Chemistry:Furan-2-ylmethanethiol
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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[1] 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.[2][3]
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.[4]
Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)
References
- ↑ Viani, Rinantonio; Petracco, Marino (2007). "Coffee". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a07_315.pub2. ISBN 978-3-527-30385-4.
- ↑ Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv 10.1101/2021.02.05.21251085.
- ↑ "Scientists identify 'trigger molecule' for Covid-related changes to smell.". The Guardian. 25 May 2022. https://www.theguardian.com/world/2022/may/25/scientists-identify-trigger-molecule-for-covid-related-changes-to-smell.
- ↑ "Preparation of Furfuryl mercaptan". Organic Syntheses 35: 66. 1955. doi:10.15227/orgsyn.035.0066. http://www.orgsyn.org/demo.aspx?prep=CV4P0491.
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