Basic Info

Common NameEthylene Oxide(F05282)
2D Structure
Description

Ethylene oxide is also called oxirane. It is a cyclic ether that is a colorless flammable gas at room temperature, with a faintly sweet odor. It is the simplest epoxide known. Because of its special molecular structure, ethylene oxide easily participates in addition reactions; e.g., opening its ring and thus easily polymerizing. Ethylene oxide is a vital industrial chemical with diverse applications, including the manufacture of polysorbate 20 and polyethylene glycol. Ethylene oxide itself is a very hazardous substance: at room temperature it is a flammable, carcinogenic, mutagenic and irritating. It is also an anaesthetic gas with a misleadingly pleasant aroma. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used industrially for making many consumer products as well as non-consumer chemicals and intermediates. Ethylene oxide is important or critical to the production of detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers and other compounds. As a poison gas that leaves no residue on items it contacts, pure ethylene oxide is a disinfectant that is widely used in hospitals and the medical equipment industry to replace steam in the sterilization of heat-sensitive tools and equipment, such as disposable plastic syringes. A very small amount (less than 1%) is used to control insects on stored agricultural products such as nuts and spices.

FRCD IDF05282
CAS Number75-21-8
PubChem CID6354
FormulaC2H4O
IUPAC Name

oxirane

InChI Key

IAYPIBMASNFSPL-UHFFFAOYSA-N

InChI

InChI=1S/C2H4O/c1-2-3-1/h1-2H2

Canonical SMILES

C1CO1

Isomeric SMILES

C1CO1

WikipediaEthylene Oxide
Synonyms
        
            ETHYLENE OXIDE
        
            Dimethylene oxide
        
            Oxirane
        
            Epoxyethane
        
            75-21-8
        
            1,2-Epoxyethane
        
            Oxacyclopropane
        
            Ethene oxide
        
            Amprolene
        
            Anprolene
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassEpoxides
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentEpoxides
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsOxacycle - Ether - Oxirane - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as epoxides. These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Properties

Property NameProperty Value
Molecular Weight44.053
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity10.3
Monoisotopic Mass44.026
Exact Mass44.026
XLogP-0.1
Formal Charge0
Heavy Atom Count3
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9843
Human Intestinal AbsorptionHIA+0.9927
Caco-2 PermeabilityCaco2+0.6925
P-glycoprotein SubstrateNon-substrate0.7751
P-glycoprotein InhibitorNon-inhibitor0.9770
Non-inhibitor0.9887
Renal Organic Cation TransporterNon-inhibitor0.8536
Distribution
Subcellular localizationLysosome0.6046
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8278
CYP450 2D6 SubstrateNon-substrate0.8788
CYP450 3A4 SubstrateNon-substrate0.7756
CYP450 1A2 InhibitorNon-inhibitor0.6504
CYP450 2C9 InhibitorNon-inhibitor0.8496
CYP450 2D6 InhibitorNon-inhibitor0.9507
CYP450 2C19 InhibitorNon-inhibitor0.7836
CYP450 3A4 InhibitorNon-inhibitor0.9899
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9308
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9165
Non-inhibitor0.9732
AMES ToxicityAMES toxic0.9415
CarcinogensNon-carcinogens0.6668
Fish ToxicityLow FHMT0.9712
Tetrahymena Pyriformis ToxicityLow TPT0.8524
Honey Bee ToxicityHigh HBT0.7481
BiodegradationReady biodegradable0.8194
Acute Oral ToxicityII0.7313
Carcinogenicity (Three-class)Warning0.5215

Model Value Unit
Absorption
Aqueous solubility0.0900LogS
Caco-2 Permeability1.8709LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7557LD50, mol/kg
Fish Toxicity2.8540pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.2076pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
SpiceNew Zealand20mg/kg

References

TitleJournalDatePubmed ID
Binary mixtures of alcohol ethoxylates, nonylphenol ethoxylates and pesticidesexhibit comparative bioactivity against three pests and toxicological risks toaquatic organisms.Chemosphere2018 Aug29649663
Nanoemulsions containing octyl methoxycinnamate and solid particles of TiO₂:preparation, characterization and in vitro evaluation of the solar protectionfactor.Drug Dev Ind Pharm2013 Sep22998354
Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae).J Econ Entomol2010 Dec21309226
Sterilization of ginseng using a high pressure CO2 at moderate temperatures.Biotechnol Bioeng2009 Feb 118726960
Experimental microbial contamination and disinfection of dry (vapour) shipperdewars designed for short-term storage and transportation of cryopreservedgermplasm and other biological specimens.Theriogenology2005 Apr 1515823351
Investigating the molecular heterogeneity of polysorbate emulsifiers by MALDI-TOFMS.J Agric Food Chem2001 Jul11453772
Assessment of parameters associated to the risk of PVC catheter reuse.J Biomed Mater Res200111505424
Safety and efficacy of hydrogen peroxide plasma sterilization for repeated use of electrophysiology catheters.J Am Coll Cardiol1998 Nov9809952
[Risk evaluation and health surveillance in hospitals: a critical review andcontributions regarding experience obtained at the S. Gerardo dei TintoriHospital in Monza].Med Lav1998 Jan-Feb9608194
Reactions of epoxide monomers in food simulants used to test plastics for migration.Food Addit Contam1997 Jan9059585
Mutation and enhanced virus transformation of cultured hamster cells by exposure to gaseous ethylene oxide.Environ Mutagen19863943498
Ethylene oxide.IARC Monogr Eval Carcinog Risk Chem Hum1985 Feb3864733
FDA prepares response to questions on sponge safety.Contracept Technol Update1983 Sep12312835
Growth response of weanling rats to heated, aged, fractionated, and chemically treated yogurts.J Dairy Sci1980 Jul7419768
The effect of feeding corn molded with Penicillium lanosum to broiler chicks.Poult Sci1980 Apr7375420
Fumigation of jute bags with ethylene oxide and methyl bromide to eradicate potato ring rot bacteria.Appl Microbiol1962 Sep13982125