Dimethyl trisulfide

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, 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, and contributes to the odor of human feces.

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

:2 CH3SH + SCl2 → CH3SSSCH3 + 2 HCl

Chemical reactions

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

Uses

Trap baits containing dimethyl trisulfide have been used to capture Calliphora loewi and other blowflies. Dimethyl trisulfide has been found to be an effective cyanide antidote in a rodent model for cyanide poisoning both against subcutaneous potassium cyanide and inhaled hydrogen cyanide, converting cyanide to much less toxic thiocyanate. It is suggested that dimethyl trisulfide can be used in a mass casualty cyanide exposure setting. In conjunction with these studies, the LD50 of dimethyl trisulfide in CD-1 mice was found to be 598.5 mg/kg, which may be compared to the LD50 of potassium cyanide of 8.0 mg/kg.

References

References

1. {{BlueBook2013
2. (2002). "Rotting smell of dead-horse arum florets". Nature.
3. (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.
4. DeLeon, SM. (2018). "DMTS is an effective treatment in both inhalation and injection models for cyanide poisoning using unanesthetized mice". [[Clinical Toxicology]].
5. (1998). "Recent progress in the synthesis, properties and reactions of trisulfanes and their oxides". Organic Preparations and Procedures International.
6. Ralf Steudel. (2002). "The Chemistry of Organic Polysulfanes R−S_n−R (n > 2)". Chemical Reviews.
7. (2009). "Dimethyl trisulfide as a characteristic odor associated with fungating cancer wounds". Bioscience, Biotechnology, and Biochemistry.
8. (2009). "Screening and Identification of Precursor Compounds of Dimethyl Trisulfide (DMTS) in Japanese Sake". J. Agric. Food Chem..
9. (1967). "Disproportionation of organic polysulfides". J. Am. Chem. Soc..
10. (1982). "Volatile components of Limburger cheese". J. Agric. Food Chem..
11. (1985). "Monooxidation of organic trisulfides". Chimika Chronika.