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Record Information
Version2.0
Creation Date2009-07-30 17:59:02 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3523
Identification
Common NameMethyl ethyl ketone peroxide
ClassSmall Molecule
DescriptionMethyl 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)
Compound Type
  • Explosive Agent
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2-Butanone peroxide
2-Butanone peroxide (Luperox(R) DDM-9) solution
2-Butanone peroxide (Luperox(R) Delta X-9) solution
2-Butanone peroxide (Luperox(R) DHD-9) solution
2-Butanone peroxide solution
2-Butanone, peroxide
Butanox LPT
Butanox M 105
Butanox M 50
Chaloxyd MEKP HA 1
Chaloxyd MEKP-HA 1
Chaloxyd MEKP-LA 1
dioxydibutane-2,2-diyl dihydroperoxide
Esperfoam FR
Ethyl methyl ketone peroxide
HI-Point 180
HI-Point 90
HI-Point PD-1
Kayamek a
Kayamek m
Ketonox
Lucidol DDM 9
Lupersol DDA 30
Lupersol DDM
Lupersol del
Lupersol DNF
Lupersol DSW
Mek peroxide
MEKP
Mekpo
Mepox
Methyl ethyl ketone hydroperoxide
Methyl ethyl ketone peroxide
Methyl ethyl ketone peroxide solution
Methylethylketonhydroperoxide
Permek g
Permek n
Quickset extra
Quickset super
RCRA waste no. U160
RCRA waste number U160
Sprayset mekp
Superox 46-710
Thermacure
Trigonox M 50
Chemical FormulaC8H18O6
Average Molecular Mass210.225 g/mol
Monoisotopic Mass210.110 g/mol
CAS Registry Number1338-23-4
IUPAC Name2-[(2-hydroperoxybutan-2-yl)peroxy]butane-2-peroxol
Traditional Namemethyl ethyl ketone peroxide
SMILESCCC(C)(OO)OOC(C)(CC)OO
InChI IdentifierInChI=1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3
InChI KeyInChIKey=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-.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic hydroperoxides
Sub ClassNot Available
Direct ParentOrganic hydroperoxides
Alternative Parents
Substituents
  • Dialkyl peroxide
  • Hydroperoxide
  • Alkyl hydroperoxide
  • Peroxol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless, oily liquid. (1)
Experimental Properties
PropertyValue
Melting Point-8°C (265°K, 18°F)
Boiling Point109 °C (382°K, 228 °F)
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.1 g/LALOGPS
logP1.45ALOGPS
logP2.28ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)11.27ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.38 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity47.66 m³·mol⁻¹ChemAxon
Polarizability20.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-8910000000-7f6861858aedd790f3f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9200000000-04147036a8bcb00d5769JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-9100000000-9f931cca86833bd07940JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5690000000-5486055835347600b63eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kg9-9710000000-9806ded99c9b6ca61485JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-b41c155f6435f9ea8426JSpectraViewer
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityMEPK toxicity could occur through lipid peroxidation. (2)
MetabolismNot Available
Toxicity ValuesLD50: 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 DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIn 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 LevelNot Available
Health EffectsMEKP 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)
SymptomsSymptoms 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)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID3672772
ChEMBL IDCHEMBL1562553
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMethyl ethyl ketone peroxide
PDB IDNot Available
ACToR ID3949
Wikipedia LinkMethyl_ethyl_ketone_peroxide
References
Synthesis ReferenceNot Available
MSDST3D3523.pdf
General References
  1. Wikipedia. Methyl ethyl ketone peroxide. Last Updated 22 January 2009. [Link]
  2. National Toxicity Program (1993). Toxicity report number 18. Methyl ethyl ketone peroxide in dimethyl phtalate. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available