ContaminantDB: Methyl ethyl ketone peroxide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:59:02 UTC

Update Date

2016-11-09 01:08:53 UTC

Accession Number

CHEM002526

Identification

Common Name

Methyl ethyl ketone peroxide

Class

Small Molecule

Description

Methyl ethyl ketone peroxide (MEKP) is an unstable organic peroxide used in the manufacture of acrylic resins, as a hardening agent for fiberglass-reinforced plastics, and as a curing agent for unsaturated polyester resins. It is commercially available as a 40% to 60% solution in dimethyl phthalate (DMP). MEKP is a severe skin irritant and can cause progressive corrosive damage or blindness. (1) (2)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
OECD HPV Chemicals
OSHA Hazardous Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Explosive Agent
Household Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl ethyl ketone peroxide	MeSH
Ketonox	MeSH

Chemical Formula

C₈H₁₈O₆

Average Molecular Mass

210.225 g/mol

Monoisotopic Mass

210.110 g/mol

CAS Registry Number

1338-23-4

IUPAC Name

2-[(2-hydroperoxybutan-2-yl)peroxy]butane-2-peroxol

Traditional Name

methyl ethyl ketone peroxide

SMILES

CCC(C)(OO)OOC(C)(CC)OO

InChI Identifier

InChI=1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3

InChI Key

WFUGQJXVXHBTEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic hydroperoxides. These are organic compounds comprising the hydroperoxide functional group, with the general formula [O-O]2-.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic hydroperoxides

Sub Class

Not Available

Direct Parent

Organic hydroperoxides

Alternative Parents

Substituents

Dialkyl peroxide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless, oily liquid. (1)

Experimental Properties

Property	Value
Melting Point	-8°C (265°K, 18°F)
Boiling Point	109 °C (382°K, 228 °F)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	18.1 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.28	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	47.66 m³·mol⁻¹	ChemAxon
Polarizability	20.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9500000000-de6f5b13da7ca43b16bc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-8910000000-7f6861858aedd790f3f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-9200000000-04147036a8bcb00d5769	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-9100000000-9f931cca86833bd07940	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-5690000000-5486055835347600b63e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kg9-9710000000-9806ded99c9b6ca61485	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-b41c155f6435f9ea8426	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9010000000-d8dbadac1ef368b3071e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-eaf111dd55d88fc7a711	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-3f057785e536903a657c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-9430000000-5fb30eccdaa47253817d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-9210000000-48110e6f35bf809e5c49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9000000000-5f030ec36d90cdd6120e	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (2) ; inhalation (2) ; dermal (2)

Mechanism of Toxicity

MEPK toxicity could occur through lipid peroxidation. (2)

Metabolism

Not Available

Toxicity Values

LD50: 65 mg/kg (Intraperitoneal, Rat) (2) LD50: 484 mg/kg (Oral, Rat) (2) LC50: 200 mg/kg (Inhalation, Rat) (2) LC50: 170 mg/kg (Inhalation, Mouse) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

In the work environment, human exposure to MEKP occurs by inhalation of, and dermal exposure to, aerosolized MEKP during the spraying procedure used in some manufacturing processes, or by dermal exposure to the liquid substance. (2)

Minimum Risk Level

Not Available

Health Effects

MEKP is highly irritating and corrosive to skin and mucous membranes. A number of cases in which people accidentally or deliberately ingested MEKP solutions, occasionally with fatal results, have been reported. (2)

Symptoms

Symptoms of acute MEKP poisoning by ingestion have included gastrointestinal bleeding, abdominal bums, necrosis, perforation of the stomach, stricture of the esophagus, severe metabolic acidosis, rapid hepatic failure, rhabdomyolysis, and respiratory insufficiency. Temporary cardiac arrest and toxic myocarditis have also been reported. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0245041

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Methyl ethyl ketone peroxide

Chemspider ID

2905622

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Methyl ethyl ketone peroxide (CHEM002526)

Structure for CHEM002526: Methyl ethyl ketone peroxide