Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2020-02-24 19:11:05 UTC
Primary IDFDB000262
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHydroxycaffeic acid
DescriptionHydroxycaffeic acid, also known as hydroxycaffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Hydroxycaffeic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Hydroxycaffeic acid can be found in olive, which makes hydroxycaffeic acid a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(2,3,4-Trihydroxyphenyl)prop-2-enoateGenerator
HydroxycaffeateGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.43 g/LALOGPS
logP1.48ALOGPS
logP1.23ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49 m³·mol⁻¹ChemAxon
Polarizability18.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O5
IUPAC name(2E)-3-(2,3,4-trihydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O5/c10-6-3-1-5(2-4-7(11)12)8(13)9(6)14/h1-4,10,13-14H,(H,11,12)/b4-2+
InChI KeyRHGWNBSOWGUGPA-DUXPYHPUSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=C(O)C(O)=C(O)C=C1)C(O)=O
Average Molecular Weight196.1568
Monoisotopic Molecular Weight196.037173366
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • 5-unsubstituted pyrrogallol
  • Benzenetriol
  • Pyrogallol derivative
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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 logPNot Available
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-MSHydroxycaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ufs-1900000000-f90579cd732eaf93951cSpectrum
Predicted GC-MSHydroxycaffeic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0i7i-3028900000-2e7d7d73b43bed14df37Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-e26fc3bbcdced026f8c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug1-1900000000-bfe1dd5222889b90412cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9400000000-d36e8a0e6a200edd32e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-79a7fe792b5d5deda87bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-94666712b50cc3055c89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9800000000-650695baff2f8917f304Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID503
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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— 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.