2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester (CHEM012751)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:01:15 UTC
Update Date2016-10-28 10:03:00 UTC
Accession NumberCHEM012751
Identification
Common Name2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester
ClassSmall Molecule
DescriptionOctinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. It is often combined with nanoparticles or other water-resistant liposomes in formulations to increase the localization at the epidermis and decrease the risk of percutaneous absorption. Its use in pharmaceutical and cosmetic formulations is approved by FDA.
Contaminant Sources
  • Cosmetic Chemicals
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Octyl methoxycinnamateKegg
ParsolKegg
Octyl methoxycinnamic acidGenerator
Octyl 4-methoxycinnamateGenerator
OCTINOXic acidHMDB
Heliopan newHMDB
OMC cinnamateHMDB
Parsol MCXHMDB
OctylmethoxycinnamateHMDB
2-Ethylhexyl-4-methoxycinnamateHMDB
2-Ethylhexyl-p-methoxycinnamateHMDB
Escalol 557HMDB
Octyl-methoxycinnamateHMDB
Chemical FormulaC18H26O3
Average Molecular Mass290.397 g/mol
Monoisotopic Mass290.188 g/mol
CAS Registry Number5466-77-3
IUPAC Name2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate
Traditional Nameparsol
SMILES[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC
InChI IdentifierInChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+
InChI KeyYBGZDTIWKVFICR-JLHYYAGUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentCinnamic acid esters
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • 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 Solubility0.00045 g/LALOGPS
logP5.62ALOGPS
logP5.38ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.44 m³·mol⁻¹ChemAxon
Polarizability34.84 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-9530000000-dfb5bc7b1b0717378513Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001i-0900000000-d4a1e41c086413d0cf67Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001i-0900000000-47b5b9c89e092811dc9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0900000000-f61c750cc4eee5641214Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-bef6ca3443465e6c192eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0900000000-9b48952b6721ccf2a0d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-04c530c6956b0f1f054fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0950000000-7c75a171098f061df1d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3910000000-999432b0b3a154dc16c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r6-9400000000-f0de61dd27ceae8cac50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-0970000000-9b1d54a8c418b0e3d7ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-0910000000-29fe696309912eb4ba3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r2-3900000000-58e02602b0c98e57a09cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r6-4970000000-a670cd89d51c4faa0f4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08ir-5910000000-378dcd5411abe5d4d831Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9200000000-9025b50b69c626ee01d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0790000000-dffcbb803f602e4748f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0920000000-f1683c652bffc0f2fcadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-17d9a346b3a4b2ac552fSpectrum
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 IDDB09496
HMDB IDHMDB0061861
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5355130
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lee GS, Widjaja A, Ju YH: Enzymatic synthesis of cinnamic acid derivatives. Biotechnol Lett. 2006 Apr;28(8):581-5.