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Showing metabocard for (Chloromethyl)oxirane (HMDB0034232)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:02:10 UTC
Update Date2023-02-21 17:24:03 UTC
HMDB IDHMDB0034232
Secondary Accession Numbers
  • HMDB34232
Metabolite Identification
Common Name(Chloromethyl)oxirane
Description(Chloromethyl)oxirane, also known as alpha-epichlorohydrin or 1-chloro-2,3-epoxypropane, 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). Based on a literature review a significant number of articles have been published on (Chloromethyl)oxirane.
Structure
Data?1677000243
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034232 ((Chloromethyl)oxirane)


  Mrv1652305261923502D          

  5  5  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
M  END
Download

3D MOL for HMDB0034232 ((Chloromethyl)oxirane)

HMDB0034232
     RDKit          3D
(Chloromethyl)oxirane
 10 10  0  0  0  0  0  0  0  0999 V2000
    2.6652   -0.2277   -0.2455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.4250    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -0.4477   -0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.0754   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636   -1.2387    0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    0.6336    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    1.4222   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -0.8982   -1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.2144   -0.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.6212    0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  3  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
M  END
Download

3D SDF for HMDB0034232 ((Chloromethyl)oxirane)


  Mrv1652305261923502D          

  5  5  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034232

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCC1CO1

> <INCHI_IDENTIFIER>
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2

> <INCHI_KEY>
BRLQWZUYTZBJKN-UHFFFAOYSA-N

> <FORMULA>
C3H5ClO

> <MOLECULAR_WEIGHT>
92.524

> <EXACT_MASS>
92.002892489

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
8.381723948729508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(chloromethyl)oxirane

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.6772814056666667

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.187369150675658

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
20.057

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epichlorohydrin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0034232 ((Chloromethyl)oxirane)

HMDB0034232
     RDKit          3D
(Chloromethyl)oxirane
 10 10  0  0  0  0  0  0  0  0999 V2000
    2.6652   -0.2277   -0.2455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.4250    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -0.4477   -0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.0754   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636   -1.2387    0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    0.6336    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    1.4222   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -0.8982   -1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.2144   -0.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.6212    0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  3  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
M  END
Download

PDB for HMDB0034232 ((Chloromethyl)oxirane)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -0.889   3.969   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0      -0.325   0.325   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    5                                                  
CONECT    4    1                                                            
CONECT    5    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    5    0   10    0
END
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3D PDB for HMDB0034232 ((Chloromethyl)oxirane)

COMPND    HMDB0034232
HETATM    1 CL1  UNL     1       2.665  -0.228  -0.245  1.00  0.00          CL  
HETATM    2  C1  UNL     1       1.087   0.425   0.238  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.009  -0.448  -0.296  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.379  -0.075  -0.004  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.764  -1.239   0.541  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.021   0.634   1.313  1.00  0.00           H  
HETATM    7  H2  UNL     1       0.993   1.422  -0.281  1.00  0.00           H  
HETATM    8  H3  UNL     1       0.204  -0.898  -1.279  1.00  0.00           H  
HETATM    9  H4  UNL     1      -2.142  -0.214  -0.782  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.678   0.621   0.794  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    6    7
CONECT    3    4    5    8
CONECT    4    5    9   10
END
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SMILES for HMDB0034232 ((Chloromethyl)oxirane)

ClCC1CO1
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INCHI for HMDB0034232 ((Chloromethyl)oxirane)

InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
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View in JSmolView NMR AssignmentsView Stereo Labels
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
EpichlorhydrinHMDB
Epichlorohydrin, (+-)-isomerHMDB
Epichlorohydrin, (S)-isomerHMDB
(+/-)-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
EpichlorhydrineHMDB
EpichlorohydrinHMDB
EpichlorophydrinHMDB
Epoxy-3-chloropropaneHMDB
Epoxypropyl chlorideHMDB
Glycerol epichlorhydrinHMDB
Glycerol epichlorohydrinHMDB
Glycidyl chlorideHMDB
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
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
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleEnvironmental role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-57.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility65.9 mg/mL at 25 °CNot Available
LogP0.45Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+124.62530932474
DeepCCS[M-H]-122.7330932474
DeepCCS[M-2H]-158.14130932474
DeepCCS[M+Na]+132.54730932474
AllCCS[M+H]+120.632859911
AllCCS[M+H-H2O]+115.632859911
AllCCS[M+NH4]+125.232859911
AllCCS[M+Na]+126.532859911
AllCCS[M-H]-125.732859911
AllCCS[M+Na-2H]-130.332859911
AllCCS[M+HCOO]-135.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Chloromethyl)oxiraneClCC1CO11186.2Standard polar33892256
(Chloromethyl)oxiraneClCC1CO1656.9Standard non polar33892256
(Chloromethyl)oxiraneClCC1CO1744.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Chloromethyl)oxirane GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-2522505dfae837fe94b42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Chloromethyl)oxirane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Chloromethyl)oxirane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-9000000000-cf79f4df316c1a34590c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 10V, Positive-QTOFsplash10-0006-9000000000-b6bb0cdac54d9608a8c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 20V, Positive-QTOFsplash10-0006-9000000000-593f62fd67709fb160bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 40V, Positive-QTOFsplash10-0a4i-9000000000-aa2e1dcd9bf189b5f3f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 10V, Negative-QTOFsplash10-0006-9000000000-9ba5e5c03ddff67e1a872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 20V, Negative-QTOFsplash10-0a4l-9000000000-5463bc269c8f0a27e94d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 40V, Negative-QTOFsplash10-0a4i-9000000000-bfcd9dffcd4d2de9041a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 10V, Positive-QTOFsplash10-00dl-9000000000-c5367172f332120538f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 20V, Positive-QTOFsplash10-03di-9000000000-d48e553dccbe6be572e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 40V, Positive-QTOFsplash10-03di-9000000000-04ef6303d628f7046a2d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 10V, Negative-QTOFsplash10-001i-9000000000-b0c837ec56b2dada1b502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Chloromethyl)oxirane 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .