戊酸,2-甲基-4-羰基-,甲基酯,(2S)- | 2380-28-1

• 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: 戊酸,2-甲基-4-羰基-,甲基酯,(2S)-
• 英文名称: methyl 13-oxooctadecanoate
• 英文别名: 13-Oxo-octadecansaeure-methylester；Methyl-13-oxo-stearat；13-Ketostearinsaeuremethylester；Methyl 13-oxostearate
• CAS: 2380-28-1
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: PJELCFQUQJJWGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	tridecanedioic acid monomethyl ester	3927-59-1	C14H26O4	258.358
  十三碳二酸二甲酯	dimethyl 1,11-undecanedicarboxylate	1472-87-3	C15H28O4	272.385
  13-氧代十八烷酸	13-oxooctadecanoic acid	2389-06-2	C18H34O3	298.466
  己酰乙酸甲酯	methyl 3-oxooctanoate	22348-95-4	C9H16O3	172.224
  ——	12-(Methoxycarbonyl)dodecanoyl Chloride	24525-25-5	C14H25ClO3	276.804
  11-碘十一烷酸乙酯	ethyl 11-iodoundecanoate	53821-20-8	C13H25IO2	340.245

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  13-氧代十八烷酸	13-oxooctadecanoic acid	2389-06-2	C18H34O3	298.466
  甲基13-羟基硬脂酸酯	13-hydroxyoctadecadienoic acid methyl ester	2540-76-3	C19H38O3	314.509
  13-羟基十八酸	13-hydroxyoctadecanoic acid	17773-34-1	C18H36O3	300.482

反应信息

• 作为反应物：
  描述：

  戊酸,2-甲基-4-羰基-,甲基酯,(2S)- 在 甲醇 、 镍 作用下， 生成 甲基13-羟基硬脂酸酯
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴戊烷 在 magnesium 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.5h， 生成 戊酸,2-甲基-4-羰基-,甲基酯,(2S)-
  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

文献信息

• NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part IV: Studies on ketophospholipids
  作者：Michal Afri、Carmit Alexenberg、Pinchas Aped、Efrat Bodner、Sarit Cohen、Michal Ejgenberg、Shlomi Eliyahu、Pessia Gilinsky-Sharon、Yifat Harel、Miriam E. Naqqash、Hani Porat、Ayala Ranz、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2014.07.003

  日期：2014.12

  ketophospholipids was prepared in which the above n-oxooctadecanoic acids were attached to the sn-2 position of a phosphatidylcholine with a palmitic acid chain at sn-1. To assist in assignment and detection several derivatives were prepared 13C-enriched in both carbonyls. The various homologs were intercalated into DMPC liposomes and give points specifically in the missing area of the previous polarity–penetration

  在我们的同伴论文中，我们描述了两种同源的二羰基化合物系列（正氧十八烷酸甲酯和相应的正氧十八烷酸（n  = 4-16））的制备和插入到DMPC脂质体中。使用E T（30）溶剂极性-化学位移相关性表和相应的计算穿透深度（以Å为单位），分析了各种羰基的13 C NMR化学位移。数据点的迭代最佳拟合分析揭示了E T之间的指数相关性（30）微极性和脂质体双层的渗透深度（以Å为单位）。但是，这项研究仍不完整，因为该图在中等极性的重要区域内，即在E T（30）范围为41-45.5 kcal / mol的范围内，缺少数据点。为了纠正这一缺陷，制备了一个酮磷脂家族，其中上述n-氧代十八碳烯酸被连接到在sn -1处具有棕榈酸链的磷脂酰胆碱的sn -2位置。为了协助进行赋值和检测，准备了几种衍生物13C富含两个羰基。将各种同系物插入DMPC脂质体中，并在先前的极性-穿透相关图的缺失区域中明确给出点。有趣的是，完
• Soybean Lipoxygenase-Mediated Oxygenation of Monounsaturated Fatty Acids to Enones
  作者：Charles H. Clapp、Susan E. Senchak、Theodore J. Stover、Thomas C. Potter、Peter M. Findeis、Mark J. Novak

  DOI：10.1021/ja0032071

  日期：2001.1.1
• Chemoselective Hydrogenation of Unsaturated Peroxides
  作者：Patrick H. Dussault、Scott Kreifels、In Quen Lee

  DOI：10.1080/00397919508011807

  日期：1995.9

  Chemoselective hydrogenation of unsaturated monoperoxyketals provides new methodology for the synthesis of saturated and allyl hydroperoxides.
• GULACAR, FAZIL O.;BUCHS, ARMAND;SUSINI, ALBERTO, J. CHROMATOGR., 479,(1989) N, C. 61-72
  作者：GULACAR, FAZIL O.、BUCHS, ARMAND、SUSINI, ALBERTO

  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：——