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Record Information
Version1.0
Creation Date2016-07-13 19:22:14 UTC
Update Date2016-07-20 21:02:58 UTC
LmdbLMDB00007
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Hydroxyphenylacetic acid
Descriptionp-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or 4-carboxymethylphenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). p-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. p-hydroxyphenylacetic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, p-hydroxyphenylacetic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, p-Hydroxyphenylacetic acid is found, on average, in the highest concentration within a few different foods, such as olives, american cranberries, and grape wines and in a lower concentration in corns, beers, and oats. p-Hydroxyphenylacetic acid has also been detected, but not quantified in, several different foods, such as common wheats, herbs and spices, cocoa beans, dandelions, and evening primroses. This could make p-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. p-Hydroxyphenylacetic acid is a potentially toxic compound. p-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, perillyl alcohol administration for cancer treatment, crohn's disease, and ulcerative colitis; p-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria.
Structure
Thumb
Synonyms
ValueSource
(p-Hydroxyphenyl)acetic acidChEBI
4-CarboxymethylphenolChEBI
4-Hydroxybenzeneacetic acidChEBI
4-HydroxyphenylacetateChEBI
4-Hydroxyphenylacetic acidKegg
(p-Hydroxyphenyl)acetateGenerator
4-HydroxybenzeneacetateGenerator
p-HydroxyphenylacetateGenerator
(4-Hydroxy-phenyl)-acetateHMDB
(4-Hydroxy-phenyl)-acetic acidHMDB
(4-Hydroxy-phenyl)-essigsaeureHMDB
(4-Hydroxyphenyl)acetateHMDB
(4-Hydroxyphenyl)acetic acidHMDB
(p-Hydroxyphenyl)-acetateHMDB
(p-Hydroxyphenyl)-acetic acidHMDB
4-Hydroxy-benzeneacetateHMDB
4-Hydroxy-benzeneacetic acidHMDB
4-Hydroxyphenyl-acetic acidHMDB
Parahydroxy phenylacetateHMDB
Parahydroxy phenylacetic acidHMDB
ParahydroxyphenylacetateHMDB
Para-hydroxyphenylacetic acidHMDB
p-Hydroxyphenylacetic acidChEBI
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxyphenylacetic acid
CAS Registry Number156-38-7
SMILES
OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyXQXPVVBIMDBYFF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01ta-1930000000-57c9e8ddaa10569055aaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0h01-0940000000-a14203384331e709252fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-678591f03aba45c2a6aeSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0h0r-2940000000-760b6c506072a61059c0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2900000000-3939c62b0d7f649ff402Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-fdb73325a31c758496e9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gyk-0980000000-ed36f36969e4d51b9a8dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ta-1930000000-57c9e8ddaa10569055aaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0h01-0940000000-a14203384331e709252fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9410000000-678591f03aba45c2a6aeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h0r-2940000000-760b6c506072a61059c0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1931100000-50456fed0c5ef95ecb57Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-b6f6363476ffa290862fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-abf5245dd22d012d04f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-0900000000-e3dfb4b180d858b3a854Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-056r-9400000000-9a6cb39e019a0b40a666Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0kdl-9400000000-35ecc22161defddc7b21Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a4i-2900000000-3939c62b0d7f649ff402Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0a4i-6900000000-fdb73325a31c758496e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-4900000000-88da569804a98e1a99eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-88da569804a98e1a99eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-02cd23fa5ff37594d2beSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-bbac468eb7ce6ea99123Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-05d18e7bb4163e35e2aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-9a0086561d6f8a169670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-398dff08b5b2a56e658cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-5f75ea6de2d6bad624d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-7ce02fea5a9ef38024f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-12e388b0927ed1c6e166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-ae1870eee4853c57a447Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Plasma
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
DrugBank IDNot Available
HMDB IDHMDB0000020
FooDB IDFDB010534
Phenol Explorer ID573
KNApSAcK IDNot Available
BiGG ID35599
BioCyc ID4-HYDROXYPHENYLACETATE
METLIN ID130
PDB IDNot Available
Wikipedia Link4-hydroxyphenylacetic_acid
Chemspider ID124
ChEBI ID18101
PubChem Compound ID127
Kegg Compound IDC00642
YMDB IDYMDB01486
ECMDB IDM2MDB004468
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available