Malic acid

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O5
Molecular Weight	134.0874
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C4H6O5
Molecular Weight	134.0874
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://gov.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/FR330.pdf | https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdfhttp://www.cosmeticsinfo.org/ingredient/sodium-malate | https://www.food.gov.uk/science/additives/enumberlist#h_7 | https://www.ncbi.nlm.nih.gov/pubmed/11358110 | https://www.ncbi.nlm.nih.gov/pubmed/9477166

Malic acid is a tart-tasting organic dicarboxylic acid that contributes to the taste of many sour or tart foods such as apples. Sodium Malate is the sodium salt of Malic Acid. Malic Acid and Sodium Malate can be found in a wide range of cosmetics and personal care products. Sodium Malate functions as a skin conditioning agent-humectant. As a food additive, Sodium Malate has the E number E350. Sodium Malate has demonstrated protective effect on cisplatin-induced toxicity in mice. Sodium malate could become a useful agent for the reduction of CDDP-induced toxicity, particularly nephrotoxicity and hepatotoxicity.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cisplatin-induced toxicity 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9477166 https://www.ncbi.nlm.nih.gov/pubmed/9514605	Secondary	Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8974556 https://www.ncbi.nlm.nih.gov/pubmed/1458176	Preventing	Preclinical	Unknown Approved Use Unknown
Skin injuries 8 Sources: https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf	Curative	Approved 8583	ACERBINE Approved Use Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.

Doses

Dose	Population	Adverse events
1 % 8 times / day multiple, topical Studied dose Dose: 1 %, 8 times / day Route: topical Route: multiple Dose: 1 %, 8 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22926481/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/22926481/	Sources: https://pubmed.ncbi.nlm.nih.gov/22926481/
600 mg 2 times / day multiple, oral Studied dose Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8587088/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8587088/	Sources: https://pubmed.ncbi.nlm.nih.gov/8587088/

PubMed

Title	Date	PubMed
Assimilation of D-malate by Rhodobacter capsulatus E1F1.	2001-09	11400062
Structural analyses of a malate dehydrogenase with a variable active site.	2001-08-17	11389141
Alteration of the specificity of malate dehydrogenase by chemical modulation of an active site arginine.	2001-08-17	11389140
Characterization of a novel complex from halophilic archaebacteria, which displays chaperone-like activities in vitro.	2001-08-10	11395490
Effect of an antidiabetic extract of Catharanthus roseus on enzymic activities in streptozotocin induced diabetic rats.	2001-08	11448549
Carbohydrate deprivation reduces NADPH-production in fish liver but not in adipose tissue.	2001-08	11404182
Metabolic flux analysis for succinic acid production by recombinant Escherichia coli with amplified malic enzyme activity.	2001-07-20	11369997
[Properties of gluconeogenesis enzymes from flatworms].	2001-07-17	11452789
pH-dependent investigations of vanadium(V)-peroxo-malate complexes from aqueous solutions. In search of biologically relevant vanadium(V)-peroxo species.	2001-07-16	11442368
The first examples of (S)-2-hydroxyacid dehydrogenases catalyzing the transfer of the pro-4S hydrogen of NADH are found in the archaea.	2001-07-09	11451450
Transcriptome meets metabolome: hierarchical and metabolic regulation of the glycolytic pathway.	2001-07-06	11445079
Relationships between inhibition constants, inhibitor concentrations for 50% inhibition and types of inhibition: new ways of analysing data.	2001-07-01	11415458
Malo-ethanolic fermentation in grape must by recombinant strains of Saccharomyces cerevisiae.	2001-07	11447602
Thyroid hormone--sympathetic interaction and adaptive thermogenesis are thyroid hormone receptor isoform--specific.	2001-07	11435461
Massive sequence comparisons as a help in annotating genomic sequences.	2001-07	11435413
Altered expression and function of mitochondrial beta-oxidation enzymes in juvenile intrauterine-growth-retarded rat skeletal muscle.	2001-07	11420423
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.	2001-06-29	11434921
[Lactate and malate dehydrogenase activity in the sterlet and Russian sturgeon under conditions of the widespread muscular pathology].	2001-06-27	11424523
Tricarboxylic acid cycle enzymes of the ectomycorrhizal basidiomycete, Suillus bovinus.	2001-06-26	11421446
Myoadenylate deaminase deficiency does not affect muscle anaplerosis during exhaustive exercise in humans.	2001-06-15	11410643
Histochemical study of acute and chronic intraperitoneal nicotine effects on several glycolytic and Krebs cycle dehydrogenase activities in the frontoparietal cortex and subcortical nuclei of the rat brain.	2001-06-15	11398187
Enzymatic computing.	2001-06-02	11386878
The effect of nucleotides and mitochondrial chaperonin 10 on the structure and chaperone activity of mitochondrial chaperonin 60.	2001-06	11422376
Two-dimensional electrophoresis and characterization of antigens from Paracoccidioides brasiliensis.	2001-06	11418327
Inducible and constitutive expression using new plasmid and integrative expression vectors for Thermus sp.	2001-06	11412354
Aluminum speciation studies in biological fluids. Part 7. A quantitative investigation of aluminum(III)-malate complex equilibria and their potential implications for aluminum metabolism and toxicity.	2001-06	11410234
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001-06	11405809
Energetic determinants of tyrosine phosphorylation of focal adhesion proteins during hypoxia/reoxygenation of kidney proximal tubules.	2001-06	11395393
A pre-genetic study of the isoforms of malic enzyme associated with lipid accumulation in Mucor circinelloides.	2001-06	11390681
An NMR and enzyme study of the carbon metabolism of Neisseria meningitidis.	2001-06	11390678
Determination of organic acids and inorganic anions in wine by isotachophoresis on a planar chip.	2001-05-04	11382288
Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide.	2001-05-03	11348236
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.	2001-05	11440113
Induction of a peroxisomal malate dehydrogenase isoform in liver of starved rats.	2001-05	11405883
Partial amino acid catabolism leading to the formation of alanine in Periophthalmodon schlosseri (mudskipper): a strategy that facilitates the use of amino acids as an energy source during locomotory activity on land.	2001-05	11398750
New phenolic constituents from the fruit juice of Phyllanthus emblica.	2001-05	11383602
Magnesium ameliorates aluminum rhizotoxicity in soybean by increasing citric acid production and exudation by roots.	2001-05	11382822
Comprehensive chemical profiling of gramineous plant root exudates using high-resolution NMR and MS.	2001-05	11382236
Cloning and functional characterization of the 5' flanking region of the human mitochondrial malic enzyme gene. Regulatory role of Sp1 and AP-2.	2001-05	11358520
Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex.	2001-05	11351103
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.	2001-05	11351102
Survey of normal appearing mouse strain which lacks malic enzyme and Nad+-linked glycerol phosphate dehydrogenase: normal pancreatic beta cell function, but abnormal metabolite pattern in skeletal muscle.	2001-04	11451371
Single-cell dissection and microdroplet chemistry.	2001-04	11373308
Physiological basis of reduced AL tolerance in ditelosomic lines of Chinese Spring wheat.	2001-04	11346958
Inhibiting expression of a tomato ripening-associated membrane protein increases organic acids and reduces sugar levels of fruit.	2001-04	11346954
Reevaluating the free-ion activity model of trace metal toxicity toward higher plants: experimental evidence with copper and zinc.	2001-04	11345467
Non-photosynthetic 'malic enzyme' from maize: a constituvely expressed enzyme that responds to plant defence inducers.	2001-03	11352460
Variation of isoenzyme and RAPD patterns in Candida albicans morphological mutants with altered colony ultrastructure.	2001	11426863
Metabolic regulation of pH in plant cells: role of cytoplasmic pH in defense reaction and secondary metabolism.	2001	11407758
Final report on the safety assessment of Malic Acid and Sodium Malate.	2001	11358110

Patents

Sample Use Guides

In Vivo Use Guide

Apply Acerbine solution (malic acid, salicylic acid, benzoic acid) to the wound or damaged skin two or more times daily or moisten the dressing again. Once scar formation begins, one application a day is generally sufficient.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:51 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:51 GMT 2025`
Record UNII	817L1N4CKP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Malic acid

Official Name

English

E-296

Preferred Name

English

MALIC ACID [USP IMPURITY]

Common Name

English

MALIC ACID, DL-

Common Name

English

POMALOUS ACID

Common Name

English

INS NO.296

Code

English

MALIC ACID [VANDF]

Common Name

English

MALATE

Common Name

English

MALIC ACID [USP-RS]

Common Name

English

DL-MALIC ACID

Common Name

English

HYDROXYBUTANEDIOIC ACID, (±)-

Systematic Name

English

MALIC ACID [FCC]

Common Name

English

NSC-25941

Code

English

INS NO. 296

Code

English

E296

Code

English

(±)-MALIC ACID

Common Name

English

MALIC ACID [II]

Common Name

English

MALIC ACID [EP MONOGRAPH]

Common Name

English

HYDROXYBUTANEDIOIC ACID [HSDB]

Common Name

English

INS-296

Code

English

MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]

Common Name

English

D,L-MALIC ACID

Common Name

English

Malic acid [WHO-DD]

Common Name

English

HYDROXYSUCCINIC ACID

Common Name

English

MALIC ACID [MI]

Common Name

English

2-HYDROXYBUTANEDIOIC ACID

Systematic Name

English

MALIC ACID [NF]

Common Name

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-296