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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:38 UTC
HMDB IDHMDB0000822
Secondary Accession Numbers
  • HMDB00822
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. 4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol. p-Hydroxymandelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752158
Synonyms
ValueSource
4-Hydroxyphenylglycolic acidChEBI
4-Hydroxymandelic acidKegg
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
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
Disposition

Source:

Biological location:

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
Water Solubility7.69 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1970000000-156d51ef8c0ad0f76d64Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1970000000-156d51ef8c0ad0f76d64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-8900000000-b062f43216386832ddedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1091000000-70622b0e5331b2fe290fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4i-0900000000-da456e31e91f9a9b7c34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-bb2667f5c8ef34847d41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fv-9600000000-c7c25ea1fa9244b02d82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-0853088e78547b002394Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r7-4900000000-4fd0952fc81ec79b040fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-6c7af63bb32592f280faSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Retina
  • Vitreous humor
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.844 (0.511-6.0959) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.91-1.7 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.98-1.5 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified4.1 (0.1-4.9) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified3.7 (1.3-6.8) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified4.3 (1.4-10.0) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    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
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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)Download (PDF)
    General References
    1. Couch MW, Greer DM, Williams CM: Excretion of octopamine metabolites in neuroblastoma. Clin Chim Acta. 1986 Jul 15;158(1):109-14. [PubMed:3091293 ]
    2. 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. [PubMed:8087979 ]
    3. Niwa T, Ohki T, Maeda K, Saito A, Ohta K, Kobayashi K: A gas chromatographic-mass spectrometric assay for nine hydroxyphenolic acids in uremic serum. Clin Chim Acta. 1979 Sep 3;96(3):247-54. [PubMed:487594 ]
    4. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
    5. Arai K, Jin D, Kusu F, Takamura K: Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1997 Jun;15(9-10):1509-14. [PubMed:9226583 ]
    6. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
    7. Crowley JR, Couch MW, Williams CM, Threatte RM, Fregly MJ: Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clin Chim Acta. 1981 Jan 22;109(2):125-31. [PubMed:7471493 ]