Malic acid

Malic acid
	; DL-Malic acid
Names
	Preferred IUPAC name 2-Hydroxybutanedioic acid
	Other names Hydroxybutanedioic acid; 2-Hydroxysuccinic acid; (L/D)-Malic acid; (±)-Malic acid; (S/R)-Hydroxybutanedioic acid;
Identifiers
CAS Number	6915-15-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6650 ; CHEBI:30796 D-(+); CHEBI:30797 L-(–);
ChEMBL	ChEMBL1455497 ;
ChemSpider	510 ; 83793 D-(+)-malic acid ; 193317 L-(–)-malic acid ;
ECHA InfoCard	100.027.293
EC Number	230-022-8;
E number	E296 (preservatives)
IUPHAR/BPS	2480;
KEGG	C00711 ; C00497 D-(+); C00149 L-(–);
PubChem CID	525; 92824 D-(+); 222656 L-(–);
UNII	817L1N4CKP ;
CompTox Dashboard (EPA)	DTXSID0027640 ;
	InChI InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N ; InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) Key: BJEPYKJPYRNKOW-UHFFFAOYAM;
	SMILES O=C(O)CC(O)C(=O)O;
Properties
Chemical formula	C4H6O5
Molar mass	134.09 g/mol
Appearance	Colorless
Density	1.609 g⋅cm−3
Melting point	130 °C (266 °F; 403 K)
Solubility in water	558 g/L (at 20 °C)
Acidity (pKa)	pKa1 = 3.40; pKa2 = 5.20; pKa3 = 14.5
Hazards
	GHS labelling:
Pictograms
Flash point	203 °C
Related compounds
Other anions	Malate
Related carboxylic acids	Succinic acid; Tartaric acid; Fumaric acid
Related compounds	Butanol; Butyraldehyde; Crotonaldehyde; Sodium malate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ "chemBlink Database of Chemicals from Around the World". chemblink.com. Archived from the original on 2009-01-22.
^ Data for biochemical research (3rd ed.). Oxford: Clarendon Press. 1986. ISBN 0-19-855358-7. OCLC 11865673.
^ Silva, Andre M. N.; Kong, Xiaole; Hider, Robert C. (2009). "Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems". BioMetals. 22 (5): 771–778. doi:10.1007/s10534-009-9224-5. ISSN 0966-0844. PMID 19288211.
^ "DL-Malic acid - (DL-Malic acid) SDS". Merck Millipore.

Names


DL-Malic acid
Preferred IUPAC name 2-Hydroxybutanedioic acid
Other names Hydroxybutanedioic acid 2-Hydroxysuccinic acid (L/D)-Malic acid (±)-Malic acid (S/R)-Hydroxybutanedioic acid
Identifiers
CAS Number	6915-15-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6650^Y CHEBI:30796 D-(+) CHEBI:30797 L-(–)
ChEMBL	ChEMBL1455497^N
ChemSpider	510^Y 83793 D-(+)-malic acid^Y 193317 L-(–)-malic acid^Y
ECHA InfoCard	100.027.293
EC Number	230-022-8
E number	E296 (preservatives)
IUPHAR/BPS	2480
KEGG	C00711^N C00497 D-(+) C00149 L-(–)
PubChem CID	525 92824 D-(+) 222656 L-(–)
UNII	817L1N4CKP^Y
CompTox Dashboard (EPA)	DTXSID0027640
InChI InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)^Y Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N^Y InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) Key: BJEPYKJPYRNKOW-UHFFFAOYAM
SMILES O=C(O)CC(O)C(=O)O
Properties
Chemical formula	C₄H₆O₅
Molar mass	134.09 g/mol
Appearance	Colorless
Density	1.609 g⋅cm⁻³
Melting point	130 °C (266 °F; 403 K)
Solubility in water	558 g/L (at 20 °C)^[1]
Acidity (pK_a)	pK_a1 = 3.40 pK_a2 = 5.20^[2] pK_a3 = 14.5^[3]
Hazards
GHS labelling:
Pictograms
Flash point	203 °C^[4]
Related compounds
Other anions	Malate
Related carboxylic acids	Succinic acid Tartaric acid Fumaric acid
Related compounds	Butanol Butyraldehyde Crotonaldehyde Sodium malate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references