6-hydroxymethyl-1-propylpyrrolidinium-3-olate | 220467-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-hydroxymethyl-1-propylpyrrolidinium-3-olate
• 英文别名: 6-hydroxymethyl-1-propylpyridinium-3-olate；6-(Hydroxymethyl)-1-propylpyridin-1-ium-3-olate
• CAS: 220467-22-1
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: WAGRZTJURVTYKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxymethyl-1-propylpyrrolidinium-3-olate 在 manganese(IV) oxide 作用下， 以 甲醇 、 水 为溶剂， 反应 27.0h， 生成 6-(N-propyl)-carbimino-1-propylpyridinium-3-olate
  参考文献：
  名称：

  己糖与伯胺反应形成吡啶甜菜碱

  摘要：

  摘要葡萄糖或果糖与伯胺的反应和葡萄糖的Amadori产物的热降解导致形成6-甲酰基-1-烷基吡啶-3-油酸酯（5），其中6-甲酰基-1-丙基吡啶-3从反应混合物中分离出β-油酸酯。参比物质可以分两步从5-（羟甲基）-2-呋喃醛制备。与典型的食品加工和生理条件相比，这些甜菜碱相对于其他吸收紫外线的产品具有较高的收成。与伯胺一起，甜菜碱容易形成席夫碱，该席夫碱在水溶液中加热时会发生斯特雷克型降解。

  DOI：

  10.1016/s0008-6215(98)00251-1
• 作为产物：
  描述：

  正丙胺 、 5-羟甲基糠醛 以 乙醇 、 水 为溶剂， 反应 72.0h， 以43%的产率得到6-hydroxymethyl-1-propylpyrrolidinium-3-olate
  参考文献：
  名称：

  己糖与伯胺反应形成吡啶甜菜碱

  摘要：

  摘要葡萄糖或果糖与伯胺的反应和葡萄糖的Amadori产物的热降解导致形成6-甲酰基-1-烷基吡啶-3-油酸酯（5），其中6-甲酰基-1-丙基吡啶-3从反应混合物中分离出β-油酸酯。参比物质可以分两步从5-（羟甲基）-2-呋喃醛制备。与典型的食品加工和生理条件相比，这些甜菜碱相对于其他吸收紫外线的产品具有较高的收成。与伯胺一起，甜菜碱容易形成席夫碱，该席夫碱在水溶液中加热时会发生斯特雷克型降解。

  DOI：

  10.1016/s0008-6215(98)00251-1

文献信息

• Characterization of an Intense Bitter-Tasting 1<i>H</i>,4<i>H</i>-Quinolizinium-7-olate by Application of the Taste Dilution Analysis, a Novel Bioassay for the Screening and Identification of Taste-Active Compounds in Foods
  作者：O. Frank、H. Ottinger、T. Hofmann

  DOI：10.1021/jf0010073

  日期：2001.1.1

  Thermal treatment of aqueous solutions of xylose and primary amino acids led to rapid development of a bitter taste of the reaction mixture. To characterize the key compound causing this bitter taste, a novel bioassay, which is based on the determination of the taste threshold of reaction products in serial dilutions of HPLC fractions, was developed to select the most intense taste compounds in the complex mixture of Maillard reaction products. By application of this so-called taste dilution analysis (TDA) 21 fractions were obtained, among which 1 fraction was evaluated with by far the highest taste impact. Carefully planned LC-MS as well as 1D and 2D NMR experiments were, therefore, focused on the compound contributing the most to the intense bitter taste of the Maillard mixture and led to its unequivocal identification as the previously unknown 3-(2-furyl)-8-[(2-furyl)methyl]4-hydroxymethyl-1-oxo-1H,4H-quinolizinium-7-olate. This novel compound, which we name quinizolate, exhibited an intense bitter taste at an extraordinarily low detection threshold of 0.00025 mmol/kg of water. As this novel taste compound was found to have 2000- and 28-fold lower threshold concentrations than the standard bitter compounds caffeine and quinine hydrochloride, respectively, quinizolate might be one;of the most intense bitter compounds reported so far.