Dimethyl trisulfide

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Dimethyl trisulfide
Dimethyl trisulfide.svg
Dimethyl-trisulfide-DFT-Mercury-3D-balls.png
Identifiers
CAS number 3658-80-8 YesY
PubChem 19310
ChemSpider 18219 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H6S3
Molar mass 126.26 g/mol
Density 1.1978 g/cm3
Melting point -68.05 °C
Boiling point 170 °C; 65–68 °C (25 Torr)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide.[1][2] It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.[3]

Occurrence[edit]

Dimethyl trisulfide has been found in volatiles emitted from cooked onion, leek and other Allium species, from broccoli and cabbage, as well as from Limburger cheese,[4] and is involved in the unpalatable aroma of aged beer and stale Japanese sake.[5] It is a decomposition product from bacterial decomposition, including from the early stages of human decomposition,[6] and is a major attractant for blowflies looking for hosts. Dimethyl trisulfide along with dimethyl sulfide and dimethyl disulfide have been confirmed as volatile compounds given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus). These flies are attracted to the odor of fetid meat and help pollinate this plant.[7] DMTS contributes to the foul odor given off by the fungus Phallus impudicus, also known as the common stinkhorn. DMTS causes the characteristic malodorous smell of a fungating lesion, e.g., from cancer wounds,[3] and contributes to the odor of human feces.[8]

DMTS can be synthesized by the reaction of methanethiol with hydrogen sulfide (in the presence of copper (II))[9] and with sulfur dichloride,[10] among other methods:[2]

2 CH3SH + SCl2 → CH3SSSCH3 + HCl

Chemical reactions[edit]

On heating at 80 °C, DMTS slowly decomposes to a mixture of dimethyl di-, tri-, and tetrasulfides.[10] The reactivity of DMTS is related to its weak sulfur-sulfur bond (ca. 45 kcal/mol).[1] Dimethyl tetrasulfide, which is thermally more reactive than dimethyl trisulfide, has a still weaker (central) sulfur-sulfur bond (ca. 36 kcal/mol).[10] Oxidation of DMTS by meta-chloroperoxybenzoic acid (mCPBA) gives the corresponding S-monoxide, CH3S(O)SSCH3.[11]

Uses[edit]

Trap baits containing dimethyl trisulfide have been used to capture Calliphora loewi and other blowflies.[12]

References[edit]

  1. ^ a b Edward L. Clennan and Kristina L. Stensaas (1998). "Recent progress in the synthesis, properties and reactions of trisulfanes and their oxides". Organic Preparations and Procedures International 30 (5): 551–600. doi:10.1080/00304949809355321. 
  2. ^ a b Ralf Steudel (2002). "The Chemistry of Organic Polysulfanes R−Sn−R (n > 2)". Chemical Reviews 102 (11): 3905–3945. doi:10.1021/cr010127m. 
  3. ^ a b Shirasu, Mika; Nagai, Shunji; Hayashi, Ryuichi; Ochiai, Atsushi; Touhara, Kazushige (2009). "Dimethyl trisulfide as a characteristic odor associated with fungating cancer wounds". Bioscience, Biotechnology, and Biochemistry 73 (9): 2117–20. doi:10.1271/bbb.90229. PMID 19734656. 
  4. ^ Thomas H. Parliament, Michael G. Kolor and Donald J. Rizzo (1982). "Volatile components of Limburger cheese". J. Agric. Food Chem. 30 (6): 1006–1008. doi:10.1021/jf00114a001. 
  5. ^ Atsuko Isogai, Ryoko Kanda, Yoshikazu Hiraga, Toshihide Nishimura, Hiroshi Iwata and Nami Goto-Yamamoto (2009). "Screening and Identification of Precursor Compounds of Dimethyl Trisulfide (DMTS) in Japanese Sake". J. Agric. Food Chem. 57 (1): 189–195. doi:10.1021/jf802582p. PMID 19090758. 
  6. ^ M. Statheropoulosa, A. Agapioua, C. Spiliopoulou, G.C. Pallis and E. Sianos (2007). "Environmental aspects of VOCs evolved in the early stages of human decomposition.". Science of The Total Environment 385 (1-3): 221–227. doi:10.1016/j.scitotenv.2007.07.003. 
  7. ^ Marcus C. Stensmyr, Isabella Urru, Ignazio Collu, Malin Celander, Bill S. Hansson, Anna-Maria Angioy (2002). "Rotting smell of dead-horse arum florets". Nature 420: 625–626. doi:10.1038/420625a. PMID 12478279. 
  8. ^ J.G. Moore, L.D. Jessop and D.N. Osborne DN. (1987). "Gas-chromatographic and mass-spectrometric analysis of the odor of human feces.". Gastroenterology 93 (6): 1321–1329. PMID 3678751. 
  9. ^ Mustapha Nedjma and Norbert Hoffmann (1996). "Hydrogen Sulfide Reactivity with Thiols in the Presence of Copper(II) in Hydroalcoholic Solutions or Cognac Brandies: Formation of Symmetrical and Unsymmetrical Dialkyl Trisulfides.". J. Agric. Food Chem. 44 (12): 3935–3938. doi:10.1021/jf9602582. 
  10. ^ a b c Timothy L. Pickering, K. J. Saunders and Arthur V. Tobolsky (1967). "Disproportionation of organic polysulfides". J. Am. Chem. Soc. 89 (10): 2364–2367. doi:10.1021/ja00986a021. 
  11. ^ J. Auger, Y. Koussourakos and E. Thibout (1985). "Monooxidation of organic trisulfides". Chimika Chronika 14 (4): 263–264. 
  12. ^ Nilssen, Arne C., Bjǿrn Åge Tǿmmerås, Rudolf Schmid, and Sissel Barli Evensen. “Dimethyl trisulphide is a strong attractant for some calliphorids and a muscid but not for the reindeer oestrids Hypoderma tarandi and Cephenemyia trompe.” Entomologia Experimentalis et Applicata. 79:2 (1996): 211–218. https://commerce.metapress.com/content/g5581l8416133344/resource-secured/?target=fulltext.pdf&sid=tdguxe55dk00gp55xq1tnwrd&sh=www.springerlink.com