2,4-Dithiapentane

2,4-Dithiapentane
Names
	IUPAC name 2,4-Dithiapentane
	Other names Bis(methylthio)methane; Bis(methylsulfanyl)methane; Bis(methylmercapto)methane
Identifiers
CAS Number	1618-26-4 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1731143
ChemSpider	14639 ;
ECHA InfoCard	100.015.071
PubChem CID	15380;
UNII	128SGX814T ;
CompTox Dashboard (EPA)	DTXSID0061822 ;
	InChI InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 Key: LOCDPORVFVOGCR-UHFFFAOYSA-N ; InChI=1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 Key: LOCDPORVFVOGCR-UHFFFAOYAH;
	SMILES CSCSC; S(C)CSC;
Properties
Chemical formula	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)
Solubility in water	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R-phrases (outdated)	R10
S-phrases (outdated)	S16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)	2 1
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).
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	Infobox references

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.
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.
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.

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[1] "The Chemistry of Body Odours". Compound Interest.

[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.

[3] 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.

[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.

[hocus-5] Patterson, Daniel (2007-05-16). "Hocus-Pocus, and a Beaker of Truffles". The New York Times. Retrieved 2008-02-13.

[6] 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.