Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 17:42:10 UTC |
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Update Date | 2023-02-21 17:20:17 UTC |
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HMDB ID | HMDB0031295 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethyl pentyl ketone |
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Description | Ethyl pentyl ketone, also known as 3-oxooctane or EAK, 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 pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. |
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Structure | InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3 |
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Synonyms | Value | Source |
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3-Oxooctane | ChEBI | Amyl ethyl ketone | ChEBI | EAK | ChEBI | Ethyl amyl ketone | ChEBI | Ethyl N-amyl ketone | ChEBI | Ethyl N-pentyl ketone | ChEBI | N-Amyl ethyl ketone | ChEBI | Octan-3-one | ChEBI | 3-Octanon | HMDB | 3-Octanone | HMDB | Ethyl N-amylketone | HMDB | FEMA 2803 | HMDB | N-Octanone-3 | HMDB | Ethyl pentyl ketone | ChEBI |
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Chemical Formula | C8H16O |
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Average Molecular Weight | 128.212 |
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Monoisotopic Molecular Weight | 128.120115134 |
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IUPAC Name | octan-3-one |
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Traditional Name | 3-octanone |
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CAS Registry Number | 106-68-3 |
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SMILES | CCCCCC(=O)CC |
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InChI Identifier | InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3 |
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InChI Key | RHLVCLIPMVJYKS-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 | |
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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 pentyl ketone,1TMS,isomer #1 | CC=C(CCCCC)O[Si](C)(C)C | 1158.9 | Semi standard non polar | 33892256 | Ethyl pentyl ketone,1TMS,isomer #1 | CC=C(CCCCC)O[Si](C)(C)C | 1152.1 | Standard non polar | 33892256 | Ethyl pentyl ketone,1TMS,isomer #2 | CCCCC=C(CC)O[Si](C)(C)C | 1167.3 | Semi standard non polar | 33892256 | Ethyl pentyl ketone,1TMS,isomer #2 | CCCCC=C(CC)O[Si](C)(C)C | 1151.5 | Standard non polar | 33892256 | Ethyl pentyl ketone,1TBDMS,isomer #1 | CC=C(CCCCC)O[Si](C)(C)C(C)(C)C | 1376.2 | Semi standard non polar | 33892256 | Ethyl pentyl ketone,1TBDMS,isomer #1 | CC=C(CCCCC)O[Si](C)(C)C(C)(C)C | 1344.2 | Standard non polar | 33892256 | Ethyl pentyl ketone,1TBDMS,isomer #2 | CCCCC=C(CC)O[Si](C)(C)C(C)(C)C | 1379.0 | Semi standard non polar | 33892256 | Ethyl pentyl ketone,1TBDMS,isomer #2 | CCCCC=C(CC)O[Si](C)(C)C(C)(C)C | 1341.9 | Standard non 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 - Ethyl pentyl ketone EI-B (Non-derivatized) | splash10-05bf-9000000000-781901ca764a5f841104 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized) | splash10-05bf-9000000000-c5ad6888f5d8235bbcbd | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized) | splash10-05bf-9000000000-781901ca764a5f841104 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized) | splash10-05bf-9000000000-c5ad6888f5d8235bbcbd | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9000000000-c2c048174c4c8d3d8228 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-05i3-9000000000-91e0504d51c6adb6a6dc | 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 - Ethyl pentyl ketone 10V, Positive-QTOF | splash10-004i-1900000000-ffaa377d52d739ba9f44 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOF | splash10-0a6r-9400000000-f7381b3ecccb7b1c9936 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOF | splash10-0a4l-9000000000-7f234320bd480d9871b6 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOF | splash10-004i-1900000000-e4a3fd9e0a2d4bb13155 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOF | splash10-004i-7900000000-5ba281eb40ef59122e53 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOF | splash10-0avi-9100000000-0ccdc24b3e039027a03a | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOF | splash10-004i-0900000000-e8448bc978ba2df6edde | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOF | splash10-056r-9300000000-2bbefe45e3391c2f9e16 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOF | splash10-0a4i-9000000000-07772b5c8be44e02f68e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Positive-QTOF | splash10-05tf-9000000000-7376e27c0ccc450d2e87 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOF | splash10-052f-9000000000-9a9cbad9068425131f56 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOF | splash10-052f-9000000000-390b61087232d1c44369 | 2021-09-24 | 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) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | 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 | 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 ]
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