methyl-14-oxooctadecanoate | 2380-29-2

• 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: methyl-14-oxooctadecanoate
• 英文别名: 14-Oxo-octadecansaeure-methylester；Methyl-14-oxo-octadecanoat；14-oxo-octadecanoic acid methyl ester；Methyl 14-oxooctadecanoate
• CAS: 2380-29-2
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: CZIMTJBUEYHHCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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

反应信息

• 作为反应物：
  描述：

  methyl-14-oxooctadecanoate 在 sodium tetrahydroborate 作用下， 以100%的产率得到14-Hydroxy-octadecansaeure-methylester
  参考文献：
  名称：

  使用溴化磷脂和碘化磷脂进行荧光淬灭，在脂质双层中定位嵌入剂。

  摘要：

  在以前的工作中，我们已经可以使用三种光谱技术的溶剂极性敏感性来确定脂质双层中插入分子的深度：13 C NMR化学位移（δ）；荧光发射波长（λem）和ESRβ-H分裂常数（aβ-H）。在本文中，我们使用位于磷脂链已知位置的重原子（Br或I）淬灭作为荧光部分位置的探针。我们已经合成了在脂质链的各个位置上都被溴（或碘）原子取代的各种磷脂。后面的类脂与各种荧光基团依次插入DMPC脂质体，生物膜和红细胞鬼影。当重原子的位置与荧光团的位置相对应时，会发生最有效的荧光猝灭。结果表明，一般而言，荧光团插入相同的深度，而与所使用的脂质双层无关。当荧光团位于水相中或水相中时，KBr（或KI）是最有效的淬灭剂。据推测，由于碘的半径较大和自旋耦合常数较大，因此碘类似物在其淬灭的深度范围内的分辨力要小得多。

  DOI：

  10.1016/j.chemphyslip.2019.03.018
• 作为产物：
  描述：

  14-oxooctadecanoic acid 生成 methyl-14-oxooctadecanoate
  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

• Improved Yields in the Synthesis of Spin‐Labeled Fatty Acids
  作者：Janez Mravljak、Slavko Pečar

  DOI：10.1081/scc-200032488

  日期：2004.1.1

  Paramagnetic amide side products (6a–g) have been isolated from the reaction mixture in the synthesis of spin‐labeled fatty acids of the doxyl type. After their hydrolysis to the corresponding acid, 7, the overall yield of spin‐labeled fatty acids is significantly increased compared with published procedures.

  摘要 顺磁性酰胺副产物 (6a-g) 已从多西基型自旋标记脂肪酸合成中的反应混合物中分离出来。在水解成相应的酸 7 后，与已发表的程序相比，自旋标记脂肪酸的总产率显着增加。
• 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：——