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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-09-13 08:28:37 UTC
Update Date2019-03-20 17:17:46 UTC
HMDB IDHMDB0004983
Secondary Accession Numbers
  • HMDB0006702
  • HMDB04983
  • HMDB06702
Metabolite Identification
Common NameDimethyl sulfone
DescriptionDimethyl sulfone (DMSO2) or methylsulfonylmethane (MSM), is an organic sulfur compound belonging to a class of chemicals known as sulfones. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a metabolite occurring in plasma and CSF of normal human. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. (PMID 15996001 ). Dimethyl sulfone can be found in Afipia (Wikipedia).
Structure
Data?1547234309
Synonyms
ValueSource
Dimethyl sulphoneChEBI
MethylsulfonylmethaneChEBI
SulfonylbismethaneChEBI
SulphonylbismethaneChEBI
MethylsulphonylmethaneGenerator
(Methylsulfonyl)methaneHMDB
DimethylsulfoneHMDB
Lignisul MSMHMDB
Methyl sulfoneHMDB
Opti MSMHMDB
Sulfonylbis-methaneHMDB
Methyl sulfonmethaneHMDB
Dimethyl sulfone, 13C-labeledHMDB
Dimethyl sulfoneChEBI
SulphonyldimethaneGenerator
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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
Water Solubility55.8 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-3e72edc8bd8e168298a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-9896ec507f104ada81f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-aad0ad2e46e9a93df295JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-8cb5ee5ae152833c1e84JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-fb26633c75e592809868JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3a6db80e12370ab204a9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9000000000-c5c35fbdd4193d0ece0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-c0a7fe921fa7e601fb70JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-113ab821ffdae95a6086JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-9000000000-2ef5cb880f6a43bd9df3JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.5-16.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8.8 +/- 7.3 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.3 +/- 6.2 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified13.53 +/- 5.14 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified8.0 (1.3-49.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.6 (2.5-7.5) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified11.371 +/- 7.16 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.06 (3.56) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified4.78 (2.73) uMAdult (>18 years old)FemalePregnancy details
Cerebrospinal Fluid (CSF)Detected and Quantified574.0 uMAdult (>18 years old)Both
Methionine adenosyltransferase (MAT) I/III deficiency
details
UrineDetected and Quantified10.047 +/- 14.963 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Dimethyl sulfone supplementation
  1. 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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
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. 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 ]
  2. Rogovin JL: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2002 Mar 28;129(3):263; author reply 265. [PubMed:11888710 ]
  3. Rose SE, Chalk JB, Galloway GJ, Doddrell DM: Detection of dimethyl sulfone in the human brain by in vivo proton magnetic resonance spectroscopy. Magn Reson Imaging. 2000 Jan;18(1):95-8. [PubMed:10642107 ]
  4. Lin A, Nguy CH, Shic F, Ross BD: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2001 Sep 15;123(2-3):169-77. [PubMed:11641045 ]