Milk Composition Database: Showing metabocard for Dimethyl sulfone (BMDB0004983)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:22 UTC

Update Date

2020-06-04 20:48:45 UTC

MCDB ID

BMDB0004983

Secondary Accession Numbers

BMDB04983

Metabolite Identification

Common Name

Dimethyl sulfone

Description

Dimethyl 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dimethyl sulphone	ChEBI
Methylsulfonylmethane	ChEBI
Sulfonylbismethane	ChEBI
Sulphonylbismethane	ChEBI
Methylsulphonylmethane	Generator
Dimethyl sulfone, 13C-labeled	MeSH
Methyl sulfone	MeSH
Methyl sulfonmethane	MeSH
(Methylsulfonyl)methane	HMDB
Dimethylsulfone	HMDB
Lignisul MSM	HMDB
Opti MSM	HMDB
Sulfonylbis-methane	HMDB
Dimethyl sulfone	ChEBI
Sulphonyldimethane	Generator, HMDB

Chemical Formula

C₂H₆O₂S

Average Molecular Weight

94.133

Monoisotopic Molecular Weight

94.008850126

IUPAC Name

methanesulfonylmethane

Traditional Name

methylsulfonylmethane

CAS Registry Number

67-71-0

SMILES

CS(C)(=O)=O

InChI Identifier

InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3

InChI Key

HHVIBTZHLRERCL-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.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfonyls

Sub Class

Sulfones

Direct Parent

Sulfones

Alternative Parents

Substituents

Sulfone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfone (CHEBI:9349 )
a sulfone (CPD-10437 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	109 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.41	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.95	ALOGPS
logP	-1.3	ChemAxon
logS	-0.23	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.53 m³·mol⁻¹	ChemAxon
Polarizability	8.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-3e72edc8bd8e168298a0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-9000000000-9896ec507f104ada81f3	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-aad0ad2e46e9a93df295	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-8cb5ee5ae152833c1e84	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-fb26633c75e592809868	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-3a6db80e12370ab204a9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9000000000-c5c35fbdd4193d0ece0d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-c0a7fe921fa7e601fb70	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-113ab821ffdae95a6086	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fu-9000000000-2ef5cb880f6a43bd9df3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-f0302cfc5bddee62ebdf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-f0302cfc5bddee62ebdf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-902b68745378a21a3ae9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-dd5ad5c474bf2a0fc2ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-dd5ad5c474bf2a0fc2ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-d82cbf78ceb7825835f9	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.00142 +/- 0.00153 uM	PMID: 12463694	details
Detected and Quantified	0.001 +/- 0.002 uM	PMID: 12463694	details
Detected and Quantified	0.001 +/- 0.001 uM	PMID: 12463694	details
Detected and Quantified	1.423 uM	PMID: 16840607	details
Detected and Quantified	8.426 uM	PMID: 16840607	details
Detected and Quantified	8.097 uM	PMID: 16840607	details
Detected and Quantified	15.21 uM	PMID: 16840607	details
Detected and Quantified	2.517 uM	PMID: 16840607	details
Detected and Quantified	11 uM	PMID: 16840607	details
Detected and Quantified	52 uM	PMID: 16840607	details
Detected and Quantified	24 uM	PMID: 16840607	details
Detected and Quantified	13 uM	PMID: 16840607	details
Detected and Quantified	29 uM	PMID: 16840607	details
Detected and Quantified	8.535 uM	PMID: 16840607	details
Detected and Quantified	14 uM	PMID: 16840607	details
Detected and Quantified	23 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	31 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	33 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	26 +/- 3 uM	PMID: 30994344	details
Detected and Quantified	28 +/- 8 uM	PMID: 29642378	details
Detected and Quantified	46 +/- 13 uM	PMID: 29642378	details
Detected and Quantified	12 +/- 2 uM	PMID: 29642378	details
Detected but not Quantified	Not Applicable	PMID: 23394630	details

External Links

HMDB ID

HMDB0004983

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006725

KNApSAcK ID

Not Available

Chemspider ID

5978

KEGG Compound ID

C11142

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylsulfonylmethane

METLIN ID

7236

PubChem Compound

6213

PDB ID

Not Available

ChEBI ID

9349

References

Synthesis Reference

Douglas, 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

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 ]
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 ]
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 ]
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 ]
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 ]
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.

Showing metabocard for Dimethyl sulfone (BMDB0004983)

Structure for BMDB0004983 (Dimethyl sulfone)