4-hydroxyphenyl S-(hydroxymethyl) sulfide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-hydroxyphenyl S-(hydroxymethyl) sulfide
• 英文别名: 4-(Hydroxymethylsulfanyl)phenol
• 化学式: C₇H₈O₂S
• 分子量: 156.205
• InChiKey: RIOGWZANIDIHOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  guanosine 5'-monophosphate disodium 、 4-hydroxyphenyl S-(hydroxymethyl) sulfide 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 N2-(4-hydroxyphenylthiomethyl)guanosine 5'-monophosphate
  参考文献：
  名称：

  Human Taste and Umami Receptor Responses to Chemosensorica Generated by Maillard-type N²-Alkyl- and N²-Arylthiomethylation of Guanosine 5′-Monophosphates

  摘要：

  Structural modification of the exocyclic amino function of guanosine 5'-monophosphate (5'-GMP) by Maillard-type reactions with reducing carbohydrates was recently found to increase the umami-enhancing activity of the nucleotide upon S-N-2-1-carboxyalkylation and S-N-2-(1-alkylamino)carbonylalkylation, respectively. Since the presence of sulfur atoms in synthetic N-2-alkylated nucleotides was reported to be beneficial for sensory activity, a versatile Maillard-type modification of 5'-GMP upon reaction with glycines Strecker aldehyde formaldehyde and organic thiols was performed in the present study. A series of N-2-(alkylthiomethyl)guanosine and N-2-(arylthiomethyl)guanosine 5'-monophosphates was generated and the compounds were evaluated to what extent they enhance the umami response to monosodium l-glutamate in vivo by a paired-choice comparison test using trained human volunteers and in vitro by means of cell-based umami taste receptor assay. Associated with a high umami-enhancing activity (beta-value 5.1), N-2-(propylthiomethyl)guanosine 5'-monophosphate could be generated when 5'-GMP reacted with glucose, glycine, and the onion-derived odorant 1-propanethiol, thus opening a valuable avenue to produce high-potency umami-enhancing chemosensorica from food-derived natural products by kitchen-type chemistry.

  DOI：

  10.1021/jf504686s
• 作为产物：
  描述：

  聚合甲醛 、 4-羟基苯硫酚 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到4-hydroxyphenyl S-(hydroxymethyl) sulfide
  参考文献：
  名称：

  Pastor, Stephen D.; Odorisio, Paul A.; Ravichandran, Ramanathan, Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 67 - 72

  摘要：

  DOI：

文献信息

• Pastor, Stephen D.; Odorisio, Paul A.; Ravichandran, Ramanathan, Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 67 - 72
  作者：Pastor, Stephen D.、Odorisio, Paul A.、Ravichandran, Ramanathan

  DOI：——

  日期：——
• Human Taste and Umami Receptor Responses to Chemosensorica Generated by Maillard-type <i>N</i>²-Alkyl- and <i>N</i>²-Arylthiomethylation of Guanosine 5′-Monophosphates
  作者：Barbara Suess、Anne Brockhoff、Andreas Degenhardt、Sylvia Billmayer、Wolfgang Meyerhof、Thomas Hofmann

  DOI：10.1021/jf504686s

  日期：2014.11.26

  Structural modification of the exocyclic amino function of guanosine 5'-monophosphate (5'-GMP) by Maillard-type reactions with reducing carbohydrates was recently found to increase the umami-enhancing activity of the nucleotide upon S-N-2-1-carboxyalkylation and S-N-2-(1-alkylamino)carbonylalkylation, respectively. Since the presence of sulfur atoms in synthetic N-2-alkylated nucleotides was reported to be beneficial for sensory activity, a versatile Maillard-type modification of 5'-GMP upon reaction with glycines Strecker aldehyde formaldehyde and organic thiols was performed in the present study. A series of N-2-(alkylthiomethyl)guanosine and N-2-(arylthiomethyl)guanosine 5'-monophosphates was generated and the compounds were evaluated to what extent they enhance the umami response to monosodium l-glutamate in vivo by a paired-choice comparison test using trained human volunteers and in vitro by means of cell-based umami taste receptor assay. Associated with a high umami-enhancing activity (beta-value 5.1), N-2-(propylthiomethyl)guanosine 5'-monophosphate could be generated when 5'-GMP reacted with glucose, glycine, and the onion-derived odorant 1-propanethiol, thus opening a valuable avenue to produce high-potency umami-enhancing chemosensorica from food-derived natural products by kitchen-type chemistry.