2-methyl-3-furyl 2-oxo-3-pentyl disulfide

• 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: 2-methyl-3-furyl 2-oxo-3-pentyl disulfide
• 英文别名: 3-<(2-methyl-3-furyl)dithio>-2-pentanone；1-Propyldecyl cyclopentanecarboxylate；3-[(2-methylfuran-3-yl)disulfanyl]pentan-2-one
• 化学式: C₁₀H₁₄O₂S₂
• 分子量: 230.352
• InChiKey: HUNHUMWMMZADPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 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 、 2-甲基-3-呋喃硫醇 在 copper(II) sulfate 作用下， 以 乙醚 为溶剂， 反应 0.58h， 生成 2-methyl-3-furyl 2-oxo-3-pentyl disulfide
  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

• Formation of Aroma Compounds from Ribose and Cysteine during the Maillard Reaction
  作者：Christoph Cerny、Tomas Davidek

  DOI：10.1021/jf026123f

  日期：2003.4.1

  (13)C(5)-labeled, suggesting that it stems from ribose and that 4-hydroxy-5-methyl-3(2H)-furanone is unimportant as an intermediate. Whereas 2-mercapto-3-pentanone was found unlabeled and hence originated from 4-hydroxy-5-methyl-3(2H)-furanone, its isomer 3-mercapto-2-pentanone was formed from both 4-hydroxy-5-methyl-3(2H)-furanone and ribose. A new reaction pathway from ribose via its 1,4-dideoxyosone is

  通过顶空SPME检测了由半胱氨酸的磷酸盐缓冲液（pH 5）和核糖与[（13）C（5）]核糖的1 + 1混合物在95°C加热4 h产生的顶空挥发物。与GC-MS结合使用。MS数据表明核糖的断裂在硫香气化合物2-甲基-3-呋喃硫醇，2-糠硫醇和3-巯基-2-戊酮的形成中没有显着作用，其中核糖的碳骨架保持完整。2-甲基-3-（甲硫基）呋喃的甲基呋喃部分起源于核糖，而甲硫基碳原子部分来自核糖，部分来自半胱氨酸。在3-巯基-2-丁酮中，一个碳单元从核糖链上分开。另一方面，3-噻吩硫醇中的所有碳原子均来自半胱氨酸。在另一个试验中，半胱氨酸 使4-羟基-5-甲基-3（2H）-呋喃酮与[（13）C（5）]核糖在相同条件下反应。所得的2-甲基-3-呋喃硫醇主要是（13）C（5）标记的，表明它起源于核糖，而4-羟基-5-甲基-3（2H）-呋喃酮作为中间体并不重要。发现2-巯基-3-戊酮未标记，因此起源于4-羟
• 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.
• Sulfur-Containing Furans in Commercial Meat Flavorings
  作者：Joachim Ruther、Werner Baltes

  DOI：10.1021/jf00046a032

  日期：1994.10

  The volatiles of eight commercially available meat flavorings were enriched by dynamic headspace extraction. The resulting aroma extracts were analyzed by high-resolution gas chromatography and gas chromatography/mass spectrometry (GC/MS). Among the compounds identified were 16 sulfur-containing furans. 2-Methyl-3-(ethyldithio)furan, 1-[(2-methyl-3-furyl)dithio]-2-propanone, and the spectroscopic data of 3-[(2-methyl-3-furyl)dithio]-2-butanone, 2-[(2-methyl-3-furyl)dithio]-3-pentanone and 3-[(2-methyl-3-furyl)dithio]-2-pentanone are reported here for the first time. Possible formation pathways are discussed.
• 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.