Furan-2-ylmethanethiol explained

Furan-2-ylmethanethiol (2-Furanmethanethiol) is an organic compound containing a furan substituted with a sulfanylmethyl group. It is a clear colourless liquid when pure, but it becomes yellow coloured upon prolonged standing. 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.[1] [2]

Synthesis

Furan-2-ylmethanethiol is easily prepared by reacting furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt which is hydrolized to the thiol by heating with sodium hydroxide.[3]

Notes and References

  1. Parker JK, Kelly CE, Gane SB . Molecular Mechanism of Parosmia. . 5 February 2021 . 21251085 . 10.1101/2021.02.05.21251085.
  2. Web site: Scientists identify 'trigger molecule' for Covid-related changes to smell. . Devlin H . The Guardian . 25 May 2022 .
  3. Preparation of furfuryl mercaptane . Organic Syntheses . 1955 . 35 . 66 . 10.15227/orgsyn.035.0066 .