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) | |
| Names | |
|---|---|
| IUPAC name 2,4-Dithiapentane | |
| Other names Bis(methylthio)methane Bis(methylsulfanyl)methane Bis(methylmercapto)methane | |
| Identifiers | |
3D model (JSmol) | |
| 1731143 | |
| ChemSpider | |
| ECHA InfoCard | 100.015.071  |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
SMILES
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| Properties | |
| C3H8S2 | |
| Molar mass | 108.22 g·mol−1 |
| Appearance | Liquid |
| Density | 1.059 g/cm3, liquid |
| Melting point | −20.5 °C (−4.9 °F; 252.7 K) |
| Boiling point | 147 °C (297 °F; 420 K) |
| Immiscible | |
Refractive index (nD) | 1.53 |
| Viscosity | 0.00113 Pa s |
| Hazards | |
| Safety data sheet | External MSDS |
| R-phrases (outdated) | R10 |
| S-phrases (outdated) | S16 |
| NFPA 704 (fire diamond) | |
| Flash point | 43.89 °C (111.00 °F; 317.04 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
2,4-Dithiapentane is an organosulfur compound. It is a colorless liquid with a strong odor.
2,4-Dithiapentane is the dimethyldithioacetal of formaldehyde. It is prepared by the acid-catalyzed addition of methyl mercaptan, the main aromatic compound in both halitosis and foot odor and a secondary compound in flatulence,[1] to formaldehyde.
- 2 CH3SH + H2C=O → CH3SCH2SCH3 + H2O
2,4-Dithiapentane is found as an aromatic component in some truffle varietals.[2][3][4] A synthetic version is used as the primary aromatic additive in commercial truffle products, such as truffle oil, truffle butter, truffle salt, pastes, etc.[5] It has also been found to occur naturally in rotting wood of some species in genus Lecythis.[6]
Notes and references
- ^ "The Chemistry of Body Odours". Compound Interest.
- ^ A. Fiecchi; M. Galli Kienle; A. Scala & P. Cabella (1967). "Bis-methylthiomethane, an odorous substance from white truffle, tuber magnatum pico". Tetrahedron Lett. 18: 1681–1682. doi:10.1016/S0040-4039(00)90698-1.
- ^ Franco Bellesia; Adriano Pinetti; Alberto Bianchi andBruno Tirillini (1996). "Volatile Compounds of the White Truffle (Tuber magnatum Pico) from Middle Italy". Flavour and Fragrance Journal. 11 (4): 239–243. doi:10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A.
- ^ Richard Splivallo & Susan E. Ebeler (2015). "Sulfur volatiles of microbial origin are key contributors to human-sensed truffle aroma". Biotechnological Products and Process Engineering: Applied Microbiology and Biotechnology. 99 (6): 2583–2592. doi:10.1007/s00253-014-6360-9. PMID 25573471. S2CID 16749990.
- ^ Patterson, Daniel (2007-05-16). "Hocus-Pocus, and a Beaker of Truffles". The New York Times. Retrieved 2008-02-13.
- ^ Amy Berkov; Barbara Meurer-Grimes; Kenneth L. Purzycki (2000). "Do Lecythidaceae Specialists (Coleoptera, Cerambycidae) Shun Fetid Tree Species?" (PDF). Biotropica. 32 (3): 440–451. doi:10.1646/0006-3606(2000)032[0440:dlsccs]2.0.co;2.