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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:03 UTC
Update Date2019-01-11 19:42:51 UTC
HMDB IDHMDB0031558
Secondary Accession Numbers
  • HMDB31558
Metabolite Identification
Common NameMethyloxirane
DescriptionEtherification agent for food starc
Structure
Data?1547235771
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 epoxideMeSH
Chemical FormulaC3H6O
Average Molecular Weight58.0791
Monoisotopic Molecular Weight58.041864814
IUPAC Name2-methyloxirane
Traditional Namepropylene oxide
CAS Registry Number75-56-9
SMILES
CC1CO1
InChI Identifier
InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3
InChI KeyGOOHAUXETOMSMM-UHFFFAOYSA-N
Chemical Taxonomy
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).
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
Ontology
Disposition

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-111.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590 mg/mL at 25 °CNot Available
LogP0.03Not Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-14a67668e01cd34da6f5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-2809da7584a192d3c952JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-e04a808a6c7ea551fe07JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6d95bc4ff8c653f74440JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-f6193463d18cb059b706JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-fe386cbd774acc334110JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ba65edaf304df379c2baJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-75c4313f7dba690a8a68JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008171
KNApSAcK IDNot Available
Chemspider ID6138
KEGG Compound IDC15508
BioCyc ID12-EPOXYPROPANE
BiGG IDNot Available
Wikipedia LinkPropylene_oxide
METLIN IDNot Available
PubChem Compound6378
PDB IDNot Available
ChEBI ID38685
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. 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. [PubMed:17875671 ]
  3. 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. [PubMed:18536396 ]
  4. 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. [PubMed:17554930 ]
  5. 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. [PubMed:23266270 ]
  6. 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. [PubMed:18772284 ]
  7. 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. [PubMed:20302306 ]
  8. 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. [PubMed:17577196 ]
  9. 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. [PubMed:17194116 ]
  10. 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. [PubMed:18590938 ]
  11. 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. [PubMed:17436634 ]
  12. 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. [PubMed:17112018 ]
  13. 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. [PubMed:22243419 ]
  14. 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. [PubMed:18510976 ]
  15. 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. [PubMed:19430773 ]
  16. 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. [PubMed:21721614 ]
  17. 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. [PubMed:18051879 ]
  18. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .