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Showing Compound 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (FDB024152)

Record Information
Version1.0
Creation date2011-09-21 00:40:40 UTC
Update date2017-04-03 05:02:17 UTC
Primary IDFDB024152
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Description2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, also known as 4,alpha-dihydroxycinnamic acid or 4-hydroxy-enol-phenylpyruvate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-hydroxy-3-(4-hydroxyphenyl)propenoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid.
CAS Number104594-70-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4,alpha-Dihydroxycinnamic acidChEBI
4-Hydroxy-enol-phenylpyruvateKegg
4,a-DihydroxycinnamateGenerator
4,a-Dihydroxycinnamic acidGenerator
4,alpha-DihydroxycinnamateGenerator
4,Α-dihydroxycinnamateGenerator
4,Α-dihydroxycinnamic acidGenerator
4-Hydroxy-enol-phenylpyruvic acidGenerator
2-Hydroxy-3-(4-hydroxyphenyl)propenoateGenerator
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidhmdb
4,α-dihydroxycinnamateGenerator
4,α-dihydroxycinnamic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP1.28ALOGPS
logP1.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.01 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O4
IUPAC name(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-
InChI KeyGQYBCIHRWMPOOF-YVMONPNESA-N
Isomeric SMILESOC(=O)C(\O)=C\C1=CC=C(O)C=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Enol-phenylpyruvate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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-MS2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-1900000000-10c51d0329cb2a35dbb8Spectrum
Predicted GC-MS2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gi-6259000000-cdf2744454615081e02fSpectrum
Predicted GC-MS2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu0-0900000000-a08730e02c84f43e79262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2eb4f2eaa5d547249a3e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-7900000000-63f2942443ac7bfdce482017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8576bdecf0b58e989df62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-46e515a63da5ddf92de92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-3c0a27f480b5bb59093c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-02f0fa9241cf4b1591c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9800000000-0e7b12140d77aa62a5122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-4900000000-6f21f2ecdec85109e7d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qi-0900000000-28cf4812bb35ce056a152021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1900000000-bd40f97e341181046c0f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9200000000-c7f40face58730829b4a2021-09-22View Spectrum
NMRNot Available
ChemSpider ID552441
ChEMBL IDNot Available
KEGG Compound IDC05350
Pubchem Compound ID636708
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06915
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
Enzymes
NameGene NameUniProt ID
Macrophage migration inhibitory factorMIFP14174
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference