Ethyl (Z)-11-hexadecanoate | 130074-73-6

• 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: Ethyl (Z)-11-hexadecanoate
• 英文别名: (Z)-ethyl hexadec-11-enoate；ethyl (11Z)-hexadec-11-enoate；ethyl cis-11-hexadecenoate；Ethyl (11z)-11-hexadecenoate；ethyl (Z)-hexadec-11-enoate
• CAS: 130074-73-6
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: ORDVGMQAZDTLDF-FPLPWBNLSA-N

物化性质

• 沸点：
  348.7±11.0 °C(Predicted)
• 密度：
  0.875±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  Ethyl (Z)-11-hexadecanoate 在 水 、 sodium hydroxide 作用下， 反应 3.0h， 生成 (11Z)-11-十六碳烯酸
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105
• 作为产物：
  描述：

  ethyl 11-hydroxyundecanoate 在 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 反应 2.25h， 生成 Ethyl (Z)-11-hexadecanoate
  参考文献：
  名称：

  宿主防御兴奋剂马鞭草苷的全合成

  摘要：

  通过以光化学芳族环化为关键步骤的途径，已经实现了宿主防御刺激剂马鞭草苷的有效全合成。

  DOI：

  10.1016/0040-4039(90)80007-9

文献信息

• Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2
  作者：Shannon N. Mostyn、Jane E. Carland、Susan Shimmon、Renae M. Ryan、Tristan Rawling、Robert J. Vandenberg

  DOI：10.1021/acschemneuro.7b00105

  日期：2017.9.20

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.
• Total synthesis of the host defense stimulant maesanin
  作者：Rick L. Danheiser、Don D. Cha

  DOI：10.1016/0040-4039(90)80007-9

  日期：1990.1

  An efficient total synthesis of the host defense stimulant maesanin has been achieved by a route featuring a photochemical aromatic annulation as a key step.

  通过以光化学芳族环化为关键步骤的途径，已经实现了宿主防御刺激剂马鞭草苷的有效全合成。