You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0000750
Secondary Accession Numbers
  • HMDB00750
Metabolite Identification
Common Name3-Hydroxymandelic acid
Description3-Hydroxymandelic acid, also known as m-hydroxymandelate or MHMA, is a 2-hydroxy monocarboxylic acid. 3-Hydroxymandelic acid is the dehydroxylated (positions 2 and 3’) derivative of phenylacetic acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It derives from a mandelic acid. Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway. Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Derivatives of mandelic acid, such as 3-hydroxymandelic acid, are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.
Structure
Data?1582752154
Synonyms
ValueSource
2-Hydroxy-2-(3-hydroxyphenyl)acetic 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, MeSH
MHMAHMDB
2-Hydroxy-2-(3'-hydroxyphenyl)acetic acidHMDB
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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available136.81331661259
DarkChem[M-H]-PredictedNot Available131.36431661259
AllCCS[M+H]+PredictedNot Available136.62532859911
AllCCS[M-H]-PredictedNot Available131.3132859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
3-Hydroxymandelic acid,1TMS,#11734.7573https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,1TMS,#21705.7993https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,1TMS,#31687.9436https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TMS,#11729.3838https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TMS,#21747.4127https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TMS,#31689.4302https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,3TMS,#11753.8215https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,1TBDMS,#11985.8225https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,1TBDMS,#21945.3263https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,1TBDMS,#31935.9851https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TBDMS,#12174.019https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TBDMS,#22229.6355https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,2TBDMS,#32176.5444https://arxiv.org/abs/1905.12712
3-Hydroxymandelic acid,3TBDMS,#12391.4885https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9800000000-bf3bd36839dcaaf08ef92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1091000000-8a56583c49f940049f672017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0900000000-10beec4c3472d3afb28c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5a6c0f2c681a7da489f02012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-49e33a7a57260ed160a52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-0900000000-72199f89fe731fcb25d02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-72199f89fe731fcb25d02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-09041ce83fd7828817c22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-c7391a6d5d26c34d6ff12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-006x-9800000000-ac2ed19d66c39053866d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4i-0900000000-33388d527863717e6b522017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-d7968efcab4fad804ea02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0592-9500000000-c87d3eeded18820fc89e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-78dab78100ab6d939f862017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r7-4900000000-953e2a0259bd8f0d8e1a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-360650692ca61f88e3552017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-d80ec9d424fdb79051802021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-6900000000-e627c37fec0d676dca1a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-a4dc421433c86804a2282021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-24344bf18e403a55dd052021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-7900000000-031a2963cd0c05ff534f2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-87934a19509c4f25a0792021-09-09View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified10.527 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10.527 +/- 0.0595 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.023 +/- 0.014 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified700.0 (670.0 - 1030.0) uMAdult (>18 years old)Both
Kidney disease
    • Nieren- und Hochd...
details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. (). Nieren- und Hochdruckkrankheiten (1978), 7(2), 62-74 (translated from German Kidney and Hypertension). . .
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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. Midgley JM, Couch MW, Crowley JR, Williams CM: Identification and quantitative determination of o- and m-hydroxymandelic acid in human urine. Biomed Mass Spectrom. 1979 Nov;6(11):485-90. [PubMed:534686 ]
  2. Ibrahim KE, Midgley JM, Crowley JR, Williams CM: The mammalian metabolism of R-(-)-m-synephrine. J Pharm Pharmacol. 1983 Mar;35(3):144-7. [PubMed:6132969 ]
  3. Gumbhir K, Mason WD: Determination of m-hydroxymandelic acid, m-hydroxyphenylglycol and their conjugates in human plasma using liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1994 Jul;12(7):943-9. [PubMed:7981325 ]
  4. 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 ]