Caffeic acid ester (CHEM025521)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:26:46 UTC
Update Date2016-11-09 01:18:06 UTC
Accession NumberCHEM025521
Identification
Common NameCaffeic acid ester
ClassSmall Molecule
DescriptionAn alkyl caffeate ester in which 2-phenylethyl is the alkyl component.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylateChEBI
2-Phenylethyl caffeateChEBI
Caffeic acid phenethyl esterChEBI
CAPEChEBI
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylic acidGenerator
2-Phenylethyl caffeic acidGenerator
Caffeate phenethyl esterGenerator
Phenethyl caffeic acidGenerator
CAPE compoundMeSH
CAPEEEMeSH
Caffeic acid phenyl esterMeSH
Phenyl caffeateMeSH
Caffeate esterGenerator
Phenethyl caffeateMeSH
Chemical FormulaC17H16O4
Average Molecular Mass284.307 g/mol
Monoisotopic Mass284.105 g/mol
CAS Registry NumberNot Available
IUPAC Name2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Namecaffeic acid phenethyl ester
SMILES[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OCCC1=CC=CC=C1
InChI IdentifierInChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+
InChI KeySWUARLUWKZWEBQ-VQHVLOKHSA-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 Solubility0.063 g/LALOGPS
logP3.65ALOGPS
logP3.92ChemAxon
logS-3.7ALOGPS
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 Count6ChemAxon
Refractivity81.16 m³·mol⁻¹ChemAxon
Polarizability30.74 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-03di-3900000000-62548c49c8e49f1179deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0970000000-3ead949a4b33ddf83a47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0910000000-edce37422aca70f6e004Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5900000000-7a448f8c4402b3836f79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0970000000-65a7d0af8a3310ebf8f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0910000000-4bdc18e559b25d305c03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g3-6900000000-8270b803edf414dd7802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-ce73056df2bcf6d3c1f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-1930000000-dfff28b8878e5d52b8c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2900000000-c94cd4513f24a8bba089Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-0690000000-3387ce31518f152b80adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-2940000000-2bcbc9c2181629ef7a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-2900000000-4a20e5d83c4c38f6530dSpectrum
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 IDHMDB0302344
FooDB IDFDB004209
Phenol Explorer IDNot Available
KNApSAcK IDC00002766
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCaffeic_acid_phenethyl_ester
Chemspider ID4445100
ChEBI ID8062
PubChem Compound ID5281787
Kegg Compound IDC10484
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22206942
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22610380
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22646141
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22964505
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22996076
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23231684
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23291456
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23313590
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23462369
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23466879
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23511289
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23548785
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23561222
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23571777
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23589406
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23611786
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23615471
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23659443
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23662124
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23727925
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23847089
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23876066
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23927014