Structure via PubChem · Public domain (PubChem)
furfuryl mercaptan
Sign in to saveAlso known as furan-2-ylmethanethiol, 2-furanmethanethiol, (2-furanyl)methylmercaptan, 2-(mercaptomethyl)furan, 2-furfurylmercaptan, 2-furfurylthiol, 2-furylmethanethiol, 2-furylmethyl mercaptan
Furan-2-ylmethanethiol (2-furanmethanethiol) is an organosulfur compound. It is classified as a furan substituted with a methylthiol group. It is a colourless liquid, but impure samples can appear yellow. It possesses a strong odour of roasted coffee and a bitter taste. It is a key component of the aroma of roasted coffee. It has been identified as a trigger molecule for parosmia following COVID-19 infection.
Chemical data
- Formula
- C5H6OS
- Molecular weight
- 114.17 g/mol
- IUPAC name
- furan-2-ylmethanethiol
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
42 papers- Sulfur Hydrogen Bonding in Isolated Monohydrates: Furfuryl Mercaptan versus Furfuryl Alcohol.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018
- Degradation of the coffee flavor compound furfuryl mercaptan in model Fenton-type reaction systems.Journal of agricultural and food chemistry · 2002
- Studies on the metabolism of the thiofurans furfuryl mercaptan and 2-methyl-3-furanthiol in rat liver.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association · 2003
- Short-term toxicity of furfuryl mercaptan in rats.Food and cosmetics toxicology · 1977
- Elucidating salt-reduction mechanisms of aroma-active compounds from yeast extracts through sensomics approaches and electroencephalography.Food chemistry: X · 2024
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 114.014
Show 4 more facts
- chemical formula
- C₅H₆OS
- canonical SMILES
- C1=COC(=C1)CS
- subject has role
- flavor enhancer
- Commons category
- 2-Furanmethanethiol
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Furan-2-ylmethanethiol (2-furanmethanethiol) is an organosulfur compound. It is classified as a furan substituted with a methylthiol group. It is a colourless liquid, but impure samples can appear yellow. It possesses a strong odour of roasted coffee and a bitter taste. It is a key component of the aroma of roasted coffee. It has been identified as a trigger molecule for parosmia following COVID-19 infection.
==Synthesis == Furan-2-ylmethanethiol is prepared by treating furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt, which is hydrolized to the thiol by heating with sodium hydroxide. 520px|left|Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)
Excerpted from Wikipedia’s “furfuryl mercaptan” article, available under the CC BY-SA 4.0 licence.