trans-Permethrin (CHEM020854)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:30:10 UTC
Update Date2016-11-09 01:17:18 UTC
Accession NumberCHEM020854
Identification
Common Nametrans-Permethrin
ClassSmall Molecule
Descriptiontrans-Permethrin with configuration 1S,3R.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1S-trans-PermethrinChEBI
(3-Phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acidGenerator
NRDC147MeSH
NittiforMeSH
cis PermethrinMeSH
Permethrin, (1S-cis)-isomerMeSH
Permethrin, (trans)-isomerMeSH
NRDC 147MeSH
Permethrin, (1R-trans)-isomerMeSH
Permethrin, trans-(1Rs)-isomerMeSH
trans PermethrinMeSH
(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH
3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH
Permethrin, (1R-cis)-isomerMeSH
Permethrin, cis-(1Rs)-isomerMeSH
NRDC-147MeSH
Permethrin, (trans-(+-))-isomerMeSH
trans-PermethrinMeSH
NRDC143MeSH
PermethrinMeSH
Permethrin, (1S-trans)-isomerMeSH
cis-(1Rs)-PermethrinMeSH
3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, esterMeSH
NRDC 143MeSH
Permethrin, (cis)-isomerMeSH
Permethrin, (cis-(+-))-isomerMeSH
trans-(1Rs)-PermethrinMeSH
AmbushMeSH
ElimiteMeSH
NRDC-143MeSH
cis-PermethrinMeSH
Chemical FormulaC21H20Cl2O3
Average Molecular Mass391.290 g/mol
Monoisotopic Mass390.079 g/mol
CAS Registry Number61949-77-7
IUPAC Name(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameelimite
SMILES[H][C@]1(C=C(Cl)Cl)[C@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C
InChI IdentifierInChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19+/m0/s1
InChI KeyRLLPVAHGXHCWKJ-PKOBYXMFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Chloroalkene
  • Haloalkene
  • Ether
  • Vinyl halide
  • Monocarboxylic acid or derivatives
  • Vinyl chloride
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.9e-05 g/LALOGPS
logP6.24ALOGPS
logP5.7ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.28 m³·mol⁻¹ChemAxon
Polarizability40.02 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-fdac422c546f05b83cebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1709000000-f755eb7d0bee859d0bb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-97e9860533a91746241dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0519000000-0f6eb9a687fe3c0d66c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1923000000-a400c6833ac566d7a622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-2900000000-7758be41aece58f5d5d1Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-13112
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID62523
PubChem Compound ID40159
Kegg Compound IDC19864
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15123619
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19581484