triacontanedioic acid dimethyl ester | 24397-43-1

• 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: triacontanedioic acid dimethyl ester
• 英文别名: dimethyl triacontanedioate；Triacontandisaeure-dimethylester
• CAS: 24397-43-1
• 化学式: C₃₂H₆₂O₄
• 分子量: 510.842
• InChiKey: TVLUURPTIMUJNX-UHFFFAOYSA-N

物化性质

• 沸点：
  503.0±18.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  36
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  triacontanedioic acid dimethyl ester 在 sodium hydroxide 、 草酰氯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 Triacontanedioyl dichloride
  参考文献：
  名称：

  Synthesis and Properties of a Bipolar, Bisphosphatidyl Ethanolamine That Forms Stable 2-Dimensional Self-Assembled Bilayer Systems and Liposomes

  摘要：

  Phosphatidyl ethanolamine is one of the most common naturally occurring phospholipids. The presence of an amino group also makes it one of the most straightforward to functionalize. Unfortunately however, it tends to form micelles and hexagonal clusters instead of forming lamellar systems such as sheets and vesicles (liposomes), key supramolecular structures for a variety of biomedical and other technical applications. This has been overcome by synthesizing a dimeric phosphatidyl ethanolamine molecule in which the acyl chains at the 2-position of glycerol are joined at their termini by a carbon-carbon bond, thus resulting in a trans-membrane type fatty acyl linkage. Such tail-to-tail bipolar transmembrane lipids are found in the membranes of thermophilic and other extremophilic bacteria. The dimeric phosphatidyl ethanolamine readily forms very uniformly flat self-assembled lamellar supramolecular arrays and liposomes that are stable at temperatures up to 80 degrees C. The planar systems formed by the new lipid were characterized by atomic force microscopy, and the uniformity of the vesicles was observed by laser scanning confocal microscopy, The thermal stability of the phospholipid and the vesicles formed was examined by NMR spectroscopy including proton T-1 measurements as a function of temperature. Fourier transform infrared spectroscopy indicated a much greater order of the alkyl chain in the dimer than in phosphatidyl ethanolamine. This extremely stable and readily functionalizable dimeric phospholipid has potential uses in the fabrication of biomaterials, stable membrane models, and liposome drug-delivery systems.

  DOI：

  10.1021/jo9902852
• 作为产物：
  描述：

  环十五内酯 在 palladium on activated charcoal 三甲基氯硅烷 、 氢气 、 sodium methylate 、 碳酸氢钠 、 sodium iodide 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 150.0 ℃ 、1.38 MPa 条件下， 反应 27.07h， 生成 triacontanedioic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and Properties of a Bipolar, Bisphosphatidyl Ethanolamine That Forms Stable 2-Dimensional Self-Assembled Bilayer Systems and Liposomes

  摘要：

  Phosphatidyl ethanolamine is one of the most common naturally occurring phospholipids. The presence of an amino group also makes it one of the most straightforward to functionalize. Unfortunately however, it tends to form micelles and hexagonal clusters instead of forming lamellar systems such as sheets and vesicles (liposomes), key supramolecular structures for a variety of biomedical and other technical applications. This has been overcome by synthesizing a dimeric phosphatidyl ethanolamine molecule in which the acyl chains at the 2-position of glycerol are joined at their termini by a carbon-carbon bond, thus resulting in a trans-membrane type fatty acyl linkage. Such tail-to-tail bipolar transmembrane lipids are found in the membranes of thermophilic and other extremophilic bacteria. The dimeric phosphatidyl ethanolamine readily forms very uniformly flat self-assembled lamellar supramolecular arrays and liposomes that are stable at temperatures up to 80 degrees C. The planar systems formed by the new lipid were characterized by atomic force microscopy, and the uniformity of the vesicles was observed by laser scanning confocal microscopy, The thermal stability of the phospholipid and the vesicles formed was examined by NMR spectroscopy including proton T-1 measurements as a function of temperature. Fourier transform infrared spectroscopy indicated a much greater order of the alkyl chain in the dimer than in phosphatidyl ethanolamine. This extremely stable and readily functionalizable dimeric phospholipid has potential uses in the fabrication of biomaterials, stable membrane models, and liposome drug-delivery systems.

  DOI：

  10.1021/jo9902852

文献信息

• Long chain α,ω-dicarboxylic acids from the spores of Equisetum telmateia and E. arvense
  作者：K.R. Adams、R. Bonnett

  DOI：10.1016/s0031-9422(00)86454-7

  日期：1971.8

  Abstract Ether extraction of spores of Equisetum telmateia and E. arvense gives up to 1% triacontanedioic acid (equisetolic acid) contaminated with a small proportion of octacosanedioic acid. The dimethyl ester of the C30-diacid has been isolated in a pure state by GLC and its identity confirmed by comparison with a sample prepared by anodic synthesis.

  摘要 Equisetum telmateia 和 E. arvense 孢子的乙醚提取得到高达 1% 的三十烷二酸 (equisetolic acid) 被少量二十八烷二酸污染。C30-二酸的二甲酯已通过 GLC 以纯态分离出来，并通过与阳极合成制备的样品进行比较来确认其身份。
• Ziegler; Hechelhammer, Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 133
  作者：Ziegler、Hechelhammer

  DOI：——

  日期：——
• Ruzicka; Stoll; Schinz, Helvetica Chimica Acta, 1928, vol. 11, p. 1179
  作者：Ruzicka、Stoll、Schinz

  DOI：——

  日期：——
• Yadav, Ashok K.; Singh, Arpita, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 8, p. 1724 - 1726
  作者：Yadav, Ashok K.、Singh, Arpita

  DOI：——

  日期：——