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Record Information
Version1.0
Creation Date2016-09-30 22:35:59 UTC
Update Date2020-05-11 20:57:31 UTC
MCDB ID BMDB0000750
Secondary Accession Numbers
  • BMDB00750
Metabolite Identification
Common Name3-Hydroxymandelic acid
Description3-Hydroxymandelic acid, also known as m-hydroxymandelate or mhma, 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-Hydroxymandelic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-2-(3-hydroxyphenyl)acetic acidChEBI
2-Hydroxy-2-(3-hydroxyphenyl)ethanoic acidChEBI
m-Hydroxymandelic acidChEBI
2-Hydroxy-2-(3-hydroxyphenyl)acetateGenerator
2-Hydroxy-2-(3-hydroxyphenyl)ethanoateGenerator
m-HydroxymandelateGenerator
3-HydroxymandelateGenerator
3-Hydroxyphenylglycolic acidHMDB
alpha,3-Dihydroxybenzeneacetic acidHMDB
DL-3-HydroxymandelateHMDB
DL-3-Hydroxymandelic acidHMDB
DL-Hydroxy(m-hydroxyphenyl)acetic acidHMDB
Hydroxy(3-hydroxyphenyl)acetic acidHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelateHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelic acidHMDB
Meta-hydroxymandelic acidHMDB
MHMAHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-2-(3-hydroxyphenyl)acetic acid
Traditional NameMHMA
CAS Registry Number17119-15-2
SMILES
OC(C(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyOLSDAJRAVOVKLG-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
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.89ALOGPS
logP0.59ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.68 m³·mol⁻¹ChemAxon
Polarizability15.55 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 IDHMDB0000750
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022222
KNApSAcK IDNot Available
Chemspider ID78444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid
METLIN ID732
PubChem Compound86957
PDB IDNot Available
ChEBI ID86553
References
Synthesis ReferenceFanali S; Aturki Z Further study on the use of uncharged beta-cyclodextrin polymer in capillary electrophoresis: enantiomeric separation of some alpha-hydroxy acids. Electrophoresis (1995), 16(8), 1505-9.
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 ]