4-(furan-2-ylmethyl)benzene-1,2-diol | 91344-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(furan-2-ylmethyl)benzene-1,2-diol
• 英文别名: 1,2-Dihydroxy-4-furfuryl-benzol；2-<3,4-Dihydro-benzyl>-furan；4-furfuryl-benzene-1,2-diol
• CAS: 91344-78-4
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: YTLNQLBYXROIRM-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  140-152 °C(Press: 1.5 Torr)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醇 、 邻苯二酚 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-(furan-2-ylmethyl)benzene-1,2-diol
  参考文献：
  名称：

  Identification of (furan-2-yl)methylated benzene diols and triols as a novel class of bitter compounds in roasted coffee

  摘要：

  Preliminary studies demonstrated that the identification of unknown bitter taste compounds in roasted coffee, by means of an analytical fractionation approach, is hampered by their limited oxidative, as well as chemical stability. A synthetic-constructive strategy was followed in the present investigation by performing targeted reactions of putative coffee-related precursors to give candidate bitter taste molecules. Binary mixtures of a di and trihydroxybenzene, namely pyrogallol, hydroxyhydroquinone, catechol, or 3-and 4-methylcatechole, and a furan derivative, namely furfuryl alcohol, furan-2-aldehyde, or 5-(hydroxymethyl)furan-2-aldehyde, all of which are known to be present in roasted coffee, were thermally treated. The reaction products were identified as (furan-2-yl)methylated benzene diols and triols, by means of LC-MS and NMR experiments, and their bitter taste thresholds determined by means of sensory analysis. Finally, LC-MS/MS studies verified the natural occurence of 4-(furan-2-ylmethyl)benzene-1,2-diol, 4-(furan-2-ylmethyl)benzene-1,2,3-triol, 4-(furan-2-ylmethyl)-5-methylbenzene-1,2-diol, and 3-(furan-2-ylmethyl)-6-methylbenzene-1,2-diol as a novel class of bitter taste compounds in roasted coffee. Depending on their chemical structure, the bitter taste recognition threshold of these compounds ranged between 100 and 537 mu mol/l. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2010.11.008