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2,4-Dithiapentane
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changed changed 477211334 2,4-Dithiapentane 2,4-dithiapentane.svg 160px Skeletal formula of 2,4-dithiapentane 2,4-dithiapentane-3D-balls.png Ball-and-stick model Bis(methylsulfanyl)methane Bis(methylthio)methaneBis(methylmercapto)methane2,4-Dithiapentane correct CAS 1618-26-4 1731143 167064 correct chemspider 14639 216-577-9 15380 correct FDA 128SGX814T CSCSC 1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 LOCDPORVFVOGCR-UHFFFAOYAH correct chemspider 1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 correct chemspider LOCDPORVFVOGCR-UHFFFAOYSA-N
3 8 2 Liquid 1.059 g/cm3, liquid Immiscible −20.5 147 0.00113 Pa s 1.53
External MSDS 1 2 43.89 02 07 Warning 226 315 319 335 210 233 240 241 242 243 261 264 271 280 302+352 303+361+353 304+340 305+351+338 312 321 332+313 337+313 362 370+378 403+233 403+235 405 501
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.2,4-Dithiapentane https://www.acs.org/molecule-of-the-week/archive/d/2-4-dithiapentane.html American Chemical Society 3 April 2024 en
2,4-Dithiapentane is the dimethyl dithioacetal of formaldehyde. Its synthesis was first reported in 1941.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 https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cber.19410741009 3 April 2024 subscription 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, The Chemistry of Body Odours 7 April 2014 Compound Interest http://www.compoundchem.com/2014/04/07/the-chemistry-of-body-odours-sweat-halitosis-flatulence-cheesy-feet/ with formaldehyde.
2 CH3SH + H2C=O → CH3SCH2SCH3 + H2O
2,4-Dithiapentane is found as an aromatic component in some truffle varieties. 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 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 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 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, Patterson Daniel Hocus-Pocus, and a Beaker of Truffles The New York Times 2007-05-16 https://www.nytimes.com/2007/05/16/dining/16truf.html 2008-02-13 Babich Matt July 12, 2022 The truffle industry is a big scam. Not just truffle oil, everything https://www.tasteatlas.com/truffle-industry-is-a-big-scam 2022-11-19 www.tasteatlas.com and have elevated levels of 2,4-dithiapentane compared to levels in natural truffle products.Paul Thomas Waill Elkhateeb Ghoson Daba Kandikere R. Sridhar Sunil K. Deshmukh Advances in Macrofungi 2021 CRC Press 978-1-003-09681-8 https://books.google.com/books?id=My44EAAAQBAJ 3 April 2024 en Industrial Applications of Truffles and Truffle-like Fungi It has also been found to occur naturally in rotting wood of some species in the genus Lecythis. 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
Notes and references
Category:Thioethers
Category:Methylthio compounds