methyl 11-hydroxy-12-nitrododecanoate | 1179999-46-2

• 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: methyl 11-hydroxy-12-nitrododecanoate
• CAS: 1179999-46-2
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: UAMQCKZDVXJLHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 11-hydroxy-12-nitrododecanoate 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by Nitroalkene Fatty Acids: Importance of Nitration Position and Degree of Unsaturation

  摘要：

  Nitroalkene fatty acids are potent endogenous ligand activators of PPAR gamma-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPAR gamma activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPAR gamma, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPAR gamma activation. Interestingly, at higher concentrations (> 2 mu M) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO2-18:1 [7]) deviated significantly from the saturable pattern of PPAR gamma activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).

  DOI：

  10.1021/jm900326c
• 作为产物：
  描述：

  硝基甲烷 、 methyl 11-oxoundecanoate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 24.0h， 以89%的产率得到methyl 11-hydroxy-12-nitrododecanoate
  参考文献：
  名称：

  Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by Nitroalkene Fatty Acids: Importance of Nitration Position and Degree of Unsaturation

  摘要：

  Nitroalkene fatty acids are potent endogenous ligand activators of PPAR gamma-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPAR gamma activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPAR gamma, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPAR gamma activation. Interestingly, at higher concentrations (> 2 mu M) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO2-18:1 [7]) deviated significantly from the saturable pattern of PPAR gamma activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).

  DOI：

  10.1021/jm900326c

文献信息

• Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by Nitroalkene Fatty Acids: Importance of Nitration Position and Degree of Unsaturation
  作者：Michael J. Gorczynski、Pamela K. Smitherman、Taro E. Akiyama、Harold B. Wood、Joel P. Berger、S. Bruce King、Charles S. Morrow

  DOI：10.1021/jm900326c

  日期：2009.8.13

  Nitroalkene fatty acids are potent endogenous ligand activators of PPAR gamma-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPAR gamma activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPAR gamma, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPAR gamma activation. Interestingly, at higher concentrations (> 2 mu M) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO2-18:1 [7]) deviated significantly from the saturable pattern of PPAR gamma activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).