[(Prop-2-en-1-yl)sulfanyl]methanol | 62839-43-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: [(Prop-2-en-1-yl)sulfanyl]methanol
• 英文别名: prop-2-enylsulfanylmethanol
• CAS: 62839-43-4
• 化学式: C₄H₈OS
• 分子量: 104.173
• InChiKey: LLBKXTWGRZDUPR-UHFFFAOYSA-N

物化性质

• 沸点：
  162.9±23.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(Prop-2-en-1-yl)sulfanyl]methanol 、 guanosine 5'-monophosphate disodium 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 N2-(prop-2-enylthiomethyl)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 、 烯丙硫醇 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 生成 [(Prop-2-en-1-yl)sulfanyl]methanol
  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

文献信息

• 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.