活性，与β-内酯VM008 [反式-（Z）-3-（十六烷基-7-烯-1-基）-4-丙基氧杂环丁烷-2-一]是最好的生长抑制剂。

  DOI：

  10.1002/cmdc.201800720

文献信息

• General Synthesis and Physicochemical Characterisation of a Series of Peptide-Mimic Lysine-Based Amino-Functionalised Lipids
  作者：Christian Wölk、Simon Drescher、Annette Meister、Alfred Blume、Andreas Langner、Bodo Dobner

  DOI：10.1002/chem.201204529

  日期：2013.9.16

  A series of novel malonic acid diamides (second generation) with two long hydrophobic alkyl chains and an alkaline polar head group was synthesised and characterised as a new class of amino‐functionalised lipids. These peptide‐mimic lipids are suitable for polynucleotide transfer. The lipids bear a novel backbone consisting of a lysine unit and a malonic acid unit. Six different head‐group structures

  合成了一系列具有两个长的疏水性烷基链和一个碱性极性头基的新型丙二酸二酰胺（第二代），并将其表征为一类新的氨基官能化脂质。这些肽模拟脂质适合多核苷酸转移。脂质带有由赖氨酸单元和丙二酸单元组成的新型主链。六个不同的头基结构连接到主链结构上，这些头基结构的大小和可质子化的氨基数量不同。此外，使用不同的烷基链来构建亲脂性部分（即十四烷基，十六烷基和油基）。根据头基和烷基链的变化，对新化合物在pH 10的水分散液中的相变进行了分析和讨论。
• Novel Cationic Lipids Based on Malonic Acid Amides Backbone: Transfection Efficacy and Cell Toxicity Properties
  作者：Martin Heinze、Gerald Brezesinski、Bodo Dobner、Andreas Langner

  DOI：10.1021/bc9004624

  日期：2010.4.21

  Gene delivery using nonviral approaches has been extensively studied as a basic tool for intracellular gene transfer. Despite intensive research activity, the aim of creating a vector which meets all necessary demands has still not been reached. One possibility to solve the nonviral vector associated problem of low transfection efficacy is the development of new cationic amphiphiles. Therefore, the non-glycerol-based cationic lipids 1-9 have been synthesized and tested for in vitro gene delivery experiments. The backbone structure of the lipids consists of a malonic acid diamide with two long hydrophobic chains. The degree of saturation of the hydrophobic chains and the structure of the polar cationic headgroup were varied. The preparation follows an easy process and facilitates the trouble-free insertion of different alkyl chains. By studying in vitro gene delivery an increase of transfection efficacy was observed when using at least one unsaturated alkyl chain in the hydrophobic part and lysine or bis(2-aminoethyl)aminoethylamid as hydrophilic headgroup. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available LipolectAmine and Super Feet.
• Eisner et al., Bulletin de la Societe Chimique de France, 1955, p. 212,217
  作者：Eisner et al.

  DOI：——

  日期：——
• Synthesis of Long‐Chain β‐Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria
  作者：Pierre Santucci、Christina Dedaki、Alexandros Athanasoulis、Laura Gallorini、Anaïs Munoz、Stéphane Canaan、Jean‐François Cavalier、Victoria Magrioti

  DOI：10.1002/cmdc.201800720

  日期：2019.2.5

  the quest for new antibacterial agents, a series of novel long- and medium-chain mono- and disubstituted β-lactones was developed. Their activity against three pathogenic mycobacteria-M. abscessus, M. marinum, and M. tuberculosis-was assessed by the resazurin microtiter assay (REMA). Among the 16 β-lactones synthesized, only 3-hexadecyloxetan-2-one (VM005) exhibited promising activity against M. abscessus

  为了寻求新的抗菌剂，开发了一系列新颖的长链和中链单和双取代β-内酯。它们针对三种致病性分枝杆菌-M的活性。通过刃天青素微量滴定分析（REMA）评估脓肿，海藻分枝杆菌和结核分枝杆菌。在合成的16种β-内酯中，只有3-十六烷基氧杂环丁烷-2-酮（VM005）表现出对脓肿分支杆菌的有希望的活性，而大多数β-内酯表现出了有趣的抗海藻分支杆菌的活性，类似于经典抗生素，异烟肼。关于结核分枝杆菌，发现有六种化合物对这种分枝杆菌有活性，与β-内酯VM008 [反式-（Z）-3-（十六烷基-7-烯-1-基）-4-丙基氧杂环丁烷-2-一]是最好的生长抑制剂。
• Synthesis and DNA transfection properties of new head group modified malonic acid diamides
  作者：Christian Wölk、Martin Heinze、Patrick Kreideweiß、Matthias Dittrich、Gerald Brezesinski、Andreas Langner、Bodo Dobner

  DOI：10.1016/j.ijpharm.2011.02.022

  日期：2011.5

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.