2,4-Dithiapentane Explained

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.[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]

Notes and References

  1. Web site: 2,4-Dithiapentane . American Chemical Society . 3 April 2024 . en.
  2. Böhme . Horst . Marx . Robert . Zur Kenntnis der Trisulfonyl‐methane . Berichte der deutschen chemischen Gesellschaft (A and B Series) . 8 October 1941 . 74 . 10 . 1667–1675 . 10.1002/cber.19410741009 . 3 April 2024.
  3. Web site: The Chemistry of Body Odours . 7 April 2014 . .
  4. Bis-methylthiomethane, an odorous substance from white truffle, tuber magnatum pico . A. Fiecchi . M. Galli Kienle . A. Scala . P. Cabella . amp . Tetrahedron Lett . 18 . 1681–1682 . 1967. 10.1016/S0040-4039(00)90698-1 .
  5. Flavour and Fragrance Journal . 11 . 4 . 239–243 . 1996 . Volatile Compounds of the White Truffle (Tuber magnatum Pico) from Middle Italy . Franco Bellesia . Adriano Pinetti . Alberto Bianchi and Bruno Tirillini . 10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A.
  6. Biotechnological Products and Process Engineering: Applied Microbiology and Biotechnology . 2015 . 99 . 6 . 2583–2592 . Sulfur volatiles of microbial origin are key contributors to human-sensed truffle aroma . Richard Splivallo . Susan E. Ebeler . amp . 10.1007/s00253-014-6360-9. 25573471 . 16749990 .
  7. Web site: Patterson. Daniel. Hocus-Pocus, and a Beaker of Truffles. The New York Times. 2007-05-16. 2008-02-13 .
  8. Web site: Babich . Matt . July 12, 2022 . The truffle industry is a big scam. Not just truffle oil, everything . 2022-11-19 . www.tasteatlas.com.
  9. Book: Paul Thomas . Waill Elkhateeb . Ghoson Daba . Kandikere R. Sridhar . Sunil K. Deshmukh . Advances in Macrofungi . 2021 . CRC Press . 978-1-003-09681-8 . 3 April 2024 . en . Industrial Applications of Truffles and Truffle-like Fungi.
  10. Do Lecythidaceae Specialists (Coleoptera, Cerambycidae) Shun Fetid Tree Species? . Amy Berkov . Barbara Meurer-Grimes . Kenneth L. Purzycki . Biotropica . 32 . 3 . 440–451 . 2000 . 10.1646/0006-3606(2000)032[0440:dlsccs]2.0.co;2 . 198156552 .

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2,4-Dithiapentane".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.