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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 16:35:55 UTC
Update Date2020-02-26 21:26:08 UTC
HMDB IDHMDB0005879
Secondary Accession Numbers
  • HMDB05879
Metabolite Identification
Common NameDimethyldisulfide
DescriptionDimethyldisulfide, also known as 2,3-dithiabutane or sulfa-hitech, belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups. Dimethyldisulfide is possibly neutral. Dimethyldisulfide is a cabbage, citrus, and earthy tasting compound. Outside of the human body, Dimethyldisulfide is found, on average, in the highest concentration within a few different foods, such as kohlrabis, soft-necked garlics, and milk (cow). Dimethyldisulfide has also been detected, but not quantified in, several different foods, such as cauliflowers, cereals and cereal products, broccoli, allium (onion), and guava. This could make dimethyldisulfide a potential biomarker for the consumption of these foods. Dimethyldisulfide, with regard to humans, has been found to be associated with several diseases such as irritable bowel syndrome, nonalcoholic fatty liver disease, pervasive developmental disorder not otherwise specified, and ulcerative colitis; dimethyldisulfide has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1582752368
Synonyms
ValueSource
2,3-DithiabutaneChEBI
Dimethyl disulphideChEBI
Methyl disulfideChEBI
Dimethyl disulfideGenerator
Methyl disulphideGenerator
DimethyldisulphideGenerator
(Methyldisulfanyl)methaneHMDB
(Methyldithio)methaneHMDB
Disulfide dimethylHMDB
DMDSHMDB
MethyldisulfanylmethaneHMDB
MethyldisulfideHMDB
MethyldithiomethaneHMDB
Sulfa-hitechHMDB
Sulfa-hitech 0382HMDB
DimethyldisulfideChEBI
Chemical FormulaC2H6S2
Average Molecular Weight94.199
Monoisotopic Molecular Weight93.991091572
IUPAC Name(methyldisulfanyl)methane
Traditional Namedimethyl disulfide
CAS Registry Number624-92-0
SMILES
CSSC
InChI Identifier
InChI=1S/C2H6S2/c1-3-4-2/h1-2H3
InChI KeyWQOXQRCZOLPYPM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassOrganic disulfides
Sub ClassDialkyldisulfides
Direct ParentDialkyldisulfides
Alternative Parents
Substituents
  • Dialkyldisulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-85 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mL at 25 °CNot Available
LogP1.77HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility8.32 g/LALOGPS
logP1.15ALOGPS
logP1.35ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.15 m³·mol⁻¹ChemAxon
Polarizability9.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-41761824faab2335162bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-61860690131d526ccbcdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-41761824faab2335162bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-61860690131d526ccbcdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9000000000-97640eecd2e825d92614Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d07f637646d53e0944c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-26e3c12a663eae500df3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-1d9c7a25e309969d69a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-edf3b70601a5f19f86a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-9000000000-f1ba1d7c13a44ac40571Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9000000000-0d55ed2a736557bc36e7Spectrum
MSMass Spectrum (Electron Ionization)splash10-002e-9000000000-064e4dcc87016a4be743Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Crohn's disease
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Ulcerative colitis
details
FecesDetected and Quantified0.00121 (0.000616-0.00924) nmol/g wet fecesNot SpecifiedNot Specified
Crohns disease
details
FecesDetected and Quantified0.000605 (0.000117-0.00437) nmol/g wet fecesNot SpecifiedNot Specified
Irritable bowel syndrome
details
FecesDetected and Quantified0.000754 (0.000287-0.00152) nmol/g wet fecesNot SpecifiedNot Specified
Ulcerative colitis
details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Irritable bowel syndrome
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003491
KNApSAcK IDC00001245
Chemspider ID11731
KEGG Compound IDC08371
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_disulfide
METLIN IDNot Available
PubChem Compound12232
PDB IDNot Available
ChEBI ID4608
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Greenman J, Duffield J, Spencer P, Rosenberg M, Corry D, Saad S, Lenton P, Majerus G, Nachnani S, El-Maaytah M: Study on the organoleptic intensity scale for measuring oral malodor. J Dent Res. 2004 Jan;83(1):81-5. [PubMed:14691119 ]
  3. Volozhin AI, Petrovich IuA, Filatova ES, Barer GM, Fomina OL, Kreit KhN, Volozhina SA, Dieva SV: [Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients]. Stomatologiia (Mosk). 2001;80(1):9-12. [PubMed:11236158 ]
  4. Jappinen P, Kangas J, Silakoski L, Savolainen H: Volatile metabolites in occupational exposure to organic sulfur compounds. Arch Toxicol. 1993;67(2):104-6. [PubMed:8481097 ]