3-<(2-furylmethyl)dithio>-2-pentanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-<(2-furylmethyl)dithio>-2-pentanone
• 英文别名: 2-furfuryl 2-oxo-3-pentyl disulfide；3-(furan-2-ylmethyldisulfanyl)pentan-2-one
• 化学式: C₁₀H₁₄O₂S₂
• 分子量: 230.352
• InChiKey: WVURWAKIPKTGCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硫基-2-戊酮 、 糠基硫醇 在 copper(II) sulfate 作用下， 以 乙醚 为溶剂， 反应 0.58h， 生成 3-<(2-furylmethyl)dithio>-2-pentanone
  参考文献：
  名称：

  Evaluation of the Key Odorants in a Thermally Treated Solution of Ribose and Cysteine by Aroma Extract Dilution Techniques

  摘要：

  Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 degrees C; 20 min) of cysteine/ribose led to the identification of 2-furfurylthiol, 3-mercapto-2-pentanone, 2-methyl-3-furanthiol, 5-acetyl-2,3-dihydro-1,4-thiazine, 3-mercapto-2-butanone, and bis(2-methyl-3-furyl) disulfide showing the highest flavor dilution factors among the 29 odor-active volatiles. HRGC/olfactometry of decreasing headspace volumes established especially 2-furfurylthiol and 2-methyl-3-furanthiol as important odorants and revealed 2-thenyl mercaptan and ethyl mercaptan as further key contributors to the overall roasty, meatlike, sulfury odor of the model mixture. 5-Acetyl-2,3-dihydro-1,4-thiazine, identified for the first time among the volatiles of Maillard model reactions or foods, exhibited an intense roasty, popcorn-like odor at the low odor threshold of 0.06 ng/L of air, which was of the same order of magnitude as those reported in the literature for the roasty-smelling odorants 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline.

  DOI：

  10.1021/jf00056a042

文献信息

• Some Novel Meatlike Aroma Compounds from the Reactions of Alkanediones with Hydrogen Sulfide and Furanthiols
  作者：Donald S. Mottram、Marta S. Madruga、Frank B. Whitfield

  DOI：10.1021/jf00049a035

  日期：1995.1

  The products of reactions of hydrogen sulfide with 2,3-butanedione and with 2,3-pentanedione in dilute ethanolic solution were analyzed by CC-MS and CC-odor port analysis. Components were also collected from the GC column and analyzed by H-1 NMR. Mercaptoketones were formed which readily oxidized to the corresponding disulfides with traces of mono- and trisulfides. When 2-methyl-3-furanthiol or 2-furylmethanethiol was added to the reaction mixtures, a series of disulfides containing alkanone, 2-methyl-3-furyl and 2-furanmethyl moieties were formed. Some of these compounds have been found recently in the volatiles of cooked meat and in meatlike model systems. GC-odor port evaluation of the components of the reaction systems showed that disulfides containing the 2-methyl-3-furyl group had meaty aromas, whereas those without this group were sulfurous or onion-like in character.
• Evaluation of the Key Odorants in a Thermally Treated Solution of Ribose and Cysteine by Aroma Extract Dilution Techniques
  作者：Thomas Hofmann、Peter Schieberle

  DOI：10.1021/jf00056a042

  日期：1995.8

  Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 degrees C; 20 min) of cysteine/ribose led to the identification of 2-furfurylthiol, 3-mercapto-2-pentanone, 2-methyl-3-furanthiol, 5-acetyl-2,3-dihydro-1,4-thiazine, 3-mercapto-2-butanone, and bis(2-methyl-3-furyl) disulfide showing the highest flavor dilution factors among the 29 odor-active volatiles. HRGC/olfactometry of decreasing headspace volumes established especially 2-furfurylthiol and 2-methyl-3-furanthiol as important odorants and revealed 2-thenyl mercaptan and ethyl mercaptan as further key contributors to the overall roasty, meatlike, sulfury odor of the model mixture. 5-Acetyl-2,3-dihydro-1,4-thiazine, identified for the first time among the volatiles of Maillard model reactions or foods, exhibited an intense roasty, popcorn-like odor at the low odor threshold of 0.06 ng/L of air, which was of the same order of magnitude as those reported in the literature for the roasty-smelling odorants 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline.