Caffeic acid ethyl ester (CED0010396)

Record Information
Version1.0
Creation Date2016-05-25 20:45:14 UTC
Update Date2026-08-18 09:13:01 UTC
Accession NumberCHEM022950
Identification
Common NameCaffeic acid ethyl ester
ClassSmall Molecule
Description
Caffeic acid ethyl ester is an organic compound with the formula C11H12O4 and an average molecular weight of 208.21 g/mol. Caffeic acid ethyl ester belongs to the hydroxycinnamic acids and derivatives, a subclass of cinnamic acids and derivatives within the organic compounds. It is further categorized under the superclass of phenylpropanoids and polyketides. This compound has been identified in or released from one recorded source: Electrical & Electronic Equipment (Antennas).
Contaminant TypeNot Available
Chemical Structure
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 Number102-37-4
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03g0-2900000000-c16a5811eae4cc57741aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1890000000-bac15703d62d288bae8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-3910000000-851348d6ede682401375Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-9800000000-447a54bed40ab435643fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-2790000000-8a20e8b5192c8f9ba3f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-3920000000-a5cfde27b3fb97857e9eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-4900000000-1f4744d8c108b7f47fc0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-0950000000-d2c1d1796989e2b3fe1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08g1-0910000000-a4f99bb22be28136622cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00rj-6900000000-94a781fc016decb68ef5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0390000000-70f10da8be018d1b5addNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2900000000-7ab4f3330a50bf996fbaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001u-2900000000-86fade974acbd7c34700Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2471.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
506AntennasElectrical & Electronic EquipmentNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGag-Pol polyproteinQ7ZJM1Human immunodeficiency virus 1Predicted (SEA)1.86838
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)1.24559
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)1.40129
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)2.88042
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)7.55137
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)4.35956
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)2.17978
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)1.86838
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)2.56902
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)2.02408
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)9.6533
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7.39568
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)2.56902
Click to view 3D structureXanthine dehydrogenase/oxidaseP80457Bos taurusPredicted (SEA)1.08989
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)1.55698
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)2.56902
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)7.94062
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)0.778492
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)27.6365
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)146.279
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)0.856341
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)127.517
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)28.6485
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)37.8347
Click to view 3D structure17-beta-hydroxysteroid dehydrogenase type 2P37059HumansPredicted (SEA)3.50322
Concentrations
Not Available
External Links
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