2,4-Dithiapentane

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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 Edit this at Wikidata
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
Safety data sheet (SDS) External MSDS
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Signal word
 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)
1
2
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).
☒N  (what is checkY☒N ?)
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 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.[5] It has also been found to occur naturally in rotting wood of some species in genus Lecythis.[6]

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. ^ 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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