T3DB: Methyl ethyl ketone peroxide

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

Record Information

Version

2.0

Creation Date

2009-07-30 17:59:02 UTC

Update Date

2014-12-24 20:26:07 UTC

Accession Number

T3D3523

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)

Compound Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

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 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

InChIKey=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
LogP	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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9500000000-de6f5b13da7ca43b16bc	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-8910000000-7f6861858aedd790f3f4	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-9200000000-04147036a8bcb00d5769	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-9100000000-9f931cca86833bd07940	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-5690000000-5486055835347600b63e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kg9-9710000000-9806ded99c9b6ca61485	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-b41c155f6435f9ea8426	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9010000000-d8dbadac1ef368b3071e	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-eaf111dd55d88fc7a711	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-3f057785e536903a657c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-9430000000-5fb30eccdaa47253817d	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-9210000000-48110e6f35bf809e5c49	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9000000000-5f030ec36d90cdd6120e	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-12	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

3672772

ChEMBL ID

CHEMBL1562553

ChemSpider ID

Not Available

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Methyl ethyl ketone peroxide

PDB ID

Not Available

ACToR ID

3949

Wikipedia Link

Methyl_ethyl_ketone_peroxide

References

Synthesis Reference

Not Available

MSDS

T3D3523.pdf

General References

Wikipedia. Methyl ethyl ketone peroxide. Last Updated 22 January 2009. [Link]
National Toxicity Program (1993). Toxicity report number 18. Methyl ethyl ketone peroxide in dimethyl phtalate. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Methyl ethyl ketone peroxide (T3D3523)

Structure for T3D3523: Methyl ethyl ketone peroxide