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Record Information |
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Version | 4.0 |
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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 | 2019-07-23 06:09:01 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, 9CI, 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'. Thus, 4-methyl-3-penten-2-one, 9CI is considered to be an oxygenated hydrocarbon lipid molecule. 4-Methyl-3-penten-2-one, 9CI is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Methyl-3-penten-2-one, 9CI is a sweet, acrylic, and chemical tasting compound. Outside of the human body, 4-Methyl-3-penten-2-one, 9CI 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, 9CI a potential biomarker for the consumption of these foods. 4-Methyl-3-penten-2-one, 9CI is a potentially toxic compound. 4-Methyl-3-penten-2-one, 9CI, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. |
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Structure | |
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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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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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 | -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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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) | splash10-0a7i-9000000000-3661666f8de0c561e186 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a7i-9000000000-3661666f8de0c561e186 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0536-9000000000-2812ff25d24931b41744 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-9000000000-1cada987a9858a217a77 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001j-9000000000-e609ed7c7875fbd22551 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00lr-9000000000-fe1499144a8401242c76 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-623d2802baf709699403 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052b-9000000000-16572bb315d857e26b9b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7i-9000000000-59b1a0eada94cc3c451e | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-053s-9000000000-6fe7e7a277af44176ff4 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 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 | Immunoglobulin A nephropathy (IgAN) non progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Celiac disease | | details |
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Associated Disorders and Diseases |
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Disease References | Celiac disease |
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- Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
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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 | FDB008178 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8526 |
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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 | 8858 |
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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 | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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