N-oxo-kynurenic acid | 90800-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-oxo-kynurenic acid
• 英文别名: 4-Hydroxy-chinolin-carbonsaeure-(2)-N-oxid；4-Hydroxy-chinolin-carbonsaeure-(2)-oxid
• CAS: 90800-51-4
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: INROJRCTIGPTPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  邻硝基苯乙酮 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 N-oxo-kynurenic acid
  参考文献：
  名称：

  “Untypical Aging Off-Flavor” in Wine:  Synthesis of Potential Degradation Compounds of Indole-3-acetic Acid and Kynurenine and Their Evaluation as Precursors of 2-Aminoacetophenone

  摘要：

  Kynurenine (1) and indole-3-acetic acid (2) are considered as potential precursors of 2-amino-acetophenone (3), which is regarded to be the aroma impact compound causing an "untypical aging off-flavor" (UTA) in Vitis vinifera wines. The mechanism of the formation of 3 was studied using model fermentation and model sulfuration media spiked with 1 or 2 as potential precursors. Possible degradation products such as kynurenamine (4) and kynurenic acid (5), or skatole (6), 2-oxoskatole (7), 2-formamidoacetophenone (8), 2-oxindole-3-acetic acid (9), and 3-(2-formylaminophenyl)-3-oxopropionic acid (10) were evaluated by HPLC-UV of the fermentation and sulfuration media and comparison with synthesized 7, 8, 9, and 10. The synthesis of the possible precursor 4-(2-aminophenyl)-2,4-dioxobutanoic acid (111), a proposed metabolite of 1 failed because a spontaneous cyclization yields 5 and N-oxo-kynurenic acid (12), but not 11. It could be shown that the formation of 3 is triggered by an oxidative degradation of 2 after sulfuration with potassium bisulfite via the intermediates 10 and 8. However, no formation of 3 occurred during sulfuration of a model wine spiked with 1 or during fermentation of a model must spiked with 1 or 2.

  DOI：

  10.1021/jf011672r