Showing metabocard for p-Hydroxymandelic acid (BMDB0000822)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:07 UTC
Update Date2020-05-11 20:57:33 UTC
BMDB IDBMDB0000822
Secondary Accession Numbers
  • BMDB00822
Metabolite Identification
Common Namep-Hydroxymandelic acid
Descriptionp-Hydroxymandelic acid, also known as 4-hydroxymandelate or 4-hydroxyphenylglycolate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Based on a literature review a significant number of articles have been published on p-Hydroxymandelic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Hydroxyphenylglycolic acidChEBI
4-HydroxyphenylglycolateGenerator
4-HydroxymandelateGenerator
p-HydroxymandelateGenerator
(+/-)-alpha,4-dihydroxy-benzeneacetateHMDB
(+/-)-alpha,4-dihydroxy-benzeneacetic acidHMDB
(R)-4-HydroxymandelateHMDB
(RS)-p-HydroxymandelateHMDB
(RS)-p-Hydroxymandelic acidHMDB
(S)-4-HydroxymandelateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetic acidHMDB
3-Dimethylallyl-4-hydroxymandelateHMDB
3-Dimethylallyl-4-hydroxymandelic acidHMDB
4-Hydroxy-DL-mandelateHMDB
4-Hydroxy-DL-mandelic acidHMDB
alpha,4-Dihydroxy-benzeneacetateHMDB
alpha,4-Dihydroxy-benzeneacetic acidHMDB
alpha,4-DihydroxybenzeneacetateHMDB
alpha,4-Dihydroxybenzeneacetic acidHMDB
D-4-HydroxymandelateHMDB
D-p-HydroxymandelateHMDB
delta-4-HydroxymandelateHMDB
delta-p-HydroxymandelateHMDB
DL-4-HydroxymandelateHMDB
DL-4-Hydroxymandelic acidHMDB
DL-p-HydroxymandelateHMDB
DL-p-Hydroxymandelic acidHMDB
DL-p-HydroxyphenylglycolateHMDB
DL-p-Hydroxyphenylglycolic acidHMDB
Hydroxy(4-hydroxyphenyl)acetateHMDB
Hydroxy(4-hydroxyphenyl)acetic acidHMDB
L-4-HydroxymandelateHMDB
L-p-HydroxymandelateHMDB
p-Hydroxy-mandelateHMDB
p-Hydroxy-mandelic acidHMDB
p-HydroxyphenylglycolateHMDB
p-Hydroxyphenylglycolic acidHMDB
Para-hydroxymandelic acidHMDB
4-Hydroxymandelic acid, (D)-isomerHMDB
Pisolithin bHMDB
2-Hydroxy-2-(4'-hydroxyphenyl)acetic acidHMDB
2-Hydroxy-2-(4-hydroxyphenyl)acetic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxymandelic acid
CAS Registry Number1198-84-1
SMILES
OC(C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyYHXHKYRQLYQUIH-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
  • 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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point103 - 106 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.86ALOGPS
logP0.59ChemAxon
logS-1.3ALOGPS
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
Polarizability15.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Liver
  • Retina
  • Vitreous Humour
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
RetinaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Vitreous HumourExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000822
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022267
KNApSAcK IDNot Available
Chemspider ID321
KEGG Compound IDC11527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid
METLIN ID5785
PubChem Compound328
PDB IDNot Available
ChEBI ID16388
References
Synthesis ReferenceWang, Bing; Zhang, Guofeng. Synthesis and purity determination of p-hydroxymandelic acid. Qingdao Daxue Xuebao, Gongcheng Jishuban (1999), 14(1), 14-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available