| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2007-04-12 16:35:55 UTC |
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| Update Date | 2020-02-26 21:26:08 UTC |
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| HMDB ID | HMDB0005879 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Dimethyldisulfide |
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| Description | Dimethyldisulfide, 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,3-Dithiabutane | ChEBI | | Dimethyl disulphide | ChEBI | | Methyl disulfide | ChEBI | | Dimethyl disulfide | Generator | | Methyl disulphide | Generator | | Dimethyldisulphide | Generator | | (Methyldisulfanyl)methane | HMDB | | (Methyldithio)methane | HMDB | | Disulfide dimethyl | HMDB | | DMDS | HMDB | | Methyldisulfanylmethane | HMDB | | Methyldisulfide | HMDB | | Methyldithiomethane | HMDB | | Sulfa-hitech | HMDB | | Sulfa-hitech 0382 | HMDB | | Dimethyldisulfide | ChEBI |
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| Chemical Formula | C2H6S2 |
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| Average Molecular Weight | 94.199 |
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| Monoisotopic Molecular Weight | 93.991091572 |
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| IUPAC Name | (methyldisulfanyl)methane |
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| Traditional Name | dimethyl disulfide |
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| CAS Registry Number | 624-92-0 |
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| SMILES | CSSC |
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| InChI Identifier | InChI=1S/C2H6S2/c1-3-4-2/h1-2H3 |
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| InChI Key | WQOXQRCZOLPYPM-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organosulfur compounds |
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| Class | Organic disulfides |
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| Sub Class | Dialkyldisulfides |
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| Direct Parent | Dialkyldisulfides |
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| Alternative Parents | |
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| Substituents | - Dialkyldisulfide
- Sulfenyl compound
- Hydrocarbon derivative
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Biological location: Source: |
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| Role | Biological role: |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -85 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 3 mg/mL at 25 °C | Not Available | | LogP | 1.77 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Disease References | | Ulcerative colitis |
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- 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 ]
- 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 ]
- 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 |
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- 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 |
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- 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 |
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- 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 ]
- 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 |
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- 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 |
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- 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 |
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- 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 |
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- 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 ]
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| General References | - Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
- 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 ]
- 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 ]
- 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 ]
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