Record Information
Version1.0
Creation Date2016-09-30 23:14:22 UTC
Update Date2020-06-04 20:48:45 UTC
MCDB ID BMDB0004983
Secondary Accession Numbers
  • BMDB04983
Metabolite Identification
Common NameDimethyl sulfone
DescriptionDimethyl sulfone, also known as sulfonylbismethane or lignisul MSM, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms. Dimethyl sulfone exists as a solid, possibly soluble (in water), and possibly neutral molecule. Dimethyl sulfone exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
Dimethyl sulphoneChEBI
MethylsulfonylmethaneChEBI
SulfonylbismethaneChEBI
SulphonylbismethaneChEBI
MethylsulphonylmethaneGenerator
Dimethyl sulfone, 13C-labeledMeSH
Methyl sulfoneMeSH
Methyl sulfonmethaneMeSH
(Methylsulfonyl)methaneHMDB
DimethylsulfoneHMDB
Lignisul MSMHMDB
Opti MSMHMDB
Sulfonylbis-methaneHMDB
Dimethyl sulfoneChEBI
SulphonyldimethaneGenerator, HMDB
Chemical FormulaC2H6O2S
Average Molecular Weight94.133
Monoisotopic Molecular Weight94.008850126
IUPAC Namemethanesulfonylmethane
Traditional Namemethylsulfonylmethane
CAS Registry Number67-71-0
SMILES
CS(C)(=O)=O
InChI Identifier
InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
InChI KeyHHVIBTZHLRERCL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfonyls
Sub ClassSulfones
Direct ParentSulfones
Alternative Parents
Substituents
  • Sulfone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.41HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.95ALOGPS
logP-1.3ChemAxon
logS-0.23ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.53 m³·mol⁻¹ChemAxon
Polarizability8.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-3e72edc8bd8e168298a02017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-9896ec507f104ada81f32012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-aad0ad2e46e9a93df2952012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-8cb5ee5ae152833c1e842012-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-fb26633c75e5928098682017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3a6db80e12370ab204a92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9000000000-c5c35fbdd4193d0ece0d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-c0a7fe921fa7e601fb702017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-113ab821ffdae95a60862017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-9000000000-2ef5cb880f6a43bd9df32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f0302cfc5bddee62ebdf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f0302cfc5bddee62ebdf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-902b68745378a21a3ae92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-dd5ad5c474bf2a0fc2ab2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-dd5ad5c474bf2a0fc2ab2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-d82cbf78ceb7825835f92021-09-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00142 +/- 0.00153 uM details
Detected and Quantified0.001 +/- 0.002 uM details
Detected and Quantified0.001 +/- 0.001 uM details
Detected and Quantified1.423 uM details
Detected and Quantified8.426 uM details
Detected and Quantified8.097 uM details
Detected and Quantified15.21 uM details
Detected and Quantified2.517 uM details
Detected and Quantified11 uM details
Detected and Quantified52 uM details
Detected and Quantified24 uM details
Detected and Quantified13 uM details
Detected and Quantified29 uM details
Detected and Quantified8.535 uM details
Detected and Quantified14 uM details
Detected and Quantified23 +/- 2 uM details
Detected and Quantified31 +/- 2 uM details
Detected and Quantified33 +/- 2 uM details
Detected and Quantified26 +/- 3 uM details
Detected and Quantified28 +/- 8 uM details
Detected and Quantified46 +/- 13 uM details
Detected and Quantified12 +/- 2 uM details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0004983
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006725
KNApSAcK IDNot Available
Chemspider ID5978
KEGG Compound IDC11142
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylsulfonylmethane
METLIN ID7236
PubChem Compound6213
PDB IDNot Available
ChEBI ID9349
References
Synthesis ReferenceDouglas, Thomas B. Heats of formation of liquid methyl suffoxide and crystalline methyl sulfone at 18° Journal of the American Chemical Society (1946), 68 1072-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. [PubMed:12463694 ]
  2. Vazquez-Landaverde PA, Torres JA, Qian MC: Quantification of trace volatile sulfur compounds in milk by solid-phase microextraction and gas chromatography-pulsed flame photometric detection. J Dairy Sci. 2006 Aug;89(8):2919-27. doi: 10.3168/jds.S0022-0302(06)72564-4. [PubMed:16840607 ]
  3. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  4. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  5. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
  6. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.