butyl methyl ketone

General Material Information

Preferred name	butyl methyl ketone
Trivial Name	2-Hexanone
Short Description	methyl butyl ketone
Formula	C6 H12 O
CAS Number	591-78-6
ECHA Number	209-731-1
FDA UNII	6QDY60NH6N
Nikkaji Number	J3.303K
Beilstein Number	1737676
MDL	MFCD00009482
COE Number	11776
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	N- butyl methyl ketone butylmethyl ketone hexan-2-one 2-oxo hexane 2-hexanone ketone, butyl methyl MBK methyl butyl ketone methyl N-butyl ketone methylbutyl ketone propyl acetone propylacetone 2-Hexanone n-Butyl methyl ketone 2-Oxohexane

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Literature & References

	hexan-2-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	591-78-6
Pubchem (cid):	11583
Pubchem (sid):	134977464
Flavornet:	591-78-6
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Publications by PubMed
Volatile Organic Compounds during Inflammation and Sepsis in Rats: A Potential Breath Test Using Ion-mobility Spectrometry.
Reaction rate constants of H-abstraction by OH from large ketones: measurements and site-specific rate rules.
Binding of carbonyl flavours to canola, pea and wheat proteins using GC/MS approach.
Salivary microbiota and metabolome associated with celiac disease.
Combined IR/NIR and density functional theory calculations analysis of the solvent effects on frequencies and intensities of the fundamental and overtones of the C ═ O stretching vibrations of acetone and 2-hexanone.
Development of an electrospray-(63)Ni-differential ion mobility spectrometer for the analysis of aqueous samples.
[Biomonitoring of exposure to chemical products in environmental and workplace toxicology].
Furry pet allergens, fungal DNA and microbial volatile organic compounds (MVOCs) in the commercial aircraft cabin environment.
Brushed block copolymer micelles with pH-sensitive pendant groups for controlled drug delivery.
Can volatile organic metabolites be used to simultaneously assess microbial and mite contamination level in cereal grains and coffee beans?
Mass and Ion Transport in Ketones and Ketone Electrolytes: Comparison with Acetate Systems.
An endophytic Nodulisporium sp. from Central America producing volatile organic compounds with both biological and fuel potential.
Airborne molds and bacteria, microbial volatile organic compounds (MVOC), plasticizers and formaldehyde in dwellings in three North European cities in relation to sick building syndrome (SBS).
Blending synthetic pheromones of cerambycid beetles to develop trap lures that simultaneously attract multiple species.
Analysis of volatile organic compounds released from human lung cancer cells and from the urine of tumor-bearing mice.
Bioactivity of short-chain aliphatic ketones against adults of the granary weevil, Sitophilus granarius (L.).
Simplification of a complex microbial antilisterial consortium to evaluate the contribution of its flora in uncooked pressed cheese.
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.
Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth.
Thermodynamic properties of hyperbranched polymer, Boltorn U3000, using inverse gas chromatography.
Degradation of hexane and other recalcitrant hydrocarbons by a novel isolate, Rhodococcus sp. EH831.
Quantification of volatile compounds in goat milk Jack cheese using static headspace gas chromatography.
High-pressure ion mobility spectrometry.
Biocatalytical production of (5S)-hydroxy-2-hexanone.
Extraction and spectrophotometric determination of cobalt(II) with isonitroso-5-methyl-2-hexanone.
Headspace solid phase microextraction/gas chromatography-mass spectrometry combined to chemometric analysis for volatile organic compounds determination in canine hair: a new tool to detect dog contamination by visceral leishmaniasis.
Airborne concentrations of volatile organic compounds in neonatal incubators.
Aroma barrier properties of sodium caseinate-based films.
Microbial volatile organic compounds in the air of moldy and mold-free indoor environments.
Acid-catalyzed isomerization and decomposition of ketone-2,4-dinitrophenylhydrazones.
Evaluation of lipid oxidation and oxidative products as affected by pork meat cut, packaging method, and storage time during frozen storage (-10 degrees C).
Kinetic analysis of volatile formation in milk subjected to pressure-assisted thermal treatments.
Rate constants for the reaction of cl with a series of C4 to C6 ketones using the relative rate method.
[Identification of volatiles from field cotton plant under different induction treatments].
Purification and characterization of alcohol dehydrogenase reducing N-benzyl-3-pyrrolidinone from Geotrichum capitatum.
Pulsed laser photolysis vacuum UV laser-induced fluorescence kinetic study of the gas-phase reactions of Cl(2P3/2) atoms with C3-C6 ketones.
Ozone artifacts and carbonyl measurements using Tenax GR, Tenax TA, Carbopack B, and Carbopack X adsorbents.
Solid-phase microextraction: investigation of the metabolism of substances that may be abused by inhalation.
Quantitative determination of thermally derived off-flavor compounds in milk using solid-phase microextraction and gas chromatography.
Degradation characteristics of methyl ethyl ketone by Pseudomonas sp. KT-3 in liquid culture and biofilter.
Capture of female Hylotrupes bajulus as influenced by trap type and pheromone blend.
1,4-hydroxycarbonyl products of the OH radical initiated reactions of C5-C8 n-alkanes in the presence of NO.
Enhancement of attraction and trap catches of the old-house borer, Hylotrupes bajulus (Coleoptera: Cerambycidae), by combination of male sex pheromone and monoterpenes.
Tropospheric reaction of OH with selected linear ketones: kinetic studies between 228 and 405 K.
Microwave-assisted derivatization of 2,5-hexanedione in urine: evaluation using GC-MS and GC-ECD.
Synthesis of 3'-fluoro-2',3'-dideoxy-2',3'-didehydro-4'-ethynyl-D- and -L-furanosyl nucleosides.
Stereoselective oxidation of aliphatic diols and reduction of hydroxy-ketones with galactitol dehydrogenase from Rhodobacter sphaeroides D.
The prodrug activator EtaA from Mycobacterium tuberculosis is a Baeyer-Villiger monooxygenase.
Migration of volatile degradation products into ozonated water from plastic packaging materials.
Free and total 2,5-hexanedione in biological monitoring of workers exposed to n-hexane in the shoe industry.
Synthesis, structural characterization and antimicrobial studies of hydrazone derivatives of 3-hydroxyimino-5-methyl-2-hexanone.
Evaluation of 2,5-hexanedione in urine of workers exposed to n-hexane in Brazilian shoe factories.
Synthesis and antimicrobial activity of 3-hydroxyimino-5-methyl-2-hexanone(HIMH) and its dioxime derivative.
Aromatic as well as aliphatic hydrocarbon solvent axonopathy.
Determination of unique microbial volatile organic compounds produced by five Aspergillus species commonly found in problem buildings.
Detection and quantification of ochratoxin A and deoxynivalenol in barley grains by GC-MS and electronic nose.
The generalization of an olfactory-based conditioned response reveals unique but overlapping odour representations in the moth Manduca sexta.
Aroma compounds-proteins interaction using headspace techniques.
Evaluation of individual components of plum odor as potential attractants for adult plum curculios.
Positional effect of solute functional group among positional isomers in hydroxyl group-solvent and carbonyl group-solvent specific interactions in menthanol--water mixed solvents monitored by high-performance liquid chromatography.
Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes.
Regulated workplace ketones and their interference in the PFBHA method for aldehydes.
Modular representations of odorants in the glomerular layer of the rat olfactory bulb and the effects of stimulus concentration.
Effect of aeration during cell growth on ketone reactions by immobilized yeast.
NAD(+)-dependent (S)-specific secondary alcohol dehydrogenase involved in stereoinversion of 3-pentyn-2-ol catalyzed by Nocardia fusca AKU 2123.
Determination of free and glucuronated hexane metabolites without prior hydrolysis by liquid- and gas-chromatography coupled with mass spectrometry.
Evidence for an inducible nucleotide-dependent acetone carboxylase in Rhodococcus rhodochrous B276.
Water activity control: a way to improve the efficiency of continuous lipase esterification.
Determination of n-hexane metabolites by liquid chromatography/mass spectrometry. 2. Glucuronide-conjugated metabolites in untreated urine samples by electrospray ionization.
Determination of n-hexane metabolites by liquid chromatography/mass spectrometry. 1. 2,5-hexanedione and other phase I metabolites in untreated and hydrolyzed urine samples by atmospheric pressure chemical ionization.
Do endogenous volatile organic chemicals measured in breath reflect and maintain CYP2E1 levels in vivo?
Method for the simultaneous quantification of n-hexane metabolites: application to n-hexane metabolism determination.
Toxic effects of hexane derivatives on cultured rat Schwann cells.
In vitro quantitative structure-activity relationship assessment of pyrrole adducts production by gamma-diketone-forming neurotoxic solvents.
Different contributions of cytochrome P450 2E1 and P450 2B1/2 to chloroform hepatotoxicity in rat.
Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.
Induction of chromosome loss in yeast by combined treatment with neurotoxic hexacarbons and monoketones.
Sensory irritation and pulmonary irritation of n-methyl ketones: receptor activation mechanisms and relationships with threshold limit values.
A markedly diminished pleiotropic response to phenobarbital and structurally-related xenobiotics in Zucker rats in comparison with F344/NCr or DA rats.
A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat. Effects of chemicals of varied structure.
Compounds affecting mosquito oviposition: structure-activity relationships and concentration effects.
Immunochemical detection of cytochrome P450 isozymes induced in rat liver by n-hexane, 2-hexanone and acetonyl acetone.
Gonadotoxic effects of 2-hexanone and 1,2-dibromo-3-chloropropane on the enzymatic activity of rat testicular 17 alpha-hydroxylase/C17,20-lyase.
Evidence for the involvement of organelles in the mechanism of ketone-potentiated chloroform-induced hepatotoxicity.
The neurotoxic effect of carbon disulphide, N-hexane and its metabolites studied with erythrocyte and synaptosome membranes in vitro.
Induction of chromosome loss by mixtures of organic solvents including neurotoxins.
Induction of cytochromes P450IIE1 and P450IIB1 by secondary ketones and the role of P450IIE1 in chloroform metabolism.
Synthesis and pheromonal activity of 6,10,13-trimethyl-1-tetradecanol for predatory stink bug,Stiretrus anchorago (Heteroptera: Pentatomidae).
Cytoskeletal changes induced in vitro by 2,5-hexanedione: an immunocytochemical study.
Volatile methyl ketone seed-germination inhibitors fromAmaranthus palmeri S. Wats. Residues.
The relevance of 4,5-dihydroxy-2-hexanone in the excretion kinetics of n-hexane metabolites in rat and man.
The role of biotransformation-detoxication in acetone-, 2-butanone-, and 2-hexanone-potentiated chloroform-induced hepatotoxicity.
Disposition, pharmacokinetics, and metabolism of a dermal dose of [14C]2,5-hexanedione in hens.
4,5-Dihydroxy-2-hexanone: a new metabolite of N-hexane and of 2,5-hexanedione in rat urine.
Modifications in rat hepatobiliary function following treatment with acetone, 2-butanone, 2-hexanone, mirex, or chlordecone and subsequently exposed to chloroform.
Renal and hepatic interactions between 2-hexanone and carbon tetrachloride in F-344 rats.
Impairment of human polymorphonuclear leukocyte chemotaxis by 2,5-hexanedione.
Methodological investigations on the determination of n-hexane metabolites in urine.
Analysis of n-hexane, 2-hexanone, 2,5-hexanedione, and related chemicals by capillary gas chromatography and high-performance liquid chromatography.
The joint neurotoxic action of inhaled methyl butyl ketone vapor and dermally applied O-ethyl O-4-nitrophenyl phenylphosphonothioate in hens: potentiating effect.
Role of intrarenal biotransformation in chloroform-induced nephrotoxicity in rats.
Temporal analysis of rat liver injury following potentiation of carbon tetrachloride hepatotoxicity with ketonic or ketogenic compounds.
Dose-response relationships in ketone-induced potentiation of chloroform hepato- and nephrotoxicity.
Nephrotoxic interactions between ketonic solvents and halogenated aliphatic chemicals.
An electrophysiological study of 2-hexanone and 2,5-hexanedione neurotoxicity in rats.
Mechanisms in 2-hexanone potentiation of chloroform hepatotoxicity.
Anaesthetic action of esters and ketones: evidence for an interaction with the sodium channel protein in squid axons.
2-hexanone potentiation of [14C]chloroform hepatotoxicity: covalent interaction of a reactive intermediate with rat liver phospholipid.
In vitro effect of n-hexane and its metabolites on selected enzymes in glycolysis, pentose phosphate pathway and citric acid cycle.
Relationship between the carbon skeleton length of ketonic solvents and potentiation of chloroform-induced hepatotoxicity in rats.
Ultrastructural studies of the dying-back process. VI. Examination of nerve fibers undergoing giant axonal degeneration in organotypic culture.
[An experimental study on the neurotoxicity of 2-octanone and 2-hexanol, a metabolite of n-hexane].
Neurotoxicity of continuous (90 days) inhalation of technical grade methyl butyl ketone in hens.
Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione.
Microbial Oxidation of Gaseous Hydrocarbons: Production of Methylketones from Corresponding n-Alkanes by Methane-Utilizing Bacteria.
Clinical epidemiology of occupational neurotoxic disease.
Microbial production of methyl ketones. Purification and properties of a secondary alcohol dehydrogenase from yeast.
Oxidation of secondary alcohols to methyl ketones by yeasts.
Simultaneous determination of n-hexane, 2-hexanone and 2,5-hexanedione in biological tissues by gas chromatography mass spectrometry.
Peripheral nervous system in a case of canine giant axonal neuropathy.
The effect of 2-hexanone and 2-hexanone metabolites on pupillomotor activity and growth.
Toxicity and metabolism of methyl n-butyl ketone.
2-hexanone. (Methylbutyl ketone, MBK).
2-Hexanone (methyl-n-butyl ketone, n-butyl methyl ketone, propyl acetone).

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
HMDB (The Human Metabolome Database):	HMDB05842
FooDB:	FDB008079
Export Tariff Code:	2914.19.0000
Typical G.C.
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Formulations/Preparations: •grade: technical •commercial grades of mnbk vary in purity from 70 to 96%; the more dilute grades include predominantly methyl isobutyl ketone (mibk).

Suppliers

Beijing Lys Chemicals	CJ Latta & Associates
Inoue Perfumery	Penta International
Sigma-Aldrich	Synerzine
TCI AMERICA	WholeChem
Beijing Lys Chemicals Co, LTD.	CJ Latta & Associates, LLC
Penta International Corporation	Synerzine, Inc.
WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	100.16084289551
Vapor Pressure	11.6 mmHg @ 25 °C
Flash Point TCC Value	35 °C TCC
logP (o/w)	1.38
Solubility
alcohol	Yes
water, 17500 mg/L @ 20 °C (exp)	Yes
water	No

Organoleptic Properties

Odor Type: Fruity
fruity, fungal, meaty, buttery
General comment	At 1.00 % in dipropylene glycol. fruity fungal meaty buttery

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
T - Toxic.
R 10 - Flammable. R 48/23 - Toxic: danger of serious damage to health by prolonged exposure through inhalation. R 62 - Possible risk of impaired fertility. R 67 - Vapours may cause frowsiness and dizziness. S 02 - Keep out of the reach of children. S 07/09 - Keep container tightly closed and in well-ventilated place. S 16 - Keep away from sources of ignition - No Smoking. S 20/21 - When using do not eat, drink or smoke. S 23 - Do not breath vapour. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2590 mg/kg AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954. oral-mouse LD50 2430 mg/kg Toxicology Letters. Vol. 30, Pg. 13, 1986. unreported-guinea pig LD50 914 mg/kg Personnal Communication from R.L. Raleigh, Assistant Director of Health and Safety Lab., Eastman Kodak Co., Rochester, NY, Mar. 6, 1974Vol. 01MAR1974 oral-guinea pig LDLo 914 mg/kg Personnal Communication from R.L. Raleigh, Assistant Director of Health and Safety Lab., Eastman Kodak Co., Rochester, NY, Mar. 6, 1974Vol. 01MAR1974 unreported-rat LD50 914 mg/kg Personnal Communication from R.L. Raleigh, Assistant Director of Health and Safety Lab., Eastman Kodak Co., Rochester, NY, Mar. 6, 1974Vol. 01MAR1974 intraperitoneal-rat LDLo 914 mg/kg Personnal Communication from R.L. Raleigh, Assistant Director of Health and Safety Lab., Eastman Kodak Co., Rochester, NY, Mar. 6, 1974Vol. 01MAR1974
Dermal Toxicity:
skin-rabbit LD50 4800 mg/kg Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 78, 1974.
Inhalation Toxicity:
inhalation-rat LC50 8000 ppm/4H Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 78, 1974. inhalation-human TCLo 1000 ppm SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: HEADACHE GASTROINTESTINAL: NAUSEA OR VOMITING Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 78, 1974.