Furan-2-ylmethanethiol

Furan-2-ylmethanethiol

Furan-2-ylmethanethiol

Chemical compound

Quick Facts Names, Identifiers ...

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]

Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)

References

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