4-氧代十八烷酸甲酯 | 2380-19-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 4-氧代十八烷酸甲酯
• 英文名称: methyl 4-oxooctadecanoate
• 英文别名: 4-oxo-octadecanoic acid methyl ester；4-Oxo-octadecansaeure-methylester；4-Oxo-octadecansaeuremethylester；4-Oxo-stearinsaeure-methylester；4-Oxo-stearinsaeuremethylester；Methyl-4-oxo-octadecanoat；Octadecanoic acid, 4-oxo-, methyl ester
• CAS: 2380-19-0
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: UIUPUTHABPRTHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  4-氧代十八烷酸甲酯 在 甲醇 、 氢氧化钾 、 镍 作用下， 生成 4-羟基十八烷酸
  参考文献：
  名称：

  Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-heptadecanoic acid methyl ester 在 potassium carbonate 、 2-戊酮 作用下， 生成 4-氧代十八烷酸甲酯
  参考文献：
  名称：

  Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169

  摘要：

  DOI：

文献信息

• The phthienoic acids from tubercle bacillus
  作者：J. Cason、P. Tavs、A. Weiss

  DOI：10.1016/s0040-4020(01)92691-2

  日期：1962.1

  applied as an independent determination of structure and examination for homogeneity. TheC25-phthienoic acid has also been isolated, characterized, and assigned the structure, 2,4,6,-trimethyl-2-docosenic acid. Gas chromatographic analysis of previously isolated fraction of acids from the tubercle bacillus indicates the occurrence of the series of phthienoic acids ranging from C22 to C28. There are probably

  与其他研究人员先前确定的结构一致，C 27-邻苯二甲酸的氧化降解毫无疑问地确定了结构2,4,6，-三甲基-2-四十四烯酸。一种降解方法包括α，β-不饱和酸的烯丙基溴化，脱卤化氢，臭氧分解和用高锰酸钾进行氧化。一种新的降解烃链的方法，依赖于乙酸铬铬的氧化，被用作结构的独立测定和均质性检查。第25届会议还已分离，表征和表征了-邻苯二甲酸结构，即2,4,6，-三甲基-2-二十二碳六烯酸。先前从结核杆菌分离出的部分酸的气相色谱分析表明，发生了一系列范围从C 22至C 28的邻苯二酸。除了C 27-邻苯二酸以外，可能还存在另外两种C 27 -α，δ-不饱和酸。
• NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer
  作者：Michal Afri、Carmit Alexenberg、Pinchas Aped、Efrat Bodner、Sarit Cohen、Michal Ejgenburg、Shlomi Eliyahu、Pessia Gilinsky-Sharon、Yifat Harel、Miriam E. Naqqash、Hani Porat、Ayala Ranz、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2014.07.007

  日期：2014.12

  The development of "molecular rulers" would allow one to quantitatively locate the penetration depth of intercalants within lipid bilayers. To this end, an attempt was made to correlate the C-13 NMR chemical shift of polarizable "reporter" carbons (e.g., carbonyls) of intercalants within DMPC liposomal bilayers - with the polarity it experiences, and with its Angstrom distance from the interface.This requires families of molecules with two "reporter carbons" separated by a known distance, residing at various depths/polarities within the bilayer. For this purpose, two homologous series of dicarbonyl compounds, methyl n-oxooctadecanoates and the corresponding n-oxooctadecanoic acids (n = 4-16), were synthesized. To assist in assignment and detection several homologs in each system were prepared (13)C(-)enriched in both carbonyls. Within each family, the number of carbons and functional groups remains the same, with the only difference being the location of the second ketone carbonyl along the fatty acid chain. Surprisingly, the head groups within each family are not anchored near the lipid-water interface, nor are they even all located at the same depth. Nevertheless, using an iterative best fit analysis of the data points enables one to obtain an exponential curve. The latter gives substantial insight into the correlation between polarity (measured in terms of the Reichardt polarity parameter, E-T(30)) and penetration depth into the liposomal bilayer. Still missing from this curve are data points in the moderate polarity range. (C) 2014 Elsevier Ireland Ltd. All rights reserved.
• Double-Chain Surfactants with Two Quaternary Ammonium Head Groups
  作者：David A. Jaeger、Sarah G. G. Russell、Hiraku Shinozaki

  DOI：10.1021/jo00103a066

  日期：1994.12
• A New Family of Polymerizable Lyotropic Liquid Crystals:  Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure
  作者：Mary A. Reppy、David H. Gray、Brad A. Pindzola、Juston L. Smithers、Douglas L. Gin

  DOI：10.1021/ja002462i

  日期：2001.1.1

  An efficient and versatile synthesis of a series of polymerizable amphiphilic mesogens that affords control over tail length and position of the :polymerizable group is described. The synthesis employs a novel and facile method of preparing styrene ethers. The monomers are sadium salts of styrene ether-modified fatty acids that can be used to form cross-linkable inverted hexagonal (H-II) lyotropic liquid crystal (LLC) phases at ambient temperature with controllable nanometer-scale dimensions. Examination of a series of regioisomers with the same alkyl chain length but with the styrene: ether group at different locations along the chain revealed that the position of the styrene ether has a profound effect on the dimensions of the resulting HII phase at a fixed temperature and composition. Increasing overall monomer tail length also has a significant, although smaller, effect on the unit cell dimensions of the LLC phase. By controlling the structure of the LLC monomer in this manner, cross-linked HII phases with interchannel distances (ICD) ranging from 29 to 54 Angstrom can be obtained. Furthermore, changing the counterion from Na+ to tetraalkylammonium ions leads to further expansion of the H-II unit cell to a maximum ICD of 65 Angstrom, as well as to the production of a lamellar phase. Use of these monomers affords a new and unparalleled degree of control over phase structure and dimensions for the production of nanostructured organic materials.
• Brown; Farmer, Biochemical Journal, 1935, vol. 29, p. 635,636
  作者：Brown、Farmer

  DOI：——

  日期：——