2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester (CHEM013138)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:08:20 UTC
Update Date2016-10-28 10:03:00 UTC
Accession NumberCHEM013138
Identification
Common Name2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester
ClassSmall Molecule
DescriptionOctocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous, oily liquid that is clear and colorless. The extended conjugation of the acrylate portion of the molecule absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths from 280 to 320 nm, protecting the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.
Contaminant Sources
  • Cosmetic Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
OctocrileneKegg
2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoateMeSH
2-Ethylhexyl 2-cyano-3,3-diphenylacrylateMeSH
2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoic acidGenerator
Chemical FormulaC24H27NO2
Average Molecular Mass361.485 g/mol
Monoisotopic Mass361.204 g/mol
CAS Registry Number6197-30-4
IUPAC Name2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
Traditional Nameoctocrylene
SMILESCCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
InChI KeyFMJSMJQBSVNSBF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.0016 g/LALOGPS
logP6.23ALOGPS
logP6.78ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.58 m³·mol⁻¹ChemAxon
Polarizability41.37 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-8392000000-7df1849d4d11f42cbe19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0090000000-9bc63b566bcc1ee3ee78Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0ue9-0190000000-7bbeb1091ac567157bddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-720e10b4cb30b5c5651aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0090000000-2ae1f0fc8653ed8a26bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0190000000-c9c951db319416b853c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0090000000-a977ff239760b825aa77Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ufr-0490000000-bdacf2f5dfcc29d4d863Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1937000000-e991ddf4a4f445b4a358Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-4922000000-1d813a8f22fad6edc3a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9620000000-bd6cd0d7223337914f86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0759000000-57dbcea9ad84241544f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0951000000-fcb8e4ebdf526eef3704Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v00-6690000000-47a9b34fd363cf122c33Spectrum
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 IDHMDB0255910
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOctocrylene
Chemspider ID21165
ChEBI IDNot Available
PubChem Compound ID22571
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available