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Record Information
Version3.6
Creation Date2012-05-18 14:35:55 UTC
Update Date2016-02-11 01:27:20 UTC
HMDB IDHMDB13780
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimethyl trisulfide
DescriptionDimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide. It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion. 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, and is involved in the unpalatable aroma of aged beer and stale Japanese sake. It is a decomposition product from bacterial decomposition, including from the early stages of human decomposition, 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. 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. Dimethyldisulfide is a volatile organic compound. Methyl disulfide is occasionally found as a volatile component of normal human breath and biofluids. Dimethyldisulfide is one of the representative volatile components found in oral malodor. Dimethyldisulfide concentrations in breath is a practical noninvasive way to assess recent exposure to sulfur compounds in sulfate pulp mills, and therefore it should be applicable to workplaces contaminated. (PMID: 5556886 , 14691119 , 11236158 , 8481097 ).
Structure
Thumb
Synonyms
ValueSource
DMTSKegg
(Methyltrisulphanyl)methaneGenerator
(Methyldisulfanyl)methaneHMDB
(methyldithio)MethaneHMDB
1,3-Dimethyltrisulfane (acd/name 4.0)HMDB
2,3,4-TrithiapentaneHMDB
2,3-DithiabutaneHMDB
CH3SSSCH3HMDB
Dimethyl disulfideHMDB
Dimethyl disulphideHMDB
Dimethyl trisufideHMDB
Dimethyl trisulphideHMDB
DimethyldisulfideHMDB
Disulfide dimethylHMDB
DMDSHMDB
Methyl disulfideHMDB
Methyl trisulfideHMDB
MethyldisulfanylmethaneHMDB
MethyldisulfideHMDB
MethyldithiomethaneHMDB
Sulfa-hitechHMDB
Sulfa-hitech 0382HMDB
Trisulfide, dimethylHMDB
Chemical FormulaC2H6S3
Average Molecular Weight126.264
Monoisotopic Molecular Weight125.963162262
IUPAC Namedimethyltrisulfane
Traditional Namedimethyl trisulfide
CAS Registry Number3658-80-8
SMILES
CSSSC
InChI Identifier
InChI=1S/C2H6S3/c1-3-5-4-2/h1-2H3
InChI KeyInChIKey=YWHLKYXPLRWGSE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassOrganic trisulfides
Sub ClassNot Available
Direct ParentOrganic trisulfides
Alternative Parents
Substituents
  • Organic trisulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-85 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.94Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility2.2 mg/mLALOGPS
logP1.26ALOGPS
logP1.94ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.9 m3·mol-1ChemAxon
Polarizability12.46 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-004j-9400000000-4e5c63061823b6b4c4ccView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012458
KNApSAcK IDC00001246
Chemspider ID18219
KEGG Compound IDC08372
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl_trisulfide
NuGOwiki LinkHMDB13780
Metagene LinkHMDB13780
METLIN IDNot Available
PubChem Compound19310
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. Greenman J, Duffield J, Spencer P, Rosenberg M, Corry D, Saad S, Lenton P, Majerus G, Nachnani S, El-Maaytah M: Study on the organoleptic intensity scale for measuring oral malodor. J Dent Res. 2004 Jan;83(1):81-5. [14691119 ]
  3. Volozhin AI, Petrovich IuA, Filatova ES, Barer GM, Fomina OL, Kreit KhN, Volozhina SA, Dieva SV: [Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients]. Stomatologiia (Mosk). 2001;80(1):9-12. [11236158 ]
  4. Jappinen P, Kangas J, Silakoski L, Savolainen H: Volatile metabolites in occupational exposure to organic sulfur compounds. Arch Toxicol. 1993;67(2):104-6. [8481097 ]