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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:05 UTC
Update Date2019-07-23 07:17:20 UTC
HMDB IDHMDB0061861
Secondary Accession Numbers
  • HMDB61861
Metabolite Identification
Common NameOctyl 4-methoxycinnamic acid
DescriptionOctyl 4-methoxycinnamic acid, also known as parsol or 2-ethylhexyl-4-methoxycinnamate, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Octyl 4-methoxycinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Its use in pharmaceutical and cosmetic formulations is approved by FDA. Acts as a photoprotective agent that protects the skin by preventing and minimizing the damaging effects of ultraviolet (UV) rays of natural light. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. Like any other photoprotective agents, octinoxate prevents the damage to cells and deoxyribonucleic acid (DNA) by reducing the p53 protein expression following UV exposure and also increases the skin's tolerability to UV rays . UV-induced molecular breakdown of octinoxate may interfere with cellular processes or induce oxidative damage in human skin . Can be enzymatically degraded by lipases in the stratum corneum where esters undergo hydrolysis . Octinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. Absorbs UV-B (predominantly) and UV-A rays while accumulating in the outermost layer of the epidermis.
Structure
Data?1563866240
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 Weight290.3972
Monoisotopic Molecular Weight290.188194698
IUPAC Name2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate
Traditional Nameparsol
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC
InChI Identifier
InChI=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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-9530000000-dfb5bc7b1b0717378513Spectrum
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09496
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5355130
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee GS, Widjaja A, Ju YH: Enzymatic synthesis of cinnamic acid derivatives. Biotechnol Lett. 2006 Apr;28(8):581-5. [PubMed:16614896 ]