甲基16-氧代硬脂酸酯 | 2380-31-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基16-氧代硬脂酸酯
• 英文名称: 16-Oxooctadecanoic acid methyl ester
• 英文别名: methyl 16-oxooctadecanoate；16-oxo-octadecanoic acid methyl ester；16-Oxo-octadecansaeure-methylester；16-Oxo-octadecansaeuremethylester；16-Oxo-stearinsaeuremethylester；Methyl-16-oxo-octadecanoat
• CAS: 2380-31-6
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: IYSITFOIRGLNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：

  甲基16-氧代硬脂酸酯 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以40%的产率得到16-氧代硬脂酸
  参考文献：
  名称：

  NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2014.07.007
• 作为产物：
  描述：

  16-氧代硬脂酸 生成 甲基16-氧代硬脂酸酯
  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

• Natural acetylenes. Part XXIII. A C18 polyacetylenic keto-aldehyde related to falcarinone from an Umbellifer (Pastinaca sativa L.)
  作者：Ewart R. H. Jones、S. Safe、V. Thaller

  DOI：10.1039/j39660001220

  日期：——

  The structure of the polyacetylenic keto-aldehyde H2CCH·CO·[CC]2·CH2·CH[graphic omitted]CH·[CH2]7·CHO} has been determined. It is the first C18 polyacetylene to be isolated from a plant (Pastinaca sativa L.) of the main polyacetylene-producing families. Its occurrence almost certainly establishes the derivation of the C17 falcarinone and related compounds and is in harmony with Bu'Lock's hypothesis

  的聚炔酮醛的结构H 2 C ^ CH·CO·[C C] 2 ·CH 2 ·CH [图形省略] CH·[CH 2 ] 7 ·CHO}已经确定。这是第一个C 18聚乙炔被从植物（隔绝Pastinaca苜蓿主聚乙炔生产家庭L.）。它的出现几乎可以肯定地确定了C 17 falcarinone及其相关化合物的衍生物，并且与Bu'Lock关于天然乙炔的生物发生的假设相一致。
• Dolgopalets; Volkov; Kisel', Russian Journal of Organic Chemistry, 1999, vol. 35, # 10, p. 1436 - 1438
  作者：Dolgopalets、Volkov、Kisel'、Kozhevko、Kulinkovich

  DOI：——

  日期：——