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Showing Compound Caffeic acid ethyl ester (FDB000243)

Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2019-11-26 02:54:35 UTC
Primary IDFDB000243
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeic acid ethyl ester
DescriptionCaffeic acid ethyl ester, also known as (E)-ethyl 3,4-dihydroxycinnamate or (E)-ethyl caffeate, belongs to coumaric acids and derivatives class of compounds. Those 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. Caffeic acid ethyl ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ethyl ester can be found in eggplant and vinegar, which makes caffeic acid ethyl ester a potential biomarker for the consumption of these food products. Ethyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring organic compound .
CAS Number102-37-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl esterbiospider
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl esterbiospider
3-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl esterbiospider
3,4-Dihydroxycinnamic acid, ethyl esterbiospider
Caffeic acid phenethyl esterbiospider
Phenethyl caffeatebiospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12O4
IUPAC nameethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
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
Isomeric SMILESCCOC(=O)\C=C\C1=CC(O)=C(O)C=C1
Average Molecular Weight208.2106
Monoisotopic Molecular Weight208.073558872
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.56HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCaffeic acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g0-2900000000-c16a5811eae4cc57741aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1890000000-bac15703d62d288bae8b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-3910000000-851348d6ede6824013752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-447a54bed40ab435643f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2790000000-8a20e8b5192c8f9ba3f12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-3920000000-a5cfde27b3fb97857e9e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-4900000000-1f4744d8c108b7f47fc02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0950000000-d2c1d1796989e2b3fe1a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-0910000000-a4f99bb22be28136622c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-6900000000-94a781fc016decb68ef52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-70f10da8be018d1b5add2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-7ab4f3330a50bf996fba2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001u-2900000000-86fade974acbd7c347002021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10484
Pubchem Compound ID5317238
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID473
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDETHYL-CAFFEATE
BIGG IDNot Available
KNApSAcK IDC00030221
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.