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
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
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
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