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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:02:10 UTC
Update Date2019-01-11 19:48:07 UTC
HMDB IDHMDB0034232
Secondary Accession Numbers
  • HMDB34232
Metabolite Identification
Common Name(Chloromethyl)oxirane
Description(Chloromethyl)oxirane is used for cross-linking dextrose units in food starc
Structure
Data?1547236087
Synonyms
ValueSource
(Chloromethyl)ethylene oxideChEBI
(RS)-3-chloro-1,2-EpoxypropaneChEBI
1-chloro-2,3-EpoxypropaneChEBI
2,3-Epoxypropyl chlorideChEBI
3-chloro-1,2-EpoxypropaneChEBI
alpha-EpichlorohydrinChEBI
ChloromethyloxiraneChEBI
gamma-Chloropropylene oxideChEBI
a-EpichlorohydrinGenerator
α-epichlorohydrinGenerator
g-Chloropropylene oxideGenerator
γ-chloropropylene oxideGenerator
(+/-)-2-(chloromethyl)oxiraneHMDB
(+/-)-epichlorohydrinHMDB
(Chloromethyl)-oxiraneHMDB
(DL)-alpha-EpichlorohydrinHMDB
1,2-Epoxy-3-chloropropaneHMDB
1-chloro-2,3-Epoxy proponeHMDB
1-chloro-2,3-Epoxy-propaneHMDB
2-(Chloromethyl)-oxiraneHMDB
2-(Chloromethyl)oxiraneHMDB
3-chloro-1,2-Propylene oxideHMDB
3-chloro-Propylene oxideHMDB
3-Chloropropene-1,2-oxideHMDB
3-Chloropropyl epoxideHMDB
3-Chloropropylene oxideHMDB
Allyl chloride oxideHMDB
chloro-1,2-EpoxypropaneHMDB
chloro-1,2-Propylene oxideHMDB
chloro-2,3-EpoxypropaneHMDB
Chloropropene-1,2-oxideHMDB
Chloropropyl epoxideHMDB
ChloropropyleneHMDB
Chloropropylene oxideHMDB
DL-a-EpichlorohydrinHMDB
Epi-chlorohydrinHMDB
EpichloorhydrineHMDB
EpichlorhydrinHMDB
EpichlorhydrineHMDB
EpichlorohydrinHMDB
EpichlorophydrinHMDB
Epoxy-3-chloropropaneHMDB
Epoxypropyl chlorideHMDB
Glycerol epichlorhydrinHMDB
Glycerol epichlorohydrinHMDB
Glycidyl chlorideHMDB
Epichlorohydrin, (+-)-isomerMeSH
Epichlorohydrin, (S)-isomerMeSH
Chemical FormulaC3H5ClO
Average Molecular Weight92.524
Monoisotopic Molecular Weight92.002892489
IUPAC Name2-(chloromethyl)oxirane
Traditional Nameepichlorohydrin
CAS Registry Number106-89-8
SMILES
ClCC1CO1
InChI Identifier
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
InChI KeyBRLQWZUYTZBJKN-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
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-57.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility65.9 mg/mL at 25 °CNot Available
LogP0.45Not Available
Predicted Properties
PropertyValueSource
Water Solubility71.8 g/LALOGPS
logP0.35ALOGPS
logP0.68ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.06 m³·mol⁻¹ChemAxon
Polarizability8.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-2522505dfae837fe94b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-b6bb0cdac54d9608a8c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-593f62fd67709fb160bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-aa2e1dcd9bf189b5f3f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-9ba5e5c03ddff67e1a87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-5463bc269c8f0a27e94dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-bfcd9dffcd4d2de9041aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a6r-9000000000-cf79f4df316c1a34590cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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 IDFDB012543
KNApSAcK IDNot Available
Chemspider ID13837112
KEGG Compound IDC14449
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpichlorohydrin
METLIN IDNot Available
PubChem Compound7835
PDB IDNot Available
ChEBI ID37144
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cizmarikova R, Racanska E, Misikova E, Greksakova O: [Preparation and anticonvulsant activity of new potential beta-adrenoreceptor blockers]. Ceska Slov Farm. 1998 Sep;47(5):220-4. [PubMed:9818476 ]
  2. Ensign SA: Aliphatic and chlorinated alkenes and epoxides as inducers of alkene monooxygenase and epoxidase activities in Xanthobacter strain Py2. Appl Environ Microbiol. 1996 Jan;62(1):61-6. [PubMed:8572713 ]
  3. Bao YT, Loeppky RN: Blocking nitrosamine formation with polymers. Chem Res Toxicol. 1991 May-Jun;4(3):382-9. [PubMed:1912324 ]
  4. Small FJ, Tilley JK, Ensign SA: Characterization of a new pathway for epichlorohydrin degradation by whole cells of xanthobacter strain py2. Appl Environ Microbiol. 1995 Apr;61(4):1507-13. [PubMed:16535000 ]
  5. Getautis V, Daskeviciene M, Malinauskas T, Stanisauskaite A, Stumbraite J: An efficient scalable synthesis of 2,3-epoxypropyl phenylhydrazones. Molecules. 2006 Jan 31;11(1):64-71. [PubMed:17962747 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .