Caffeic acid ethyl ester (CHEM022950)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:45:14 UTC
Update Date2016-11-09 01:17:36 UTC
Accession NumberCHEM022950
Identification
Common NameCaffeic acid ethyl ester
ClassSmall Molecule
DescriptionAn ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-Ethyl 3,4-dihydroxycinnamateChEBI
(e)-Ethyl 3-(3,4-dihydroxyphenyl)acrylateChEBI
(e)-Ethyl caffeateChEBI
Ethyl (2E)-3-(3,4-dihydroxyphenyl)acrylateChEBI
Ethyl 3,4-dihydroxycinnamateChEBI
Ethyl caffeateChEBI
(e)-Ethyl 3,4-dihydroxycinnamic acidGenerator
(e)-Ethyl 3-(3,4-dihydroxyphenyl)acrylic acidGenerator
(e)-Ethyl caffeic acidGenerator
Ethyl (2E)-3-(3,4-dihydroxyphenyl)acrylic acidGenerator
Ethyl 3,4-dihydroxycinnamic acidGenerator
Ethyl caffeic acidGenerator
Ethyl trans-caffeic acidGenerator
Ethyl 1-(3'4'-dihydroxyphenyl)propenateChEMBL
Ethyl 1-(3'4'-dihydroxyphenyl)propenic acidGenerator
Ethyl cinnamic acid,3,4-dihydroxyGenerator
Caffeate ethyl esterGenerator
Ethyl trans-caffeateMeSH
Chemical FormulaC11H12O4
Average Molecular Mass208.211 g/mol
Monoisotopic Mass208.074 g/mol
CAS Registry NumberNot Available
IUPAC Nameethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Nameethyl cinnamate,3,4-dihydroxy
SMILESCCOC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+
InChI KeyWDKYDMULARNCIS-GQCTYLIASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • 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 Solubility0.81 g/LALOGPS
logP2.6ALOGPS
logP2.26ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.54 m³·mol⁻¹ChemAxon
Polarizability21.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-2900000000-c16a5811eae4cc57741aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1890000000-bac15703d62d288bae8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-3910000000-851348d6ede682401375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-447a54bed40ab435643fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2790000000-8a20e8b5192c8f9ba3f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-3920000000-a5cfde27b3fb97857e9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-4900000000-1f4744d8c108b7f47fc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0950000000-d2c1d1796989e2b3fe1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-0910000000-a4f99bb22be28136622cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-6900000000-94a781fc016decb68ef5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-70f10da8be018d1b5addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-7ab4f3330a50bf996fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001u-2900000000-86fade974acbd7c34700Spectrum
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 IDHMDB0301712
FooDB IDFDB000243
Phenol Explorer IDNot Available
KNApSAcK IDC00030221
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthyl_caffeate
Chemspider ID4476132
ChEBI ID132714
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16041399
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19813225
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23050660
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24892518
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7334427