2,4-Dithiapentane (original) (raw)

From Wikipedia, the free encyclopedia

2,4-Dithiapentane

Skeletal formula of 2,4-dithiapentaneSkeletal formula of 2,4-dithiapentane
Ball-and-stick modelBall-and-stick model
Names
Preferred IUPAC name Bis(methylsulfanyl)methane
Other namesBis(methylthio)methaneBis(methylmercapto)methane2,4-Dithiapentane
Identifiers
CAS Number 1618-26-4 checkY
3D model (JSmol) Interactive image
Beilstein Reference 1731143
ChEBI CHEBI:167064
ChemSpider 14639 checkY
ECHA InfoCard 100.015.071 Edit this at Wikidata
EC Number 216-577-9
PubChem CID 15380
UNII 128SGX814T checkY
CompTox Dashboard (EPA) DTXSID0061822 Edit this at Wikidata
InChI InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 checkYKey: LOCDPORVFVOGCR-UHFFFAOYSA-N checkYInChI=1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3Key: LOCDPORVFVOGCR-UHFFFAOYAH
SMILES CSCSC
Properties
Chemical formula 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)
Solubility in water Immiscible
Refractive index (_n_D) 1.53
Viscosity 0.00113 Pa s
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H315, H319, H335
Precautionary statements 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 diamond 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 ?) Infobox references

Chemical compound

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

[edit]

  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.