糠基硫醇-d2 | 136430-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 糠基硫醇-d2
• 中文别名: 糠基巯基-d2
• 英文名称: α,α-[2H2]-2-furfurylthiol
• 英文别名: [2H]2-2-furfurylthiol；Furfuryl Mercaptan-d2；dideuterio(furan-2-yl)methanethiol
• CAS: 136430-22-3
• 化学式: C₅H₆OS
• 分子量: 116.152
• InChiKey: ZFFTZDQKIXPDAF-APZFVMQVSA-N

物化性质

• 溶解度：
  乙腈（微溶）、氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  14.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-乙基苯磷二酚 、 糠基硫醇-d2 在 三氯化铁 作用下， 反应 1.0h， 以18%的产率得到3-{[(2-furyl)[2H]2-methyl]sulfanyl}-5-ethylcatechol
  参考文献：
  名称：

  Quantitative Studies on the Formation of Phenol/2-Furfurylthiol Conjugates in Coffee Beverages toward the Understanding of the Molecular Mechanisms of Coffee Aroma Staling

  摘要：

  To gain a more comprehensive knowledge of the contribution of recently identified phenol/thiol conjugates to the storage-induced degradation of odorous thiols, the concentrations of the sulfuryroasty smelling key odorant 2-furfurylthiol and the concentrations of the putative thiol-receptive di- and trihydroxybenzenes pyrogallol ( 1), hydroxyhydroquinone ( 2), catechol ( 3), 4-ethylcatechol ( 4), 4-methylcatechol ( 5), and 3-methylcatechol ( 6), as well as of the phenol/thiol conjugates 3-[(2-furylmethyl) sulfanyl] catechol ( 7), 3-[(2-furylmethyl) sulfanyl]-5-ethylcatechol ( 8), 4-[(2-furylmethyl)sulfanyl] hydroxyhydroquinone ( 9), and 3,4- bis[(2-furylmethyl) sulfanyl] hydroxyhydroquinone ( 10) were quantitatively determined in fresh and stored coffee beverages by means of stable isotope dilution analyses (SIDA). Although 2 was found to be the quantitatively predominant trihydroxybenzene in freshly prepared coffee brew, this compound exhibited a very high reactivity and decreased rapidly during coffee storage to generate the conjugates 9 and 10. After only 10 min, about 60% of the initial amount of 2-furfurylthiol in a coffee beverage reacted with 2 to give 9 and 10. In contrast, conjugate 7 was found to be exclusively formed during coffee roasting because its initial concentration as well as the amount of its putative precursor, phenol 3, was not affected by storage. It is interesting to note that the concentration of 8 was increased with increasing incubation time, but its putative precursor 4 was not affected, thus indicating another formation pathway most likely via the chlorogenic acid degradation product 4- vinylcatechol. This study demonstrates for the first time that the loss of 2-furfurylthiol during coffee storage is mainly due to the oxidative coupling of the odorant to hydroxyhydroquinone ( 2), giving rise to the conjugates 9 and 10.

  DOI：

  10.1021/jf070095p

文献信息

• Quantitative Studies on the Formation of Phenol/2-Furfurylthiol Conjugates in Coffee Beverages toward the Understanding of the Molecular Mechanisms of Coffee Aroma Staling
  作者：Christoph Müller、Thomas Hofmann

  DOI：10.1021/jf070095p

  日期：2007.5.1

  To gain a more comprehensive knowledge of the contribution of recently identified phenol/thiol conjugates to the storage-induced degradation of odorous thiols, the concentrations of the sulfuryroasty smelling key odorant 2-furfurylthiol and the concentrations of the putative thiol-receptive di- and trihydroxybenzenes pyrogallol ( 1), hydroxyhydroquinone ( 2), catechol ( 3), 4-ethylcatechol ( 4), 4-methylcatechol ( 5), and 3-methylcatechol ( 6), as well as of the phenol/thiol conjugates 3-[(2-furylmethyl) sulfanyl] catechol ( 7), 3-[(2-furylmethyl) sulfanyl]-5-ethylcatechol ( 8), 4-[(2-furylmethyl)sulfanyl] hydroxyhydroquinone ( 9), and 3,4- bis[(2-furylmethyl) sulfanyl] hydroxyhydroquinone ( 10) were quantitatively determined in fresh and stored coffee beverages by means of stable isotope dilution analyses (SIDA). Although 2 was found to be the quantitatively predominant trihydroxybenzene in freshly prepared coffee brew, this compound exhibited a very high reactivity and decreased rapidly during coffee storage to generate the conjugates 9 and 10. After only 10 min, about 60% of the initial amount of 2-furfurylthiol in a coffee beverage reacted with 2 to give 9 and 10. In contrast, conjugate 7 was found to be exclusively formed during coffee roasting because its initial concentration as well as the amount of its putative precursor, phenol 3, was not affected by storage. It is interesting to note that the concentration of 8 was increased with increasing incubation time, but its putative precursor 4 was not affected, thus indicating another formation pathway most likely via the chlorogenic acid degradation product 4- vinylcatechol. This study demonstrates for the first time that the loss of 2-furfurylthiol during coffee storage is mainly due to the oxidative coupling of the odorant to hydroxyhydroquinone ( 2), giving rise to the conjugates 9 and 10.