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]
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| Names | |
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| Preferred IUPAC name
(Furan-2-yl)methanethiol | |
Other names
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| Identifiers | |
3D model (JSmol)
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| 383594 | |
| ChemSpider | |
| ECHA InfoCard | 100.002.390 |
| EC Number |
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| MeSH | furfuryl+mercaptan |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 3336 |
CompTox Dashboard (EPA)
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| Properties | |
| C5H6OS | |
| Molar mass | 114.16 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Roasted coffee, Caramel, Sulfurous, Waxy |
| Density | 1.132 g cm−3 |
| Boiling point | 155 °C; 311 °F; 428 K |
| Vapor pressure | 531 Pa |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H226 | |
| Flash point | 45 °C (113 °F; 318 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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100-200 mg kg−1 (mouse) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
editFuran-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]
References
edit- ^ Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv 10.1101/2021.02.05.21251085.
- ^ Devlin H (25 May 2022). "Scientists identify 'trigger molecule' for Covid-related changes to smell". The Guardian.
- ^ "Preparation of furfuryl mercaptane". Organic Syntheses. 35: 66. 1955. doi:10.15227/orgsyn.035.0066.
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