Record Information
Version1.0
Creation date2010-04-08 22:09:10 UTC
Update date2019-11-27 17:16:17 UTC
Primary IDFDB010534
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyphenylacetic acid
Descriptionp-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or parahydroxy phenylacetate, 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 is found, on average, in the highest concentration in 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, mushrooms, evening primroses, and dandelions. 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 has been found to be associated with several diseases such as lung cancer, eosinophilic esophagitis, and epilepsy; also p-hydroxyphenylacetic acid has been linked to several inborn metabolic disorders including phenylketonuria and fumarase deficiency.
CAS Number156-38-7
Structure
Thumb
Synonyms
SynonymSource
(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
(4-hydroxy-phenyl)-acetatebiospider
(4-hydroxy-phenyl)-acetic acidbiospider
(4-hydroxyphenyl)acetatebiospider
(4-hydroxyphenyl)acetic acidbiospider
(p-hydroxyphenyl)-acetatebiospider
(p-hydroxyphenyl)-acetic acidbiospider
(p-hydroxyphenyl)acetatebiospider
(p-hydroxyphenyl)acetic acidbiospider
3pcgbiospider
4-HPAbiospider
4-Hydroxy-Benzeneacetatebiospider
4-Hydroxy-Benzeneacetic acidbiospider
4-Hydroxybenzeneacetic acid, 9CIdb_source
4-hydroxyphenyl acetatebiospider
4-hydroxyphenylacetatebiospider
Acetic acid, (p-hydroxyphenyl)-biospider
Benzeneacetic acid, 4-hydroxy-biospider
DL-para-hydroxyphenylacetic acidbiospider
p-Hydroxy-a-toluic aciddb_source
P-hydroxyphenyl acetic acidbiospider
P-hydroxyphenylacetatebiospider
P-hydroxyphenylacetic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility7.12 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H8O3
IUPAC name2-(4-hydroxyphenyl)acetic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CC1=CC=C(O)C=C1
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 63.15%; H 5.30%; O 31.55%DFC
    Melting PointMp 148-150°DFC
    Boiling PointNot Available
    Experimental Water Solubility60.7 mg/mL at 25 oCGRACIN,S & RASMUSON,AC (2002)
    Experimental logP0.75HANSCH,C ET AL. (1995)
    Experimental pKapKa 4.59 (10% EtOH aq.)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01ta-1930000000-57c9e8ddaa10569055aaView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0h01-0940000000-a14203384331e709252fView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-678591f03aba45c2a6aeView in MoNA
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0h0r-2940000000-760b6c506072a61059c0View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2900000000-3939c62b0d7f649ff402View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-fdb73325a31c758496e9View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gyk-0980000000-ed36f36969e4d51b9a8dView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ta-1930000000-57c9e8ddaa10569055aaView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0h01-0940000000-a14203384331e709252fView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9410000000-678591f03aba45c2a6aeView in MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h0r-2940000000-760b6c506072a61059c0View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1931100000-50456fed0c5ef95ecb57View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-b6f6363476ffa290862fView in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-abf5245dd22d012d04f8View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-0900000000-e3dfb4b180d858b3a854View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-056r-9400000000-9a6cb39e019a0b40a666View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0kdl-9400000000-35ecc22161defddc7b21View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a4i-2900000000-3939c62b0d7f649ff402View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0a4i-6900000000-fdb73325a31c758496e9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-4900000000-88da569804a98e1a99eaView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-88da569804a98e1a99eaView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-02cd23fa5ff37594d2beView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-bbac468eb7ce6ea99123View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-05d18e7bb4163e35e2aaView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-9a0086561d6f8a169670View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-398dff08b5b2a56e658cView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-5f75ea6de2d6bad624d8View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-7ce02fea5a9ef38024f2View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-12e388b0927ed1c6e166View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-ae1870eee4853c57a447View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1View in MoNA
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
    ChemSpider ID124
    ChEMBL IDCHEMBL1772
    KEGG Compound IDC00642
    Pubchem Compound ID127
    Pubchem Substance IDNot Available
    ChEBI ID18101
    Phenol-Explorer ID573
    DrugBank IDNot Available
    HMDB IDHMDB00020
    CRC / DFC (Dictionary of Food Compounds) IDFCL13-X:FCL13-X
    EAFUS IDNot Available
    Dr. Duke ID4-HYDROXYPHENYLACETIC-ACID|P-HYDROXYPHENYLACETIC-ACID
    BIGG ID35599
    KNApSAcK IDNot Available
    HET ID4HP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID573
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Tyrosine MetabolismSMP00006 map00350
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    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.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).