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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 | 2006-05-22 15:12:20 UTC |
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Update Date | 2020-02-26 21:24:19 UTC |
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HMDB ID | HMDB0002939 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methyl isobutyl ketone |
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Description | Methyl isobutyl ketone, also known as 4-methyl-2-pentanon or hexanone, 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, methyl isobutyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. Methyl isobutyl ketone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methyl isobutyl ketone (MIBK) is an organic solvent. Methyl isobutyl ketone is a dairy, fruity, and green tasting compound. Outside of the human body, Methyl isobutyl ketone has been detected, but not quantified in, several different foods, such as black elderberries, sweet cherries, evergreen blackberries, nuts, and fruits. This could make methyl isobutyl ketone a potential biomarker for the consumption of these foods. MIBK in urine is considered as a biological marker of occupational exposure to this solvent. Methyl isobutyl ketone is a potentially toxic compound. Methyl isobutyl ketone, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, ulcerative colitis, autism, and pervasive developmental disorder not otherwise specified; methyl isobutyl ketone has also been linked to the inborn metabolic disorder celiac disease. Visual dysfunction has been reported in workers exposed to a mixture of organic solvents containing MIBK. Memory impairment was detected in clinical observation on a 44-year-old man who had been exposed to MIBK at 100 ppm for more than 10 years. MIBK is occasionally found as a volatile component of urine. The typical toxicity effects of MIBK in humans exposed at 50 to 100 ppm are mucous membrane irritation and weak effects on the central nervous system (CNS) such as headache. Olfactory perception is significant but adaptation may occur. Regarding to the route of absorption, skin penetration of MIBK is substantial. MIBK is among the top ten most popular organic solvents used in industry. |
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Structure | |
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Synonyms | Value | Source |
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2-Methyl-4-pentanone | HMDB | 2-Methylpropyl methyl ketone | HMDB | 4-Methyl-2-oxopentane | HMDB | 4-Methyl-2-pentanon | HMDB | 4-Methyl-2-pentanone | HMDB | 4-Methyl-pentan-2-ON | HMDB | 4-Methylpentan-2-one | HMDB | 4-Metilpentan-2-one | HMDB | Ethyl iso-butyl ketone | HMDB | Hexanone | HMDB | Hexon | HMDB | Hexone | HMDB | Isobutyl methyl ketone | HMDB | Isobutyl-methylketon | HMDB | Isohexanone | HMDB | Isopropyl acetone | HMDB | Isopropylacetone | HMDB | Methyl I-butyl ketone | HMDB | Methyl-isobutyl-cetone | HMDB | Methylisobutylketon | HMDB | Methylpentan-2-one | HMDB | Metilisobutilchetone | HMDB | Metyloizobutyloketon | HMDB | Shell mibk | HMDB | Methyl isobutyl ketone | MeSH |
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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 | 4-methylpentan-2-one |
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Traditional Name | methyl isobutyl ketone |
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CAS Registry Number | 108-10-1 |
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SMILES | CC(C)CC(C)=O |
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InChI Identifier | InChI=1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 |
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InChI Key | NTIZESTWPVYFNL-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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Disposition | Route of exposure: Biological location: Source: |
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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 | -84 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 19 mg/mL at 25 °C | Not Available | LogP | 1.31 | TANII,H & HASHIMOTO,K (1986) |
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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) | splash10-0006-9000000000-5c7c989978f9e9e3684e | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-a74860e5429fbdddd4ec | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-ef9512a77e6eca91c42f | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-1df29932d3d714865bf1 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-5c7c989978f9e9e3684e | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-a74860e5429fbdddd4ec | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-ef9512a77e6eca91c42f | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-1df29932d3d714865bf1 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-79a91c01e3561d0aa8be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-014i-9200000000-0f15e3b44a8f18e6e836 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-014i-9200000000-fc3200b61e2367a1d019 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-014i-9300000000-339c8752bafa71ce0bb5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-0006-9000000000-649fb0cb4535c5185e04 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0006-9000000000-3faae6eee04013af7ff4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-052f-9000000000-33bf21fe746da25ecf7e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-052f-9000000000-1df29932d3d714865bf1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-9800000000-f93ec788a44ead85485e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-9300000000-cf3e6a2e070abcc2afaa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-451064d75185091dac8c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-305a268f865f14a7d6ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-f046f52b582c91226f66 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053u-9000000000-23dbcbb92100ffd7edde | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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 | Children (1-13 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | 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 | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Urine | 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 | 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 | Children (1-13 years old) | Both | Autism | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Pervasive Developmental Disorder Not Otherwise Specified | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative Colitis | | details | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Celiac disease | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Breast cancer | | details |
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Associated Disorders and Diseases |
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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 ]
| Autism |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Pervasive developmental disorder not otherwise specified |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| 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 ]
| Perillyl alcohol administration for cancer treatment |
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- Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
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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 | FDB008174 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7621 |
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KEGG Compound ID | C19263 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Methyl isobutyl ketone |
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METLIN ID | Not Available |
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PubChem Compound | 7909 |
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PDB ID | Not Available |
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ChEBI ID | 142806 |
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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) | Download (PDF) |
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General References | - Shim HJ, Lee ED, Yoon EJ, Lee SD, Kim WB, Yang J, Lee MG: Simultaneous determination of a new anthracycline, DA-125, and its metabolites M1, M2, M3 and M4 in plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1994 Jun 17;656(2):407-14. [PubMed:7987494 ]
- Kawai T, Zhang ZW, Takeuchi A, Miyama Y, Sakamoto K, Higashikawa K, Ikeda M: Methyl isobutyl ketone and methyl ethyl ketone in urine as biological markers of occupational exposure to these solvents at low levels. Int Arch Occup Environ Health. 2003 Feb;76(1):17-23. Epub 2002 Sep 18. [PubMed:12592578 ]
- Kubota R, Endo Y, Takeuchi A, Inoue Y, Ogata H, Ogawa M, Nakagawa T, Onda N, Endo G: SPE-GC/FTD determination of N-methyl-2-pyrrolidone and its metabolites in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jul 1;854(1-2):204-10. Epub 2007 Apr 25. [PubMed:17485256 ]
- Truchon G, Tardif R, Droz PO, Charest-Tardif G, Pierrehumbert G: Biological exposure indicators: quantification of biological variability using toxicokinetic modeling. J Occup Environ Hyg. 2006 Mar;3(3):137-43. [PubMed:16464817 ]
- Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
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