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Details

Stereochemistry ACHIRAL
Molecular Formula C4H8O
Molecular Weight 72.1057
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYL ETHYL KETONE

SMILES

CCC(C)=O

InChI

InChIKey=ZWEHNKRNPOVVGH-UHFFFAOYSA-N
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3

HIDE SMILES / InChI
Molecular Formula C4H8O
Molecular Weight 72.1057
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Methyl ethyl ketone (butanone) is an industrial solvent produced on a large scale. It is used in surface coatings, adhesives, printing inks, chemical intermediates, magnetic tapes, and lube oil dewaxing agents. Methyl ethyl ketone has a fruity odor similar to acetone. It is used as a flavor/fragrance agent in pharmaceuticals and cosmetics.

Approval Year

1998
123
PubMed

PubMed

TitleDatePubMed
The stereoselectivity and catalytic properties of Xanthobacter autotrophicus 2-[(R)-2-Hydroxypropylthio]ethanesulfonate dehydrogenase are controlled by interactions between C-terminal arginine residues and the sulfonate of coenzyme M.
2004-06-01
Treatment of MEK and toluene mixtures in biofilters: effect of operating strategy an performance during transient loading.
2004-05-20
Performance of a fungal biofilter treating gas-phase solvent mixtures during intermittent loading.
2004-05
Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis.
2004-05
Potential for the use of ultrasound in the extraction of antioxidants from Rosmarinus officinalis for the food and pharmaceutical industry.
2004-05
Assessment of microbial populations in methyl ethyl ketone degrading biofilters by denaturing gradient gel electrophoresis.
2004-05
Volatile compounds produced in cheese by Enterobacteriaceae strains of dairy origin.
2004-03
Gas chromatography-mass spectrometry of carbonyl compounds in cigarette mainstream smoke after derivatization with 2,4-dinitrophenylhydrazine.
2004-02-20
Method development for the determination of diacetyl and acetoin at a microwave popcorn plant.
2004-02-01
Determining the equilibrium partitioning coefficients of volatile organic compounds at an air-water interface.
2004-02
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].
2004
Photocatalytic: oxidation of volatile organic compounds present in airborne environment adjacent to sewage treatment plants.
2004
Evaluation of liquid chromatography column retentivity using macromolecular probes. III. Partition properties of C18 phases traced by polymers.
2003-12-12
Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents.
2003-12-06
Locating dynamic species with X-ray crystallography and NMR spectroscopy: acetone in p-tert-Butylcalix[4]arene.
2003-10-17
Proteolysis, volatile compounds, and sensory evaluation in Hispánico cheese manufactured with the addition of a thermophilic adjunct culture, nisin, and calcium alginate-nisin microparticles.
2003-10
The forensic analysis of thermal transfer printing.
2003-09
The diffusion and sorption of volatile organic compounds through kaolinitic clayey soils.
2003-09
Developmental toxicity studies of methyl ethyl ketoxime (MEKO) in rats and rabbits.
2003-08
Use of a coupled biological system to treat a chemically complex air stream.
2003-07
[Isolation and quantitative analysis of the alpha-amylase inhibitor in Lagerstroemia speciosa (L.) Pers. (Banaba)].
2003-07
Measurement and modeling of single- and multi-component adsorption equilibria of VOC on high-silica zeolites.
2003-06-01
Micropatterned polymeric gratings as chemoresponsive volatile organic compound sensors: implications for analyte detection and identification via diffraction-based sensor arrays.
2003-05-15
Sequencing batch biofilter operation for treatment of methyl ethyl ketone (MEK) contaminated air.
2003-05
Volatile organic compounds produced during irradiation of mail.
2003-04-12
Evaluation of organics leaching from solidified/stabilized hazardous wastes using a powder reactivated carbon additive.
2003-04
The effects of co-exposure to methyl ethyl ketone on the biological monitoring of occupational exposure to N,N-dimethylformamide.
2003-03
Breathing and heart rate during experimental solvent exposure of young adults with self-reported multiple chemical sensitivity (sMCS).
2003-03
An evaluation of Fourier transform infrared (FTIR) spectroscopy for detecting organic solvents in expired breath.
2003-03
Iridium-catalyzed Oppenauer oxidations of primary alcohols using acetone or 2-butanone as oxidant.
2003-02-21
Methyl isobutyl ketone and methyl ethyl ketone in urine as biological markers of occupational exposure to these solvents at low levels.
2003-02
The loss of the chemical tanker Ievoli Sun in the English Channel, October 2000.
2003-02
Activation of mitogen-activated protein kinase pathway by keratinocyte growth factor or fibroblast growth factor-10 promotes cell proliferation in human endometrial carcinoma cells.
2003-02
Peracetylated 1,6-dibromo-D-glucitol as efficient precursor of 1,6-diiodo and some mono-, disubstituted and heterocyclic D-glucitol derivatives.
2003-01-20
Nasal function in self-reported chemically intolerant individuals.
2003-01-01
Influence of solvents on the variety of crystalline forms of erythromycin.
2003
An evaluation of changes and recovery in the olfactory epithelium in mice after inhalation exposure to methylethylketoxime.
2002-12
Volatile compounds in Hispánico cheese manufactured using a mesophilic starter, a thermophilic starter, and bacteriocin-producing Lactococcus lactis subsp. lactis INIA 415.
2002-11-06
Simultaneous determination of cyanide and carbonyls in cyanogenic plants by gas chromatography-electron capture/photoionization detection.
2002-11
Determination of volatile compounds in cows' milk using headspace GC-MS.
2002-11
Volatile compounds of headspace gas in the Japanese fish sauce ishiru.
2002-10
Neuropathy in an artist exposed to organic solvents in paints: a case study.
2002-08-27
Changes in n-hexane toxicokinetics in short-term single exposure due to co-exposure to methyl ethyl ketone in volunteers.
2002-08
Toluene, xylenes and xylene isomers in urine as biological indicators of low-level exposure to each solvent; a comparative study.
2002-08
Enantioselective chemisorption on a chirally modified surface in ultrahigh vacuum: adsorption of propylene oxide on 2-butoxide-covered palladium(111).
2002-07-31
Development of a physiologically based pharmacokinetic model for methyl ethyl ketone in F344 rats.
2002-07-12
Mild and chemoselective synthesis of lactones from diols using a novel metal-ligand bifunctional catalyst.
2002-07-11
Cytogenetic analysis of buccal cells from shoe-workers and pathology and anatomy laboratory workers exposed to n-hexane, toluene, methyl ethyl ketone and formaldehyde.
2002-07-10
Reduction of ketones and alkyl iodides by SmI(2) and Sm(II)-HMPA complexes. Rate and mechanistic studies.
2002-06-19
Field dependence of mobilities for gas-phase-protonated monomers and proton-bound dimers of ketones by planar field asymmetric waveform ion mobility spectrometer (PFAIMS).
2002-06-06
Patents

Patents

03931255
1
03951876
1
03975535
1
03983239
1
03989739
2
04000193
1
04002647
7
04010279
2
04022897
3
04028379
5
04038414
8
04071511
1
04123456
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04125541
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04125714
3
04127661
1
04140713
9
04187232
4
04217305
1
04222946
4
04266063
1
04284773
1
04287341
6
04308356
1
04329300
2
04340733
4
04343949
3
04351940
6
04364954
1
04376844
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04377581
6
04397986
1
04398939
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04479900
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04480092
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04483994
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04497817
6
04510325
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04528400
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04547559
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04551169
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04565828
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04568682
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04589909
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04621090
2
04644063
1
04652563
7
04670452
2
04690931
1
04710316
1
04710506
1
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:47 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:47 GMT 2025
Record UNII
6PT9KLV9IO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYL ETHYL KETONE
HSDB   II   MART.   MI   USP-RS   VANDF  
Systematic Name English
MEK
INCI  
INCI  
Preferred Name English
METHYLETHYL KETONE
Systematic Name English
BUTANONE
Systematic Name English
ETHYL METHYL KETONE
Systematic Name English
FEMA NO. 2170
Code English
2-BUTANONE [FCC]
Common Name English
METHYL ETHYL KETONE [II]
Common Name English
METHYL ETHYL KETONE [VANDF]
Common Name English
METHYL ETHYL KETONE [HSDB]
Common Name English
METHYL ETHYL KETONE [USP-RS]
Common Name English
METHYL ETHYL KETONE [MART.]
Common Name English
2-BUTANONE
FCC   FHFI  
Systematic Name English
2-BUTANONE [FHFI]
Common Name English
METHYL ETHYL KETONE [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 6714
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
JECFA EVALUATION 2-BUTANONE
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
CFR 21 CFR 175.320
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
Code System Code Type Description
CHEBI
28398
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PRIMARY
PUBCHEM
6569
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
FDA UNII
6PT9KLV9IO
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
DAILYMED
6PT9KLV9IO
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
SMS_ID
100000089029
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
RS_ITEM_NUM
1430101
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
JECFA MONOGRAPH
406
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
WIKIPEDIA
Methyl ethyl ketone
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID3021516
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
RXCUI
1363708
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PRIMARY
EVMPD
SUB22121
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
NCI_THESAURUS
C77477
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
CONCEPT Industrial Aid
MESH
C005222
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PRIMARY
CAS
78-93-3
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PRIMARY
HSDB
99
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-159-0
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
EVMPD
SUB79627
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
MERCK INDEX
m7413
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of METHYL ETHYL KETONE
ACTIVE MOIETY
NIH
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