cis-Eicos-9-enoic acid methyl ester | 76899-35-9

• 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: cis-Eicos-9-enoic acid methyl ester
• 英文别名: methyl (9Z)-icos-9-enoate；Eicosen-(9c)-saeure-methylester；Methyl gadoleate；methyl (Z)-icos-9-enoate
• CAS: 76899-35-9
• 化学式: C₂₁H₄₀O₂
• 分子量: 324.547
• InChiKey: XEJYCWVISZMIDA-SEYXRHQNSA-N

物化性质

• 密度：
  0.8738 g/cm3
• LogP：
  9.820 (est)
• 保留指数：
  2287;2279

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-Eicos-9-enoic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(9Z)-9-二十碳烯酸
  参考文献：
  名称：

  A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

  摘要：

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

  DOI：

  10.1021/acs.jmedchem.9b01287
• 作为产物：
  描述：

  十一醛 生成 cis-Eicos-9-enoic acid methyl ester
  参考文献：
  名称：

  Bergelson,L.D. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 1785 - 1789

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins
  作者：Qinghai Zhang、Yu Fu、Yue Weng、Wen-Xu Hong

  DOI：10.1055/s-0030-1259912

  日期：2011.4

  A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization.

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。
• MIRALLES, JOSEPH;AKNIN, MAURICE;BANDIA, IBRAHIMA;BASSENE, EMMANUEL;DIAGNE+, OCEANOL. ACTA, 12,(1989) N, C. 433-436
  作者：MIRALLES, JOSEPH、AKNIN, MAURICE、BANDIA, IBRAHIMA、BASSENE, EMMANUEL、DIAGNE+

  DOI：——

  日期：——
• Biodiesel Composition and Related Process and Products
  申请人：ARGENT ENERGY GROUP LIMITED

  公开号：US20160137937A1

  公开（公告）日：2016-05-19

  There is described a biodiesel composition and process for producing biodiesel and related products. There is also described related fuels and fuel blends comprising biodiesel. The biodiesel composition may be prepared from a mixture comprising fats, oils and greases from sewer waste.
• US9868918B2
  申请人：——

  公开号：US9868918B2

  公开（公告）日：2018-01-16
• A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration
  作者：Inés González-Gil、Debora Zian、Henar Vázquez-Villa、Gloria Hernández-Torres、R. Fernando Martínez、Nora Khiar-Fernández、Richard Rivera、Yasuyuki Kihara、Isabel Devesa、Sakthikumar Mathivanan、Cristina Rosell del Valle、Emma Zambrana-Infantes、María Puigdomenech、Giovanni Cincilla、Melchor Sanchez-Martinez、Fernando Rodríguez de Fonseca、Antonio V. Ferrer-Montiel、Jerold Chun、Rubén López-Vales、María L. López-Rodríguez、Silvia Ortega-Gutiérrez

  DOI：10.1021/acs.jmedchem.9b01287

  日期：2020.3.12

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.