2,4-Dithiapentane

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
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 diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
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).
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2,4-Dithiapentane is an organosulfur compound, and is the simplest alkyl dithioether. It is a colorless liquid with a strong odor, reminiscent of freshly prepared mustard in the pure form.[1]

2,4-Dithiapentane is the dimethyldithioacetal of formaldehyde. Its synthesis was first reported in 1941.[1][2] It is industrially 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,[3] with formaldehyde.

2 CH3SH + H2C=O → CH3SCH2SCH3 + H2O

2,4-Dithiapentane is found as an aromatic component in some truffle varieties.[4][5][6] A synthetic version is used as the primary aromatic additive in commercial "truffle" products, such as truffle oil, truffle butter, truffle salt and truffle pastes, many of which contain no truffle content at all,[7][8] and have elevated levels of 2,4-dithiapentane compared to levels in natural truffle products.[9] It has also been found to occur naturally in rotting wood of some species in the genus Lecythis.[10]

  1. ^ a b "2,4-Dithiapentane". American Chemical Society. Retrieved 3 April 2024.
  2. ^ Böhme, Horst; Marx, Robert (8 October 1941). "Zur Kenntnis der Trisulfonyl-methane". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 74 (10): 1667–1675. doi:10.1002/cber.19410741009. Retrieved 3 April 2024.
  3. ^ "The Chemistry of Body Odours". Compound Interest. 7 April 2014.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ Patterson, Daniel (2007-05-16). "Hocus-Pocus, and a Beaker of Truffles". The New York Times. Retrieved 2008-02-13.
  8. ^ Babich, Matt (July 12, 2022). "The truffle industry is a big scam. Not just truffle oil, everything". www.tasteatlas.com. Retrieved 2022-11-19.
  9. ^ Paul Thomas; Waill Elkhateeb; Ghoson Daba (2021). "Industrial Applications of Truffles and Truffle-like Fungi". In Kandikere R. Sridhar; Sunil K. Deshmukh (eds.). Advances in Macrofungi. CRC Press. ISBN 978-1-003-09681-8. Retrieved 3 April 2024.
  10. ^ Amy Berkov; Barbara Meurer-Grimes; Kenneth L. Purzycki (2000). "Do Lecythidaceae Specialists (Coleoptera, Cerambycidae) Shun Fetid Tree Species?". Biotropica. 32 (3): 440–451. doi:10.1646/0006-3606(2000)032[0440:dlsccs]2.0.co;2. S2CID 198156552.