棕榈酸-D3 | 75736-53-7

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 棕榈酸-D3
• 中文别名: 棕榈酸-16,16,16-d3
• 英文名称: palmitic acid(16,16,16-d3)
• 英文别名: Hexadecanoic-16,16,16-d3 acid；16,16,16-trideuteriohexadecanoic acid
• CAS: 75736-53-7
• 化学式: C₁₆H₃₂O₂
• 分子量: 259.405
• InChiKey: IPCSVZSSVZVIGE-FIBGUPNXSA-N

物化性质

• 熔点：
  61-64°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  棕榈酸-D3 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到1-十六烷醇-D3
  参考文献：
  名称：

  氘标记的半脂质异构体的高效便捷合成及其ESI-MS表征。

  摘要：

  通过从受保护的缩水甘油基半乳糖苷3进行直接合成，同位素和化学上纯净地分别获得了在烷基或酰基链上用氘标记的半脂质1a和1b以及半乳糖基烷基酰基甘油甘油2a和2b，总收率为22％。通过NMR光谱和ESI质谱分析确定化合物的身份和纯度。这些标记的化合物作为通过质谱定量这些脂质的内标非常重要，它们还可以用于体外甚至体内系统的代谢研究。程序的扩展可以为制备相同一般类别的其他化合物的同位素异构体提供一条途径。

  DOI：

  10.1016/j.chemphyslip.2008.02.002
• 作为产物：
  描述：

  在 recombinant clysophospholipase A₂ 、 BSA 作用下， 生成 棕榈酸-D3 、 2,3-二羟丙基(2-(三甲基铵)乙基)磷酸酯
  参考文献：
  名称：

  Lysophospholipases cooperate to mediate lipid homeostasis and lysophospholipid signaling

  摘要：

  Lysophospholipids (LysoPLs) are bioactive lipid species involved in cellular signaling processes and the regulation of cell membrane structure. LysoPLs are metabolized through the action of lysophospholipases, including lysophospholipase A1 (LYPLA1) and lysophospholipase A2 (LYPLA2). A new X-ray crystal structure of LYPLA2 compared with a previously published structure of LYPLA1 demonstrated near-identical folding of the two enzymes; however, LYPLA1 and LYPLA2 have displayed distinct substrate specificities in recombinant enzyme assays. To determine how these in vitro substrate preferences translate into a relevant cellular setting and better understand the enzymes' role in LysoPL metabolism, CRISPR-Cas9 technology was utilized to generate stable KOs of Lypla1 and/or Lypla2 in Neuro2a cells. Using these cellular models in combination with a targeted lipidomics approach, LysoPL levels were quantified and compared between cell lines to determine the effect of losing lysophospholipase activity on lipid metabolism. This work suggests that LYPLA1 and LYPLA2 are each able to account for the loss of the other to maintain lipid homeostasis in cells; however, when both are deleted, LysoPL levels are dramatically increased, causing phenotypic and morphological changes to the cells.

  DOI：

  10.1194/jlr.m087890

文献信息

• Investigation of Surfactant Conformation and Order at the Liquid−Liquid Interface by Total Internal Reflection Sum-Frequency Vibrational Spectroscopy
  作者：John C. Conboy、Marie C. Messmer、Geraldine L. Richmond

  DOI：10.1021/jp953616x

  日期：1996.1.1

  The conformational order of sodium dodecyl sulfate (SDS) adsorbed at the D2O-CCl4 interface has been examined by total internal reflection sum-frequency vibrational spectroscopy. A change in conformation of the alkyl chain with increased surface coverage at the liquid-liquid interface is observed. A series of aqueous surfactant concentrations have been examined in order to determine the effect of surface coverage on the conformation of the alkyl chains at the interface. Polarization studies indicate that, for the concentration range examined, the symmetry axis of the terminal methyl group on the alkyl chain is oriented primarily along the surface normal. Identification of spectral features in the C-H region of the infrared region is facilitated by examination of the sum-frequency spectrum from an analogous deuterated compound.
• Chemosynthetic homologues of Mycoplasma pneumoniae β-glycolipid antigens for the diagnosis of mycoplasma infectious diseases
  作者：Kazuo Fukuda、Kazuhiro Matsuda、Sachie Matsuda、Sayaka Kado、Hyuma Masu、Hirofumi Dohi、Yoshihiro Nishida

  DOI：10.1016/j.bmc.2017.12.046

  日期：2018.2

  Mycoplasma pneumoniae expresses beta-glycolipids (beta-GGLs) in cytoplasmic membranes, which possess a unique beta(1 -> 6)-linked disaccharide epitope, which has high potential in biochemical and medicinal applications. In the present study, a series of beta-GGLs homologues with different acyl chains (C12, C14, C16, and C18) were prepared from a common precursor. An ELISA assay using an anti-(beta-GGLs) monoclonal antibody indicated that the synthetic homologues with long acyl chains had greater diagnostic potential in the order C18 > C16 > C14 > C12. Toward a simultaneous detection of natural glycolipids by mass spectrometry (MS), a deuterium-labeled C16 homologue (beta-GGL-C16-d3) was prepared and applied as an internal standard for a high-resolution electrospray ionization MS (ESI-MS) analysis. The ESI-MS analysis was used to identify and quantify acyl homologues (C16/C16, C16/C18, and C18/C18) of beta-GGL-C16 in cultured M. pneumoniae. A beta-GGLs homologue with a 1,2-diacetyl group (C2) was also prepared as a "water soluble" glycolipid homologue and characterized by H-1 NMR spectroscopy. We envisage that each of these chemosynthetic homologues will provide promising approaches to solve medical and biological problems associated with mycoplasma infectious diseases (MIDs). (C) 2017 Elsevier Ltd. All rights reserved.
• BOULOUSSA, O.;DENHEZ, J. P.;DIZABO, P., J. LABELLED COMPOUNDS AND RADIOPHARM, 1986, 23, N 2, 127-135
  作者：BOULOUSSA, O.、DENHEZ, J. P.、DIZABO, P.

  DOI：——

  日期：——
• DETERDING, LEESA J.;GROSS, MICHAEL L., ANAL. CHIM. ACTA, 200,(1987) N 1, 431-445
  作者：DETERDING, LEESA J.、GROSS, MICHAEL L.

  DOI：——

  日期：——
• Vaz; Doane; Neubert, Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 68, # 1-4, p. 11 - 22
  作者：Vaz、Doane、Neubert

  DOI：——

  日期：——