3-[(4'-hydroxyphenyl)amino]propane-1,2-diol | 150880-09-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[(4'-hydroxyphenyl)amino]propane-1,2-diol
• 英文别名: 3-(4-hydroxy-anilino)-propane-1,2-diol；4-(β.γ-Dioxy-propylamino)-phenol；γ-(4-Oxy-anilino)-propylenglykol；3-(4-Hydroxy-anilino)-propan-1,2-diol；3-(4-Hydroxyanilino)propane-1,2-diol
• CAS: 150880-09-4
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: WECUKSDHUPVXIU-UHFFFAOYSA-N

物化性质

• 沸点：
  460.8±40.0 °C(predicted)
• 密度：
  1.349±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苄氧基苯胺 在 palladium on activated charcoal 、 lithium trifluoromethanesulfonate 氢气 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 5.5h， 生成 3-[(4'-hydroxyphenyl)amino]propane-1,2-diol
  参考文献：
  名称：

  Biotransformation and Clearance of 3-(Phenylamino)propane-1,2-diol, a Compound Present in Samples Related to Toxic Oil Syndrome, in C57BL/6 and A/J Mice

  摘要：

  In May 1981, a massive food-borne intoxication occurred in Spain. The so-called toxic oil syndrome (TOS) was associated with the consumption of aniline-denatured and refined rapeseed oil that was illegally sold as edible olive oil. Fatty acid anilides and fatty acid derivatives of 3-(phenylamino)propane-1,2-diol were detected in oils and implicated as potential toxic agents and markers of toxic oil batches. Epidemiological evidence points to 3-(phenylamino)propane-1,2-diol derivatives as the putative toxic agents, which were generated during the refining process at the ITH refinery. Here we present the biotransformation and clearance of 3-(phenylamino)propane-1,2-diol (PAP) administered intraperitoneally to A/J and C57BL/6 mice that have been proposed as a murine model for the immunological features of TOS. Mice eliminated 6 mu Ci of [U-C-14]PAP during a 24 h period, mostly in urine. Animals exhibited urine elimination rates of 70 and 36% in A/J and C57BL/6 strains, respectively. A/J mice exhibited no increase in the elimination rate when induced with P-naphthoflavone, whereas C57BL/6 did increase the rate of elimination to 57%. Feces contributed to a lesser extent to the elimination rate (0.6 and 3.3% in A/J and C57BL/6 mice, respectively). Radioactivity remaining in organ tissues was lower than 1% (liver, lung, kidney, spleen, heart, and muscle). Metabolic species in urine were identified by HPLC coupled to UV and radioisotope detectors and further GC/MS analyses. 2-Hydroxy-3-(phenylamino)propanoic acid metabolite was the major chemical species excreted in urine in both strains, in both control and induced animal groups. This compound was the main urinary metabolite of PAP, and unmetabolized PAP excreted in urine constituted less than 1% of the total administered dose. Two additional highly polar metabolites also detected in urine were identified as 3- [(4'-hydroxyphenyl)amino] propane-1,2-diol and 2-hydroxy-3-[(4'-hydroxyphenyl) amino] propanoic acid. These findings are the first reported on PAP metabolism and clearance in mice strains and suggest that PAP can be extensively metabolized in vivo and potential reactive species can be generated.

  DOI：

  10.1021/tx990105j

文献信息

• The reaction of glycerol carbonate with primary aromatic amines in the presence of Y- and X-faujasites: the synthesis of N-(2,3-dihydroxy)propyl anilines and the reaction mechanism
  作者：Maurizio Selva、Massimo Fabris

  DOI：10.1039/b904821a

  日期：——

  At 140 °C, in the presence of alkali metal exchanged faujasites, preferably NaY, as catalysts, glycerine carbonate (GlyC) is an efficient and green alkylating agent of primary aromatic amines (p-XC6H4NH2, X = H, OMe, OH, Cl): the reaction takes place with a high conversion (∼90%) and a good selectivity (80–90%) for the formation of N-(2,3-dihydroxy)propyl anilines (p-XC6H4NHCH2CH(OH)CH2OH). The alkylation

  在140°C下 碱金属 交换八面沸石，最好是NaY 催化剂，碳酸甘油酯（GlyC）是一种高效且绿色的 烷基化剂 小学 芳香胺（p -XC 6 ħ 4 NH 2，X = H，青梅，OH，Cl）的：发生反应以高转化率（〜90％）和良好的选择性（80-90％），用于形成Ñ - （2,3-二羟基）丙基苯胺（p -XC 6 H 4 NHCH 2 CH（OH）CH 2 OH）。这烷基化 该过程不会通过排他性的亲核取代来进行 苯胺在GlyC的C5位置。证据证明，苯胺用GlyC与GlyC产生中间体，并且酯交换反应和水解反应都参与以获得最终的N-烷基衍生物。因此提出了一种机制。实验表明八面沸石是可回收的催化剂 如果他们暴露在温和的高温下 激活（70°C，18 mbar）才能重新使用。否则，如果沸石 都经过煅烧（400°C，空气）， 催化剂活性和反应选择性下降。N-（2,3-二羟基）丙基的孤立产率（60–65
• DE343151
  申请人：——

  公开号：——

  公开（公告）日：——
• DE346386
  申请人：——

  公开号：——

  公开（公告）日：——
• Biotransformation and Clearance of 3-(Phenylamino)propane-1,2-diol, a Compound Present in Samples Related to Toxic Oil Syndrome, in C57BL/6 and A/J Mice
  作者：Margarita G. Ladona、Jordi Bujons、Angel Messeguer、Coral Ampurdanés、Anna Morató、Jacint Corbella

  DOI：10.1021/tx990105j

  日期：1999.12.1

  In May 1981, a massive food-borne intoxication occurred in Spain. The so-called toxic oil syndrome (TOS) was associated with the consumption of aniline-denatured and refined rapeseed oil that was illegally sold as edible olive oil. Fatty acid anilides and fatty acid derivatives of 3-(phenylamino)propane-1,2-diol were detected in oils and implicated as potential toxic agents and markers of toxic oil batches. Epidemiological evidence points to 3-(phenylamino)propane-1,2-diol derivatives as the putative toxic agents, which were generated during the refining process at the ITH refinery. Here we present the biotransformation and clearance of 3-(phenylamino)propane-1,2-diol (PAP) administered intraperitoneally to A/J and C57BL/6 mice that have been proposed as a murine model for the immunological features of TOS. Mice eliminated 6 mu Ci of [U-C-14]PAP during a 24 h period, mostly in urine. Animals exhibited urine elimination rates of 70 and 36% in A/J and C57BL/6 strains, respectively. A/J mice exhibited no increase in the elimination rate when induced with P-naphthoflavone, whereas C57BL/6 did increase the rate of elimination to 57%. Feces contributed to a lesser extent to the elimination rate (0.6 and 3.3% in A/J and C57BL/6 mice, respectively). Radioactivity remaining in organ tissues was lower than 1% (liver, lung, kidney, spleen, heart, and muscle). Metabolic species in urine were identified by HPLC coupled to UV and radioisotope detectors and further GC/MS analyses. 2-Hydroxy-3-(phenylamino)propanoic acid metabolite was the major chemical species excreted in urine in both strains, in both control and induced animal groups. This compound was the main urinary metabolite of PAP, and unmetabolized PAP excreted in urine constituted less than 1% of the total administered dose. Two additional highly polar metabolites also detected in urine were identified as 3- [(4'-hydroxyphenyl)amino] propane-1,2-diol and 2-hydroxy-3-[(4'-hydroxyphenyl) amino] propanoic acid. These findings are the first reported on PAP metabolism and clearance in mice strains and suggest that PAP can be extensively metabolized in vivo and potential reactive species can be generated.