Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-12 03:04:17 UTC |
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Update Date | 2023-02-21 17:28:40 UTC |
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HMDB ID | HMDB0041389 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methyl 2-propenyl disulfide |
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Description | Methyl 2-propenyl disulfide, also known as 3-(methyldisulfanyl)-1-propene or allyl methyl disulphide, belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. Methyl 2-propenyl disulfide is an alliaceous, garlic, and green tasting compound. Methyl 2-propenyl disulfide is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). Methyl 2-propenyl disulfide has also been detected, but not quantified in, several different foods, such as allia (Allium), garden onions (Allium cepa), red onion, chives (Allium schoenoprasum), and welsh onions (Allium fistulosum). This could make methyl 2-propenyl disulfide a potential biomarker for the consumption of these foods. Methyl 2-propenyl disulfide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Methyl 2-propenyl disulfide. |
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Structure | InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3 |
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Synonyms | Value | Source |
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3-(Methyldisulfanyl)-1-propene | ChEBI | 3-(Methyldithio)prop-1-ene | ChEBI | 4,5-Dithia-1-hexene | ChEBI | Allyl methyl disulphide | ChEBI | Methyl allyl disulfide | ChEBI | Methylallyl disulphide | ChEBI | Allyl methyl disulfide | Kegg | 3-(Methyldisulphanyl)-1-propene | Generator | Methyl allyl disulphide | Generator | Methylallyl disulfide | Generator | Methyl 2-propenyl disulphide | Generator | Methyl 2-propenyl disulfide | ChEBI | 2-Propenylmethyldisulfide | HMDB | 3-(Methyldisulfanyl)prop-1-ene | HMDB | Disulfide, allyl methyl | HMDB | Disulfide, methyl 2-propenyl | HMDB | FEMA 3127 | HMDB |
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Chemical Formula | C4H8S2 |
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Average Molecular Weight | 120.236 |
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Monoisotopic Molecular Weight | 120.006741636 |
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IUPAC Name | 3-(methyldisulfanyl)prop-1-ene |
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Traditional Name | allyl methyl disulfide |
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CAS Registry Number | 2179-58-0 |
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SMILES | CSSCC=C |
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InChI Identifier | InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3 |
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InChI Key | XNZOTQPMYMCTBZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. |
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Kingdom | Organic compounds |
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Super Class | Organosulfur compounds |
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Class | Allyl sulfur compounds |
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Sub Class | Not Available |
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Direct Parent | Allyl sulfur compounds |
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Alternative Parents | |
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Substituents | - Allyl sulfur compound
- Dialkyldisulfide
- Organic disulfide
- 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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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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Methyl 2-propenyl disulfide | CSSCC=C | 1254.5 | Standard polar | 33892256 | Methyl 2-propenyl disulfide | CSSCC=C | 889.6 | Standard non polar | 33892256 | Methyl 2-propenyl disulfide | CSSCC=C | 927.2 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Methyl 2-propenyl disulfide EI-B (Non-derivatized) | splash10-006x-9400000000-b22656c2fc50d291c433 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl 2-propenyl disulfide EI-B (Non-derivatized) | splash10-006x-9400000000-b22656c2fc50d291c433 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-3fa975297f7692e3fe54 | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00dl-9400000000-856243b0edb1ecdb248c | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Positive-QTOF | splash10-00di-2900000000-e03c0f5ea97b029207c0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Positive-QTOF | splash10-006x-9100000000-abe867e9c4013484ac4e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Positive-QTOF | splash10-0006-9000000000-e7405b22a930dc4a3b78 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Negative-QTOF | splash10-014i-7900000000-a33d414c2259e6db3436 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Negative-QTOF | splash10-00dm-9000000000-d315cbc5a8b4f1c41d66 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Negative-QTOF | splash10-00di-9000000000-d7971f432840cb9b5c5d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Negative-QTOF | splash10-004m-9000000000-ef96b828ac069c1341a6 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Negative-QTOF | splash10-0002-9000000000-b8ccb9f6306766cb8e14 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Negative-QTOF | splash10-004i-9000000000-1d58e6810a052e42af36 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Positive-QTOF | splash10-00b9-9000000000-9af83ce6d3c6853ffc90 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Positive-QTOF | splash10-00fr-9000000000-06ae20f4fc773ea95001 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Positive-QTOF | splash10-000g-9000000000-78aa2b9636ad8c22c806 | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn's disease | | details |
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Associated Disorders and Diseases |
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Disease References | 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 ]
| Ulcerative colitis |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| Crohn's disease |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021321 |
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KNApSAcK ID | C00001257 |
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Chemspider ID | 56217 |
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KEGG Compound ID | C08383 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 62434 |
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PDB ID | Not Available |
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ChEBI ID | 6854 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1009831 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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