4-hydroxyphenylacetate (PAMDB110166)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110166
Identification
Name: 4-hydroxyphenylacetate
Description:A monocarboxylic acid anion that is obtained by removal of a proton from the carboxylic acid group of 4-hydroxyphenylacetic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 4-HPA
  • p-hydroxyphenylacetic acid
  • benzeneacetic acid
  • 4-hydroxy-
  • DL-para-hydroxyphenylacetic acid
  • 4-hydroxyphenylacetic acid
  • 4-hydroxyphenyl acetate
  • p-hydroxyphenylacetate
Chemical Formula: C8H7O3
Average Molecular Weight: 151.14
Monoisotopic Molecular Weight: 152.0473441231
InChI Key: XQXPVVBIMDBYFF-UHFFFAOYSA-M
InChI: InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)/p-1
CAS number: 156-38-7
IUPAC Name:(4-hydroxyphenyl)acetate
Traditional IUPAC Name: 4-hydroxyphenylacetic acid
SMILES:C1(C=C(O)C=CC=1CC(=O)[O-])
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Benzenoids
Sub ClassPhenols
Direct Parent 1-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 Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 148 - 150 °C
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
Water Solubility7.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m3·mol-1ChemAxon
Polarizability14.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
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)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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  • Hirota S, Takahama U, Ly TN, Yamauchi R: Quercetin-dependent inhibition of nitration induced by peroxidase/H2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition. J Agric Food Chem. 2005 May 4;53(9):3265-72. [15853358 ]
  • Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [11997029 ]
  • Kobayashi K, Koide Y, Shohmori T: Determination of p-hydroxyphenylacetic acid in cerebrospinal fluid by high-performance liquid chromatography with electrochemical detection. Clin Chim Acta. 1982 Aug 4;123(1-2):161-8. [7116636 ]
  • Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [6883916 ]
  • Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [6181210 ]
  • Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [14708889 ]
  • Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [455649 ]
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  • McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [4903899 ]
  • Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [12797864 ]
  • Takahama U, Hirota S, Nishioka T, Oniki T: Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary components 4-hydroxyphenylacetic acid and proteins. Arch Oral Biol. 2003 Oct;48(10):679-90. [12971945 ]
  • Quijano C, Hernandez-Saavedra D, Castro L, McCord JM, Freeman BA, Radi R: Reaction of peroxynitrite with Mn-superoxide dismutase. Role of the metal center in decomposition kinetics and nitration. J Biol Chem. 2001 Apr 13;276(15):11631-8. Epub 2001 Jan 4. [11152462 ]
  • Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [6085021 ]
  • Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [15721987 ]
Synthesis Reference: Qiao, 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)
External Links:
ResourceLink
CAS156-38-7
ChEBI48999
ChemSpider3881560
HMDBHMDB00020
KEGGC00642
MetaboLightsMTBLC48999
PubChem4693933