Trimethylsilyl 2-anilinoacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Trimethylsilyl 2-anilinoacetate
• 化学式: C₁₁H₁₇NO₂Si
• 分子量: 223.347
• InChiKey: GINIFXAWBVTHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 N-苯基甘氨酸 以 乙腈 为溶剂， 反应 0.25h， 生成 Trimethylsilyl 2-anilinoacetate
  参考文献：
  名称：

  Identification of four metabolites of 3-(phenylamino)alanine, a constituent in l-tryptophan products implicated in eosinophiliamyalgia syndrome, in rats

  摘要：

  3-(Phenylamino)alanine (PAA), a contaminant found in L-tryptophan tablets, has been discussed as a possible cause of eosinophilia-myalgia syndrome (EMS). We administered PAA (100 mg/kg) by gastric gavage to Wistar rats to determine its distribution and metabolism. We developed a purification procedure, using Bond Elut SCX cartridges followed by high performance liquid chromatography (HPLC) in order to determine levels of PAA. The level of PAA in blood was 4.22 mu g/ml at 5 h and urinary excretion was 21.7 mu g for 5 h and 84.6 mu g between 5 and 24 h. The amount of PAA in the contents of the large intestine at 5 h was 0.76 mu g, indicating poor transfer of PAA to the large intestine. However, the highest concentration of PAA was 12.3 mu g/g in the brain, indicating the passage of PAA through the blood-brain barrier. In addition to detecting PAA in the blood and organs, we also detected four metabolites of PAA in urine. We used gas chromatography mass spectrometry to identify PAA in rat liver, as well as N-(hydroxyphenyl)glycine, N-phenylglycine, 3-(pheylamino)lactic acid, and 3-(hydroxyphenylamino)lactic acid in rat urine. These results suggest that the degradation pathway of PAA is similar to that of phenylalanine.

  DOI：

  10.1007/s002040050102

文献信息

• Identification of four metabolites of 3-(phenylamino)alanine, a constituent in l-tryptophan products implicated in eosinophiliamyalgia syndrome, in rats
  作者：Junko Adachi、Takaya Mio、Yasuhiro Ueno、Takeaki Naito、Akiyoshi Nishimura、Satoshi Fujiwara、Kimiaki Sumino、Yoshitsugu Tatsuno

  DOI：10.1007/s002040050102

  日期：1994.8

  3-(Phenylamino)alanine (PAA), a contaminant found in L-tryptophan tablets, has been discussed as a possible cause of eosinophilia-myalgia syndrome (EMS). We administered PAA (100 mg/kg) by gastric gavage to Wistar rats to determine its distribution and metabolism. We developed a purification procedure, using Bond Elut SCX cartridges followed by high performance liquid chromatography (HPLC) in order to determine levels of PAA. The level of PAA in blood was 4.22 mu g/ml at 5 h and urinary excretion was 21.7 mu g for 5 h and 84.6 mu g between 5 and 24 h. The amount of PAA in the contents of the large intestine at 5 h was 0.76 mu g, indicating poor transfer of PAA to the large intestine. However, the highest concentration of PAA was 12.3 mu g/g in the brain, indicating the passage of PAA through the blood-brain barrier. In addition to detecting PAA in the blood and organs, we also detected four metabolites of PAA in urine. We used gas chromatography mass spectrometry to identify PAA in rat liver, as well as N-(hydroxyphenyl)glycine, N-phenylglycine, 3-(pheylamino)lactic acid, and 3-(hydroxyphenylamino)lactic acid in rat urine. These results suggest that the degradation pathway of PAA is similar to that of phenylalanine.