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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 15:37:12 UTC |
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Update Date | 2020-04-08 20:50:00 UTC |
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HMDB ID | HMDB0005842 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Oxohexane |
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Description | 2-Oxohexane, also known as hexan-2-one or MNBK, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-oxohexane is considered to be an oxygenated hydrocarbon lipid molecule. 2-Oxohexane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Oxohexane is an ethereal tasting compound. Outside of the human body, 2-Oxohexane is found, on average, in the highest concentration within a few different foods, such as hyssops, milk (cow), and corns. 2-Oxohexane has also been detected, but not quantified in, several different foods, such as green bell peppers, orange bell peppers, red bell peppers, nuts, and peppers. This could make 2-oxohexane a potential biomarker for the consumption of these foods. 2-Oxohexane is a potentially toxic compound. 2-Oxohexane, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, and nonalcoholic fatty liver disease; 2-oxohexane has also been linked to the inborn metabolic disorder celiac disease. 2-Oxohexane is absorbed via ingestion, inhalation, and dermal routes, then distributed widely throughout the body, with the highest levels in the liver and blood. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. This may include pathologies such as peripheral neuropathy and developmental defects. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. In addition, 2,5-hexanedione can covalently cross-links neurofilaments, causing large axonal swellings. 2-Oxohexane and 2,5-hexanedione may also inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase and glyceraldehyde-3-phosphate dehydrogenase, as well as certain creatine kinases and adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration. |
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Structure | |
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Synonyms | Value | Source |
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Hexan-2-one | HMDB | 2-Hexanone | HMDB | 2-Hexanone methyl N-butyl ketone | HMDB | Butyl methyl ketone | HMDB | Methyl butyl ketone | HMDB | Methyl N-butyl ketone | HMDB | MNBK | HMDB | N-Butyl methyl ketone | HMDB | N-C4H9COCH3 | HMDB | Propylacetone | HMDB | Butylmethyl ketone | HMDB | Ketone, butylmethyl | HMDB | 2 Hexanone | HMDB | Hexan 2 one | HMDB | Ketone, methyl N-butyl | HMDB | Methyl N butyl ketone | HMDB | N-Butyl ketone, methyl | HMDB | 2-Oxohexane | HMDB | MBK | HMDB |
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Chemical Formula | C6H12O |
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Average Molecular Weight | 100.1589 |
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Monoisotopic Molecular Weight | 100.088815006 |
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IUPAC Name | hexan-2-one |
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Traditional Name | hexanone |
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CAS Registry Number | 591-78-6 |
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SMILES | CCCCC(C)=O |
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InChI Identifier | InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3 |
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InChI Key | QQZOPKMRPOGIEB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Ketones |
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Alternative Parents | |
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Substituents | - Ketone
- Organic oxide
- 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 | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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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 | -55.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 17.5 mg/mL at 20 °C | Not Available | LogP | 1.38 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-a8db7120c386c93d25ff | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-858b1e62ef5dfd041baf | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-e2acd59c62ae4caefc56 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-a8db7120c386c93d25ff | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-858b1e62ef5dfd041baf | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-e2acd59c62ae4caefc56 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-0884cf76c54fac458024 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-052f-9000000000-214c4efe96ae363515d5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HP 5970) , Positive | splash10-0006-9000000000-858b1e62ef5dfd041baf | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-052f-9000000000-e2acd59c62ae4caefc56 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-8900000000-7f95c62c199ac18bb617 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f8c-9300000000-86d93f8a23031d700516 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-52c2a4eb34b81253f5b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-e69f92c1ea30b1c8b758 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-b2aac1a98aa5c3d5501e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a5c-9000000000-a65bc7e7cdfb70bec9db | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-052f-9000000000-f15df0bf9af914ce3f16 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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 | 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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected and Quantified | 0-70720.958 nmol/g wet feces | Children (1-13 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | 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 | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | 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 | Crohns disease | | 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 | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn's disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Feces | Detected and Quantified | 0-1158026.562 nmol/g wet feces | Children (1-13 years old) | Not Specified | Treated celiac disease | | details |
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Associated Disorders and Diseases |
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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 ]
- 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 ]
- 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 ]
| 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 ]
| 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 ]
| 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 ]
- 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 ]
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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 | FDB008079 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 11095 |
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KEGG Compound ID | Not Available |
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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 | 11583 |
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PDB ID | Not Available |
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ChEBI ID | 89206 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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 ]
- Griffin JW: Hexacarbon neurotoxicity. Neurobehav Toxicol Teratol. 1981 Winter;3(4):437-44. [PubMed:6278344 ]
- Lolin Y: Chronic neurological toxicity associated with exposure to volatile substances. Hum Toxicol. 1989 Jul;8(4):293-300. [PubMed:2550357 ]
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