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Dimethyl sulfoxide (M2MDB001616)

Record Information
Version2.0
Creation Date2012-07-30 14:54:57 -0600
Update Date2015-09-13 15:15:31 -0600
Secondary Accession Numbers
  • ECMDB21208
Identification
Name:Dimethyl sulfoxide
DescriptionDimethyl sulfoxide is a highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Because of its high boiling point (189
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (CH3)2SO
  • (DMSO)
  • (methanesulfinyl)methane
  • (methanesulphinyl)methane
  • (methylsulfinyl)methane
  • (methylsulphinyl)methane
  • 1,1'-Sulfinylbis-Methane
  • 1,1'-Sulphinylbis-Methane
  • N
  • Deltan
  • Demasorb
  • Demavet
  • Demeso
  • Demsodrox
  • Dermasorb
  • Diemthyl sulfoxide
  • Diemthyl sulphoxide
  • Dimethyl sulfoxide
  • Dimethyl Sulfoxide (USAN)
  • Dimethyl sulfoxide BP
  • Dimethyl sulfoxide(USAN)
  • Dimethyl sulfoxixde
  • Dimethyl sulfur oxide
  • Dimethyl sulphoxide
  • Dimethyl Sulphoxide (USAN)
  • Dimethyl sulphoxide BP
  • Dimethyl sulphoxide(USAN)
  • Dimethyl sulphoxixde
  • Dimethyl sulphur oxide
  • Dimethyl sulpoxide
  • Dimethyli sulfoxidum
  • Dimethyli sulphoxidum
  • Dimethylsulfoxid
  • Dimethylsulfoxyde
  • Dimethylsulphoxid
  • Dimethylsulphoxyde
  • Dimetil sulfoxido
  • Dimetil sulphoxido
  • Dimexide
  • Dimexidum
  • Dipirartril-tropico
  • DMSO
  • DMSO (methyl sulfoxide)
  • DMSO (methyl sulphoxide)
  • Dolicur
  • Doligur
  • Domoso
  • Dromisol
  • Durasorb
  • Gamasol 90
  • Herpid
  • Hyadur
  • Infiltrina
  • Kemsol
  • Methyl sulfoxide
  • Methyl sulphoxide
  • Methylsulfinylmethane
  • Methylsulphinylmethane
  • n
  • Rimso 50
  • S(O)Me2
  • Sclerosol
  • Somipront
  • Sulfinylbis methane
  • Sulfinylbis(methane)
  • Sulfinylbis-Methane
  • Sulfinylbismethane
  • Sulfinyldimethane
  • Sulfoxide, dimethyl
  • Sulphinylbis methane
  • Sulphinylbis(methane)
  • Sulphinylbis-Methane
  • Sulphinylbismethane
  • Sulphinyldimethane
  • Sulphoxide, dimethyl
  • Syntexan
  • Topsym
Chemical Formula:C2H6OS
Weight:Average: 78.133
Monoisotopic: 78.013935504
InChI Key:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
InChI:InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
CAS number:67-68-5
IUPAC Name:methanesulfinylmethane
Traditional IUPAC Name:dimethyl sulfoxide
SMILES:CS(C)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Sulfoxide
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:18.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mLPhysProp
LogP:-1.35; -1.35 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility65.7 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.08ALOGPS
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.73 m³·mol⁻¹ChemAxon
Polarizability7.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Dimethyl sulfoxide + Menaquinol 8 > Dimethyl sulfide + Water + Menaquinone 8
2-Demethylmenaquinol 8 + Dimethyl sulfoxide > 2-Demethylmenaquinone 8 + Dimethyl sulfide + Water
Dimethyl sulfoxide + a menaquinol > Dimethyl sulfide + Water + a menaquinone
Dimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6
Menaquinol 8 + Dimethyl sulfoxide + 2 Hydrogen ion + 2 Electron > menaquinone-8 + Dimethyl sulfide + Water +2 Hydrogen ion
SMPDB Pathways:
dimethyl sulfoxide electron transferPW001892 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
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)splash10-03fr-9000000000-f0f118841efd8b3297a3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fs-9000000000-945240052686ea267e2bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fs-9000000000-378b716bc39417224511View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fr-9000000000-f0f118841efd8b3297a3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fs-9000000000-945240052686ea267e2bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fs-9000000000-378b716bc39417224511View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-9000000000-a87469bb1afda1828bbeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-9000000000-b96781268f9bbbcb1544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-16f85b2cb3628d8d9358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03dj-9000000000-c11b31839f52d556db57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-004i-9000000000-6fd68fb341597894c9e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-c8f7a9f09c8bb456283cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-d8d98568ae59afba65e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-e0a36c290f004f302f0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-89687ba96456a97fb486View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-9000000000-04ddc1322b21e4817d57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-d90c2fed7aad139b406cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-50c596e219854897fad2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-50c596e219854897fad2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9000000000-102e2e8c382c8f4c1975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-28072bae45639cb50943View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-670c7176bed65aef23f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-9ae0f01cd17306d4ecf0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03fr-9000000000-1db858034b22d1646592View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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
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
  • 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
Synthesis Reference:Goeb, Andre. Dimethyl sulfoxide. Ger. Offen. (1976), 12 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID28262
HMDB IDHMDB02151
Pubchem Compound ID679
Kegg IDC11143
ChemSpider ID659
WikipediaDimethyl_sulfoxide
BioCyc IDDMSO
EcoCyc IDDMSO
Ligand ExpoDMS

Enzymes

Protein Details
1. Probable anaerobic dimethyl sulfoxide reductase chain ynfG
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
Protein Details
2. Anaerobic dimethyl sulfoxide reductase chain A
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.
Protein Details
3. Anaerobic dimethyl sulfoxide reductase chain B
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
Protein Details
4. Putative dimethyl sulfoxide reductase chain ynfE
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
Protein Details
5. Probable dimethyl sulfoxide reductase chain ynfF
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
Protein Details
6. Trimethylamine-N-oxide reductase 2
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(+).
Protein Details
7. Cytochrome c-type protein torY
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
Protein Details
8. Anaerobic dimethyl sulfoxide reductase chain C
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
Protein Details
9. Anaerobic dimethyl sulfoxide reductase chain ynfH
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

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
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
Protein Details
3. Outer membrane protein F
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
Protein Details
4. Outer membrane protein C
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