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 17:44:04 UTC |
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Update Date | 2023-02-21 17:20:50 UTC |
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HMDB ID | HMDB0031563 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Methyl-3-penten-2-one, 9CI |
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Description | 4-Methyl-3-penten-2-one, also known as isopropylidene acetone or (CH3)2C=chc(=o)CH3, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 4-Methyl-3-penten-2-one is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 4-methyl-3-penten-2-one is considered to be an oxygenated hydrocarbon lipid molecule. 4-Methyl-3-penten-2-one is a sweet, acrylic, and chemical tasting compound. 4-Methyl-3-penten-2-one has been detected, but not quantified, in several different foods, such as orange bell peppers, pepper (c. frutescens), herbs and spices, yellow bell peppers, and green bell peppers. This could make 4-methyl-3-penten-2-one a potential biomarker for the consumption of these foods. With regards to humans, 4-Methyl-3-penten-2-one has been linked to the inborn metabolic disorder celiac disease. |
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Structure | InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3 |
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Synonyms | Value | Source |
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(CH3)2C=chc(=o)CH3 | HMDB | 1-Methylpent-2-en-4-one | HMDB | 2,2-Dimethylvinyl methyl ketone | HMDB | 2-Methyl-2-penten-4-one | HMDB | 2-Methyl-2-pentenone-4 | HMDB | 2-Methyl-4-oxo-2-pentene | HMDB | 3-Isohexen-2-one | HMDB | 3-PENTEN,2-one,4-methyl mesityloxide | HMDB | 4-Methyl-3-penten-2-ON | HMDB | 4-Methyl-3-penten-2-one | HMDB | 4-Methyl-3-penten-2-one (mesityl oxide) | HMDB | 4-Methyl-3-pentene-2-one | HMDB | 4-Methylpent-3-en-2-one | HMDB | 4-Metil-3-penten-2-one | HMDB | FEMA 3368 | HMDB | Isobutenyl methyl ketone | HMDB | Isopropylidene acetone | HMDB | Isopropylidene-acetone | HMDB | Isopropylideneacetone | HMDB | Mesityl oxide | HMDB | Mesityloxid | HMDB | Mesityloxyde | HMDB | Methyl 2,2-dimethylvinyl ketone | HMDB | Methyl 2-methyl-1-propenyl ketone | HMDB | Methyl isobutenyl ketone | HMDB | ossido Di mesitile | HMDB | Oxyde de mesityle | HMDB |
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Chemical Formula | C6H10O |
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Average Molecular Weight | 98.143 |
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Monoisotopic Molecular Weight | 98.073164942 |
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IUPAC Name | 4-methylpent-3-en-2-one |
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Traditional Name | mesityl oxide |
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CAS Registry Number | 141-79-7 |
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SMILES | CC(C)=CC(C)=O |
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InChI Identifier | InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3 |
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InChI Key | SHOJXDKTYKFBRD-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. |
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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 | Enones |
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Alternative Parents | |
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Substituents | - Enone
- Acryloyl-group
- 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 | |
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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 | -41.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 28.9 mg/mL at 20 °C | Not Available | LogP | Not Available | Not Available |
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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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4-Methyl-3-penten-2-one, 9CI,1TMS,isomer #1 | C=C(C=C(C)C)O[Si](C)(C)C | 992.9 | Semi standard non polar | 33892256 | 4-Methyl-3-penten-2-one, 9CI,1TMS,isomer #1 | C=C(C=C(C)C)O[Si](C)(C)C | 959.2 | Standard non polar | 33892256 | 4-Methyl-3-penten-2-one, 9CI,1TBDMS,isomer #1 | C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C | 1204.1 | Semi standard non polar | 33892256 | 4-Methyl-3-penten-2-one, 9CI,1TBDMS,isomer #1 | C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C | 1194.2 | 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 - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized) | splash10-0a7i-9000000000-3661666f8de0c561e186 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized) | splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized) | splash10-0a7i-9000000000-3661666f8de0c561e186 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized) | splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive | splash10-0536-9000000000-2812ff25d24931b41744 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-053s-9000000000-6fe7e7a277af44176ff4 | 2014-09-20 | 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 - 4-Methyl-3-penten-2-one, 9CI 10V, Positive-QTOF | splash10-000t-9000000000-1cada987a9858a217a77 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Positive-QTOF | splash10-001j-9000000000-e609ed7c7875fbd22551 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Positive-QTOF | splash10-00lr-9000000000-fe1499144a8401242c76 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Negative-QTOF | splash10-0002-9000000000-623d2802baf709699403 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Negative-QTOF | splash10-052b-9000000000-16572bb315d857e26b9b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Negative-QTOF | splash10-0a7i-9000000000-59b1a0eada94cc3c451e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Negative-QTOF | splash10-0002-9000000000-21c5ae8d52f2e0f4cd33 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Negative-QTOF | splash10-0002-9000000000-eed82ff9c391c5362464 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Negative-QTOF | splash10-03fr-9000000000-c60c0aab8dedee066bd2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Positive-QTOF | splash10-000x-9000000000-87409e2f1170b30e777d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Positive-QTOF | splash10-0006-9000000000-6d052a8bde956f1f244e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Positive-QTOF | splash10-000f-9000000000-e4044459c1588578e40a | 2021-09-22 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 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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