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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2019-07-23 05:45:39 UTC
HMDB IDHMDB0002939
Secondary Accession Numbers
  • HMDB02939
Metabolite Identification
Common NameMethyl isobutyl ketone
DescriptionMethyl isobutyl ketone (MIBK) is an organic solvent. MIBK is among the top ten most popular organic solvents used in industry. MIBK is occasionally found as a volatile component of urine. MIBK in urine is considered as a biological marker of occupational exposure to this solvent. Olfactory perception is significant but adaptation may occur. 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. 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. Regarding to the route of absorption, skin penetration of MIBK is substantial. (PMID: 12592578 , 17485256 , 16464817 , 5556886 ).
Structure
Data?1563860739
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5c7c989978f9e9e3684eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a74860e5429fbdddd4ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ef9512a77e6eca91c42fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-1df29932d3d714865bf1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-5c7c989978f9e9e3684eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a74860e5429fbdddd4ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-ef9512a77e6eca91c42fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-1df29932d3d714865bf1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-79a91c01e3561d0aa8beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-9200000000-0f15e3b44a8f18e6e836JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9200000000-fc3200b61e2367a1d019JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9300000000-339c8752bafa71ce0bb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-649fb0cb4535c5185e04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-3faae6eee04013af7ff4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-33bf21fe746da25ecf7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-1df29932d3d714865bf1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9800000000-f93ec788a44ead85485eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9300000000-cf3e6a2e070abcc2afaaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-451064d75185091dac8cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-305a268f865f14a7d6aeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-f046f52b582c91226f66JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9000000000-23dbcbb92100ffd7eddeJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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 ]