Record Information |
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Version | 5.0 |
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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 | 2023-02-21 17:17:09 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 gasoline tasting compound. 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-link 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 | InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3 |
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Synonyms | Value | Source |
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Hexan-2-one | ChEMBL, HMDB, MeSH | 2-Hexanone | HMDB | 2-Hexanone methyl N-butyl ketone | HMDB | Butyl methyl ketone | HMDB | Methyl butyl ketone | HMDB | Methyl n-butyl ketone | HMDB, MeSH | MNBK | HMDB | n-Butyl methyl ketone | HMDB | N-C4H9COCH3 | HMDB | Propylacetone | HMDB | Butylmethyl ketone | MeSH, HMDB | Ketone, butylmethyl | MeSH, HMDB | 2 Hexanone | MeSH, HMDB | Hexan 2 one | MeSH, HMDB | Ketone, methyl N-butyl | MeSH, HMDB | Methyl N butyl ketone | MeSH, HMDB | N-Butyl ketone, methyl | MeSH, 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 | |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | -55.5 °C | Not Available | Boiling Point | 127.60 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 17.5 mg/mL at 20 °C | Not Available | LogP | 1.38 | HANSCH,C ET AL. (1995) |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2-Oxohexane,1TMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C | 1004.9 | Semi standard non polar | 33892256 | 2-Oxohexane,1TMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C | 952.0 | Standard non polar | 33892256 | 2-Oxohexane,1TMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C | 1007.6 | Standard polar | 33892256 | 2-Oxohexane,1TMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C | 961.4 | Semi standard non polar | 33892256 | 2-Oxohexane,1TMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C | 959.8 | Standard non polar | 33892256 | 2-Oxohexane,1TMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C | 1021.4 | Standard polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C(C)(C)C | 1208.6 | Semi standard non polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C(C)(C)C | 1158.4 | Standard non polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #1 | CCCC=C(C)O[Si](C)(C)C(C)(C)C | 1211.1 | Standard polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C(C)(C)C | 1162.9 | Semi standard non polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C(C)(C)C | 1159.4 | Standard non polar | 33892256 | 2-Oxohexane,1TBDMS,isomer #2 | C=C(CCCC)O[Si](C)(C)C(C)(C)C | 1222.9 | Standard polar | 33892256 |
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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 - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-a8db7120c386c93d25ff | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-0006-9000000000-858b1e62ef5dfd041baf | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-e2acd59c62ae4caefc56 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-a8db7120c386c93d25ff | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-0006-9000000000-858b1e62ef5dfd041baf | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Oxohexane EI-B (Non-derivatized) | splash10-052f-9000000000-e2acd59c62ae4caefc56 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Oxohexane GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-0884cf76c54fac458024 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Oxohexane GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-052f-9000000000-f15df0bf9af914ce3f16 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Oxohexane EI-B (HITACHI RMU-6M) , Positive-QTOF | splash10-052f-9000000000-b9a2ab16adfdd94ece2a | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Oxohexane EI-B (HITACHI RMU-7M) , Positive-QTOF | splash10-052f-9000000000-c9c9e98957d1fde0dce7 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Oxohexane EI-B (HITACHI M-80B) , Positive-QTOF | splash10-052f-9000000000-214c4efe96ae363515d5 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Oxohexane EI-B (HP 5970) , Positive-QTOF | splash10-0006-9000000000-858b1e62ef5dfd041baf | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Oxohexane EI-B (HITACHI RMU-6M) , Positive-QTOF | splash10-052f-9000000000-e2acd59c62ae4caefc56 | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 10V, Negative-QTOF | splash10-0002-9000000000-e69f92c1ea30b1c8b758 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 20V, Negative-QTOF | splash10-0002-9000000000-b2aac1a98aa5c3d5501e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 40V, Negative-QTOF | splash10-0a5c-9000000000-a65bc7e7cdfb70bec9db | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 10V, Negative-QTOF | splash10-0002-9000000000-658fe53778817eb82301 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 20V, Negative-QTOF | splash10-001l-9000000000-e907871a490af2e1ded7 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 40V, Negative-QTOF | splash10-0a4i-9000000000-c861cd366a7a836ef1bd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 10V, Positive-QTOF | splash10-0ue9-8900000000-7f95c62c199ac18bb617 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 20V, Positive-QTOF | splash10-0f8c-9300000000-86d93f8a23031d700516 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 40V, Positive-QTOF | splash10-0006-9000000000-52c2a4eb34b81253f5b0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 10V, Positive-QTOF | splash10-0536-9000000000-0559a7010081eca96a3d | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 20V, Positive-QTOF | splash10-0006-9000000000-e97d6cc8af942e33a198 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Oxohexane 40V, Positive-QTOF | splash10-0006-9000000000-44563a4a9f48cfa3a8d9 | 2021-09-21 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | 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]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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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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