4-(furan-2-ylmethyl)benzene-1,3-diol | 92643-88-4

• 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-1,3-diol
• 英文别名: 4-furfuryl-benzene-1,3-diol；2-<2,4-Dihydro-benzyl>-furan；US9682910, 4-(Furan-2-ylmethyl)benzene-1,3-diol (5)
• CAS: 92643-88-4
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: UGOKFADRDRUFRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  148-160 °C(Press: 1 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 、 间苯二酚 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-(furan-2-ylmethyl)benzene-1,3-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

文献信息

• SERIES OF SKIN WHITENING (LIGHTENING) COMPOUNDS
  申请人：Nandy Sandip K.

  公开号：US20100016347A1

  公开（公告）日：2010-01-21

  The present invention is directed to inhibitors of tyrosinase, pharmaceutical compositions comprising such tyrosinase inhibitors, and methods of making and using the same. Specifically, included in the present invention are compositions of matter comprised of at least one 2,4-dihydroxybenzene analog, which inhibit the activity of tyrosinase and which inhibit the overproduction of melanin.

  本发明涉及酪氨酸酶抑制剂，包含此类酪氨酸酶抑制剂的药物组合物，以及制备和使用这些药物的方法。具体而言，本发明包括至少一种2,4-二羟基苯类似物组成的物质组合物，这些组合物抑制酪氨酸酶的活性并抑制黑色素的过度产生。
• SERIES OF SKIN-WHITENING (LIGHTENING) COMPOUNDS
  申请人：Unigen, Inc.

  公开号：US20160083322A1

  公开（公告）日：2016-03-24

  The present invention is directed to inhibitors of tyrosinase, pharmaceutical compositions comprising such tyrosinase inhibitors, and methods of making and using the same. Specifically, included in the present invention are compositions of matter comprised of at least one 2,4-dihydroxybenzene analog, which inhibit the activity of tyrosinase and which inhibit the overproduction of melanin.

  本发明涉及酪氨酸酶抑制剂、包含这种酪氨酸酶抑制剂的药物组合物以及制备和使用它们的方法。具体而言，本发明包括由至少一种2,4-二羟基苯类似物组成的物质组合物，其抑制酪氨酸酶活性并抑制黑色素的过度生产。
• Series of skin whitening (lightening) compounds
  申请人：Unigen, Inc.

  公开号：US10259764B2

  公开（公告）日：2019-04-16

  The present invention is directed to inhibitors of tyrosinase, pharmaceutical compositions comprising such tyrosinase inhibitors, and methods of making and using the same. Specifically, included in the present invention are compositions of matter comprised of at least one 2,4-dihydroxybenzene analog, which inhibit the activity of tyrosinase and which inhibit the overproduction of melanin.

  本发明涉及酪氨酸酶抑制剂、包含这种酪氨酸酶抑制剂的药物组合物以及制造和使用这些药物组合物的方法。具体地说，本发明包括由至少一种 2,4-二羟基苯类似物组成的物质组合物，这种物质组合物能抑制酪氨酸酶的活性，并能抑制黑色素的过度生成。
• Series of Skin Whitening (Lightening) Compounds
  申请人：Unigen, Inc.

  公开号：US20170275224A1

  公开（公告）日：2017-09-28

  The present invention is directed to inhibitors of tyrosinase, pharmaceutical compositions comprising such tyrosinase inhibitors, and methods of making and using the same. Specifically, included in the present invention are compositions of matter comprised of at least one 2,4-dihydroxybenzene analog, which inhibit the activity of tyrosinase and which inhibit the overproduction of melanin.
• Series of Skin-Whitening (Lightening) Compounds
  申请人：Unigen, Inc.

  公开号：US20210188751A1

  公开（公告）日：2021-06-24

  The present invention is directed to inhibitors of tyrosinase, pharmaceutical compositions comprising such tyrosinase inhibitors, and methods of making and using the same. Specifically, included in the present invention are compositions of matter comprised of at least one 2,4-dihydroxybenzene analog, which inhibit the activity of tyrosinase and which inhibit the overproduction of melanin.