2,4-Dithiapentane

2,4-Dithiapentane is an organosulfur compound. It is a colorless liquid with a strong odor.

2,4-Dithiapentane
Skeletal formula of 2,4-dithiapentane
Ball-and-stick model
Names
Preferred IUPAC name
Bis(methylsulfanyl)methane
Other names
Bis(methylthio)methane
Bis(methylmercapto)methane
2,4-Dithiapentane
Identifiers
3D model (JSmol)
1731143
ChEBI
ChemSpider
ECHA InfoCard 100.015.071
EC Number
  • 216-577-9
UNII
  • InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 checkY
    Key: LOCDPORVFVOGCR-UHFFFAOYSA-N checkY
  • InChI=1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3
    Key: LOCDPORVFVOGCR-UHFFFAOYAH
  • CSCSC
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
1.53
Viscosity 0.00113 Pa s
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
2
Flash point 43.89 °C (111.00 °F; 317.04 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

2,4-Dithiapentane is the dimethyldithioacetal of formaldehyde. It is prepared by the acid-catalyzed condensation of methyl mercaptan, the main aromatic compound in both halitosis and foot odor and a secondary compound in flatulence,[1] with 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., many of which contain no truffle content at all.[5][6] It has also been found to occur naturally in rotting wood of some species in genus Lecythis.[7]

Notes and references
  1. "The Chemistry of Body Odours". Compound Interest. 7 April 2014.
  2. 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.
  3. Franco Bellesia; Adriano Pinetti; Alberto Bianchi and Bruno 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.
  4. 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.
  5. Patterson, Daniel (2007-05-16). "Hocus-Pocus, and a Beaker of Truffles". The New York Times. Retrieved 2008-02-13.
  6. Babich, Matt (July 12, 2022). "The truffle industry is a big scam. Not just truffle oil, everything". www.tasteatlas.com. Retrieved 2022-11-19.
  7. 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. S2CID 198156552.


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