malic acid (CHEBI:6650)

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ChEBI Name	malic acid

ChEBI ID	CHEBI:6650

Definition	A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB4220794, ChemicalBook:CB7220795, eMolecules:475037

Download	Molfile XML SDF

Wikipedia	License
Malic acid is an organic compound with the molecular formula HO2CCH(OH)CH2CO2H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is a metabolic intermediate in the citric acid cycle.
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Formula

C4H6O5

Net Charge

Average Mass

134.08744

Monoisotopic Mass

134.02152

InChI

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

InChIKey

BJEPYKJPYRNKOW-UHFFFAOYSA-N

SMILES

OC(CC(O)=O)C(O)=O

Metabolite of Species	Details
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyond

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):	fundamental metabolite Any metabolite produced by all living cells. food acidity regulator A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.

Application(s):	food acidity regulator A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.

ChEBI Ontology
Outgoing	malic acid (CHEBI:6650) has functional parent succinic acid (CHEBI:15741) malic acid (CHEBI:6650) has role food acidity regulator (CHEBI:64049) malic acid (CHEBI:6650) has role fundamental metabolite (CHEBI:78675) malic acid (CHEBI:6650) is a 2-hydroxydicarboxylic acid (CHEBI:50263) malic acid (CHEBI:6650) is a C4-dicarboxylic acid (CHEBI:66873) malic acid (CHEBI:6650) is conjugate acid of malate (CHEBI:25115) malic acid (CHEBI:6650) is conjugate acid of malate(2−) (CHEBI:15595)

Incoming	2,3-dimethylmalic acid (CHEBI:15590) has functional parent malic acid (CHEBI:6650) 2-(ω-methylthio)alkylmalic acid (CHEBI:134530) has functional parent malic acid (CHEBI:6650) 2-(p-coumaroyl)malic acid (CHEBI:134253) has functional parent malic acid (CHEBI:6650) 2-hydroxy-3-(2-methylidenecyclopropyl)butanedioic acid (CHEBI:133310) has functional parent malic acid (CHEBI:6650) 2-phosphinomethylmalic acid (CHEBI:81403) has functional parent malic acid (CHEBI:6650) 3-(ω-methylthio)alkylmalic acid (CHEBI:134532) has functional parent malic acid (CHEBI:6650) 3-carboxy-3-hydroxypropanoyl-CoA (CHEBI:137700) has functional parent malic acid (CHEBI:6650) malate ester (CHEBI:36188) has functional parent malic acid (CHEBI:6650) (R)-malic acid (CHEBI:30796) is a malic acid (CHEBI:6650) (S)-malic acid (CHEBI:30797) is a malic acid (CHEBI:6650) malate (CHEBI:25115) is conjugate base of malic acid (CHEBI:6650) malate(2−) (CHEBI:15595) is conjugate base of malic acid (CHEBI:6650)

IUPAC Name

2-hydroxybutanedioic acid

Synonyms	Sources
2-Hydroxybutanedioic acid	KEGG COMPOUND
2-Hydroxyethane-1,2-dicarboxylic acid	HMDB
2-Hydroxysuccinic acid	HMDB
α-hydroxysuccinic acid	HMDB
Äpfelsäure	ChEBI
apple acid	NIST Chemistry WebBook
DL-Malic acid	HMDB
E296	ChEBI
H₂mal	IUPAC
hydroxybutanedioic acid	NIST Chemistry WebBook
hydroxysuccinic acid	NIST Chemistry WebBook
Malic acid	KEGG COMPOUND

Citations

Last Modified

07 July 2017