Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2007-04-12 15:34:50 UTC |
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Update Date | 2023-02-21 17:17:09 UTC |
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HMDB ID | HMDB0005841 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethyl isobutyl ketone |
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Description | Ethyl isobutyl ketone 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, ethyl isobutyl ketone is considered to be an oxygenated hydrocarbon. Ethyl isobutyl ketone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make ethyl isobutyl ketone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ethyl isobutyl ketone. |
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Structure | InChI=1S/C7H14O/c1-4-7(8)5-6(2)3/h6H,4-5H2,1-3H3 |
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Synonyms | Value | Source |
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2-Methyl-4-hexanone | HMDB | 5-Methyl-3-hexanone | HMDB | 5-Methylhexan-3-one | HMDB | Isobutyl ethyl ketone | HMDB |
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Chemical Formula | C7H14O |
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Average Molecular Weight | 114.1855 |
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Monoisotopic Molecular Weight | 114.10446507 |
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IUPAC Name | 5-methylhexan-3-one |
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Traditional Name | 5-methyl-3-hexanone |
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CAS Registry Number | 623-56-3 |
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SMILES | CCC(=O)CC(C)C |
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InChI Identifier | InChI=1S/C7H14O/c1-4-7(8)5-6(2)3/h6H,4-5H2,1-3H3 |
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InChI Key | DXVYLFHTJZWTRF-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 | Not Available |
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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 | |
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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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Ethyl isobutyl ketone,1TMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C | 1025.3 | Semi standard non polar | 33892256 | Ethyl isobutyl ketone,1TMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C | 1007.2 | Standard non polar | 33892256 | Ethyl isobutyl ketone,1TMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C | 1044.5 | Standard polar | 33892256 | Ethyl isobutyl ketone,1TMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C | 1028.3 | Semi standard non polar | 33892256 | Ethyl isobutyl ketone,1TMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C | 1008.6 | Standard non polar | 33892256 | Ethyl isobutyl ketone,1TMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C | 1061.3 | Standard polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C(C)(C)C | 1241.5 | Semi standard non polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C(C)(C)C | 1208.3 | Standard non polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #1 | CCC(=CC(C)C)O[Si](C)(C)C(C)(C)C | 1233.7 | Standard polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C(C)(C)C | 1234.5 | Semi standard non polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C(C)(C)C | 1201.9 | Standard non polar | 33892256 | Ethyl isobutyl ketone,1TBDMS,isomer #2 | CC=C(CC(C)C)O[Si](C)(C)C(C)(C)C | 1244.2 | Standard 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 - Ethyl isobutyl ketone EI-B (Non-derivatized) | splash10-0a6r-9000000000-20f5957b32aa208000d9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Ethyl isobutyl ketone EI-B (Non-derivatized) | splash10-0a6r-9000000000-20f5957b32aa208000d9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyl isobutyl ketone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4l-9000000000-f01a97b7c30840ff4d25 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyl isobutyl ketone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyl isobutyl ketone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | 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 - Ethyl isobutyl ketone 10V, Positive-QTOF | splash10-014i-5900000000-fc098450c84e4393fdd6 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 20V, Positive-QTOF | splash10-0a4i-9200000000-ce8d55f0147c2a74c17d | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 40V, Positive-QTOF | splash10-0a4i-9000000000-819d4f467ae6024900e0 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 10V, Negative-QTOF | splash10-03di-2900000000-b1a0593ae0e25cbaf63a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 20V, Negative-QTOF | splash10-03di-9800000000-dd86cec9286248f0027d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 40V, Negative-QTOF | splash10-0a4i-9000000000-448aeb86ef5d8473431f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 10V, Negative-QTOF | splash10-03di-1900000000-b49cb3627f7b6c740aea | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 20V, Negative-QTOF | splash10-0a4i-9100000000-c9c959820461844ffcd6 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 40V, Negative-QTOF | splash10-052f-9000000000-29398e0997d217111f10 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 10V, Positive-QTOF | splash10-0a4i-9100000000-324444d0af69bdc3978d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 20V, Positive-QTOF | splash10-0a4i-9000000000-029d01ec0daecb03c64d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl isobutyl ketone 40V, Positive-QTOF | splash10-052f-9000000000-23fbdabc624e7c81c195 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | 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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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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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 |
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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 ]
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Associated OMIM IDs | None |
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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 | FDB023779 |
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KNApSAcK ID | C00051562 |
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Chemspider ID | 11687 |
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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 | 12187 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | rw1129381 |
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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 ]
- 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 ]
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