CHEBI:35825 - mandelic acid

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ChEBI Name mandelic acid
ChEBI ID CHEBI:35825
Definition A 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25149, CHEBI:32801
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Formula C8H8O3
Net Charge 0
Average Mass 152.14732
Monoisotopic Mass 152.047
InChI InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
InChIKey IWYDHOAUDWTVEP-UHFFFAOYSA-N
SMILES OC(C(O)=O)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial agent
A substance that kills or slows the growth of bacteria.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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ChEBI Ontology
Outgoing mandelic acid (CHEBI:35825) has functional parent acetic acid (CHEBI:15366)
mandelic acid (CHEBI:35825) has role antibacterial agent (CHEBI:33282)
mandelic acid (CHEBI:35825) has role human xenobiotic metabolite (CHEBI:76967)
mandelic acid (CHEBI:35825) is a 2-hydroxy monocarboxylic acid (CHEBI:49302)
mandelic acid (CHEBI:35825) is a benzenes (CHEBI:22712)
mandelic acid (CHEBI:35825) is conjugate acid of mandelate (CHEBI:25147)
Incoming 3,4-dihydroxymandelic acid (CHEBI:27637) has functional parent mandelic acid (CHEBI:35825)
3,4-methylenedioxymandelic acid (CHEBI:65054) has functional parent mandelic acid (CHEBI:35825)
3-dimethylallyl-4-hydroxymandelic acid (CHEBI:31112) has functional parent mandelic acid (CHEBI:35825)
3-hydroxymandelic acid (CHEBI:86553) has functional parent mandelic acid (CHEBI:35825)
4-hydroxymandelic acid (CHEBI:16388) has functional parent mandelic acid (CHEBI:35825)
cyclandelate (CHEBI:3988) has functional parent mandelic acid (CHEBI:35825)
ethyl hydroxy(phenyl)acetate (CHEBI:38750) has functional parent mandelic acid (CHEBI:35825)
vanillylmandelic acid (CHEBI:20106) has functional parent mandelic acid (CHEBI:35825)
(R)-mandelic acid (CHEBI:17656) is a mandelic acid (CHEBI:35825)
(S)-mandelic acid (CHEBI:32800) is a mandelic acid (CHEBI:35825)
mandelate (CHEBI:25147) is conjugate base of mandelic acid (CHEBI:35825)
IUPAC Name
hydroxy(phenyl)acetic acid
Synonyms Sources
(RS)-Mandelic acid HMDB
2-Hydroxy-2-phenylacetic acid HMDB
2-Hydroxy-2-phenylethanoic acid HMDB
α-hydroxybenzeneacetic acid NIST Chemistry WebBook
DL-Mandelic acid HMDB
Mandelsäure ChEBI
Database Links Databases
1629 DrugCentral
HMDB0000703 HMDB
Mandelic_acid Wikipedia
View more database links
Registry Numbers Types Sources
218213 Gmelin Registry Number Gmelin
510011 Beilstein Registry Number Beilstein
510011 Reaxys Registry Number Reaxys
90-64-2 CAS Registry Number NIST Chemistry WebBook
90-64-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22770225 PubMed citation Europe PMC
24278065 PubMed citation Europe PMC
4813698 PubMed citation Europe PMC
Last Modified
07 July 2017
General Comment
2014-03-11 Mandelic acid in found in urine samples of humans that have been exposed to styrene.