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Record Information
Version1.0
Creation Date2016-09-30 22:30:47 UTC
Update Date2020-06-04 20:13:07 UTC
MCDB ID BMDB0000440
Secondary Accession Numbers
  • BMDB00440
Metabolite Identification
Common Name3-Hydroxyphenylacetic acid
Description3-Hydroxyphenylacetic acid, also known as (m-hydroxyphenyl)acetate or 3-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 3-Hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3-Hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. 3-Hydroxyphenylacetic acid has been found to be associated with several diseases known as colorectal cancer and eosinophilic esophagitis; also 3-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.
Structure
Thumb
Synonyms
ValueSource
(m-Hydroxyphenyl)acetic acidChEBI
3-Hydroxybenzeneacetic acidChEBI
m-Hydroxyphenylacetic acidChEBI
(m-Hydroxyphenyl)acetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
3-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
Meta-hydroxyphenylacetic acidHMDB
3-Hydroxyphenylacetic acidKEGG
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(3-hydroxyphenyl)acetic acid
Traditional Name3-hydroxyphenylacetic acid
CAS Registry Number621-37-4
SMILES
OC(=O)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyFVMDYYGIDFPZAX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 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
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000440
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylacetic acid
METLIN ID5429
PubChem Compound12122
PDB IDNot Available
ChEBI ID17445
References
Synthesis ReferenceStaudenmaier, Horst Ralf; Hauer, Bernhard; Ladner, Wolfgang; Mueller, Ursula; Pressler, Uwe; Meyer, Joachim. Fermentative manufacture of 3-hydroxyphenylacetic acid. Ger. Offen. (1993), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]