2,4-Dithiapentane

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2,4-Dithiapentane
Skeletal formula of 2,4-dithiapentane
Ball-and-stick model
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 Edit this at Wikidata
  • 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
  • S(C)CSC
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
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).
☒N verify (what is checkY☒N ?)

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

  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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  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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