(±)-Malic acid (CED0002106)

Record Information

Version

1.0

Creation Date

2016-05-26 00:08:54 UTC

Update Date

2026-04-17 19:49:16 UTC

Accession Number

CHEM027998

Identification

Common Name

(±)-Malic acid

Class

Small Molecule

Description

(±)-Malic acid is an organic compound with the chemical formula C4H6O5 and an average molecular weight of 134.09 g/mol. (±)-Malic acid belongs to the beta hydroxy acids and derivatives, a subclass of hydroxy acids and derivatives within the organic compounds. In industrial applications, the compound serves as a pH regulating agent, a chelating agent, and a nutrient and flavouring agent. It is identified in 24 recorded sources across various sectors. Within the category of food, food processing and cookware, it is found in the preparation of wort, vinegar, and malt, as well as the preparation of wine or sparkling wine and agglomerated sugar products. In the realm of household cleaning and consumer products, it is present in tobacco product cases, tobacco pipes, pipe accessories, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in building and construction materials, specifically ceilings, and in electrical and electronic equipment, including magnets, emergency protective devices, discharge lamps, contacts, and antennas.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-L-Malic acid	ChEBI
(S)-(-)-Hydroxysuccinic acid	ChEBI
L-2-Hydroxybutanedioic acid	ChEBI
L-Apple acid	ChEBI
Malate	ChEBI
Malic acid	ChEBI
S-2-Hydroxybutanedioic acid	ChEBI
L-Malate	Kegg
(-)-L-Malate	Generator
(S)-(-)-Hydroxysuccinate	Generator
L-2-Hydroxybutanedioate	Generator
S-2-Hydroxybutanedioate	Generator
(-)-(S)-Malate	HMDB
(-)-(S)-Malic acid	HMDB
(-)-Hydroxysuccinate	HMDB
(-)-Hydroxysuccinic acid	HMDB
(-)-Malic acid	HMDB
(2S)-2-Hydroxybutanedioate	HMDB
(2S)-2-Hydroxybutanedioic acid	HMDB
(S)-Hydroxy-butanedioate	HMDB
(S)-Hydroxy-butanedioic acid	HMDB
(S)-Hydroxybutanedioate	HMDB
(S)-Hydroxybutanedioic acid	HMDB
(S)-Malic acid	HMDB
Apple acid	HMDB
L-(-)-Malic acid	HMDB
L-Hydroxybutanedioate	HMDB
L-Hydroxybutanedioic acid	HMDB
L-Hydroxysuccinate	HMDB
L-Hydroxysuccinic acid	HMDB
S-(-)-Malate	HMDB
S-(-)-Malic acid	HMDB
(S)-Malate	HMDB
L-Malic acid	ChEBI
(2S)-2-Hydroxysuccinic acid	HMDB
(2S)-Malic acid	HMDB
(S)-2-Hydroxysuccinic acid	HMDB
2-Hydroxybutanedioic acid	HMDB
2-Hydroxyethane-1,2-dicarboxylic acid	HMDB
2-Hydroxysuccinic acid	HMDB
Deoxytetraric acid	HMDB
Hydroxybutanedioic acid	HMDB
Hydroxysuccinic acid	HMDB
Monohydroxybutanedioic acid	HMDB
alpha-Hydroxysuccinic acid	HMDB
α-Hydroxysuccinic acid	HMDB

Chemical Formula

C₄H₆O₅

Average Molecular Mass

134.087 g/mol

Monoisotopic Mass

134.022 g/mol

CAS Registry Number

617-48-1

IUPAC Name

(2S)-2-hydroxybutanedioic acid

Traditional Name

(-)-malic acid

SMILES

O[C@@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

InChI Key

BJEPYKJPYRNKOW-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

malic acid (CHEBI:30797 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	218 g/L	ALOGPS
logP	-0.87	ALOGPS
logP	-1.1	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.88 m³·mol⁻¹	ChemAxon
Polarizability	10.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-000t-0940000000-142d6f5fc2efbf0d5109	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0002-0920000000-505483ce10ee3c4c9d20	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00di-9710000000-8f263d045d715ae9fe2b	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-000t-0940000000-142d6f5fc2efbf0d5109	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0002-0920000000-505483ce10ee3c4c9d20	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00di-9710000000-8f263d045d715ae9fe2b	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0002-0910000000-fadd80af55894555ea72	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9100000000-aba7652c885a434930ef	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-02j9-7191000000-b78c78194b39deee0ca4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-9300000000-acd7d0159b8bb70b80fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0096-9000000000-7359292556d9d393d8f4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0097-9000000000-a111335688b3219c1fc1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00lr-0942120000-9504700a82dcf5dc3adb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0900000000-45e58d8a75d957cc5c41	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-4ec56105367de7bf0027	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-1decf12f117200e0f28d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-4900000000-86fd329658581c81c0ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9100000000-82ffef2aa053f77cdbc5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9000000000-424bd54bc81a9db65a55	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-a916941735427ee3c48d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-1decf12f117200e0f28d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-4900000000-86fd329658581c81c0ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9100000000-82ffef2aa053f77cdbc5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9000000000-424bd54bc81a9db65a55	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-a916941735427ee3c48d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-afdfdad3edeeb90cb3e4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-4900000000-01b3a756de8f5a3ae6de	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-4900000000-5fc3f0befc374a6fcdd6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-7900000000-2a07c36db6acea9015af	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00rj-9200000000-316c7803efd1dfb76523	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-9000000000-a442bcaaacb6f4eec14d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-9800000000-03bfaee5de56f72ed927	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0079-9200000000-26a075efe73adc63a189	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-059f-9000000000-a3281a79477ac14e2eae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00y0-9400000000-b346287170f4b47937d9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00du-9000000000-94fcc5032bed94eae77e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9000000000-43c40f8a7715a996c55b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ri-9400000000-a20ca040dba0bb25ae2b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0095-9000000000-90064952bc6def150ecc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9000000000-4dd1a07ea5d3aab2c6ea	Not Available	View Spectrum
MS	MS Spectrum	splash10-0076-9000000000-ad60ea592282d09e4bd8	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, H₂O, experimental)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5241.0	Log mg/kg	[2900:9300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
495	Ceilings	Building & Construction	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
512	Contacts	Electrical & Electronic Equipment	Not Available
514	Discharge Lamps	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
536	Superconductive Or Hyperconductive Conductors Cables Or Transmission Lines	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
538	Thin Magnetic Films	Electrical & Electronic Equipment	Not Available
541	Agglomerated Sugar Products	Food, food processing & cookware	Not Available
547	Preparation Of Malt	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
550	Preparation Of Wort	Food, food processing & cookware	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
553	Treatment Of Hops	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
566	Tobacco Pipes	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
568	Tobacco Product Moisture Control	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
589	Life Buoys	Marine, shipping & aquaculture	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
631	Anthraquinone Dyes	Textiles, leather & furnishings	Not Available
638	Decorating Textiles	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available

Pathways

33 pathways

Citric Acid Cycle

Pyruvate Metabolism

Leigh Syndrome

Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)

Pyruvate Dehydrogenase Complex Deficiency

Transfer of Acetyl Groups into Mitochondria

Congenital Lactic Acidosis

Fumarase Deficiency

Mitochondrial Complex II Deficiency

2-Ketoglutarate Dehydrogenase Complex Deficiency

Pyruvate Dehydrogenase Deficiency (E3)

Pyruvate Dehydrogenase Deficiency (E2)

View all 33 pathways

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glutamate transporter homolog	O59010	Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)	Predicted (SEA)	0.467095
Click to view 3D structure	Asc-type amino acid transporter 1	P63116	Rat	Predicted (SEA)	2.64687
Click to view 3D structure	Mast cell carboxypeptidase A	P15088	Humans	Predicted (SEA)	17.9832
Click to view 3D structure	Olfactory receptor 51E2	Q9H255	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	N-acetylaspartylglutamate synthase A	Q8IXN7	Humans	Predicted (SEA)	8.25202
Click to view 3D structure	Metabotropic glutamate receptor 8	P47743	Mus musculus	Predicted (SEA)	4.5931
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P39086	Humans	Predicted (SEA)	5.83869
Click to view 3D structure	Metabotropic glutamate receptor 2	P31421	Rattus norvegicus	Predicted (SEA)	41.9607
Click to view 3D structure	Excitatory amino acid transporter 3	P43005	Humans	Predicted (SEA)	23.6662
Click to view 3D structure	Beta-lactamase VIM-1	Q9XAY4	Pseudomonas aeruginosa	Predicted (SEA)	1.24559
Click to view 3D structure	Metabotropic glutamate receptor 6	P35349	Rattus norvegicus	Predicted (SEA)	17.2047
Click to view 3D structure	Metabotropic glutamate receptor 3	P31422	Rattus norvegicus	Predicted (SEA)	39.0025
Click to view 3D structure	Dihydroxyacetone phosphate acyltransferase	O15228	Humans	Predicted (SEA)	20.3186
Click to view 3D structure	Metabotropic glutamate receptor 4	P31423	Rattus norvegicus	Predicted (SEA)	116.54
Click to view 3D structure	Metabotropic glutamate receptor 2	Q14416	Humans	Predicted (SEA)	110.234
Click to view 3D structure	Glutamate receptor 4	P48058	Humans	Predicted (SEA)	6.53933
Click to view 3D structure	Metabotropic glutamate receptor 6	O15303	Humans	Predicted (SEA)	41.4158
Click to view 3D structure	Metabotropic glutamate receptor 1	Q13255	Humans	Predicted (SEA)	81.3524
Click to view 3D structure	Excitatory amino acid transporter 1	P43003	Humans	Predicted (SEA)	15.3363
Click to view 3D structure	Ribose-5-phosphate isomerase B	P9WKD7	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	0.856341
Click to view 3D structure	Sodium- and chloride-dependent GABA transporter 2	P31646	Rattus norvegicus	Predicted (SEA)	4.04816
Click to view 3D structure	Metabotropic glutamate receptor 8	P70579	Rattus norvegicus	Predicted (SEA)	46.5538
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P22756	Rattus norvegicus	Predicted (SEA)	23.2769
Click to view 3D structure	Metabotropic glutamate receptor 4	Q14833	Humans	Predicted (SEA)	257.837
Click to view 3D structure	Succinate receptor 1	Q99MT6	Mus musculus	Predicted (SEA)	0.934191