10-D,L-Hydroxy-<10-D,L-H>stearinsaeure-methylester | 80863-13-4

• 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: 10-D,L-Hydroxy-<10-D,L-H>stearinsaeure-methylester
• CAS: 80863-13-4
• 化学式: C₁₉H₃₈O₃
• 分子量: 315.501
• InChiKey: ZWOMTUQOMSFPSL-VAAKKRCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  10-D,L-Hydroxy-<10-D,L-H>stearinsaeure-methylester 在 4-二甲氨基吡啶 、 硼氘化钠 、 水 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 [10,10-2H2]-4-nitrophenyl octadecanoate
  参考文献：
  名称：

  NMR-based conformational analysis of sphingomyelin in bicelles

  摘要：

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.001
• 作为产物：
  描述：

  10-氧代十八烷酸甲酯 在 硼氘化钠 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 以79%的产率得到10-D,L-Hydroxy-<10-D,L-H>stearinsaeure-methylester
  参考文献：
  名称：

  NMR-based conformational analysis of sphingomyelin in bicelles

  摘要：

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.001