Page last updated: 2024-11-05

methyl isobutyl ketone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

MIBK is a colorless liquid ketone with a sweet odor. It is a common industrial solvent used in many applications, including paint thinners, adhesives, and coatings. MIBK is also used in the production of other chemicals, such as pharmaceuticals and pesticides. It is synthesized through a process called aldol condensation, where acetone and isobutylene react in the presence of a catalyst. MIBK is a relatively non-toxic solvent, but it can be irritating to the skin, eyes, and respiratory system. Prolonged exposure to high levels of MIBK can cause damage to the liver and kidneys. It is studied for its potential applications in various fields, such as organic synthesis, extraction, and separation processes. Its importance lies in its versatility as a solvent and its ability to dissolve a wide range of compounds. It is also a valuable starting material for the synthesis of other chemicals.'

Cross-References

ID SourceID
PubMed CID7909
CHEMBL ID285323
CHEBI ID82344
SCHEMBL ID13341539
SCHEMBL ID15458
MeSH IDM0047019

Synonyms (153)

Synonym
wln: 1y1 & 1v1
metyloizobutyloketon
4-methyl-pentan-2-on(dutch, german)
ketone, isobutyl methyl
mik
2-methyl-4-pentanone
2-methylpropyl methyl ketone
108-10-1
2-pentanone, 4-methyl-
4-methyl-2-pentanone
methyl-isobutyl-cetone
methylisobutylketon(dutch, german)
4-methyl-2-pentanon
isopropylacetone
isobutyl-methylketon
4-metilpentan-2-one
methyl isobutyl ketone
mibk
nsc-5712
hexone
nsc5712
isobutyl methyl ketone
4-methyl-2-oxopentane
hexon
metilisobutilchetone
methyl isobutyl ketone (nf)
D04989
inchi=1/c6h12o/c1-5(2)4-6(3)7/h5h,4h2,1-3h
4-methylpentan-2-one
2-pentanone,4-methyl methyl,isobutyl,ketone
NCGC00091475-01
isopropyl acetone
shell mibk
fema number 2731
rcra waste no. u161
4-metilpentan-2-one [italian]
ccris 2052
methylisobutylketon [dutch, german]
hexon [czech]
nsc 5712
rcra waste number u161
epa pesticide chemical code 044105
4-methyl-2-pentanon [czech]
ai3-01229
einecs 203-550-1
metilisobutilchetone [italian]
un1245
isobutyl-methylketon [czech]
methyl-isobutyl-cetone [french]
4-methyl-2-pentanone (natural)
brn 0605399
caswell no. 574aa
isohexanone
4-methyl-pentan-2-on [dutch, german]
metyloizobutyloketon [polish]
hsdb 148
fema no. 2731
4-methyl-2-pentanone, >=99%, fcc
4-methyl-2-pentanone, puriss. p.a., acs reagent, >=99.0% (gc)
CHEMBL285323
chebi:82344 ,
AKOS000118793
M0389
A801806
NCGC00091475-02
methylisobutylketon
methyl isobutyl ketone [nf]
methyl isobutyl ketone [un1245] [flammable liquid]
4-01-00-03305 (beilstein handbook reference)
unii-u5t7b88cnp
ec 203-550-1
4-methyl-pentan-2-on
u5t7b88cnp ,
C19263
LMFA12000033
tox21_201108
dtxcid701889
cas-108-10-1
dtxsid5021889 ,
NCGC00258660-01
4-methyl-pentan-2-one
methylisobutylketone
FT-0628744
methyl isobutyl ketone [hsdb]
methyl isobutyl ketone [iarc]
methyl isobutyl ketone [mart.]
4-methyl-2-pentanone [fcc]
mibk [inci]
methyl isobutyl ketone [usp-rs]
4-methyl-2-pentanone [fhfi]
methylisobutylketone [usp-rs]
isopropylacetone [mi]
isobutylmethyl ketone
SCHEMBL13341539
SCHEMBL15458
BP-13453
4-methyl 2-pentanone
methyl-iso-butylketone
methylisobutyketone
4-methyl-2pentanone
4-methylpentane-2-one
iso-butylmethylketone
isobutylmethylketone
methylisobutyl keton
methyl-isobutyl ketone
methylisobutyl-keton
methyl-isobutylketone
methy isobutyl ketone
methylisobutlyketone
methyl iso-butyl ketone
4-methyl- 2-pentanone
methyl iso-butylketone
methyl isobutylketone
methyl isobutyl keton
i-bucome
methylisobutyl ketone
Q-200495
ethyl iso-butyl ketone
methyl-2-pentanon,4-
un 1245
methyl i-butyl ketone
iso-c4h9coch3
2-methyl-4-pentanal
mfcd00008938
J-515799
F1908-0087
4-methyl-2-pentanone, hplc grade
4-methyl-2-pentanone, for hplc, >=99.5%
4-methyl-2-pentanone, acs reagent, >=98.5%
4-methyl-2-pentanone, analytical standard
4-methyl-2-pentanone, saj first grade, >=99.0%
methyl isobutyl ketone, united states pharmacopeia (usp) reference standard
4-methyl-2-pentanone, jis special grade, >=99.5%
4-methyl-2-pentanone, suitable for atomic absorption spectrometry, >=99.5%
4-methyl-2-pentanone, >=99%
methylpentan-2-one
methyl isobutyl ketone, pharmaceutical secondary standard; certified reference material
4-methyl-2-pentanone, lr, >=99%
4-methyl-2-pentanone, puriss., acs reagent, reag. ph. eur., 99.0%
4-methyl-2-pentanone, ar, >=99%
4-methyl-2-pentanone, technical grade, 95%
methyl isobutyl ketone, p.a., acs reagent, 98.5%
methyl isobutyl ketone, acs grade
4-methyl-2-pentanone(mibk)
Q418104
AMY11098
alfa-[(phenylmethoxy)carbonyl]oxy-1-piperidineaceticacidmethylester
methylisobutylketone (usp-rs)
methyl 2-methylpropyl ketone
methyl isobutyl ketone (usp-rs)
methyl isobutyl ketone (iarc)
methyl isobutyl ketone (mart.)
isobutyl methyl ketone (methyl isobutyl ketone)

Research Excerpts

Overview

Methyl isobutyl ketone (MIBK) is a solvent used in numerous products and processes. It may be present in the air of the workplace as a vapor.

ExcerptReferenceRelevance
"Methyl isobutyl ketone (MIBK) is a solvent used in numerous products and processes and may be present in the air of the workplace as a vapor. "( Simulation of repeated dose kinetics of methyl isobutyl ketone in humans from experimental single-dose inhalation exposure.
Rick, DL; Saghir, SA, 2008
)
2.06

Effects

ExcerptReferenceRelevance
"Methyl isobutyl ketone (MIBK) has recently been shown to potentiate the cholestasis induced by manganese-bilirubin (Mn-BR) or manganese (Mn) in rats. "( Methyl isobutyl ketone metabolites and potentiation of the cholestasis induced in rats by a manganese-bilirubin combination or manganese alone.
Plaa, GL; Vézina, M, 1988
)
3.16

Toxicity

ExcerptReferenceRelevance
" The 14 weeks of exposure had no adverse effect on the clinical health or growth of rats or mice."( A 14-week vapor inhalation toxicity study of methyl isobutyl ketone.
Dodd, DE; Fowler, EH; Kary, CD; Moran, EJ; O'Donoghue, J; Phillips, RD, 1987
)
0.53
" MIBK was not toxic via the oral or dermal route of exposure in acute, short-term, or subchronic animal studies, except that nephrotoxicity was observed in rats dosed with 1 g/kg in a short-term study."( Safety assessment of MIBK (methyl isobutyl ketone).
Johnson, W, 2004
)
0.62
" There was a dose-related increase in adult animals with no or a decreased response to a sound stimulus at 1000 and 2000 ppm; however, no adverse clinical signs occurred 1 h after exposure, suggesting this was a transient sedative effect."( Inhalation two-generation reproductive toxicity study of methyl isobutyl ketone in rats.
Gingell, R; Harris, SB; Nemec, MD; Pavkov, KL; Pitt, JA; Rauckman, EJ; Topping, DC,
)
0.38
" In order to evaluate the potential of MIBK to induce toxic and carcinogenic effects following chronic exposure, groups of 50 male and 50 female F344/N rats and B6C3F1 mice were exposed to MIBK at concentrations of 0, 450, 900, or 1800ppm by inhalation, 6h/day, 5 days per week for 2 years."( Toxicity and carcinogenicity of methyl isobutyl ketone in F344N rats and B6C3F1 mice following 2-year inhalation exposure.
Bucher, JR; Chhabra, RS; Herbert, RA; Kissling, GE; Roycroft, JH; Stout, MD; Suarez, F, 2008
)
0.63

Dosage Studied

ExcerptRelevanceReference
" Moreover, the minimally effective dosage needed to potentiate CHCl3-induced hepatotoxicity was approximately 5 mmol/kg for the three compounds."( Potentiation of chloroform-induced hepatotoxicity by methyl isobutyl ketone and two metabolites.
du Souich, P; Greselin, E; Kobusch, AB; Plaa, GL; Vézina, M, 1990
)
0.53
" The importance of the CCl4 dosage in these combinations, however, has not been explored."( Potentiation of CCl4-induced liver injury by ketonic and ketogenic compounds: role of the CCl4 dose.
Brodeur, J; Pilon, D; Plaa, GL, 1988
)
0.27
" Dose-response relationships for A, MEK, and MiBK potentiation of CCl4-induced hepatotoxicity and CHCl3-induced nephrotoxicity were compared."( Ketone potentiation of haloalkane-induced hepato- and nephrotoxicity. I. Dose-response relationships.
Plaa, GL; Raymond, P, 1995
)
0.29
" MIBK was not toxic via the oral or dermal route of exposure in acute, short-term, or subchronic animal studies, except that nephrotoxicity was observed in rats dosed with 1 g/kg in a short-term study."( Safety assessment of MIBK (methyl isobutyl ketone).
Johnson, W, 2004
)
0.62
" The results indicated that the continuous dosing (0."( Potential impact of methyl isobutyl ketone (MIBK) on phenols degradation in an UASB reactor and its degradation properties.
Hu, Z; Sierra, JM; Wang, W; Yang, K; Yuan, S; Zhang, X, 2017
)
0.78
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ketoneA compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency50.11870.004023.8416100.0000AID485290
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency12.58930.011212.4002100.0000AID1030
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.48560.000229.305416,493.5996AID743080
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency50.11870.001019.414170.9645AID588537
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency15.84890.01789.637444.6684AID588834
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID159270Toxicity determined using Microtox Test1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Using theoretical descriptors in quantitative structure-activity relationships: some toxicological indices.
AID167125Eye irritation potential accessed using Draize in vivo rabbit eye irritation test2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Mapping property distributions of molecular surfaces: algorithm and evaluation of a novel 3D quantitative structure-activity relationship technique.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (106)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (22.64)18.7374
1990's27 (25.47)18.2507
2000's26 (24.53)29.6817
2010's21 (19.81)24.3611
2020's8 (7.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 75.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index75.90 (24.57)
Research Supply Index4.78 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index130.33 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (75.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.72%)5.53%
Reviews4 (3.45%)6.00%
Case Studies2 (1.72%)4.05%
Observational0 (0.00%)0.25%
Other108 (93.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]