Record Information
Version1.0
Creation date2011-09-21 00:09:52 UTC
Update date2015-10-09 22:27:17 UTC
Primary IDFDB022191
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number90-64-2
Structure
Thumb
Synonyms
SynonymSource
(S)-2-Hydroxy-2-phenylacetic acidChEBI
(S)-alpha-Hydroxybenzeneacetic acidChEBI
(S)-MandelsaeureChEBI
L-Mandelic acidChEBI
(S)-2-Hydroxy-2-phenylacetateKegg
(S)-a-HydroxybenzeneacetateGenerator
(S)-a-Hydroxybenzeneacetic acidGenerator
(S)-alpha-HydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetic acidGenerator
L-MandelateGenerator
(S)-MandelateGenerator
MandelateGenerator, HMDB
(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
(S)-Mandelic acidKEGG
(S)-α-hydroxybenzeneacetateGenerator
(S)-α-hydroxybenzeneacetic acidGenerator
Mandelic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m³·mol⁻¹ChemAxon
Polarizability14.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H8O3
IUPAC name(2S)-2-hydroxy-2-phenylacetic acid
InChI IdentifierInChI=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 KeyIWYDHOAUDWTVEP-ZETCQYMHSA-N
Isomeric SMILESO[C@H](C(O)=O)C1=CC=CC=C1
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
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
Substituents
  • 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
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-2d141c7d9cfc97cc9b76JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2910000000-de71bbd7bcfd35e2bbe5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-31443907299c1634fe9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pdi-4900000000-d32dc8f06b5e94c7b3b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-1900000000-f1e179f7f6654c244250JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-15fb1f5429449730eb57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9500000000-6d480b6841c2a90ea872JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-15fb1f5429449730eb57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9500000000-96b7d7c57c085b66c0aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0900000000-dc883eccc7ede3626274JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-43028c230f4ad5a4568cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9500000000-d3b486d397a2e852f3a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-d3c9a003466ac58be74fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdi-5900000000-cadf8b3761e31a6e33c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-b906b74a2aa4ffe7faccJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID388690
ChEMBL IDCHEMBL58910
KEGG Compound IDC01984
Pubchem Compound ID439616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID958
DrugBank IDDB03357
HMDB IDHMDB00703
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSMN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMandelic acid
Phenol-Explorer Metabolite ID958
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference