Record Information
Version2.0
Creation Date2012-07-30 14:54:56 -0600
Update Date2015-06-03 17:20:53 -0600
Secondary Accession Numbers
  • ECMDB21207
Identification
Name:Dimethyl sulfide
DescriptionDimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37
Structure
Thumb
Synonyms:
  • (methylsulfanyl)methane
  • (methylsulphanyl)methane
  • 1,1'-Thiobis-Methane
  • 2-Thiapropane
  • 2-Thiopropane
  • Dimethyl monosulfide
  • Dimethyl monosulphide
  • Dimethyl sulfide
  • Dimethyl sulfide (natural)
  • Dimethyl sulfide [UN1164] [Flammable liquid]
  • Dimethyl sulfoxide(Reduced)
  • Dimethyl sulphide
  • Dimethyl sulphide (natural)
  • Dimethyl sulphide [UN1164] [Flammable liquid]
  • Dimethyl sulphoxide(Reduced)
  • Dimethyl thioether
  • Dimethylsulfid
  • Dimethylsulfide
  • Dimethylsulphid
  • Dimethylsulphide
  • DMS
  • Exact-S
  • Methanethiomethane
  • Methyl monosulfide
  • Methyl monosulphide
  • Methyl sulfide
  • Methyl sulphide
  • Methyl thioether
  • Methyl-Sulfide
  • Methyl-Sulphide
  • Methylthiomethane
  • Methylthiomethyl radical
  • MSM
  • Reduced dimethyl sulfoxide
  • Reduced dimethyl sulphoxide
  • Reduced-dmso
  • Sulfure de methyle
  • Sulphure de methyle
  • Thiobis-Methane
  • Thiobismethane
  • Thiopropane
  • [SMe2]
Chemical Formula:C2H6S
Weight:Average: 62.134
Monoisotopic: 62.019020882
InChI Key:QMMFVYPAHWMCMS-UHFFFAOYSA-N
InChI:InChI=1S/C2H6S/c1-3-2/h1-2H3
CAS number:75-18-3
IUPAC Name:(methylsulfanyl)methane
Traditional IUPAC Name:dimethyl sulfide
SMILES:CSC
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassDialkylthioethers
Direct ParentDialkylthioethers
Alternative Parents
Substituents
  • Dialkylthioether
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:-98.3 °C
Experimental Properties:
PropertyValueSource
Water Solubility:22 mg/mL at 25 deg CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility18.5 g/LALOGPS
logP0.59ALOGPS
logP1.22ChemAxon
logS-0.53ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.89 m³·mol⁻¹ChemAxon
Polarizability7.24 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
dimethyl sulfoxide electron transferPW001892 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • NADH to dimethyl sulfoxide electron transfer PWY0-1348
  • formate to dimethyl sulfoxide electron transfer PWY0-1356
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-8ed5810ef2a492b40ae1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-aab0fb854ed08a99a142View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-b8e506cefc1462c55765View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-8ed5810ef2a492b40ae1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-aab0fb854ed08a99a142View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-9000000000-b8e506cefc1462c55765View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-9000000000-452048d3bfa7a40636c4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-01ot-9000000000-8ed5810ef2a492b40ae1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ot-9000000000-360d47e40fcfcf205bf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-01ot-9000000000-b8e506cefc1462c55765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-ae1ff184cb043d43cd3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-189f32d3eb2bb107bad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-5579d822eaf64cbda3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-45a7990a4b612cb72664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9000000000-3bb7835f1011f708503eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-d5b5c0545e3e2ec5e98eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-f865abc3930f083f5ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-f865abc3930f083f5ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-efaeb46b008ef59dd3deView in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ot-9000000000-3da3b740e54dd0695ac8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. Pubmed: 15996001
  • Gahl WA, Ingelfinger J, Mohan P, Bernardini I, Hyman PE, Tangerman A: Intravenous cysteamine therapy for nephropathic cystinosis. Pediatr Res. 1995 Oct;38(4):579-84. Pubmed: 8559613
  • Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. J Pediatr Gastroenterol Nutr. 2001 May;32(5):534-41. Pubmed: 11429513
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Murata T, Fujiyama Y, Yamaga T, Miyazaki H: Breath malodor in an asthmatic patient caused by side-effects of medication: a case report and review of the literature. Oral Dis. 2003 Sep;9(5):273-6. Pubmed: 14628896
  • Rosen RT, Hiserodt RD, Fukuda EK, Ruiz RJ, Zhou Z, Lech J, Rosen SL, Hartman TG: The determination of metabolites of garlic preparations in breath and human plasma. Biofactors. 2000;13(1-4):241-9. Pubmed: 11237188
  • Terazawa K, Kaji H, Akabane H, Takatori T: Determination of dimethyl sulphide in blood and adipose tissue by headspace gas analysis. J Chromatogr. 1991 Apr 19;565(1-2):453-6. Pubmed: 1874893
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yeung CK, Lang DH, Thummel KE, Rettie AE: Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab Dispos. 2000 Sep;28(9):1107-11. Pubmed: 10950857
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17437
HMDB IDHMDB02303
Pubchem Compound ID1068
Kegg IDC00580
ChemSpider ID1039
WikipediaDimethyl_sulfide
BioCyc IDCPD-7670
EcoCyc IDCPD-7670
Ligand ExpoMSM

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfG
Uniprot ID:
P0AAJ1
Molecular weight:
22752
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
Gene Name:
dmsA
Uniprot ID:
P18775
Molecular weight:
90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol.
General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
dmsB
Uniprot ID:
P18776
Molecular weight:
22869
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfE
Uniprot ID:
P77374
Molecular weight:
89779
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfF
Uniprot ID:
P77783
Molecular weight:
89986
General function:
Involved in oxidoreductase activity
Specific function:
Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions. Can also reduce other N- and S-oxide compounds such as 4-methylmorpholine-N-oxide and biotin sulfoxide (BSO), but with a lower catalytic efficiency
Gene Name:
torZ
Uniprot ID:
P46923
Molecular weight:
88964
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+).
General function:
Involved in iron ion binding
Specific function:
Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torZ. Required for electron transfer to the torZ terminal enzyme
Gene Name:
torY
Uniprot ID:
P52005
Molecular weight:
40286
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
Gene Name:
dmsC
Uniprot ID:
P18777
Molecular weight:
30826
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. The C subunit anchors the other two subunits to the membrane and stabilize the catalytic subunits
Gene Name:
ynfH
Uniprot ID:
P76173
Molecular weight:
30523

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368