E/Z-13-methyltetradec-11-enoic acid

• 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: E/Z-13-methyltetradec-11-enoic acid
• 英文别名: 13-methyltetradec-11-enoic acid
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: DGOVYJSMPGKVMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  17.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  E/Z-13-methyltetradec-11-enoic acid 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 13-甲基十四烷酸
  参考文献：
  名称：

  Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity

  摘要：

  We report on the efficient synthesis of linear trehalose diesters (TDEs) and iso-branched TDEs (maradolipids or iso-TDEs) and their ability to activate bone marrow-derived macrophages (BMDMs) as determined by cytokine (IL-1 beta, IL-12, IL-6, IL-10) and chemokine (MIP-2) production. Both classes of TDEs were found to activate BMDMs in a Mincle-dependent manner, with longer-chain (>= C18) lipids leading to a robust inflammatory response. On the whole, the iso-branched TDEs led to greater cytokine production and a faster immune response when compared to their linear counterparts. Moreover, C12-TDE and iso-C12-TDE elicited the production of MIP-2 by BMDMs, thereby providing the first example of TDEs with a chain length of <= C12 leading to a Mincle-dependent immune response and one that is less inflammatory in nature. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.11.076
• 作为产物：
  描述：

  11-溴十一酸 以 环己烷 、 二甲基亚砜 为溶剂， 反应 3.84h， 生成 E/Z-13-methyltetradec-11-enoic acid
  参考文献：
  名称：

  Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity

  摘要：

  We report on the efficient synthesis of linear trehalose diesters (TDEs) and iso-branched TDEs (maradolipids or iso-TDEs) and their ability to activate bone marrow-derived macrophages (BMDMs) as determined by cytokine (IL-1 beta, IL-12, IL-6, IL-10) and chemokine (MIP-2) production. Both classes of TDEs were found to activate BMDMs in a Mincle-dependent manner, with longer-chain (>= C18) lipids leading to a robust inflammatory response. On the whole, the iso-branched TDEs led to greater cytokine production and a faster immune response when compared to their linear counterparts. Moreover, C12-TDE and iso-C12-TDE elicited the production of MIP-2 by BMDMs, thereby providing the first example of TDEs with a chain length of <= C12 leading to a Mincle-dependent immune response and one that is less inflammatory in nature. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.11.076

文献信息

• Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity
  作者：Ayesha Khan、Kristel Kodar、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.tet.2017.11.076

  日期：2018.3

  We report on the efficient synthesis of linear trehalose diesters (TDEs) and iso-branched TDEs (maradolipids or iso-TDEs) and their ability to activate bone marrow-derived macrophages (BMDMs) as determined by cytokine (IL-1 beta, IL-12, IL-6, IL-10) and chemokine (MIP-2) production. Both classes of TDEs were found to activate BMDMs in a Mincle-dependent manner, with longer-chain (>= C18) lipids leading to a robust inflammatory response. On the whole, the iso-branched TDEs led to greater cytokine production and a faster immune response when compared to their linear counterparts. Moreover, C12-TDE and iso-C12-TDE elicited the production of MIP-2 by BMDMs, thereby providing the first example of TDEs with a chain length of <= C12 leading to a Mincle-dependent immune response and one that is less inflammatory in nature. (C) 2017 Elsevier Ltd. All rights reserved.