14-oxooctadecanoic acid | 16694-36-3

• 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: 14-oxooctadecanoic acid
• 英文别名: 14-Oxo-octadecanoic acid
• CAS: 16694-36-3
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: SNTUZKPEHBBWOS-UHFFFAOYSA-N

物化性质

• 沸点：
  431.2±18.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-oxooctadecanoic acid 在 甲醇 、 镍 作用下， 生成 14-Hydroxy-octadecansaeure-methylester
  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：

  14-Hydroxy-octadecansaeure 在 硫酸 、 Cr₂O₇^(2-)*2K⁽¹⁺⁾*2H₂O 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以30%的产率得到14-oxooctadecanoic acid
  参考文献：
  名称：

  Comparison of Dipolar, H-Bonding, and Dispersive Interactions on Gelation Efficiency of Positional Isomers of Keto and Hydroxy Substituted Octadecanoic Acids

  摘要：

  A systematic study of the importance of functional group position and type on the gelator efficiencies of structurally simple, low molecular mass gelators is reported. Thus, the gelation abilities of a series of positional isomers of ketooctadecanoic acid (n-KSA) are compared in a wide range of liquids. The gelation abilities of the n-KSA as a function of n, the keto group position along the chain, are characterized by several structural, thermal, and rheological techniques and are compared with those of the corresponding hydroxyoctadecanoic acid isomers (n-HSA) and the parent molecule, octadecanoic acid (SA). Analyses of the gels according to the strengths of functional group interactions along the alkyl chain in terms of group position and type are made. The conclusions derived from the study indicate that gel stability is enhanced when the functional group is located relatively far from the carboxylic headgroup and when group-group interactions are stronger (i.e., hydrogen bonding interactions are stronger in the n-HSA than dipole interactions in the n-KSA, which are stronger than the London dispersion interactions in SA). Co-crystals of the keto- and hydroxy-substituted octadecanoic acids are found to be less efficient gelators than even the ketooctadecanoic acids, due to molecular packing and limited group interactions within the gelator networks.

  DOI：

  10.1021/la400664q

文献信息

• Influence of Positional Isomers on the Macroscale and Nanoscale Architectures of Aggregates of Racemic Hydroxyoctadecanoic Acids in Their Molecular Gel, Dispersion, and Solid States
  作者：Shibu Abraham、Yaqi Lan、Ricky S. H. Lam、Douglas A. S. Grahame、Jennifer Jae Hee Kim、Richard G. Weiss、Michael A. Rogers

  DOI：10.1021/la204412t

  日期：2012.3.20

  Inter/intramolecular hydrogen bonding of a series of hydroxystearic acids (HSAs) are investigated. Self-assembly of molecular gels obtained from these fatty acids with isomeric hydroxyl groups is influenced by the position of the secondary hydroxyl group. 2-Hydroxystearic acid (2HSA) does not form a molecular dimer, as indicated by FT-IR, and growth along the secondary axis is inhibited because the secondary hydroxyl

  研究了一系列羟基硬脂酸（HSA）的分子间/分子间氢键。由这些具有异构羟基的脂肪酸获得的分子凝胶的自组装受到仲羟基位置的影响。如FT-IR所示，2-羟基硬脂酸（2HSA）不会形成分子二聚体，并且由于仲羟基无法形成分子间的H键，因此沿仲轴的生长受到抑制。同样，XRD长间隔短于羟基硬脂酸的二聚体长度。3-羟基硬脂酸（3HSA）形成无环二聚体，并且羟基无法氢键结合，从而阻止了晶体结构沿副轴生长。最后，异构体6HSA，8HSA，10HSA，12HSA和14HSA具有相似的XRD和FT-IR模式，这表明这些分子都以相似的方式自组装。单体形成羧基环状二聚体，并且仲羟基促进沿仲轴的生长。
• Lipid constituents of Tridax procumbens
  作者：Ram K. Verma、Madan M. Gupta

  DOI：10.1016/0031-9422(88)83120-0

  日期：1988.1

  Abstract Eight new compounds, isolated from Tridax procumbens , have been characterized as methyl 14-oxooctadecanoate, methyl 14-oxononacosanoate, 3-methylnonadecylbenzene, heptacosanyl cyclohexane car☐ylate, 1(2,2-dimethyl-3-hydroxypropyl)-2-isobutyl phthalate, 12-hydroxytetracosan- 15-one, 32-methyl-30-oxotetratriacont-31-en-1-ol and 30-methyl-28-oxodotriacont-29-en-1-oic acid by spectral data and

  摘要 从 Tridax procumbens 中分离出的 8 种新化合物已被表征为 14-氧代十八酸甲酯、14-氧代二十烷酸甲酯、3-甲基十九烷基苯、七十二烷基环己烷羧酸酯、1(2,2-二甲基-3-羟丙基)-2-异丁基通过光谱数据和化学研究，邻苯二甲酸酯、12-羟基四十二烷-15-one、32-methyl-30-oxotetratricont-31-en-1-ol 和 30-methyl-28-oxodotriacont-29-en-1-oic 酸。首次从该植物中分离出的 9 种已知化合物被鉴定为 dottricontanol、β-amyrone、Δ 12-dehydrolupen-3-one、β-amyrin、羽扇豆醇、岩藻甾醇、9-氧代十七烷、10-氧代十一烷和谷甾醇。尽管 Δ 12 -dehydrolupen-3-one 是合成报道的，但这是该化合物来自天然来源的首次报道。
• 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.
• VERMA, RAM K.;GUPTA, MADAN M., PHYTOCHEMISTRY, 27,(1988) N 2, 459-463
  作者：VERMA, RAM K.、GUPTA, MADAN M.

  DOI：——

  日期：——
• Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169
  作者：Bergstroem et al.

  DOI：——

  日期：——