dihexadecylmalonic acid diethyl ester | 138950-58-0

• 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: dihexadecylmalonic acid diethyl ester
• 英文别名: Dihexadecyl-malonsaeure-diaethylester；Diethyl 2,2-dihexadecylpropanedioate
• CAS: 138950-58-0
• 化学式: C₃₉H₇₆O₄
• 分子量: 609.03
• InChiKey: IEZPTJHNAWTBID-UHFFFAOYSA-N

物化性质

• 熔点：
  34.5-35 °C
• 沸点：
  305-310 °C(Press: 2-2.5 Torr)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.7
• 重原子数：
  43
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihexadecylmalonic acid diethyl ester 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2-十六烷基十八烷酸
  参考文献：
  名称：

  Tris(2-aminoethyl)amine-based α-branched fatty acid amides – Synthesis of lipids and comparative study of transfection efficiency of their lipid formulations

  摘要：

  The synthesis of a new class of cationic lipids, tris(2-aminoethyl)amine-based alpha-branched fatty acid amides, is described resulting in a series of lipids with specific variations in the lipophilic as well as the hydrophilic part of the lipids. In-vitro structure/transfection relationships were established by application of complexes of these lipids with plasmid DNA (pDNA) to different cell lines. The a-branched fatty acid amide bearing two tetradecyl chains and two lysine molecules (T14diLys) in mixture with the co-lipid 1,2-di-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phosphoethanolamine (DOPE) (1/2, n/n) exhibits effective pDNA transfer in three different cell lines, namely Hep-G2, A549, and COS-7. The presence of 10% serum during lipoplex incubation of the cells did not affect the transfection efficiency. Based on that, detailed investigations of the complexation of pDNA with the lipid formulation T14diLys/DOPE 1/2 (n/n) were carried out with respect to particle size and charge using dynamic light scattering (DLS), C-potential measurements, and transmission electron microscopy (TEM). Additionally, the lipoplex uptake was investigated by confocal laser scanning microscopy (CLSM). Overall, lipoplexes prepared from T14diLys/DOPE 1/2 (n/n) offer large potential as lipid-based polynucleotide carriers and further justify advanced examinations. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejpb.2015.08.011
• 作为产物：
  描述：

  十六烷基丙二酸二乙酯 、 溴代十六烷 在 sodium hydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 10.0h， 生成 dihexadecylmalonic acid diethyl ester
  参考文献：
  名称：

  Tris(2-aminoethyl)amine-based α-branched fatty acid amides – Synthesis of lipids and comparative study of transfection efficiency of their lipid formulations

  摘要：

  The synthesis of a new class of cationic lipids, tris(2-aminoethyl)amine-based alpha-branched fatty acid amides, is described resulting in a series of lipids with specific variations in the lipophilic as well as the hydrophilic part of the lipids. In-vitro structure/transfection relationships were established by application of complexes of these lipids with plasmid DNA (pDNA) to different cell lines. The a-branched fatty acid amide bearing two tetradecyl chains and two lysine molecules (T14diLys) in mixture with the co-lipid 1,2-di-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phosphoethanolamine (DOPE) (1/2, n/n) exhibits effective pDNA transfer in three different cell lines, namely Hep-G2, A549, and COS-7. The presence of 10% serum during lipoplex incubation of the cells did not affect the transfection efficiency. Based on that, detailed investigations of the complexation of pDNA with the lipid formulation T14diLys/DOPE 1/2 (n/n) were carried out with respect to particle size and charge using dynamic light scattering (DLS), C-potential measurements, and transmission electron microscopy (TEM). Additionally, the lipoplex uptake was investigated by confocal laser scanning microscopy (CLSM). Overall, lipoplexes prepared from T14diLys/DOPE 1/2 (n/n) offer large potential as lipid-based polynucleotide carriers and further justify advanced examinations. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejpb.2015.08.011

文献信息

• Temperature-dependent chlorosomal self-aggregation of bacteriochlorophyll<i>-d</i> analogs with a branched alkyl chain in a single 1-chlorooctane solvent
  作者：Nobuyuki Hara、Hitoshi Tamiaki

  DOI：10.1093/bulcsj/uoae032

  日期：2024.3.28

  solvents or aqueous solutions. To obtain the most aggregation models, a concentrated solution of the pigments in a polar organic solvent was diluted with a large amount of a nonpolar organic solvent or water. Here, bacteriochlorophyll-d analogs possessing branched alkyl chains of different lengths at the peripheral 17-propionate residue on the core chlorin π-system were prepared and their highly soluble

  最近，在低极性有机溶剂或水溶液中证明了模拟自然光捕获装置 （chlorosome） 的叶绿素色素的超分子聚合。为了获得最多的聚集模型，用大量非极性有机溶剂或水稀释颜料在极性有机溶剂中的浓缩溶液。在这里，在核心氯π系统上的外围 17-丙酸盐残基上制备了具有不同长度的支链烷基链的细菌叶绿素-d 类似物，并在单个 1-氯辛烷作为低极性溶剂中生产其高可溶性绿素超分子。采用温度依赖性电子吸收和圆二色光谱分析它们的自聚集和解聚机制。合成类似物在高温下是单体的，并且在热溶液冷却过程中通过非 S 形途径自聚集。通过加热均相溶液，将获得的绿素自聚集体可逆单聚体化。将解聚途径拟合到同速序列模型，其熔点取决于烷基链长度。
• Synthesis of new lipophilic ortho-dicarboranes
  作者：Emmanuelle Garrigues、Jean-Pierre Souchard、Françoise Nepveu

  DOI：10.1016/s0040-4039(98)00870-3

  日期：1998.6

  The synthesis of several new lipoidal dicarborane compounds prepares by reaction of decarborane with several fatty mono- and bis-alkyl-1,3-diols is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Buu-Hoi; Cagniant, Bulletin de la Societe Chimique de France, 1943, vol. <5> 10, p. 477,482
  作者：Buu-Hoi、Cagniant

  DOI：——

  日期：——
• Staudinger; Kern, Chemische Berichte, 1933, vol. 66, p. 378
  作者：Staudinger、Kern

  DOI：——

  日期：——
• Tris(2-aminoethyl)amine-based α-branched fatty acid amides – Synthesis of lipids and comparative study of transfection efficiency of their lipid formulations
  作者：Nicole Erdmann、Christian Wölk、Ingo Schulze、Christopher Janich、Manuela Folz、Simon Drescher、Matthias Dittrich、Annette Meister、Jürgen Vogel、Thomas Groth、Bodo Dobner、Andreas Langner

  DOI：10.1016/j.ejpb.2015.08.011

  日期：2015.10

  The synthesis of a new class of cationic lipids, tris(2-aminoethyl)amine-based alpha-branched fatty acid amides, is described resulting in a series of lipids with specific variations in the lipophilic as well as the hydrophilic part of the lipids. In-vitro structure/transfection relationships were established by application of complexes of these lipids with plasmid DNA (pDNA) to different cell lines. The a-branched fatty acid amide bearing two tetradecyl chains and two lysine molecules (T14diLys) in mixture with the co-lipid 1,2-di-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phosphoethanolamine (DOPE) (1/2, n/n) exhibits effective pDNA transfer in three different cell lines, namely Hep-G2, A549, and COS-7. The presence of 10% serum during lipoplex incubation of the cells did not affect the transfection efficiency. Based on that, detailed investigations of the complexation of pDNA with the lipid formulation T14diLys/DOPE 1/2 (n/n) were carried out with respect to particle size and charge using dynamic light scattering (DLS), C-potential measurements, and transmission electron microscopy (TEM). Additionally, the lipoplex uptake was investigated by confocal laser scanning microscopy (CLSM). Overall, lipoplexes prepared from T14diLys/DOPE 1/2 (n/n) offer large potential as lipid-based polynucleotide carriers and further justify advanced examinations. (C) 2015 Elsevier B.V. All rights reserved.