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Record Information
Version1.0
Creation Date2016-09-30 22:18:32 UTC
Update Date2019-02-05 20:35:42 UTC
MCDB ID BMDB00020
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Hydroxyphenylacetic acid
Description4-Hydroxyphenylacetic acid, also known as (p-hydroxyphenyl)acetate or 4-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-Hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylacetic acid is a potentially toxic compound. 4-Hydroxyphenylacetic acid has been found to be associated with several diseases known as lung cancer, crohn's disease, spina bifida, and epilepsy; also 4-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.7 mg/mLNot Available
LogP0.75HANSCH,C ET AL. (1995)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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-1930000000-57c9e8ddaa10569055aaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0h01-0940000000-a14203384331e709252fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-678591f03aba45c2a6aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0h0r-2940000000-760b6c506072a61059c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2900000000-3939c62b0d7f649ff402JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-fdb73325a31c758496e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gyk-0980000000-ed36f36969e4d51b9a8dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ta-1930000000-57c9e8ddaa10569055aaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0h01-0940000000-a14203384331e709252fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1930000000-80c21819072fb01958dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9410000000-678591f03aba45c2a6aeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h0r-2940000000-760b6c506072a61059c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fs-1931100000-50456fed0c5ef95ecb57JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-b6f6363476ffa290862fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-abf5245dd22d012d04f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-0900000000-e3dfb4b180d858b3a854JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-056r-9400000000-9a6cb39e019a0b40a666JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0kdl-9400000000-35ecc22161defddc7b21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a4i-2900000000-3939c62b0d7f649ff402JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0a4i-6900000000-fdb73325a31c758496e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-4900000000-88da569804a98e1a99eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-0900000000-369a695f2c7bcf3a4a5cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-88da569804a98e1a99eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-eef23e2f30d876f4a1f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0a95379b7cea57386b0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-dd0a48d9d6528f6a0a6aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-02cd23fa5ff37594d2beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-bbac468eb7ce6ea99123JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-05d18e7bb4163e35e2aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-1900000000-9a0086561d6f8a169670JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-398dff08b5b2a56e658cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-5f75ea6de2d6bad624d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-7ce02fea5a9ef38024f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-12e388b0927ed1c6e166JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-ae1870eee4853c57a447JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000020
DrugBank IDNot Available
Phenol Explorer Compound ID573
FoodDB IDFDB010534
KNApSAcK IDNot Available
Chemspider ID124
KEGG Compound IDC00642
BioCyc ID4-HYDROXYPHENYLACETATE
BiGG ID35599
Wikipedia Link4-hydroxyphenylacetic_acid
METLIN ID130
PubChem Compound127
PDB IDNot Available
ChEBI ID18101
References
Synthesis ReferenceQiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang. Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid. Hebei Gongye Keji (2005), 22(5), 264-266.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]