Dimethyl trisulfide

Dimethyl trisulfide
Names
IUPAC name
dimethyltrisulfane[1]
Other names
2,3,4-trithiapentane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.828
Properties
C2H6S3
Molar mass 126.26 g/mol
Density 1.1978 g/cm3
Melting point −68.05 °C (−90.49 °F; 205.10 K)
Boiling point 170 °C (338 °F; 443 K) (65–68 °C @ 25 Torr)
Except where otherwise noted, 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.[2][3] It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.[4]

Occurrence

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,[5] and is involved in the unpalatable aroma of aged beer and stale Japanese sake.[6] It is a decomposition product of bacterial decomposition, including the early stages of human decomposition,[7] 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.[8] 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,[4] and contributes to the odor of human feces.[9]

DMTS can be synthesized by the reaction of methanethiol with hydrogen sulfide (in the presence of copper (II))[10] and with sulfur dichloride,[11] among other methods:[3]

2 CH3SH + SCl2 → CH3SSSCH3 + HCl

Chemical reactions

On heating at 80 °C, DMTS slowly decomposes to a mixture of dimethyl di-, tri-, and tetrasulfides.[11] The reactivity of DMTS is related to its weak sulfur-sulfur bond (ca. 45 kcal/mol).[2] Dimethyl tetrasulfide, which is thermally more reactive than dimethyl trisulfide, has a still weaker (central) sulfur-sulfur bond (ca. 36 kcal/mol).[11] Oxidation of DMTS by meta-chloroperoxybenzoic acid (mCPBA) gives the corresponding S-monoxide, CH3S(O)SSCH3.[12]

Uses

Trap baits containing dimethyl trisulfide have been used to capture Calliphora loewi and other blowflies.[13]

References

  1. ↑ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-68.4.1.1". In Favre, Henri A.; Powell, Warren H. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
  2. 1 2 Edward L. Clennan; 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.
  3. 1 2 Ralf Steudel (2002). "The Chemistry of Organic Polysulfanes R−Sn−R (n > 2)". Chemical Reviews. 102 (11): 3905–3945. doi:10.1021/cr010127m.
  4. 1 2 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.
  5. ↑ Thomas H. Parliament; Michael G. Kolor; Donald J. Rizzo (1982). "Volatile components of Limburger cheese". J. Agric. Food Chem. 30 (6): 1006–1008. doi:10.1021/jf00114a001.
  6. ↑ Atsuko Isogai; Ryoko Kanda; Yoshikazu Hiraga; Toshihide Nishimura; Hiroshi Iwata; 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.
  7. ↑ M. Statheropoulosa; A. Agapioua; C. Spiliopoulou; G.C. Pallis; 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.
  8. ↑ 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 (6916): 625–626. doi:10.1038/420625a. PMID 12478279.
  9. ↑ J.G. Moore; L.D. Jessop; D.N. Osborne DN. (1987). "Gas-chromatographic and mass-spectrometric analysis of the odor of human feces". Gastroenterology. 93 (6): 1321–1329. PMID 3678751.
  10. ↑ Mustapha Nedjma; 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.
  11. 1 2 3 Timothy L. Pickering; K. J. Saunders; Arthur V. Tobolsky (1967). "Disproportionation of organic polysulfides". J. Am. Chem. Soc. 89 (10): 2364–2367. doi:10.1021/ja00986a021.
  12. ↑ J. Auger; Y. Koussourakos; E. Thibout (1985). "Monooxidation of organic trisulfides". Chimika Chronika. 14 (4): 263–264.
  13. ↑ Nilssen Arne C.; Åge Tǿmmerås Bjǿrn; Schmid Rudolf; Barli Evensen Sissel (1996). "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): 211–218. doi:10.1111/j.1570-7458.1996.tb00828.x.
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