4,9-dihydroxy-2-nonenoic acid | 218462-88-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 4,9-dihydroxy-2-nonenoic acid
• 英文别名: 4,9-Dihydroxynon-2-enoic acid
• CAS: 218462-88-5
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: NCEMXVVEHUOYMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,9-dihydroxy-2-nonenoic acid 在 sodium hydroxide 作用下， 以 甲醇 、 phosphate buffer 、 水 为溶剂， 反应 26.5h， 生成 4,9-dihydroxy-2-nonenoic mercapturic acid
  参考文献：
  名称：

  Identification of Novel Urinary Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in Rats

  摘要：

  Following iv administration of 4-hydroxy-2-nonenal (HNE) and [4-H-3]HNE to rats, 15 polar urinary metabolites accounting for about 50% of the urinary radioactivity were separated by HPLC, Among them, eight major compounds and tritiated water were quantified. The metabolites were unequivocally characterized using GC/MS and ESI/MS/MS/MS. Most of "HNE polar metabolites" originate from omega-oxidation of 4-hydroxy-2-nonenoic acid(HNA): 9-hydroxy-HNA, its mercapturic acid conjugate, and two diastereoisomers of the corresponding lactone. The oxidation of 9-hydroxy-HNA by alcohol and aldehyde dehydrogenases leads to the excretion of 9-carboxy-HNA and of the corresponding lactone mercapturic acid conjugate. 1,4-Dihydroxy-2-nonene (DHN) originating from the reduction of HNE by alcohol dehydrogenase was to a lesser extent omega-hydroxylated, leading to 9-hydroxy-DHN which was excreted as a mercapturic acid conjugate (two diastereoisomers).

  DOI：

  10.1021/tx980068g
• 作为产物：
  描述：

  4-羟基-2-壬烯酸 在 glucose-6-phosphate dehydrogenase Α-D-吡喃葡萄糖6-磷酸 、 rat liver microsomal protein (clofibrate-treated rat) 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 phosphate buffer 为溶剂， 反应 2.0h， 生成 4,9-dihydroxy-2-nonenoic acid
  参考文献：
  名称：

  Identification of Novel Urinary Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in Rats

  摘要：

  Following iv administration of 4-hydroxy-2-nonenal (HNE) and [4-H-3]HNE to rats, 15 polar urinary metabolites accounting for about 50% of the urinary radioactivity were separated by HPLC, Among them, eight major compounds and tritiated water were quantified. The metabolites were unequivocally characterized using GC/MS and ESI/MS/MS/MS. Most of "HNE polar metabolites" originate from omega-oxidation of 4-hydroxy-2-nonenoic acid(HNA): 9-hydroxy-HNA, its mercapturic acid conjugate, and two diastereoisomers of the corresponding lactone. The oxidation of 9-hydroxy-HNA by alcohol and aldehyde dehydrogenases leads to the excretion of 9-carboxy-HNA and of the corresponding lactone mercapturic acid conjugate. 1,4-Dihydroxy-2-nonene (DHN) originating from the reduction of HNE by alcohol dehydrogenase was to a lesser extent omega-hydroxylated, leading to 9-hydroxy-DHN which was excreted as a mercapturic acid conjugate (two diastereoisomers).

  DOI：

  10.1021/tx980068g