Methyloxirane (CHEM003168)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:53:02 UTC
Update Date2026-04-17 19:01:39 UTC
Accession NumberCHEM003168
Identification
Common NameMethyloxirane
ClassSmall Molecule
DescriptionEtherification agent for food starch. Methyloxirane belongs to the family of Epoxides. These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Cigarette Toxin
  • Ether
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2-Propylene oxideChEBI
2,3-EpoxypropaneChEBI
EpoxypropaneChEBI
MethyloxacyclopropaneChEBI
Propylene oxideChEBI
(+/-)-methyloxiraneHMDB
(+/-)-propylene oxideHMDB
(S)-(-)-Propylene oxideHMDB
1,2-Epoxy-propaneHMDB
1,2-EpoxypropaneHMDB
2-Methyl oxiraneHMDB
2-Methyl-oxiraneHMDB
2-MethyloxiranHMDB
2-MethyloxiraneHMDB
3-Methyl-1,2-epoxypropaneHMDB
AD 6 (suspending agent)HMDB
EpihydrinHMDB
Epoxy-propaneHMDB
Methyl ethylene oxideHMDB
Methyl oxiraneHMDB
Methyl-(S)-oxiraneHMDB
Methyl-ethylene oxideHMDB
Methyl-oxiraneHMDB
Methylethylene oxideHMDB
Oxyde de propyleneHMDB
Propene oxideHMDB
Propylene epoxideHMDB
PropyleneoxideHMDB
S(-)-MethyloxiraneHMDB
Propene epoxideHMDB
MethyloxiraneChEBI
Chemical FormulaC3H6O
Average Molecular Mass58.079 g/mol
Monoisotopic Mass58.042 g/mol
CAS Registry Number75-56-9
IUPAC Name2-methyloxirane
Traditional Namepropylene oxide
SMILESCC1CO1
InChI IdentifierInChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3
InChI KeyGOOHAUXETOMSMM-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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-111.9°C
Boiling PointNot Available
Solubility590 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility201 g/LALOGPS
logP0.04ALOGPS
logP0.37ChemAxon
logS0.54ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.46 m³·mol⁻¹ChemAxon
Polarizability6.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-14a67668e01cd34da6f5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-2809da7584a192d3c952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-e04a808a6c7ea551fe07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6d95bc4ff8c653f74440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-f6193463d18cb059b706Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-fe386cbd774acc334110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ba65edaf304df379c2baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-6e3379842f4da69e8e2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-45e03d09a7c1ac5eac00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-9d4ef0a746c7edc8e992Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-9000000000-7f5c1c6cb93e5f3b85bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-337a1ac0d8b7e346c518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-440ea18042dc425b6ae3Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-75c4313f7dba690a8a68Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (18)
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031558
FooDB IDFDB008171
Phenol Explorer IDNot Available
KNApSAcK IDC00012262
BiGG IDNot Available
BioCyc ID12-EPOXYPROPANE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropylene_oxide
Chemspider ID6138
ChEBI ID38685
PubChem Compound ID6378
Kegg Compound IDC15508
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23803541
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24699862
3. Boyd JM, Clark DD, Kofoed MA, Ensign SA: Mechanism of inhibition of aliphatic epoxide carboxylation by the coenzyme M analog 2-bromoethanesulfonate. J Biol Chem. 2010 Aug 13;285(33):25232-42. doi: 10.1074/jbc.M110.144410. Epub 2010 Jun 15.
4. Chen LJ, Lebetkin EH, Nwakpuda EI, Burka LT: Metabolism and disposition of n-butyl glycidyl ether in F344 rats and B6C3F1 mice. Drug Metab Dispos. 2007 Dec;35(12):2218-24. Epub 2007 Sep 17.
5. Li Y, Li P, Xiao HB, Hu D, Yuan CY: [Detonation temperature measurement of epoxypropane using instantaneous spectrum method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2008 Mar;28(3):490-3.
6. Qian SH, Xiang LJ, Deng HB, Xiao M, Lin H, Li XQ: [Preconcentration of trace Pd (II) on crosslinked chitosan and determination by graphite furnace atomic absorption spectrometry]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Mar;27(3):592-4.
7. Kim KN, Ko YJ, Kang MC, Yang HM, Roh SW, Oda T, Jeon YJ, Jung WK, Heo SJ, Yoon WJ, Kim D: Anti-inflammatory effects of trans-1,3-diphenyl-2,3-epoxypropane-1-one mediated by suppression of inflammatory mediators in LPS-stimulated RAW 264.7 macrophages. Food Chem Toxicol. 2013 Mar;53:371-5. doi: 10.1016/j.fct.2012.12.021. Epub 2012 Dec 21.
8. Krishnakumar AM, Sliwa D, Endrizzi JA, Boyd ES, Ensign SA, Peters JW: Getting a handle on the role of coenzyme M in alkene metabolism. Microbiol Mol Biol Rev. 2008 Sep;72(3):445-56. doi: 10.1128/MMBR.00005-08.
9. Sliwa DA, Krishnakumar AM, Peters JW, Ensign SA: Molecular basis for enantioselectivity in the (R)- and (S)-hydroxypropylthioethanesulfonate dehydrogenases, a unique pair of stereoselective short-chain dehydrogenases/reductases involved in aliphatic epoxide carboxylation. Biochemistry. 2010 Apr 27;49(16):3487-98. doi: 10.1021/bi100294m.
10. Dai R, Nie X, Li H, Saeed MK, Deng Y, Yao G: Investigation of beta-CD-derivatized erythromycin as chiral selector in CE. Electrophoresis. 2007 Aug;28(15):2566-72.
11. Zhao Y, Truhlar DG: How well can new-generation density functionals describe protonated epoxides where older functionals fail? J Org Chem. 2007 Jan 5;72(1):295-8.
12. Olender D, Zwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, Zaprutko L: Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. Eur J Med Chem. 2009 Feb;44(2):645-52. doi: 10.1016/j.ejmech.2008.05.016. Epub 2008 May 28.
13. Luo MF, Wu H, Wang L, Xing XH: [Study on the structure and function of a stable methane-oxidizing mixed microbial consortium]. Wei Sheng Wu Xue Bao. 2007 Feb;47(1):103-9.
14. Li P, Hu D, Yuan CY, Dai SH, Xiao HB: [Using instantaneous spectra to determine dominant species in the DDT process of epoxypropane]. Guang Pu Xue Yu Guang Pu Fen Xi. 2006 Sep;26(9):1569-72.
15. Karmali PP, Chao Y, Park JH, Sailor MJ, Ruoslahti E, Esener SC, Simberg D: Different effect of hydrogelation on antifouling and circulation properties of dextran-iron oxide nanoparticles. Mol Pharm. 2012 Mar 5;9(3):539-45. doi: 10.1021/mp200375x. Epub 2012 Feb 2.
16. Mao W, Zangerl AR, Berenbaum MR, Schuler MA: Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. Insect Biochem Mol Biol. 2008 Jun;38(6):645-51. doi: 10.1016/j.ibmb.2008.03.013. Epub 2008 Apr 9.
17. Owens CR, Karceski JK, Mattes TE: Gaseous alkene biotransformation and enantioselective epoxyalkane formation by Nocardioides sp. strain JS614. Appl Microbiol Biotechnol. 2009 Sep;84(4):685-92. doi: 10.1007/s00253-009-2019-3. Epub 2009 May 9.
18. Rizzo A, Vahtras O: Ab initio study of excited state electronic circular dichroism. Two prototype cases: methyl oxirane and R-(+)-1,1'-bi(2-naphthol). J Chem Phys. 2011 Jun 28;134(24):244109. doi: 10.1063/1.3602219.
19. Li SJ, Sun YL, Hu DD, Chen C, Cui YL: [Preparation of metal chelate affinity chromatographic medium and its application in the purification of 6 x histidine-tagged protein]. Sheng Wu Gong Cheng Xue Bao. 2007 Sep;23(5):941-6.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.