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Showing metabocard for Methyl isobutyl ketone (HMDB0002939)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2020-02-26 21:24:19 UTC
HMDB IDHMDB0002939
Secondary Accession Numbers
  • HMDB02939
Metabolite Identification
Common NameMethyl isobutyl ketone
DescriptionMethyl 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.
Structure
Data?1582752259
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methyl-4-pentanoneHMDB
2-Methylpropyl methyl ketoneHMDB
4-Methyl-2-oxopentaneHMDB
4-Methyl-2-pentanonHMDB
4-Methyl-2-pentanoneHMDB
4-Methyl-pentan-2-ONHMDB
4-Methylpentan-2-oneHMDB
4-Metilpentan-2-oneHMDB
Ethyl iso-butyl ketoneHMDB
HexanoneHMDB
HexonHMDB
HexoneHMDB
Isobutyl methyl ketoneHMDB
Isobutyl-methylketonHMDB
IsohexanoneHMDB
Isopropyl acetoneHMDB
IsopropylacetoneHMDB
Methyl I-butyl ketoneHMDB
Methyl-isobutyl-cetoneHMDB
MethylisobutylketonHMDB
Methylpentan-2-oneHMDB
MetilisobutilchetoneHMDB
MetyloizobutyloketonHMDB
Shell mibkHMDB
Methyl isobutyl ketoneMeSH
Chemical FormulaC6H12O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
IUPAC Name4-methylpentan-2-one
Traditional Namemethyl isobutyl ketone
CAS Registry Number108-10-1
SMILES
CC(C)CC(C)=O
InChI Identifier
InChI=1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3
InChI KeyNTIZESTWPVYFNL-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-84 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility19 mg/mL at 25 °CNot Available
LogP1.31TANII,H & HASHIMOTO,K (1986)
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP1.31ALOGPS
logP1.54ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)19.61ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.97 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5c7c989978f9e9e3684eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a74860e5429fbdddd4ecSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ef9512a77e6eca91c42fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-1df29932d3d714865bf1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5c7c989978f9e9e3684eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a74860e5429fbdddd4ecSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ef9512a77e6eca91c42fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-1df29932d3d714865bf1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-79a91c01e3561d0aa8beSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-9200000000-0f15e3b44a8f18e6e836Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9200000000-fc3200b61e2367a1d019Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9300000000-339c8752bafa71ce0bb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-649fb0cb4535c5185e04Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-3faae6eee04013af7ff4Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-33bf21fe746da25ecf7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-1df29932d3d714865bf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9800000000-f93ec788a44ead85485eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9300000000-cf3e6a2e070abcc2afaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-451064d75185091dac8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-305a268f865f14a7d6aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-f046f52b582c91226f66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9000000000-23dbcbb92100ffd7eddeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis		 details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008174
KNApSAcK IDNot Available
Chemspider ID7621
KEGG Compound IDC19263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isobutyl ketone
METLIN IDNot Available
PubChem Compound7909
PDB IDNot Available
ChEBI ID142806
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]