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2,4-Dithiapentane

Bis(methylmercapto)methane 2,4-Dithiapentane"},"Section1":{"wt":"{{Chembox Identifiers\n| CASNo_Ref = {{cascite|correct|CAS}}\n| CASNo = 1618-26-4\n| Beilstein = 1731143\n| ChEB...

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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]

Notes and references

  1. 12"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 y P. Cabella (1967). "Bis-metiltiometano, una sustancia olorosa de la trufa blanca, tuber magnatum pico". Tetraedro Lett . 18 : 1681–1682.doi : 10.1016 / S0040-4039(00)90698-1 .
  5. ↑ Franco Bellesia; Adriano Pinetti; Alberto Bianchi y Bruno Tirillini (1996). "Compuestos volátiles de la trufa blanca (Tuber magnatum Pico) del centro de Italia". 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 y Susan E. Ebeler (2015). "Los compuestos volátiles de azufre de origen microbiano son contribuyentes clave al aroma de la trufa percibido por el ser humano". 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 (16 de mayo de 2007). "Hocus-Pocus y un vaso de trufas" . The New York Times . Consultado el 13 de febrero de 2008 .
  8. ↑ Babich, Matt (12 de julio de 2022). "La industria de la trufa es una gran estafa. No solo el aceite de trufa, todo" . www.tasteatlas.com . Consultado el 19 de noviembre de 2022 .
  9. ↑ Paul Thomas; Waill Elkhateeb; Ghoson Daba (2021). «Aplicaciones industriales de las trufas y hongos similares a las trufas». En Kandikere R. Sridhar; Sunil K. Deshmukh (eds.). Avances en macrohongos . CRC Press. ISBN 978-1-003-09681-8Consultado el 3 de abril de 2024 .
  10. ↑ Amy Berkov; Barbara Meurer-Grimes; Kenneth L. Purzycki (2000). "¿Los especialistas de Lecythidaceae (Coleoptera, Cerambycidae) evitan las especies de árboles fétidos?". Biotropica . 32 (3): 440– 451. doi : 10.1646/0006-3606(2000)032 [ 0440:dlsccs ] 2.0.co ; 2 . S2CID 198156552 .