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Record Information
Version3.6
Creation Date2006-05-22 15:12:20 UTC
Update Date2016-02-11 01:05:54 UTC
HMDB IDHMDB02939
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
2-Methyl-4-pentanalHMDB
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
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 KeyInChIKey=NTIZESTWPVYFNL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility11.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.97 m3·mol-1ChemAxon
Polarizability12.05 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-9200000000-0f15e3b44a8f18e6e836View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9200000000-fc3200b61e2367a1d019View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9300000000-339c8752bafa71ce0bb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-649fb0cb4535c5185e04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-3faae6eee04013af7ff4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-33bf21fe746da25ecf7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-1df29932d3d714865bf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9800000000-f93ec788a44ead85485eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9300000000-cf3e6a2e070abcc2afaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-451064d75185091dac8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-305a268f865f14a7d6aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-f046f52b582c91226f66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9000000000-23dbcbb92100ffd7eddeView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableChildren (1-13 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
SalivaDetected but not QuantifiedNot ApplicableChildren (1-13 years old)BothCeliac disease details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008174
KNApSAcK IDNot Available
Chemspider ID7621
KEGG Compound IDC19263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isobutyl ketone
NuGOwiki LinkHMDB02939
Metagene LinkHMDB02939
METLIN IDNot Available
PubChem Compound7909
PDB IDNot Available
ChEBI ID142806
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. 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. [7987494 ]
  3. 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. [12592578 ]
  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. [16464817 ]
  5. 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. [17485256 ]