2-甲基-3-噻吩硫醇 | 2527-76-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇盐
• 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: 2-甲基-3-噻吩硫醇
• 英文名称: 2-methyl-3-furanthiol
• 英文别名: 2-methylthiophene-3-thiol
• CAS: 2527-76-6
• 化学式: C₅H₆S₂
• 分子量: 130.235
• InChiKey: AQXLMAYNBMTBHD-UHFFFAOYSA-N

物化性质

• 沸点：
  189℃
• 密度：
  1.208
• 闪点：
  68℃
• LogP：
  2.394 (est)
• 保留指数：
  1030;1034;1034;1034;1034;1030;1030;1030

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-甲基-3-噻吩硫醇 、 碘甲烷 在 sodium thiosulfate 作用下， 以 乙醇 、 水 、 乙醚 为溶剂， 反应 8.0h， 生成 2-methyl-3-(methyldithio)furan
  参考文献：
  名称：

  Identification of the Key Aroma Compounds in Cocoa Powder Based on Molecular Sensory Correlations

  摘要：

  Isolation of the volatile fraction from cocoa powder (50 g; 20% fat content) by a careful extraction/distillation process followed by application of an aroma extract dilution analysis revealed 35 odoractive constituents in the flavor dilution (FD) factor range of 8-4096. Among them, 4-hydroxy-2,5dimethyl-3(2H)-furanone (caramel-like), 2- and 3-methylbutanoic acid (sweaty, rancid), dimethyl trisulfide (cooked cabbage), 2-ethyl-3,5-dimethylpyrazine(potato-chip-like), and phenylacetaldehyde (honey-like) showed the highest FD factors. Quantitation of 31 key odorants by means of stable isotope dilution assays, followed by a calculation of their odor activity values (OAVs) (ratio of concentration to odor threshold) revealed OAVs > 100 for the five odorants acetic acid (sour), 3-methylbutanal (malty), 3-methylbutanoic acid, phenylacetaldehyde, and 2- methylbutanal (malty). In addition, another 19 aroma compounds showed OAVs > 1. To establish their contribution to the overall aroma of the cocoa powder, these 24 compounds were added to a reconstructed cocoa matrix in exactly the same concentrations as they occurred in the cocoa powder. The matrix was prepared from deodorized cocoa powder, which was adjusted to 20% fat content using deodorized cocoa butter. The overall sensory evaluation of this aroma recombinate versus the cocoa powder clearly indicated that the 24 compounds represented the typical sweet, cocoa-like odor of the real sample.

  DOI：

  10.1021/jf060728k
• 作为产物：
  描述：

  3-溴-2-甲基噻吩 在 正丁基锂 、 sulfur 作用下， 生成 2-甲基-3-噻吩硫醇
  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

• Flammang, Robert; Barbieux-Flammang, Monique; Gerbaux, Pascal, Journal of the Chemical Society. Perkin transactions II, 1997, # 7, p. 1261 - 1264
  作者：Flammang, Robert、Barbieux-Flammang, Monique、Gerbaux, Pascal、Pedersen, Carl Th.

  DOI：——

  日期：——
• Investigation of the Aroma-Active Compounds Formed in the Maillard Reaction between Glutathione and Reducing Sugars
  作者：Sang Mi Lee、Ye-Jin Jo、Young-Suk Kim

  DOI：10.1021/jf9043327

  日期：2010.3.10

  Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene-2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.
• MARCHAND, G.;DECROIX, B.;MOREL, J., CHEM. SCR., 1984, 23, N 2, 80-86
  作者：MARCHAND, G.、DECROIX, B.、MOREL, J.

  DOI：——

  日期：——
• 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.
• Identification of the Key Aroma Compounds in Cocoa Powder Based on Molecular Sensory Correlations
  作者：Felix Frauendorfer、Peter Schieberle

  DOI：10.1021/jf060728k

  日期：2006.7.1

  Isolation of the volatile fraction from cocoa powder (50 g; 20% fat content) by a careful extraction/distillation process followed by application of an aroma extract dilution analysis revealed 35 odoractive constituents in the flavor dilution (FD) factor range of 8-4096. Among them, 4-hydroxy-2,5dimethyl-3(2H)-furanone (caramel-like), 2- and 3-methylbutanoic acid (sweaty, rancid), dimethyl trisulfide (cooked cabbage), 2-ethyl-3,5-dimethylpyrazine(potato-chip-like), and phenylacetaldehyde (honey-like) showed the highest FD factors. Quantitation of 31 key odorants by means of stable isotope dilution assays, followed by a calculation of their odor activity values (OAVs) (ratio of concentration to odor threshold) revealed OAVs > 100 for the five odorants acetic acid (sour), 3-methylbutanal (malty), 3-methylbutanoic acid, phenylacetaldehyde, and 2- methylbutanal (malty). In addition, another 19 aroma compounds showed OAVs > 1. To establish their contribution to the overall aroma of the cocoa powder, these 24 compounds were added to a reconstructed cocoa matrix in exactly the same concentrations as they occurred in the cocoa powder. The matrix was prepared from deodorized cocoa powder, which was adjusted to 20% fat content using deodorized cocoa butter. The overall sensory evaluation of this aroma recombinate versus the cocoa powder clearly indicated that the 24 compounds represented the typical sweet, cocoa-like odor of the real sample.