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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:15 UTC
HMDB IDHMDB00703
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
ValueSource
(S)-2-Hydroxy-2-phenylacetic acidKegg
(S)-2-Hydroxy-2-phenylacetateKegg
(S)-Mandelic acidKegg
MandelateGenerator
(S)-MandelateGenerator
(RS)-MandelateHMDB
(RS)-Mandelic acidHMDB
2-Hydroxy-2-phenylacetateHMDB
2-Hydroxy-2-phenylacetic acidHMDB
2-Hydroxy-2-phenylethanoateHMDB
2-Hydroxy-2-phenylethanoic acidHMDB
2-Phenyl-2-hydroxyacetateHMDB
2-Phenyl-2-hydroxyacetic acidHMDB
2-PhenylglycolateHMDB
2-Phenylglycolic acidHMDB
a-Hydroxy-a-toluateHMDB
a-Hydroxy-a-toluic acidHMDB
a-HydroxybenzeneacetateHMDB
a-Hydroxybenzeneacetic acidHMDB
a-HydroxyphenylacetateHMDB
a-Hydroxyphenylacetic acidHMDB
Almond acidHMDB
alpha-Hydroxy-alpha-toluateHMDB
alpha-Hydroxy-alpha-toluic acidHMDB
alpha-HydroxybenzeneacetateHMDB
alpha-Hydroxybenzeneacetic acidHMDB
alpha-HydroxyphenylacetateHMDB
alpha-Hydroxyphenylacetic acidHMDB
AmygdalateHMDB
Amygdalic acidHMDB
DL-AmygdalateHMDB
DL-Amygdalic acidHMDB
DL-Hydroxy(phenyl)acetateHMDB
DL-Hydroxy(phenyl)acetic acidHMDB
DL-MandelateHMDB
DL-Mandelic acidHMDB
ParamandelateHMDB
Paramandelic acidHMDB
PhenylglycolateHMDB
Phenylglycolic acidHMDB
PhenylhydroxyacetateHMDB
Phenylhydroxyacetic acidHMDB
UromalineHMDB
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
SMILES
O[C@H](C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
InChI KeyInChIKey=IWYDHOAUDWTVEP-ZETCQYMHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility181.0 mg/mLNot Available
LogP0.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP0.66ALOGPS
logP0.9ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m3·mol-1ChemAxon
Polarizability14.66 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-31443907299c1634fe9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pdi-4900000000-d32dc8f06b5e94c7b3b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-1900000000-f1e179f7f6654c244250View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-15fb1f5429449730eb57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9500000000-6d480b6841c2a90ea872View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified4.407 +/- 2.009 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.966 +/- 0.669 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 958
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
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
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified10.129 +/- 10.329 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified123.8 +/- 2.8 umol/mmol creatinineAdult (>18 years old)BothOccupational exposure to styrene details
UrineDetected and Quantified8.00 +/- 9.00 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  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. [2091926 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID958
FoodDB IDFDB022191
KNApSAcK IDNot Available
Chemspider ID388690
KEGG Compound IDC01984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelic acid
NuGOwiki LinkHMDB00703
Metagene LinkHMDB00703
METLIN ID5671
PubChem Compound439616
PDB IDSMN
ChEBI ID32800
References
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. 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. [8945737 ]
  2. 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. [10203155 ]
  3. 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. [12569541 ]
  4. 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. [7086169 ]
  5. 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. [9815755 ]
  6. 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. [2060253 ]
  7. 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. [7614680 ]
  8. 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. [2265798 ]
  9. 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. [10392560 ]
  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. [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. [12576693 ]