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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:14:18 UTC
Secondary Accession Numbers
  • HMDB00703
Metabolite Identification
Common NameMandelic acid
DescriptionIt is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents. Mandelic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism.
(S)-2-Hydroxy-2-phenylacetic acidChEBI
(S)-alpha-Hydroxybenzeneacetic acidChEBI
L-Mandelic acidChEBI
(S)-Mandelic acidKegg
(S)-a-Hydroxybenzeneacetic acidGenerator
(S)-Α-hydroxybenzeneacetic acidGenerator
(RS)-Mandelic acidHMDB
2-Hydroxy-2-phenylacetic acidHMDB
2-Hydroxy-2-phenylethanoic acidHMDB
2-Phenyl-2-hydroxyacetic acidHMDB
2-Phenylglycolic acidHMDB
a-Hydroxy-a-toluic acidHMDB
a-Hydroxybenzeneacetic acidHMDB
a-Hydroxyphenylacetic acidHMDB
Almond acidHMDB
alpha-Hydroxy-alpha-toluic acidHMDB
alpha-Hydroxybenzeneacetic acidHMDB
alpha-Hydroxyphenylacetic acidHMDB
Amygdalic acidHMDB
DL-Amygdalic acidHMDB
DL-Hydroxy(phenyl)acetic acidHMDB
DL-Mandelic acidHMDB
Paramandelic acidHMDB
Phenylglycolic acidHMDB
Phenylhydroxyacetic acidHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name(2S)-2-hydroxy-2-phenylacetic acid
Traditional Name(S)-mandelic acid
CAS Registry Number90-64-2
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Biological location:



Industrial application:

Physical Properties
Experimental Properties
Melting Point120 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility181 mg/mLNot Available
LogP0.62HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility16.8 g/LALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m³·mol⁻¹ChemAxon
Polarizability14.66 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-2d141c7d9cfc97cc9b76Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2910000000-de71bbd7bcfd35e2bbe5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-31443907299c1634fe9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pdi-4900000000-d32dc8f06b5e94c7b3b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-1900000000-f1e179f7f6654c244250Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-15fb1f5429449730eb57Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9500000000-6d480b6841c2a90ea872Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-15fb1f5429449730eb57Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9500000000-96b7d7c57c085b66c0aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0900000000-dc883eccc7ede3626274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-43028c230f4ad5a4568cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9500000000-d3b486d397a2e852f3a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-d3c9a003466ac58be74fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdi-5900000000-cadf8b3761e31a6e33c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-b906b74a2aa4ffe7faccSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.565 (0.164-3.608) nmol/g wet fecesAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.407 +/- 2.009 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected and Quantified0.966 +/- 0.669 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.27-0.48 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 958 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.23-0.40 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.817 +/- 0.520 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.115 +/- 0.817 umol/mmol creatinineInfant (0-1 year old)Both
UrineDetected and Quantified1.486 +/- 0.966 umol/mmol creatinineInfant (0-1 year old)Both
UrineDetected and Quantified0.063 (0.053-1.746) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.4 (1.1-1.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified10.129 +/- 10.329 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
UrineDetected and Quantified123.8 +/- 2.8 umol/mmol creatinineAdult (>18 years old)BothOccupational exposure to styrene details
UrineDetected and Quantified14.119 +/- 5.722 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified34.182 +/- 22.293 umol/mmol creatinineChildren (1-13 years old)Both
UrineDetected and Quantified35.669 +/- 20.0636 umol/mmol creatinineChildren (1-13 years old)Both
UrineDetected and Quantified8.00 +/- 9.00 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria 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 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB03357
Phenol Explorer Compound IDNot Available
FooDB IDFDB022191
KNApSAcK IDC00037426
Chemspider ID388690
KEGG Compound IDC01984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelic acid
PubChem Compound439616
PDB IDNot Available
ChEBI ID32800
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000228
Synthesis ReferenceChen, Jianfeng; Chen, Hao. Process for preparation of mandelic acid by membrane separation technology. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 7pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Krivankova L, Pantuckova P, Gebauer P, Bocek P, Caslavska J, Thormann W: Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes. Electrophoresis. 2003 Jan;24(3):505-17. [PubMed:12569541 ]
  2. Crespi H, Armando I, Tumilasci O, Levin G, Massimo J, Barontini M, Perec C: Catecholamines levels and parotid secretion in children with chronic atopic dermatitis. J Invest Dermatol. 1982 Jun;78(6):493-7. [PubMed:7086169 ]
  3. Cheung IY, Cheung NK: Molecular detection of GAGE expression in peripheral blood and bone marrow: utility as a tumor marker for neuroblastoma. Clin Cancer Res. 1997 May;3(5):821-6. [PubMed:9815755 ]
  4. Strittmatter M, Isenberg E, Grauer MT, Hamann G, Schimrigk K: CSF substance P somatostatin and monoaminergic transmitter metabolites in patients with narcolepsy. Neurosci Lett. 1996 Nov 1;218(2):99-102. [PubMed:8945737 ]
  5. Kaniwa N, Ogata H, Aoyagi N, Ejima A, Takahashi T, Uezono Y, Imazato Y: Effect of food on the bioavailability of cyclandelate from commercial capsules. Clin Pharmacol Ther. 1991 Jun;49(6):641-7. [PubMed:2060253 ]
  6. Vodicka P, Bastlova T, Vodickova L, Peterkova K, Lambert B, Hemminki K: Biomarkers of styrene exposure in lamination workers: levels of O6-guanine DNA adducts, DNA strand breaks and mutant frequencies in the hypoxanthine guanine phosphoribosyltransferase gene in T-lymphocytes. Carcinogenesis. 1995 Jul;16(7):1473-81. [PubMed:7614680 ]
  7. Suarez A, Rico F, Clavero-Nunez JA, Garcia-Barreno P: Amniotic fluid catecholamine metabolites in maternal smoking. Gynecol Obstet Invest. 1990;30(3):143-6. [PubMed:2265798 ]
  8. Kolstad HA, Bonde JP, Spano M, Giwercman A, Zschiesche W, Kaae D, Larsen SB, Roeleveld N: Change in semen quality and sperm chromatin structure following occupational styrene exposure. ASCLEPIOS. Int Arch Occup Environ Health. 1999 May;72(3):135-41. [PubMed:10392560 ]
  9. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
  10. Corona GL, Cucchi ML, Frattini P, Santagostino G, Schinelli S, Romani A, Pola A, Zerbi F, Savoldi F: Clinical and biochemical responses to therapy in Alzheimer's disease and multi-infarct dementia. Eur Arch Psychiatry Neurol Sci. 1989;239(2):79-86. [PubMed:2478368 ]
  11. Fukuda T, Ito H, Mukainaka T, Tokuda H, Nishino H, Yoshida T: Anti-tumor promoting effect of glycosides from Prunus persica seeds. Biol Pharm Bull. 2003 Feb;26(2):271-3. [PubMed:12576693 ]