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Record Information
Version2.0
Creation Date2014-08-29 05:52:57 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4207
Identification
Common NameEthylene Oxide
ClassSmall Molecule
DescriptionEthylene 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.
Compound Type
  • Cigarette Toxin
  • Ether
  • Flavouring Agent
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,2-Epoxyaethan
1,2-Epoxyethane
Aethylenoxid
alpha,beta-Oxidoethane
Amprolene
Anprolene
Anproline
D.E.R. 732 Epoxy resin
D.E.R. 736 Epoxy resin
Dihydro-Oxirene
Dihydrooxirene
Dimethylene oxide
E.O.
Epoxyethane
Ethene oxide
Ethox
Ethyleenoxide
Ethylene oxide
Ethylene oxide, 8CI
ETO
Etylenu tlenek
FEMA 2433
Merpol
Oxacyclopropane
Oxide, ethylene
Oxidoethane
Oxiraan
Oxiran
Oxirane
Oxyfume
Oxyfume 12
Polypropylene glycol, (chloromethyl)oxirane polymer
Qazi-ketcham
Sterilizing gas ethylene oxide 100%
T-Gas
Chemical FormulaC2H4O
Average Molecular Mass44.053 g/mol
Monoisotopic Mass44.026 g/mol
CAS Registry Number75-21-8
IUPAC Nameoxirane
Traditional Nameethylene oxide
SMILESC1CO1
InChI IdentifierInChI=1S/C2H4O/c1-2-3-1/h1-2H2
InChI KeyInChIKey=IAYPIBMASNFSPL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassNot Available
Direct ParentEpoxides
Alternative Parents
Substituents
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateGas
AppearanceColorless
Experimental Properties
PropertyValue
Melting Point-113 °C
Boiling Point10.7 °C
Solubility1000 mg/mL at 25°C
LogP-0.3
Predicted Properties
PropertyValueSource
Water Solubility294 g/LALOGPS
logP-0.47ALOGPS
logP-0.047ChemAxon
logS0.82ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.04 m³·mol⁻¹ChemAxon
Polarizability4.42 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0002-9000000000-7850335287c5b168b8bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-33b13e6bd63460f9b653JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-2867bc220ce9bf1b323fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-e8991e4190d018f8bd8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-4df8eec690273990ee52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a5c1cb4e821e6122d292JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00ou-9000000000-cd007c0e626a6cf3a55aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureInhalation, Dermal
Mechanism of ToxicityEthylene oxide is an alkylating agent. The addition of alkyl groups to proteins, DNA, and RNA by binding to the sulfhydryl and hydroxyl, amino, and carboxyl groups, prevents normal cellular metabolism and ultimately kills cells. It is likely that the carcinogenicity of ethylene oxide in laboratory animals arises primarily as a result of its direct alkylation of DNA and RNA. In vivo exposure to ethylene oxide induced mutations (5- to 5.6-fold) at the Hprt locus in splenic T-lymphocytes in rats and mice.
MetabolismThe metabolism of ethylene oxide is not completely known. Data from animal studies indicate two possible pathways for the metabolism of ethylene oxide: hydrolysis to ethylene glycol and glutathione conjugation to form mercapturic acid and meththio-metabolites.
Toxicity ValuesEthylene oxide is toxic by inhalation with an U.S. OSHA permissible exposure limit calculated over 8 hours of 1 ppm, and a short term exposure over 15 minutes of 5 ppm.
Lethal DoseLD50 values are 72 mg/kg (rat, oral) and 187 mg/kg (rat, subcutaneous injection)
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (6)
Uses/SourcesEthylene oxide is an industrial chemical that 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. It is also used as a sterilizing agent, a fumigant, a fungicide and as an insecticide. Ethylene oxide ranks 26th in volume among the major industrial chemicals produced in the United States. About 65% of ethylene oxide is used for synthesis of ethylene glycol, an antifreeze product.
Minimum Risk Level<1 ppm
Health EffectsAt high doses (>200 ppm) ethylene oxide irritates mucous membranes of the nose and throat; higher concentrations cause damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause pulmonary edema and damage the cardiovascular system. Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, the gas will already be at toxic concentrations when it can be smelled. Ethylene oxide is carcinogenic, mutagenic and an irritant. With chronic low doses, an increased incidence of brain tumors and mononuclear cell leukemia was found in rats that had inhaled ethylene oxide at concentrations of 10, 33, or 100 mL/m3 over a period of two years. Studies of workers exposed to ethylene oxide in ethylene oxide factories or hospital sterilizing rooms have shown an increased incidence of leukemia, stomach cancer, cancer of the pancreas and Hodgkin's disease.
SymptomsThe major effects seen in workers exposed to ethylene oxide at low levels for several months or years are irritation of the eyes, skin, and mucous membranes and problems in the functioning of the brain and nerves. Acute exposure leads to central nervous system effects. Headache, nausea and vomiting are often evident. Peripheral neuropathy, impaired hand-eye coordination and memory loss have been reported in more recent case studies of chronically-exposed workers at estimated average exposure levels as low as 3 ppm. Ethylene oxide easily penetrates through the clothing and footwear, causing skin irritation and dermatitis with the formation of blisters, fever and leukocytosis. High concentrations can cause pulmonary edema and damage the cardiovascular system.
TreatmentThere is no antidote for ethylene oxide poisoning. Treatment is supportive of respiratory and cardiovascular functions.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6354
ChEMBL IDCHEMBL1743219
ChemSpider ID6114
KEGG IDC06548
UniProt IDNot Available
OMIM ID
ChEBI ID27561
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkOxirane
References
Synthesis ReferenceNot Available
MSDST3D4207.pdf
General References
  1. Boutefnouchet S, Minh NT, Putrus R, Pfeiffer B, Leonce S, Pierre A, Michel S, Tillequin F, Lallemand MC: Synthesis and cytotoxic activity of psorospermin and acronycine analogues in the 3-propyloxy-acridin-9(10H)-one and -benzo[b]acridin-125H-one series. Eur J Med Chem. 2010 Feb;45(2):581-7. doi: 10.1016/j.ejmech.2009.10.045. Epub 2009 Nov 4. [19926174 ]
  2. Ethylene oxide--a review. J Environ Health. 2005 Nov;68(4):50. [16334098 ]
  3. Kolman A, Chovanec M, Osterman-Golkar S: Genotoxic effects of ethylene oxide, propylene oxide and epichlorohydrin in humans: update review (1990-2001). Mutat Res. 2002 Dec;512(2-3):173-94. [12464351 ]
  4. Thier R, Bolt HM: Carcinogenicity and genotoxicity of ethylene oxide: new aspects and recent advances. Crit Rev Toxicol. 2000 Sep;30(5):595-608. [11055837 ]
  5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available