Np mrd loader

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Record Information
Version1.0
Created at2006-05-22 14:17:47 UTC
Updated at2021-08-19 23:59:07 UTC
NP-MRD IDNP0001419
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethylsulfide
DescriptionDimethylsulfide is the predominant volatile sulfur compound (VSC) in breadth malodor, a metabolite of suplatast tosilate (a dimethylsulphonium compound for the treatment of asthma) in patients that regularly take that medication. (PMID 14628896 ). Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. In vapor form it is produced by cooking of certain vegetables, notably corn and cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate, and is also produced by the bacterial metabolism of methanethiol. Dimethylsulfide in concentrated liquid form is insoluble and a flammable. This is a microbial metabolite that can be found in Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID: 25807229 ).
Structure
Thumb
Synonyms
ValueSource
(METHYLsulfanyl)methaneChEBI
2-ThiapropaneChEBI
[SMe2]ChEBI
Dimethyl sulphideChEBI
DMSChEBI
Methyl sulfideChEBI
Methyl thioetherChEBI
(METHYLsulphanyl)methaneGenerator
Dimethyl sulfideGenerator
Methyl sulphideGenerator
DimethylsulphideGenerator
Dimethyl sulfoxide(reduced)HMDB
MethylthiomethaneHMDB
2-ThiopropaneHMDB
Dimethyl monosulfideHMDB
Dimethyl sulfide (natural)HMDB
Dimethyl thioetherHMDB
DimethylsulfidHMDB
MethanethiomethaneHMDB
Methyl monosulfideHMDB
Methylthiomethyl radicalHMDB
MSMHMDB
Reduced-dmsoHMDB
Thiobis-methaneHMDB
ThiopropaneHMDB
Chemical FormulaC2H6S
Average Mass62.1340 Da
Monoisotopic Mass62.01902 Da
IUPAC Name(methylsulfanyl)methane
Traditional Namedimethyl sulfide
CAS Registry Number75-18-3
SMILES
CSC
InChI Identifier
InChI=1S/C2H6S/c1-3-2/h1-2H3
InChI KeyQMMFVYPAHWMCMS-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, cyclohexane, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-98.3 °CNot Available
Boiling Point37.30 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility22 mg/mL at 25 °CNot Available
LogP0.977 (est)The Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0002303
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003591
KNApSAcK IDC00053130
Chemspider ID1039
KEGG Compound IDC00580
BioCyc IDCPD-7670
BiGG IDNot Available
Wikipedia LinkDimethyl_sulfide
METLIN ID6603
PubChem Compound1068
PDB IDNot Available
ChEBI ID17437
Good Scents IDrw1022341
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Carrion O, Curson ARJ, Kumaresan D, Fu Y, Lang AS, Mercade E, Todd JD: A novel pathway producing dimethylsulphide in bacteria is widespread in soil environments. Nat Commun. 2015 Mar 25;6:6579. doi: 10.1038/ncomms7579. [PubMed:25807229 ]