2527-76-6

Basic information

• Product Name: 2-methylthiophene-3-thiol
• Synonyms: 2-methylthiophene-3-thiol;methyl-thiophenethiol,2-methyl-3-thiophenethiol;3-Thiophenethiol, 2-methyl-;2-Methyl-3-thiophenethiol;2-Methyl-3-mercaptothiophene;2-Methyl-3-thienylthiol
• CAS NO: 2527-76-6
• Molecular Formula: C₅H₆S₂
• Molecular Weight: 130.23114
• EINECS: 219-770-6
• Product Categories: Heterocycle-oher series
• Mol File: 2527-76-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 189℃
• Flash Point: 68℃
• Appearance: /
• Density: 1.208
• Vapor Pressure: 0.789mmHg at 25°C
• Refractive Index: 1.615
• PKA: 6.57±0.48(Predicted)
• CAS DataBase Reference: 2-methylthiophene-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylthiophene-3-thiol(2527-76-6)
• EPA Substance Registry System: 2-methylthiophene-3-thiol(2527-76-6)

Safety Data

• Hazardous Substances Data: 2527-76-6(Hazardous Substances Data)

Usage

General Description

2-Methylthiophene-3-thiol is a chemical compound also known as 3-Methyl-2-(methylthio)thiophene. It is typically characterized by its strong odor, often similar to a blend of coffee and skunk, which derives from traces of sulfur in the compound. Due to its strong, aromatic smell, 2-Methylthiophene-3-thiol has applications in industry as an odorant for natural gas and other fuels, as well as certain chemical applications in the synthesis of other compounds. It occurs naturally in some foods and drinks, including beer, where it can contribute to its characteristic flavor profile, though it can also be synthetically produced. Due to its powerful scent and potential volatility, it is often handled and stored with caution.

InChI:InChI=1/C5H6S2/c1-4-5(6)2-3-7-4/h2-3,6H,1H3

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Relevant articles and documents

Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars

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-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.

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

Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 deg 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.Keywords: Aroma extract dilution analysis; nonenzymatic browning; Maillard reaction; ribose; cysteine; flavor; 5-acetyl-2,3-dihydro-1,4-thiazine