Malic Acid

10/4/2020 Malic acid | C4H6O5 - PubChem
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COMPOUND SUMMARY
Malic acid
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PubChem CID: 525
Structure:
2D 3D
Find Similar Structures
Chemical Safety:
Irritant
Laboratory Chemical Safety Summary (LCSS) Datasheet
Molecular Formula: C4H6O5
malic acid
DL-malic acid
6915-15-7
Synonyms: 2-Hydroxybutanedioic acid
2-Hydroxysuccinic acid
More...
Molecular Weight: 134.09 g/mol
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Dates:
2020-04-04 2004-09-16
Malic acid is a 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a
hydroxy group. It has a role as a food acidity regulator and a fundamental metabolite. It is a 2-hydroxydicarboxylic acid and a C4-
dicarboxylic acid. It derives from a succinic acid. It is a conjugate acid of a malate(2-) and a malate.
ChEBI
Source: ChEBI
Record Name: Malic acid
URL: http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6650
Description: Chemical Entities of Biological Interest (ChEBI) is a database and ontology of molecular entities focused on 'small' chemical
compounds, that is part of the Open Biomedical Ontologies effort. The term "molecular entity" refers to any constitutionally or isotopically distinct
atom, molecule, ion, ion pair, radical, radical ion, complex, conformer, etc., identifiable as a separately distinguishable entity.
https://pubchem.ncbi.nlm.nih.gov/compound/525 1/72
Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an
intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions.
Human Metabolome Database (HMDB)
Malic acid has been used in trials studying the treatment of Xerostomia, Depression, and Hypertension.
DrugBank
Contents
1 Structures
2 Names and Identifiers
3 Chemical and Physical Properties
4 Spectral Information
5 Related Records
6 Chemical Vendors
7 Drug and Medication Information
8 Food Additives and Ingredients
9 Pharmacology and Biochemistry
10 Use and Manufacturing
11 Identification
12 Safety and Hazards
13 Toxicity
14 Literature
15 Patents
16 Biomolecular Interactions and Pathways
17 Biological Test Results
18 Classification
19 Information Sources
1 Structures
1.1 2D Structure
Chemical Structure
Depiction
PubChem
1.2 3D Conformer
Interactive Chemical
Structure Model
Ball and Stick
Sticks
Wire-Frame
Space-Filling
Show Hydrogens
Animate
PubChem
2 Names and Identifiers
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxybutanedioic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)
PubChem
2.1.2 InChI
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
PubChem
2.1.3 InChI Key
BJEPYKJPYRNKOW-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
PubChem
2.1.4 Canonical SMILES
C(C(C(=O)O)O)C(=O)O
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)
PubChem
2.2 Molecular Formula

C4H6O5
EU Food Improvement Agents; PubChem
2.3 Other Identifiers
2.3.1 CAS
6915-15-7
ChemIDplus; DrugBank; EPA Chemicals under the TSCA; EPA DSSTox; European Chemicals Agency (ECHA); HSDB; Human Metabolome Database (HMDB)
78644-42-5
ChemIDplus
617-48-1
DTP/NCI; European Chemicals Agency (ECHA)
17482-42-7
European Chemicals Agency (ECHA)
2.3.2 Related CAS
676-46-0 (di-hydrochloride salt)
ChemIDplus
2.3.3 Deprecated CAS
41308-42-3, 617-48-1, 623158-98-5, 879715-44-3, 1334703-48-8
ChemIDplus
2.3.4 European Community (EC) Number
EC Number
230-022-8, 210-514-9, 202-601-5
EU Food Improvement Agents
210-514-9
230-022-8
241-498-1
2.3.5 NSC Number
25941
DTP/NCI
2.3.6 DSSTox Substance ID
DTXSID0027640
EPA DSSTox
2.3.7 Wikipedia
DL-malic acid
Wikipedia
2.4 Synonyms
2.4.1 MeSH Entry Terms
calcium (hydroxy-1-malate) hexahydrate

malate
malic acid
malic acid, (R)-isomer
malic acid, calcium salt, (1:1), (S)-isomer
malic acid, disodium salt
malic acid, disodium salt, (R)-isomer
malic acid, disodium salt, (S)-isomer
malic acid, magnesium salt (2:1)
malic acid, monopotassium salt, (+-)-isomer
malic acid, potassium salt, (R)-isomer
malic acid, sodium salt, (+-)-isomer
MeSH
2.4.2 Depositor-Supplied Synonyms
malic acid Malic acid, DL- FEMA No. 2655 (+-)-Hydroxysuccinic acid
DL-malic acid Musashi-no-Ringosan FEMA Number 2655 DL-2-hydroxybutanedioic acid
6915-15-7 alpha-Hydroxysuccinic acid Kyselina hydroxybutandiova [Czech] butanedioic acid, 2-hydroxy-
2-Hydroxybutanedioic acid Hydroxybutandisaeure Malic acid [NF] BUTANEDIOIC ACID, HYDROXY-, (S)-
2-Hydroxysuccinic acid dl-Hydroxybutanedioic acid EPA Pesticide Chemical Code 051101 MLS000084707
malate Caswell No. 537 CCRIS 2950 CHEBI:6650
617-48-1 Monohydroxybernsteinsaeure CCRIS 6567 (+/-)-2-Hydroxysuccinic acid
Butanedioic acid, hydroxy- Succinic acid, hydroxy- AI3-06292 (+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
hydroxysuccinic acid R,S(+-)-Malic acid HSDB 1202 Hydroxybutanedioic acid, (+-)-
Kyselina jablecna 2-Hydroxyethane-1,2-dicarboxylic acid EINECS 210-514-9 BJEPYKJPYRNKOW-UHFFFAOYSA-N
Deoxytetraric acid Kyselina jablecna [Czech] EINECS 230-022-8 NSC25941
hydroxybutanedioic acid FDA 2018 NSC 25941 Malic acid (NF)
Pomalus acid (+-)-Malic acid (-)-Malic acid Malic acid, L-
PubChem
3 Chemical and Physical Properties
3.1 Computed Properties
Property Name Property Value Reference
Molecular Weight 134.09 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3 -1.3 Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count 5 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass 134.021523 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass 134.021523 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area 94.8 Å² Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count 9 Computed by PubChem
Formal Charge 0 Computed by PubChem
Complexity 129 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count 0 Computed by PubChem
Defined Atom Stereocenter Count 0 Computed by PubChem
Undefined Atom Stereocenter Count 1 Computed by PubChem
Defined Bond Stereocenter Count 0 Computed by PubChem
Undefined Bond Stereocenter Count 0 Computed by PubChem
Covalently-Bonded Unit Count 1 Computed by PubChem
Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04)
PubChem
3.2 Experimental Properties
3.2.1 Physical Description
DryPowder; OtherSolid, Liquid
EPA Chemicals under the TSCA
White or nearly white crystalline powder or granules
Solid
3.2.2 Color/Form
Colorless crystals
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 783
HSDB
White, crystalline triclinic crystals

Blair GT, DeFraties JJ; Hydroxy Dicarboxylic Acids. Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2015). New York, NY: John Wiley & Sons. Online
Posting Date: Dec 4, 2000.
HSDB
3.2.3 Odor
Characteristic
ECHA; Search for Chemicals. Malic Acid (CAS 6915-15-7) Registered Substances Dossier. European Chemical Agency. Available from, as of Mar 17, 2015:
http://echa.europa.eu/
HSDB
3.2.4 Taste
Smoothly tart
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 240
HSDB
Sour taste
HSDB
3.2.5 Boiling Point
Decomposes at >225 °C and <235 °C (BP not determinable) /OECD Guideline 103 (Boiling point/boiling range)/
HSDB
3.2.6 Melting Point
131.0 °C
EPA DSSTox
127-132 °C
130.97 °C /OECD Guideline 102 (Melting point / Melting Range)/

HSDB
131-133°C
3.2.7 Solubility
Water Solubility
5.79 M
BEILSTEIN
EPA DSSTox
In water, 55.8 g/100 g water at 20 °C

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1060
HSDB
In water, 592,000 mg/L at 25 °C

Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 99
HSDB
Solubility in g/100 g solvent at 20 °C: methanol 82.70; diethyl ether 0.84; ethanol 45.53; acetone 17-75; dioxane 22.70
HSDB
It is highly soluble in methanol, ethanol, acetone, ether, and other polar solvents
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA13 515
HSDB
1000.0 mg/mL
3.2.8 Density
1.601 g/ cu cm at 20 °C
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-340
HSDB
3.2.9 Vapor Pressure
3.28e-08 mmHg
EPA DSSTox
3.28X10-8 mm Hg at 25 °C (extrapolated)
Yaws CL; Handbook of Vapor Pressure. Volume 1 - C1 to C4 Compounds. Gulf Publishing Co., Houston, TX (1994)
HSDB
3.2.10 Octanol/Water Partition Coefficient
-1.26 (LogP)
HANSCH,C ET AL. (1995)
EPA DSSTox
log Kow = -1.26
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 9
HSDB
-1.26
HANSCH,C ET AL. (1995)
3.2.11 Stability/Shelf Life
Stable under recommended storage conditions.

Sigma-Aldrich; Material Safety Data Sheet for Malic acid, Product Number: 240176, Version 5.3 (Revision Date 12/01/2014). Available from, as of February 20,
2015: http://www.sigmaaldrich.com/safety-center.html
HSDB
3.2.12 Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.

Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2273
HSDB
3.2.13 Viscosity
6.5 mPa.s (= cP) 50% aqueous solution at 25 °C

HSDB
3.2.14 Heat of Combustion
-1.340 MJ/mol at 20 °C
HSDB
3.2.15 pH
pH of a 0.001% aqueous solution is 3.80, that of 0.1% solution is 2.80, and that of a 1.0% solution is 2.34
HSDB
3.2.16 Dissociation Constants
Ionization constants: K1 = 4X10-4; K2 = 9X10-6

HSDB
pKa1 = 3.51; pKa2 = 5.03 at 20 °C /OECD Guideline 112 (Dissociation Constants in Water)/
HSDB
3.2.17 Kovats Retention Index
Standard non-polar 944
NIST Mass Spectrometry Data Center
3.2.18 Other Experimental Properties
Nearly odorless (sometimes a faint, acrid odor) /L-Malic Acid/

Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 3rd Edition, Volumes 1-2. Boca Raton, FL: CRC Press 1994-1995., p. 1049
HSDB
Exhibits isomeric forms (dl, l, and d)

HSDB
Density: 1.601 (d or l form); MP: 128 °C (d or l form); BP: 140 °C with decomposition (d or l form)
HSDB
Crystals from acetone, or acetone + chloroform; mp 100 °C; Decomposes at about 140 °C; specific optical rotation: -2.3 deg (conc = 8.5 g
1100 ml water); Solubilities at 20 °C: 60.66 g/100 g acetone, 74.35 g/100 g dioxane, 36.35 g/100 g water, practically insoluble in benzene,
197.22 g/100 g methanol, 2.70 g/100 g diethyl ether, 86.60 g/100 ethanol; L-(-)-Form/
HSDB
Crystals; MP: 101 °C /D(+)-Form/

HSDB
BUFFERING INDEX: 3.26

HSDB
SPECIFIC OPTICAL ROTATION: -5.7 DEG /L-FORM/, +5.2 DEG /D-FORM/ @ 18 °C (IN ACETONE)
Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co.,
1975., p. 326
HSDB
IR: 2:275F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI) /Malic acid (+-), CAS 617-48-1/
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 1805
HSDB
IR: 2:275H (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI) /Malic acid (l), CAS 97-67-6/
HSDB
IR: 2:275G (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI) /Malic acid (d), CAS 636-61-3/
HSDB
Light brown color /Commercial product/

Sax, N.I. and R.J. Lewis, Sr. (eds.). Hawley's Condensed Chemical Dictionary. 11th ed. New York: Van Nostrand Reinhold Co., 1987., p. 565
HSDB
Henry's Law constant = 8.4X10-13 atm-cu m/mol at 25 °C (est)

US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
HSDB
Hydroxyl radical reaction rate constant = 8.3X10-12 cu cm/molecule-sec at 25 °C (est)

US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
HSDB
4 Spectral Information
4.1 1D NMR Spectra
1D NMR Spectrum 1267 - Malic acid (HMDB0000744)

1D NMR Spectra
4.1.1 1H NMR Spectra
Copyright © 2006-2018 Bio-Rad Laboratories, Inc. Portions provided by BioMagResBank(BMRB) and the Board of Regents
Copyright
of the University of Wisconsin System. All Rights Reserved.
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SpectraBase
4.1.2 13C NMR Spectra
Showing 2 of 7 View More
Copyright © 2006-2018 Bio-Rad Laboratories, Inc. Portions provided by BioMagResBank(BMRB) and the Board of Regents
Copyright
of the University of Wisconsin System. All Rights Reserved.
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SpectraBase
Source of Sample Chem Service, Inc., West Chester, Pennsylvania
Copyright Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
Thumbnail
SpectraBase
4.2 2D NMR Spectra

2D NMR Spectra
4.3 Mass Spectrometry
4.3.1 GC-MS
GC-MS Spectrum 634 - Malic acid (HMDB0000744)

GC-MS GC-MS Spectrum 30147 - Malic acid (HMDB0000744)
MoNA ID GLS00162
MS Category Experimental
MS Type GC-MS
yp
MS Level MS1
Instrument GCMS-2010 Plus, Shimadzu
Instrument Type EI-B
Ionization Mode positive
Splash splash10-0002-0930000000-6a116527910d172eb561
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Submitter Hiromi Miyagawa, GL Sciences Inc.
MassBank of North America (MoNA)
4.3.2 MS-MS
MS-MS Spectrum 1056 - Malic acid (HMDB0000744)

MS-MS MS-MS Spectrum 1057 - Malic acid (HMDB0000744)
MS-MS Spectrum 1058 - Malic acid (HMDB0000744)
NIST Number 1052306
Instrument Type IT/ion trap
Collision Energy 0
Spectrum Type MS2
Precursor Type [M-H]-
Precursor m/z 133.0142
Total Peaks 7
m/z Top Peak 115
m/z 2nd Highest 87.1
m/z 3rd Highest 71.1
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NIST Mass Spectrometry Data Center
4.3.3 LC-MS
MoNA ID FiehnHILIC002812
MS Type LC-MS
MS Level MS2
precursor m/z 133.0124
Instrument SCIEX TripleTOF 6600
Instrument Type LC-ESI-QTOF
Ionization Mode negative
Collision Energy 35 eV
Splash splash10-00di-9000000000-5f7f69603423e401ecef
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Submitter Megan Showalter, University of California, Davis
MoNA ID HMDB0000744_ms_ms_1056
MS Type LC-MS
MS Level MS2
Instrument Type Quattro_QQQ
Splash splash10-03e9-3900000000-6112a756a8c8c7c7cd50
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Submitter David Wishart, University of Alberta
4.3.4 EI-MS
EI-MS EI-MS Spectrum 1853 - Malic acid (HMDB0000744)
4.3.5 Other MS
MoNA ID CCMSLIB00000479713
MS Level MS2
precursor m/z 115.02
Instrument Orbitrap
Splash splash10-00di-9000000000-590cdd511e8ecb4107bc
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Submitter GNPS Team, University of California, San Diego
4.4 IR Spectra
4.4.1 FTIR Spectra
Instrument Name Bruker Tensor 27 FT-IR
Technique KBr1
Source of Spectrum Bio-Rad Laboratories, Inc.
Source of Sample TCI Chemicals India Pvt. Ltd.
Catalog Number M0020
Lot Number 4WNZF-GB
Copyright Copyright © 2016-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
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SpectraBase
Technique KBr WAFER
Source of Sample Lachat Chemicals, Inc., Chicago Heights, Illinois
Copyright Copyright © 1980, 1981-2018 Bio-Rad Laboratories, Inc. All Rights Reserved.
Thumbnail
SpectraBase
4.4.2 ATR-IR Spectra
Instrument Name Bruker Tensor 27 FT-IR
Technique ATR-Neat (DuraSamplIR II)
Lot Number 4WNZF-GB
Thumbnail
SpectraBase
4.5 Raman Spectra
Instrument Name Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique FT-Raman
Lot Number 4WNZF-GB
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SpectraBase
5 Related Records
5.1 Related Compounds with Annotation
PubChem
5.2 Related Compounds
Same Connectivity 19 Records
Same Stereo 8 Records
Same Isotope 3 Records
Same Parent, Connectivity 362 Records
Same Parent, Stereo 275 Records
Same Parent, Isotope 344 Records
Same Parent, Exact 268 Records
Mixtures, Components, and

1,423 Records
Neutralized Forms
Similar Compounds 768 Records
Similar Conformers 1,894 Records
PubChem
5.3 Substances
5.3.1 Related Substances
All 3,449 Records
Same 351 Records
Mixture 3,098 Records
PubChem
5.3.2 Substances by Category
PubChem
5.4 Entrez Crosslinks
PubMed 4,010 Records
Protein Structures 20 Records
Taxonomy 3 Records
Gene 4 Records
PubChem
5.5 Associated Chemicals

Malic acid (dl); 617-48-1
HSDB
Malic acid (l); 97-67-6
HSDB
Malic acid (d); 636-61-3
HSDB
5.6 NCBI LinkOut
NCBI
6 Chemical Vendors
PubChem
7 Drug and Medication Information
7.1 Drug Indication

Parenteral nutrition
European Medicines Agency (EMA)
7.2 Clinical Trials
7.2.1 ClinicalTrials.gov
ClinicalTrials.gov
7.2.2 EU Clinical Trials Register
EU Clinical Trials Register
7.3 EMA Drug Information

10/4/2020
g Malic acid | C4H6O5 - PubChem
Soybean oil, Medium-chain triglycerides, Olive oil, Fish oil, Acetyl-cysteine, Alanine, Arginine /Glycine, Histidine, Isoleucin,
Leucine, Lysine acetate, Methionine, Phenylalanine, Proline, Serine/ Threonine, Tryptophan, Tyrosine, Valine, glucose,
Active Substance
calcium chloride, Sodium glycerophosphate /Magnesium sulphate, potassium chloride, Sodium acetate, Zinc sulphate,
Malic acid
Therapeutic Area Nutrition
Decision Type W: decision granting a waiver in all age groups for all conditions/indications
Decision Date 2017-06-07
7.4 Therapeutic Uses

EXPL THER An efficcacy and safety test of a tablet containing 200 mg malic acid (and 50 mg magnesium) was conducted using patients with
primary fibromyalgia syndrome. In the first part of the test, 24 patients were given three tablets twice daily (bid) for 4 weeks. In the second
part, 16 patients started with three tablets bid and increased the dosage every 3 to 5 days as necessary; at month 6, the average dose was
8.8 tablets per day. (For a 50-kg person, ingestion of six tablets would be equivalent to 24 mg of malate/kg of body weight). In the first part
of the study, one test patient reported diarrhea, one reported nausea, and one reported dyspepsia. (In the placebo group, two patients
reported diarrhea and one reported dyspepsia.) In the second part of the study, five test patients reported diarrhea, one reported nausea,
one reported dyspepsia, one reported panic attacks, and one reported dizziness.
Fuime MZ; Int J Toxicol 20 (Suppl 1): 47-55 (2001)
HSDB
EXPL THER Organic acids in Chinese herbs, the long-neglected components, have been reported to possess antioxidant, anti-inflammatory,
and antiplatelet aggregation activities; thus they may have potentially protective effect on ischemic heart disease. Therefore, this study aims
to investigate the protective effects of two organic acids, that is, citric acid and L-malic acid, which are the main components of Fructus
Choerospondiatis, on myocardial ischemia/reperfusion injury and the underlying mechanisms. In in vivo rat model of myocardial
ischemia/reperfusion injury, we found that treatments with citric acid and L-malic acid significantly reduced myocardial infarct size, serum
levels of TNF-alpha, and platelet aggregation. In vitro experiments revealed that both citric acid and L-malic acid significantly reduced LDH
release, decreased apoptotic rate, downregulated the expression of cleaved caspase-3, and upregulated the expression of phosphorylated
Akt in primary neonatal rat cardiomyocytes subjected to hypoxia/reoxygenation injury. These results suggest that both citric acid and L-
malic acid have protective effects on myocardial ischemia/reperfusion injury; the underlying mechanism may be related to their anti-
inflammatory, antiplatelet aggregation and direct cardiomyocyte protective effects. These results also demonstrate that organic acids,
besides flavonoids, may also be the major active ingredient of Fructus Choerospondiatis responsible for its cardioprotective effects and
should be attached great importance in the therapy of ischemic heart disease. /L-Malic Acid/
PMID:23737849
Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3666396
Tang X et al; Evid Based Complement Alternat Med. (2013) Published online 2013 May 14. doi: 10.1155/2013/820695
HSDB
EXPL THER Objectives: Assessing the clinical effectiveness of a topical sialogogue on spray (malic acid, 1%) in the treatment of xerostomia
induced by antihypertensive drugs. Study Design: This research has been carried out through a randomized double-blind clinical trial. 45
patients suffering from hypertensive drugs-induced xerostomia were divided into 2 groups: the first group (25 patients) received a topical
sialogogue on spray (malic acid, 1%) whereas the second group (20 patients) received a placebo. Both of them were administered on
demand for 2 weeks. Dry Mouth Questionnaire (DMQ) was used in order to evaluate xerostomia levels before and after product/placebo
application. Unstimulated and stimulated salivary flows rates, before and after application, were measured. All the statistical analyses were
performed by using SPSS software v17.0. Different DMQ scores at the earliest and final stage of the trial were analysed by using Mann-
Whitney U test, whereas Student's T-test was used to analyse salivary flows. Critical p-value was established at p<0.05. Results: DMQ scores
increased significantly (clinical recovery) from 1.21 to 3.36 points (p<0.05) after malic acid (1%) application whereas DMQ scores increased
from 1.18 to 1.34 points (p>0.05) after placebo application. After two weeks of treatment with malic acid, unstimulated salivary flow
increased from 0.17 to 0.242 mL/min whereas the stimulated one increased from 0.66 to 0.92 mL/min (p<0.05). After placebo application
unstimulated flow ranged from 0.152 to 0.146 mL/min and stimulated flow increased from 0.67 to 0.70 mL/min (p>0.05). Conclusions: Malic
acid 1% spray improved antihypertensive-induced xerostomia and stimulated the production of saliva.
Gomez-Moreno G et al; Med Oral Patol Oral Cir Bucal. 18 (1): e49-e55 (2013)
HSDB
Fourteen patients, 11 males and 3 females, with various forms of ichthyosiformdermatoses were used to evaluate the therapeutic potential
of more than 60 chemicals, including malic acid. Malic acid was dissolved in either water or ethanol and incorporated into a hydrophilic
ointment of plain petrolatum. The ointment, containing 5% malic acid (pH not specified), was applied twice daily to the appropriate test site
for 2 weeks. Daily to weekly observations were made. Malic acid provided 3+ (disappearance of scales from lesions) or 4+ (restoration to
normal looking skin) improvement in all patients except one with epidermolytic hyperkeratosis.
HSDB
8 Food Additives and Ingredients
8.1 Food Additive Classes

JECFA Functional Classes
Flavouring Agent: FLAVOURING_AGENT Food Additives: ACIDITY_REGULATOR
FAO/WHO Food Additive Evaluations (JECFA)
8.2 FDA Substances Added to Food
Substance MALIC ACID
Used for (Technical Effect) SYNERGIST
Document Number (21 CFR) 184.1069
FDA Center for Food Safety and Applied Nutrition (CFSAN)
8.3 Evaluations of the Joint FAO/WHO Expert Committee on Food Additives - JECFA
Chemical Name DL-MALIC ACID
ADI NOT SPECIFIED
Evaluation Year 1969
Included in the group ADI for malic acid and its sodium, potassium and calcium salts; in the case of D(-)-malic acid and its
Comments
salts, the ADI is not applicable to very young infants
Report NMRS 46/TRS 445-JECFA 13/16
9 Pharmacology and Biochemistry
9.1 Bionecessity
Malic acid is an intermediate in the citric acid cycle. It is formed from fumaric acid and is oxidized to oxaloacetic acid. It is also metabolized
to pyruvic acid by malic enzyme which is present in many biologic systems, including bacteria and plants. L-Malic and dl-malic acid are both
rapidly metabolized in the rat. Orally or ip administered l- or dl-malic acid was extensively eliminated as carbon dioxide (83 to 92%). No
differences between the two forms were found in the rates (90 to 95% in 24 hr) or routes of excretion.
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.,
p. 4942
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Malate occurs in all living organisms as an intermediate in the citric acid cycle. It occurs in relatively high amounts in many fruits and
vegetables. Malic acid has two stereoisomeric forms (L- and D-enantiomers), although only the L-isomer exists naturally.
EFSA Journal 12 (2): 3563 (2014)
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9.2 Absorption, Distribution and Excretion

Upon oral and IP administration of radioactive malic acid to rats, most of the radioactivity was excreted as carbon dioxide.
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9.3 Metabolism/Metabolites
Acidulents. Like l-(14)C4 malic acid, dl-(14)C4 malic acid, when admin ip or orally to rats was extensively metabolized; 90-95% of (14)C was
excreted through lungs as (14)CO2. ... Metabolized at same rate irrespective of route admin ... . /L- & dl-malic acid/
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The
Chemical Society, 1970., p. 246
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Malic acid is an intermediate in the citric acid cycle. It is formed from fumaric acid and is oxidized to oxaloacetic acid. It is also metabolized
to pyruvic acid by malic enzyme which is present in many biologic systems, including bacteria and plants. L-Malic and dl-malic acid are both
rapidly metabolized in the rat. Orally or ip administered l- or dl-malic acid was extensively eliminated as carbon dioxide (83 to 92%). No
differences between the two forms were found in the rates (90 to 95% in 24 hr) or routes of excretion.
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.,
p. 4942
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Malates are normal constituents of the diet of humans and animals and, when ingested, are rapidly and completely metabolized to CO2.
/Malates/
EFSA Journal 12 (2): 3563 (2014)
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... Both enantiomers of malic acid are readily metabolised by laboratory animals and humans and that there was no reason to distinguish
between L-malic acid and DL-malic acid when considering their safe use in food.
EFSA Journal 12 (2): 3563 (2014)
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Upon oral and IP administration of radioactive Malic Acid to rats, most of the radioactivity was excreted as carbon dioxide.
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9.4 Human Metabolite Information
9.4.1 Metabolite Description
Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an
intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions.
9.4.2 Cellular Locations
Cytoplasm
9.4.3 Metabolite Pathways
Fructose-1,6-diphosphatase deficiency
Gluconeogenesis
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Glycogenosis, Type IA. Von gierke disease
Glycogenosis, Type IB
Glycogenosis, Type IC
Malate-Aspartate Shuttle
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
The Oncogenic Action of Fumarate
Triosephosphate isomerase
Total 10 pathways, visit the HMDB page for details
9.4.4 Associated Disorders and Diseases
Diseases References
PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709,

22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383,
28587349
Colorectal cancer Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule
Claus. Metabolomics of fecal samples: A practical consideration. Trends in
Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255:
http://www.sciencedirect.com/science/article/pii/S0924224416301984
PubMed: 115032, 7126379, 2480613, 17276036, 11877547, 12796220,

7595563, 20814316, 25004141, 24713860, 23823132, 2415198, 1694425,
Schizophrenia 7711000, 19390223, 22024767, 22007635, 21483431, 3741918, 11979513,
20206656, 436860, 19401681, 6184954, 26952797, 22800120, 24789758,
22944140, 22892715, 17440431, 25729574, 22257447
Sugimoto et al. (2013) Physiological and environmental parameters

Temporomandibular joint disorder
associated with mass spectrometry-based salivary metabolomic profiles.
Diseases References
PubMed: 15185309, 7119120, 20347721
Adriana Nori de Macedo. Robust capillary electrophoresis methods for

Cystic fibrosis biomarker discovery and routine measurements in clinical and
epidemiological applications. March 2017:
https://macsphere.mcmaster.ca/handle/11375/21248
Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and

PubMed: 17994565
Seizures Syndrome
10 Use and Manufacturing
10.1 Overview
IDENTIFICATION: Malic acid is a colorless to white, crystalline solid. It has a sour taste. It is very soluble in water. Malic acid is present
naturally in many plants, including flowers, fruits and vegetables, spices, and wine grapes. It is a component in tobacco. It may be formed in
the air by reaction of other chemicals with light. Malic acid is formed naturally in animals and humans and used in the process of breaking
down sugar into energy in the body. USE: Malic acid is an important commercial chemical used in canning fruits and vegetables to prevent
them from spoiling. It is used in various other foods, dry beverage powders, carbonated beverages, and food packaging materials to control
acidity. Malic acid is an ingredient in some household cleaners, hair coloring, nail enamels, human and specialty pet shampoos. EXPOSURE:
Workers in the food, cleaning and personal care industries may be exposed to malic acid through skin contact and breathing in mists or
malic acid salt dusts. The general population is exposed to malic acid from eating foods consumed in a normal diet that contain malic acid.
People may breathe in mists or have skin contact while household and personal care products that contain malic acid. If malic acid is
released to air, it can be broken down by reaction with other chemicals and some may be in or on particles that eventually fall to the
ground. If released to water or soil, it is not expected to bind sediments. It is expected to move easily through soil. Malic acid is not
expected to move into air from wet soils or water surfaces. Malic acid is expected to be broken down by microorganisms and is not
expected to build up in tissues of aquatic organisms. RISK: Severe skin and eye irritation can occur with direct contact to malic acid or its
salts. Allergic skin reactions have been reported in some individuals after eating foods containing malic acid. Erosion of tooth enamel may
occur from drinking acidic soft drinks containing malic acid. Weakness, incoordination, convulsions, and breathing difficulties occurred in
laboratory animals given very high oral doses of malic acid. Death occurred in some animals. No health problems occurred in laboratory
animals, dogs, or cattle fed low-to-moderate doses over time. Malic acid did not cause birth defects or reproductive effects in laboratory
animals. The potential for malic acid to cause cancer has not been assessed in laboratory animals. The potential for malic acid to cause
cancer in humans has not been assessed by the U.S. EPA IRIS program, the International Agency for Research on Cancer, the U.S. National
Toxicology Program 13th Report on Carcinogens, or the California Office of Environmental Health Hazard Assessment. (SRC)
FOR MORE INFORMATION: (1) National Library of Medicine Hazardous Substances Data Bank. Available from, as of Mar 17, 2105:
http://toxnet.nlm.nih.gov/newtoxnet/hsdb.htm (2) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Available from, as of Mar
16, 2015: http://monographs.iarc.fr/ENG/Classification/index.php (3) National Library of Medicine Household Products Database. Available from, as of Mar 16,
2015: http://hpd.nlm.nih.gov/ (4) National Toxicology Program. Thirteenth Report on Carcinogens. Available from, as of Mar 16, 2015:
http://ntp.niehs.nih.gov/pubhealth/roc/index.html (5) US EPA; High Production Volume Information System (HPVIS). Butanedioic acid, hydroxy. 6915-15-7.
Available from, as of Mar 16, 2015: http://www.epa.gov/hpv/hpvis/index.html (6) USEPA/IRIS Integrated Risk Information System. Available from, as of Mar 16,
2015: http://www.epa.gov/iris/ (7) California Off Environ Health Hazard Assessment. Available from, as of Mar 18, 2015: http://oehha.ca.gov/ (8) Select
Committee on GRAS Substances (SCOGS) Opinion. Available from, as of Mar 17, 2015: http://www.accessdata.fda.gov/scripts/fcn/fcnNavigation.cfm?
rpt=scogslisting
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10.2 Use Classification

EPA Safer Chemical Functional Use Classes
Processing Aids and Additives
EPA Safer Choice
Safer Chemical Classes
Green circle - The chemical has been verified to be of low concern
EPA Safer Choice
Human Drugs -> EU pediatric investigation plans
JECFA Functional Classes -> Flavouring Agent: FLAVOURING_AGENT Food Additives: ACIDITY_REGULATOR
10.3 Uses
EPA CPDat Chemical and Product Categories
EPA Chemical and Products Database (CPDat)
Use Classification
Food additives
For malic acid (USEPA/OPP Pesticide Code: 051101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved
pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's Database on Malic Acid (6915-15-7). Available from, as of February 27, 2015:
http://npirspublic.ceris.purdue.edu/ppis/
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The active ingredient is no longer contained in any registered pesticide product ... "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.324 (Spring, 1998) EPA 738-R-98-002
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Intermediate in chemical synthesis. Chelating and buffering agent. Flavoring agent, flavor enhancer and acidulant in foods.
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Manufacture of various esters and salts, wine manufacture, chelating agent, food acidulant, flavoring.
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Malic acid is used primarily as an ingredient in hard candys and other sweets, jams, jellies, and various canned fruits and vegetables.
Miltenberger K; Hydroxycarboxylic Acids, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2014). NY, NY: John Wiley & Sons. Online
Posting Date: June 15, 2000
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Metal cleaning and finishing; chemical plating and electroplating; applications in cosmetics, pharmaceuticals, and dentifrices
CHEMICAL PRODUCTS SYNOPSIS: Malic acid, 1984
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Malic acid is a particularly desirable acidulant in certain beverage selections, specifically those sweetened with the artificial sweetener
aspartame.
Felthouse TR et al; Maleic Anhydride, Maleic Acid, and Fumaric Acid. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2014). John Wiley & Sons, Inc.
Online Posting Date: October 18, 2001
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Coumarin is formed by reaction of phenol with malic, maleic, or fumaric acids in the presence of concentrated sulfuric acid.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V7 650
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The impregnation of packing materials for foodstuffs such as cheese or the acidification required during the preparation of baked goods. It
is widely used in the food industry as an acidulant and, to a lesser degree, as an acidity regulator.
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It can serve as synergist with antioxidants in a wide variety of foods to prevent fats & oils from becoming rancid, & as agent for releasing oil
from gum contaminants in refining of edible fatty oils.
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... Improving whipping properties of egg white & of gelatin ... fatty alc monoesters ... antispattering agents in cooking fats. Dl-malic acid ...
flavoring agent & discoloration inhibitor in ... pie & other fruit fillings, in bakers' jellies & preserves, frozen pies, & frosting & meringue
mixes ... .
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... Employed in extracting pectin, in production of sour dough, & in synthesis of emulsifying agents which inhibit development of rancidity
in oils. ... Used as acidifying agent in canning tomatoes.
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... Recommended as ideal additive for stabilizing color of apple, grape & other fruit-juice drinks, & for bringing out overall taste of fruit-
flavored carbonated drinks, including cream sodas.
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DL-malic acid ... used ... for its flavor-contributing characteristics in nonalcoholic beverages, in imitation jams & jellies & in candy. ... Low mp
compared to other solid acidulants & high solubility in water cause it to dissolve very readily when ... used in mfr of hard candies. /DL-malic
acid/
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Malic acid is considered effective as a feed preservative.

EFSA Journal 12 (2): 3563 (2014)
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MEDICATION
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Reported uses (ppm): /l-Malic acid/

Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994)
Food Category Usual Max.
Baked goods 0.30 1.50
Frozen dairy 25.00 390.00
Nonalcoholic beverages 90.00 380.00
Soft candy 25.00 420.00
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1113
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10.3.1 Industry Uses
Flavoring, buffer, anti-microbial

Intermediates
Plating agents and surface treating agents
Processing aids, not otherwise listed
https://www.epa.gov/chemical-data-reporting
10.3.2 Consumer Uses
Electrical and electronic products

FOOD
Food packaging
Ink, toner, and colorant products
Metal products not covered elsewhere
Non-TSCA use
10.4 Methods of Manufacturing

dl-Malic acid is mfr by hydrating maleic and fumaric acids in presence of suitable catalysts & separating malic acid from equilibrium product
mixture. In US ... continuous process which is much more economical than older batch type. /dl-Malic acid/
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By hydration of maleic acid; by fermentation from sugars. /l-Malic acid/

Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1113
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Microbial production of l-form

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Made synthetically by catalytic oxidation of benzene to maleic acid, which is converted to malic acid by heating with steam under pressure.
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Malic acid is prepared commercially in the United States and Canada by hydration of maleic anhydride. ... In this process maleic acid is
heated at ca 180 °C (under a pressure of ca 1 MPa), malic acid is yielded as the main product. Byproducts are maleic and fumaric acids. The
latter can be separated by filtration and returned to the process stream because of its low water solubility. The filtrate is then concentrated;
this causes separation of the malic acid, which is purified by multiple washings, evaporation, and recrystallization until the contents of
fumaric and maleic acids are reduced to 7.5 and <500 ppm, respectively. Additional purification is required to prepare pharmacological-
grade material.
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Isolated from natural sources by resolution of (R,S)-malic acid with the aid of an optically active base. /(R)-(+)- and (S)-(-) malic acid/
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(S)-(-)-Malic acid is ... available through microbiological fermentation of fumaric acid. /(S)-(-)-Malic acid/
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Purification of malic /acid/ can be /performed/ by a two-stage crystallization process which first removes fumaric acid from the slurry and
subsequently crystallizes washed malic acid after carbon and ion exchange treatment
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Malic acid is synthesised by hydration of maleic anhydride under high temperature and pressure to form malic and fumaric acid. The
precipitate of the less soluble fumaric acid is separated by centrifugation and the resulting solution is concentrated to form crystals of crude
malic acid, which are separated, re-dissolved in water and passed through a decolourization unit containing activated charcoal. After
concentration of the solution, pure crystals of malic acid are formed, which are separated and dried.
EFSA Journal 12 (2): 3563 (2014)
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Hydration of fumaric acid proceeds at high temperatures and pressures to give dl-malic acid.
Felthouse TR et al; Maleic Anhydride, Maleic Acid, and Fumaric Acid. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2014). John Wiley & Sons, Inc.
Online Posting Date: October 18, 2001
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10.5 Impurities
... contents of fumaric and maleic acids are ... 7.5 and <500 ppm, respectively.
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10.6 Formulations/Preparations
Uva ursi, this is volatile oil containing a glucoside, arbutin, tannin, & gallic & malic acids.
Arena, J.M. Poisoning: Toxicology-Symptoms Treatments. Third Edition. Springfield, Illinois: Charles C. Thomas, 1974., p. 601
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Grades: Technical, active and inactive; Food Chemical Codex. The natural material is levorotatory, but the synthetic material is /optically/
inactive.
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10.7 Consumption Patterns

Dry beverage powders 50%; carbonated & still beverages, 25%; food & candy, 15%; metal cleaning & finishing, 5%; miscellaneous, 5%
(1983)
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10.8 U.S. Production

Aggregated Product Volume (EPA CDR 2016)
10,000,000 - 50,000,000 lb
(1984) 4.99X10+9 g (est)

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Butanedioic acid, hydroxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or
imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR
part 710 subpart B; 51FR21438).
EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Butanedioic acid, hydroxy- (6915-15-7). Available from, as of
February 26, 2015: http://www.epa.gov/hpv/pubs/general/opptsrch.htm
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Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Butanedioic acid, 2-hydroxy-.
Aggregated National Production Volume: 1 to < 10 million pounds.
US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Butanedioic acid, 2-hydroxy- (6915-15-7). Available from, as of
February 27, 2015: http://cfpub.epa.gov/iursearch/index.cfm
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Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into
the United States. Chemical: Butanedioic acid, 2-hydroxy-. National Production Volume: Withheld.
USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. Butanedioic acid, 2-hydroxy- (6915-15-7). Available from, as of February 27,
2015: http://java.epa.gov/oppt_chemical_search/
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10.9 U.S. Imports
(1983) Less than 4.54X10+8 g (est)

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10.10 General Manufacturing Information

Industry Processing Sectors
Electrical equipment, appliance, and component manufacturing

Food, beverage, and tobacco product manufacturing
Miscellaneous manufacturing
Printing ink manufacturing
resale of chemicals
EPA TSCA Commercial Activity Status
Butanedioic acid, 2-hydroxy-: ACTIVE

https://www.epa.gov/tsca-inventory
Malic acid [6915-15-7] (hydroxysuccinic acid, hydroxybutanedioic acid, or 1-hydroxy-1,2-ethanedicarboxylic acid), C4H6O5, is a white,
crystalline material. The levorotatory isomer, S(-)-malic acid [97-67-6] (l-malic acid), is a natural constituent and common metabolite of
plants and animals. The racemic compound, R,S-malic acid [617-48-1] (dl-malic acid), is a widely used food acidulant. This material is also
used in some industrial applications as a sequestrant and as a buffer for pH control. R(+)-Malic acid [636-61-3] (d-malic acid) is available
only as a laboratory chemical.
Blair GT, DeFraties JJ; Hydroxy Dicarboxylic Acids. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2014). John Wiley & Sons, Inc. Online Posting Date:
December 4, 2000
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In the United States, Canada, and Europe, only the synthetic R,S-malic acid is produced commercially, whereas both the S and R,S forms are
produced in Japan.
Blair GT, DeFraties JJ; Hydroxy Dicarboxylic Acids. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2014). John Wiley & Sons, Inc. Online Posting Date:
December 4, 2000
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Although its degree of ionization in water ... is same as citric acid, it has much stronger apparent acidic taste. ... Smaller amt are usually
required to obtain same taste effect. It does not have as strong an apparent taste ... as fumaric acid.
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... One of ingredients specified by internal revenue service for rendering volatile fruit-flavored concn nonpotable when they contain 6 to
15% alcohol & have to be transferred from place of mfr to winery.
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Stock soln containing 50% of this acid can readily be prepared for use at room temp, as in mfr of carbonated beverages.
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With many flavoring materials, it gives taste effect which closely resembles that of citric acid. With others, it tends to accentuate flavor ...
natural overall savor. ... Appears to have flavor-fixing qualities ... overcome undesirable aftertastes.
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Its ideal blending properties ... advantage when ... used in fruit-flavored foods & drinks, syrups, essences & ginger. It does not affect natural
or artificial coloring or permanence of color ... or cause sediment with ... "acid-proof" caramel.
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11 Identification
11.1 Analytic Laboratory Methods

9.123, 22.073. CORDIALS & LIQUEURS /OF/ ... TOTAL MALIC ACID (LEVO & INACTIVE) /DETERMINED/ BY CHROMATOGRAPHIC METHOD.
9.124, 22.081. CORDIALS & LIQUEURS /OF/ LEVO-MALIC ACID /DETERMINED BY/ POLARIZATION. /L-MALIC ACID/
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists,
1965. New editions through 13th ed. plus supplements, 1982., p. 13/160
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12.020, 22.073. BEVERAGES: NONALCOHOLIC & CONCENTRATES /OF/ TOTAL MALIC ACID /DETERMINED BY/ CHROMATOGRAPHIC
METHODS. 12.021, 22.081. BEVERAGES: NONALCOHOLIC & CONCENTRATES /OF/ LEVO MALIC ACID /DETERMINED BY/ POLARIZATION. /L-
MALIC ACID/
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11.047, 22.088. BEVERAGES: WINES /OF/ ... CITRIC & MALIC ACIDS /DETERMINED BY/ POLARIZATION.
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31.184-31.188. MAPLE PRODUCTS /OF/ MALIC ACID, /DETERMINED BY/ SPECTROPHOTOMETRY @ 390 NM.
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For more Analytic Laboratory Methods (Complete) data for MALIC ACID (8 total), please visit the HSDB record page.
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12 Safety and Hazards
12.1 Hazards Identification
12.1.1 GHS Classification
Pictogram(s)
Irritant
Signal Warning
Aggregated GHS information provided by 1947 companies from 19 notifications to the ECHA C&L Inventory. Each
notification may be associated with multiple companies.
Reported as not meeting GHS hazard criteria by 7 of 1947 companies. For more detailed information, please visit ECHA
C&L website
Of the 18 notification(s) provided by 1940 of 1947 companies with hazard statement code(s):
GHS Hazard Statements
H315 (84.12%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (94.79%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in
parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with
percentage values above 10% are shown.
Precautionary Statement P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362
Codes (The corresponding statement to each P-code can be found at the GHS Classification page.)
12.1.2 EPA Safer Chemical
Chemical: Malic acid
Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.
EPA Safer Choice
12.1.3 Skin, Eye, and Respiratory Irritations
A skin and eye irritant

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12.2 Fire Fighting
12.2.1 Fire Fighting Procedures
Wear self-contained breathing apparatus for firefighting if necessary.

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Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide

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12.3 Accidental Release Measures
12.3.1 Cleanup Methods
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
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Do not let product enter drains.

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ACCIDENTAL RELEASE MEASURES /Personal precautions, protective equipment and emergency procedures/ Use personal protective
equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid
breathing dust.
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12.3.2 Disposal Methods
SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the
chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life;
and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with
less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
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/Product/ Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service
to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an
afterburner and scrubber. /Contaminated packaging/ Dispose of as unused product.
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12.3.3 Preventive Measures
Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of
combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs.
Provide appropriate exhaust ventilation at places where dust is formed.
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SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated
contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and
safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away
from the worker.
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SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing
contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of
the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances
whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases,
contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
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Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
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Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact
with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry
hands.
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12.4 Handling and Storage
12.4.1 Storage Conditions
Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids.
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12.5 Exposure Control and Personal Protection
12.5.1 Personal Protective Equipment (PPE)
/Skin protection/ Handle with gloves.

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/Eye/face protection/ Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government
standards such as NIOSH (US) or EN 166(EU).
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/Respiratory protection/ Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100
(US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a
full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as
NIOSH (US) or CEN (EU).
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/Body Protection/ Complete suit protecting against chemicals, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
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12.6 Stability and Reactivity
12.6.1 Hazardous Reactivities and Incompatibilities
Bases, oxidizing agents, reducing agents, alkali metals.

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12.7 Regulatory Information
12.7.1 Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic
Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and
reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC,
considering costs, non air quality health and environmental impact and energy requirements. Malic acid is produced, as an intermediate or a
final product, by process units covered under this subpart.
40 CFR 60.489 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 25, 2015:
http://www.ecfr.gov
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12.7.2 FIFRA Requirements
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and
environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer
health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the
pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection
Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three
lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List
C, and with List C containing pesticides of greater concern than those on List D. Malic acid is found on List D. Case No: 4062; Case Status: No
products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may
voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet
certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Malic acid; AI Status:
The active ingredient is no longer contained in any registered products ... "cancelled."
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special
Review. (1998) EPA 738-R-98-002, p. 324
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12.7.3 FDA Requirements
Malic acid is an indirect food additive for use only as a component of adhesives.
21 CFR 175.105 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 25, 2015:
http://www.ecfr.gov
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Substance added directly to human food affirmed as generally recognized as safe (GRAS).
http://www.ecfr.gov
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Malic acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used
in accordance with good manufacturing or feeding practice.
http://www.ecfr.gov
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Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their
intended use, within the meaning of section 409 of the Act. 1-Malic acid is included on this list.
http://www.ecfr.gov
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12.8 Other Safety Information
12.8.1 Toxic Combustion Products
Carbon oxides
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12.8.2 Other Hazardous Reactions
/Conditions to avoid/ Heat.

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12.8.3 Special Reports
Fuime MZ; Final report on the safety assessment of Malic Acid and Sodium Malate. Int J Toxicol 20 (Suppl 1): 47-55 (2001)[Fuime MZ; Int J
Toxicol 20 (Suppl 1): 47-55 (2001)]
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13 Toxicity
13.1 Toxicological Information
13.1.1 Acute Effects
ChemIDplus
13.1.2 Interactions
The influence of some frequent dietary constituents on gastrointestinal absorption of aluminum from drinking water and diet was
investigated in mice. Eight groups of male mice received lactic (57.6 mg/kg/day), tartaric (96 mg/kg/day), gluconic (125.4 mg/kg/day), malic
(85.8 mg/kg/day), succinic (75.6 mg/kg/day), ascorbic (112.6 mg/kg/day), citric (124 mg/kg/day), and oxalic (80.6 mg/kg/day) acids in the
drinking water for one month. At the end of this period, animals were killed and aluminum concentrations in liver, spleen, kidney, brain, and
bone were determined. All the dietary constituents significantly increased the aluminum levels in bone, whereas brain aluminum
concentrations were also raised by the intake of lactic, gluconic, malic, citric, and oxalic acids. The levels of aluminum found in spleen were
significantly increased by gluconic and ascorbic acids, whereas gluconic and oxalic acids also raised the concentrations of aluminum found
in kidneys.
PMID:8480083
Domingo JL et al; Res Commun Chem Pathol Pharmacol 79 (3): 377-80 (1993)
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The interactions of aqueous solutions of chlorine with some fruit acids (citric acid, DL-malic acid, and L-tartaric acid) different pH values
were studied diethyl ether extraction followed by GC/MS analysis indicated that a number of mutagens certain chlorinated propanones and
chloral hydrate) are present as major products in some of these samples. A number of fruit juices (orange, grape, apple, pineapple, and
grapefruit) were also treated with aqueous solutions of chlorine at their pH values. The products were analyzed by GC/MS. The same
mutagens that were formed by the pure acids (citric acid and DL-malic acid) were identified as major products in ether extracts of these
samples. All of the major products observed in the chlorination of all five fruit juices are potentially derived from reactions aqueous
solutions of chlorine with citric or malic acid and with trace amounts of acetaldehyde and acetone in the juices.
Chang TL et al; Interaction of Aqueous Solutions of Chlorine with Malic Acid, Tartaric Acid, and Various Fruit Juices A Source of Mutagens; Govt Reports
Announcements & Index (GRA&I) (6): (1991)
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The relative efficacy of citric, malic, malonic, oxalic and succinic acids, and deferoxamine mesylate (DFOA) on the toxicity, distribution and
excretion in mice exposed to aluminum were compared. To determine the effect of the various chelators on the toxicity of aluminum
various doses of aluminum nitrate (938-3l88 mg/kg) were administered intraperitoneally, followed by one of the chelators. Survival was
recorded at the end of 14 days. Malic and succinic acids were the most effective. Malic and succinic acids were the most effective in
increasing the urinary excretion of aluminum.
PMID:3391623
Domingo JL et al; Hum Toxicol 7 (3): 259-62 (1988)
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Eight groups of female Sprague-Dawley rats were treated with 281 mg aluminum hydroxide/kg/day by gastric intubation five times a week
for fives weeks. Concurrently, animals in seven groups received ascorbic acid (56.3 mg/kg/day), citric acid (62 mg/kg/day), gluconic acid
(62.7 mg/kg/day), lactic acid (28.8 mg/kg/day), malic acid (42.9 mg/kg/day), oxalic acid (28.8 mq/kg/day), and tartaric acid (48 mg/kg/day)
in the drinking water. The eighth group did not receive any dietary constituent in the water and was designated as the control group.
Animals were placed in plastic metabolic cages and urine was collected during the treatment period. The liver, spleen, kidney, brain and
bone aluminum levels of each rat were measured, as well as the total amount of aluminun excreted into urine. All the dietary constituents
significantly increased the aluminum concentrations in most of the tissues, with ascorbic and citric acids showing the highest rate of
aluminum accumulation.
PMID:2051716
Domingo JL et al; Kidney Int 39 (4): 598-601 (1991)
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13.1.3 Toxicity Summary
IDENTIFICATION AND USE: Malic acid forms colorless crystals with a characteristic sour taste. It is used as a cosmetic and food ingredient.
Malic acid has been tested as experimental therapy for various conditions. HUMAN EXPOSURE AND TOXICITY: Malic acid and its salts are
considered as strongly irritant to the skin and mucosa and as a particular risk to the eyes. Exposure via inhalation for those handling the
additives is also considered to present a risk. Malic acid was irritating in clinical tests, with less irritation seen as pH of the applied material
increased. Patients patch tested with malic acid, placed on a diet that avoided foods containing malic or citric acid, and then challenged
with a diet high in malic and citric acid had both immediate urticarial and delayed contact dermatitis reactions. In the absence of data on
inhalation toxicity, inhalation of the malate additive should be considered as hazardous. Because of the particle size distribution of the
additives and the high dusting potential of the malate salts, it is likely that handling the additives could result in a production of respirable
dust that could present a risk to unprotected workers. ANIMAL STUDIES: Malic acid is a component of the Kreb's cycle. Malic acid was
relatively nontoxic in acute toxicity studies using animals. In a chronic oral study, feeding malic acid to rats resulted only in weight gain
changes and changes in feed consumption. Malic acid did not cause reproductive toxicity in mice, rats, or rabbits. Malic acid was a
moderate to strong skin irritatant in animal tests, and was a strong ocular irritant. Malic acid was not mutagenic across a range of
genotoxicity tests.
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13.1.4 Antidote and Emergency Treatment
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration,
preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately
flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side
(head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body
temperature. Obtain medical attention. /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p.
176
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/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs
of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for
pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with
water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and
administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated
charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after
decontamination ... . /Organic acids and related compounds/
176-7
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/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe
pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary.
Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... .
Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as
necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs
of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is
hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... .
/Organic acids and related compounds/
177
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13.1.5 Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ The effect of malic acid on cell renewal was assessed using the dansyl chloride method. Two mg/sq cm of 1
M malic acid in a simple liquid vehicle (15% ethanol [SD 40], 5% ethoxydiglycol, and 5% butylene glycol) was applied to the volar forearm
which was stained with dansyl chloride twice daily until all the stain was removed. An 18%, 10%, and 5% increase in cell renewal was
observed at pH 3, 5, and 7, respectively.
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/HUMAN EXPOSURE STUDIES/ Thirty-four patients with atopic dermatitis were tested to determine their sensitivity to foods containing
malic (and citric) acid. The patients were first patch tested with malic (and citric) acid applied as a 10% aqueous solution under occlusive
patches for 48 hours. For 2 weeks, the patients followed a diet that avoided processed foods in which malic (and citric) Acid were used, and
then challenged themselves with a diet high in malic (and citric) acid the during the third week. Eighteen patients reacted to both malic and
citric acid and 6 patients reacted to only malic acid. Both immediate reactions (seasonal allergic rhinitis and urticaria) and delayed reactions
(contact dermatitis) were present. Patch-test results were reliable in predicting results of the challenge with diet.
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/HUMAN EXPOSURE STUDIES/ The subjective skin irritation potential of malic acid was evaluated by applying 2 mg/sq cm of 1 M malic acid
in vehicle (15% ethanol [SD40], 5% ethoxydiglycol, and 5% butylene glycol) to the nasal fold area of at least 10 subjects. Irritation was
graded on a scale of 0 to 4 everyminute for 15 minutes. The irritation scores, as an average of the summation of each individual irritation
score over the 15-minute test period, were 39.4, 37.1, and 23.1 for pH 3, 5, and 7, respectively.
Fuime MZ; Int. J. Toxicol. 20 (Suppl10): 47-55 (2001)
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/SIGNS AND SYMPTOMS/ Malic acid and its salts are considered as strongly irritant to the skin and mucosa and as a particular risk to the
eyes. Exposure via inhalation for those handling the additives is also considered to present a risk.
EFSA Journal 12 (2): 3563 (2014)
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For more Human Toxicity Excerpts (Complete) data for MALIC ACID (6 total), please visit the HSDB record page.
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13.1.6 Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ The signs of acute poisoning in rats and mice were weakness, retraction of the abdomen,
respiratory distress, and cyanosis.
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/LABORATORY ANIMALS: Acute Exposure/ The oral LD50 values of malic acid for albino CD-1 outbred mice, albino Wistar rats, and Dutch-
Belted rabbits were approximately 2.66, 3.5, and 3 g/kg respectively. Each study used 50 animals, consisting of five groups of 5 males and 5
females, and malic acid was administered as a 25% aqueous solution. Mortality was observed for 14 days. Signs of toxicity included ataxia,
prostration, convulsions, and death.
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/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In two 28-day experiments with beef cattle, reduced feed intakes were
observed following the inclusion of DL-malic acid at 22,000 mg/kg complete feed, the lowest dose tested . Dietary supplementation with
DL-malic acid or the mixed salts of malic acid at a level of 3,500 mg/kg complete feed did not result in any significant changes in the
performance of growing/finishing bull calves (Belgian Blue) over a 148-day period. Performance parameters of average daily weight gain,
daily feed intake and feed-to-gain ratio were unaffected by either product when compared with a control group fed unsupplemented feed.
EFSA Journal 12 (2): 3563 (2014)
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/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ A 104-week feeding study with DL-malic acid was conducted in beagle
dogs... The dogs (four/sex/group) were provided diets supplemented with 0, 500, 5 000 or 50 000 mg/kg malic acid without any reported
adverse effects. Body gains were reported to be normal for all animals and no significant changes in haematological, blood or urine
parameters were observed. No significant lesions were detected upon macro- or microscopic examinations and no dose-dependent
changes in absolute or relative organ weights were reported.
EFSA Journal 12 (2): 3563 (2014)
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For more Non-Human Toxicity Excerpts (Complete) data for MALIC ACID (10 total), please visit the HSDB record page.
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13.1.7 Non-Human Toxicity Values
LD50 Mouse oral 1600-3200 mg/kg

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LD50 Mouse ip 50-100 mg/kg

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LD50 Rat oral greater than 3200 mg/kg

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LD50 Rat ip 100-200 mg/kg

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LD50 Rabbit oral 3000 mg/kg

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13.1.8 Ongoing Test Status
EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version
of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data
generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title
compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS
Dashboard Application; Available from, as of December 8, 2014: http://actor.epa.gov/dashboard/]
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13.2 Ecological Information
13.2.1 Environmental Fate/Exposure Summary
Malic acid's production and use as a chemical intermediate in the synthesis of esters, salts and compounds, as a chelating and buffering
agent and as a flavoring agent and acidulant in foods may result in its release to the environment through various waste streams. Malic acid
has been identified as chemical component of tobacco smoke which releases the compound directly to the environment. Malic acid occurs
in apples and many other fruits and plants. Its occurrence and detection in the ambient atmosphere may result from the photooxidation of
atmospheric hydrocarbons. It may also reach the atmosphere through volatilization from plants. If released to air, an extrapolated vapor
pressure of 3.28X10-8 mm Hg at 25 °C indicates malic acid will exist in both the vapor and particulate phases in the atmosphere. Vapor-
phase malic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this
reaction in air is estimated to be 2 days. Particulate-phase malic acid will be removed from the atmosphere by wet and dry deposition. Malic
acid has been detected in atmospheric particulate matter and in rain and snow. Malic acid does not absorb at wavelengths >290 nm and,
therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, malic acid is expected to have very high
mobility based upon an estimated Koc of 1. The pKa values of malic acid are 3.51 and 5.03, indicating that this compound will exist partially
in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their
neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated
Henry's Law constant of 8.4X10-13 atm-cu m/mole. Malic acid is not expected to volatilize from dry soil surfaces based upon its vapor
pressure. Results of screening studies have determined that malic acid biodegrades readily which indicates that biodegradation is expected
to be an important fate process in both soil and water. If released into water, malic acid is not expected to adsorb to suspended solids and
sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this
compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low.
Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under
environmental conditions. Occupational exposure to malic acid may occur through inhalation and dermal contact with this compound at
workplaces where malic acid is produced or used. Monitoring data indicate that the general population may be exposed to malic via
inhalation of ambient air and tobacco smoke, ingestion of food and beverages, and dermal contact with consumer products containing
malic acid. (SRC)
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13.2.2 Natural Pollution Sources
Malic acid occurs in apples and many other fruits and plants(1). Malic acid occurs in plants such as apricot, mango, rose, plum, elderberry,
buckwheat, strawberry, pineapple, papaya, orange, tangerine, potato, grape, soybean, grapefruit, lettuce, onion, celery, oats, cauliflower,
cabbage, brussel sprouts, tobacco, carrot, olive, sunflower, tomato, ginseng, opium poppy, pea, raspberry, sage, and corn(2). Malic acid may
occur in atmospheric samples as a result of volatilization from naturally occurring sources or from the atmospheric oxidation of precursor
aldehydes(3). Malic acid and other dicarboxylic acids are probably formed in the atmosphere via photooxidation of organic compounds that
occur in the atmosphere(4,5).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 1060 (2013) (2) USDA; Dr. Duke's Phytochemical and Ethnobotanical
Databases. Plants with a chosen chemical. Malic acid. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Mar 18, 2015: http://www.ars-
grin.gov/duke/ (3) Hoffman WAJr, Tanner RL; Detection of Organic Acids in Atmospheric Precipitation (BNL-51922). (NTIS DE86-00594) Brookhaven National
Labs (1986) (4) Kawamura K, Ikushima K; Environ Sci Technol 27: 2227-35 (1993) (5) Yu LE et al; Environ Sci Technol 39: 707-15 (2005)
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13.2.3 Artificial Pollution Sources
Malic acid's production and use as a chemical intermediate in the synthesis of esters, salts and compounds, as a chelating and buffering
agent and as a flavoring agent and acidulant in foods(1,2) may result in its release to the environment through various waste streams(SRC).
Malic acid's identification as a chemical component of tobacco smoke(2) will result in its direct release to the environment(SRC).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 1060 (2013) (2) Lewis, RJ Sr; Hawley's Condensed Chemical Dictionary
15th ed. New York, NY: John Wiley & Sons, Inc. p. 783 (2007) (2) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke, Second
Edition. Boca Raton, FL: CRC Press, p. 1774 (2013)
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13.2.4 Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation
method(2), indicates that malic acid is expected to have very high mobility in soil(SRC). The pKa values of malic acid are 3.51 and 5.03(3),
indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to
soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of malic acid from moist soil surfaces is not
expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-13 atm-cu m/mole(SRC), using a
fragment constant estimation method(2). Malic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated
vapor pressure of 3.28X10-8 mm Hg at 25 °C(5). A 73% of theoretical BOD in 2 weeks using activated sludge in the Japanese MITI test
indicates that malic acid is readily biodegradable(6). Results of other screening studies also indicate that malic acid biodegrades readily(7,8).
Using C14-radio-labeled malic acid and a 1-hr incubation period, a 6.7% CO2 evolution was observed in a natural soil degradation study(9)
demonstrating that biodegradation is expected to be an important fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) ECHA; Search for Chemicals. Malic Acid (CAS 6915-15-7) Registered Substances Dossier. European
Chemical Agency. Available from, as of Mar 17, 2015: http://echa.europa.eu/ (4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for
Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000) (5) Yaws CL; Handbook of Vapor Pressure. Volume 1 - C1 to C4 Compounds. Gulf
Publishing Co., Houston, TX (1994) (6) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech
Eval. Available from, as of Mar 18, 2015: http://www.safe.nite.go.jp/english/db.html (7) Fischer WK et al; Wasser-Und Abwasser-Forchung 7: 99-118 (1974) (8)
Malaney GW, Gerhold RM; J Water Pollut Control Fed 41: R18-R33 (1969) (9) Fournier JC et al; Sci Total Environ 123/124: 325-32 (1992)
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AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2),
indicates that malic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not
expected(3) based upon an estimated Henry's Law constant of 8.4X10-13 atm-cu m/mole(SRC), developed using a fragment constant
estimation method(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -1.26(5) and a regression-
derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 73% of theoretical BOD in 2 weeks
using activated sludge in the Japanese MITI test indicates that malic acid is readily biodegradable(6). Results of other screening studies also
indicate that malic acid biodegrades readily(7,8). Malic acid is not expected to undergo hydrolysis in the environment due to the lack of
functional groups that hydrolyze under environmental conditions(3).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer
Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990) (4) Franke C et al; Chemosphere 29: 1501-14 (1994) (5) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic,
and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 9 (1995) (6) NITE; Chemical Risk Information Platform
(CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of Mar 18, 2015: http://www.safe.nite.go.jp/english/db.html
(7) Fischer WK et al; Wasser-Und Abwasser-Forchung 7: 99-118 (1974) (8) Malaney GW, Gerhold RM; J Water Pollut Control Fed 41: R18-R33 (1969)
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ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), malic acid,
which has an extrapolated vapor pressure of 3.28X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient
atmosphere. Vapor-phase malic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the
half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 8.3X10-12 cu cm/molecule-sec at 25
°C(SRC) that was derived using a structure estimation method(3). Particulate-phase malic acid may be removed from the air by wet and dry
deposition(SRC). Malic acid has been detected in atmospheric particulate matter and in rain and snow(4,5). Malic acid does not absorb at
wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) Yaws CL; Handbook of Vapor Pressure. Volume 1 - C1 to C4 Compounds. Gulf Publishing Co.,
Houston, TX (1994) (3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (4) Kawamura K, Ikushima K; Environ Sci Technol 27: 2227-35 (1993) (5) Sempere R, Kawamura K;
Atmos Environ 28: 449-459 (1994) (6) Brittain HG, ed; Analytical Profiles of Drug Substances and Excipients. Academic Press, San Diego CA (ISBN 0-12-260828-
3), p. 177 (2001)
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13.2.5 Environmental Biodegradation
AEROBIC: In an aerobic closed bottle screening study using activated sludge and soil inoculum, malic acid had 5-, 15- and 30-day
theoretical BODs of 68, 81 and 100% respectively(1). In a Warburg respirometer study using an activated sludge inoculum, theoretical BODs
of 6.0-9.6% and 20.8-55.5% were observed over respective incubation periods of 4 and 24 hrs(2). In a Warburg respirometer study using a
sewage sludge inoculum, a theoretical BOD of 47.2% was observed over an incubation period of 5 days(3). A theoretical BOD of 56.3% was
observed in a standard BOD dilution test using a sewage inoculum(4). In a Warburg respirometer study using a phenol acclimated activated
sludge inoculum, a theoretical BOD of 46% was observed over an incubation period of 12 hrs(5). Using C14-radio-labeled malic acid and a
1-hr incubation period, a 6.7% CO2 evolution was observed in a natural soil degradation study(6); when the soil was sterilized via
autoclaving, the CO2 evolution was only 0.1%(6). DL-Malic acid, present at 100 mg/L, reached 73% of its theoretical BOD in 2 weeks using
an activated sludge inoculum at 30 mg/L in the Japanese MITI test which classified the compound as readily biodegradable(7).
(1) Fischer WK et al; Wasser-Und Abwasser-Forchung 7: 99-118 (1974) (2) Malaney GW, Gerhold RM; J Water Pollut Control Fed 41: R18-R33 (1969) (3)
Heukelekian H, Rand MC; J Water Pollut Contr Assoc 27: 1040-53 (1955) (4) Swope HG, Kenna M; Sewage Ind Waste 21: 467-8 (1950) (5) McKinney RE et al; Sew
Indust Waste 28: 547-57 (1956) (6) Fournier JC et al; Sci Total Environ 123/124: 325-32 (1992) (7) NITE; Chemical Risk Information Platform (CHRIP).
Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of Mar 18, 2015: http://www.safe.nite.go.jp/english/db.html
HSDB
13.2.6 Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of malic acid with photochemically-produced hydroxyl radicals has been estimated as
8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2
days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the reaction of malic acid with
hydroxyl radicals in aqueous solutions at pH 1.5-14 is 8.2X10+8 L/mol-sec(2); this corresponds to an aquatic half-life of 2.6 years at an
aquatic concentration of 1X10-17 hydroxyl radicals per liter(3). Malic acid does not absorb at wavelengths >290 nm(4) and, therefore, is not
expected to be susceptible to direct photolysis by sunlight(SRC). Malic acid is not expected to undergo hydrolysis in the environment due to
the lack of functional groups that hydrolyze under environmental conditions(5).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (2) Buxton GV et al; J Phys Chem Ref Data 17: 513-882 (1988) (3) Mill T et al; Science 207: 886-887
(1980) (4) Brittain HG, ed; Analytical Profiles of Drug Substances and Excipients. Academic Press, San Diego CA (ISBN 0-12-260828-3), p. 177 (2001) (5) Lyman
WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
HSDB
13.2.7 Environmental Bioconcentration
An estimated BCF of 3 was calculated in fish for malic acid(SRC), using a log Kow of -1.26(1) and a regression-derived equation(2). According
to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p.
9 (1995) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 17, 2015:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) Franke C et al; Chemosphere 29: 1501-14 (1994)
HSDB
13.2.8 Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of malic acid can be estimated to be 1(SRC).
According to a classification scheme(2), this estimated Koc value suggests that malic acid is expected to have very high mobility in soil. The
pKa values of malic acid are 3.51 and 5.03(3), indicating that this compound will exist partially in anion form in the environment and anions
generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (2) Swann RL et al; Res Rev 85: 17-28 (1983) (3) ECHA; Search for Chemicals. Malic Acid (CAS 6915-
15-7) Registered Substances Dossier. European Chemical Agency. Available from, as of Mar 17, 2015: http://echa.europa.eu/ (4) Doucette WJ; pp. 141-188 in
Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
HSDB
13.2.9 Volatilization from Water/Soil
The Henry's Law constant for malic acid is estimated as 8.4X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1).
This Henry's Law constant indicates that malic acid is expected to be essentially nonvolatile from water surfaces(2). In addition, the pKa
values of malic acid are 3.51 and 5.03(3), indicating that this compound will exist partially in anion form in the environment and the anion
form of malic acid will not volatilize from water(SRC). Malic acid's Henry's Law constant indicates that volatilization from moist soil surfaces
will not occur(SRC). Malic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of
3.28X10-8 mm Hg(4).
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer
Chem Soc pp. 15-1 to 15-29 (1990) (3) ECHA; Search for Chemicals. Malic Acid (CAS 6915-15-7) Registered Substances Dossier. European Chemical Agency.
Available from, as of Mar 17, 2015: http://echa.europa.eu/ (4) Yaws CL; Handbook of Vapor Pressure. Volume 1 - C1 to C4 Compounds. Gulf Publishing Co.,
Houston, TX (1994)
HSDB
13.2.10 Environmental Water Concentrations
RAIN/SNOW: Malic acid was detected in rainwater samples collected from New Brunswick, NJ during 1999-2000 sampling(1). Snow, sleet
and rain samples collected in Tokyo Japan in 1992 contained malic acid concentrations of 0.49-6.76 ug/L(2).
(1) Seitzinger SP et al; Environ Sci Technol 37: 131-7 (2003) (2) Sempere R, Kawamura K; Atmos Environ 28: 449-59 (1994)
HSDB
13.2.11 Effluent Concentrations
Aerosol samples collected from a Hong Kong roadway tunnel during 2003-2004 monitoring contained malic acid levels of 2.2-9.1 ng/cu
m(1); apparent occurrence of malic acid was reported as not detected to 6.63 ug/vehicle-km(1).
(1) Wang H et al; Environ Sci Technol 40: 6255-60 (2006)
HSDB
13.2.12 Sediment/Soil Concentrations
SOIL: Maleic acid was qualitatively detected in German soil samples(1).

(1) Cordt T, Kussmaul H; Vom Wasser 74: 287-98 (1990)
HSDB
13.2.13 Atmospheric Concentrations
URBAN/SUBURBAN: In a monitoring study sampling the atmospheric aerosol in the atmosphere of urban Tokyo, Japan during 1988 and
1989, malic acid was detected at concentrations ranging from 3.2 to 100 ng/cu m with an average concentration of 23 ng/cu m(1). Ambient
aerosol monitoring conducted throughout 1982 in the Los Angeles, CA area found respective annual ambient average malic acid
concentrations of 7.8, 14.3, 16.0, 22.1 and <0.02 ng/cu m at West Los Angeles, downtown Los Angeles, Pasadena, Rubidoux and San Nicolas
Island, respectively(2). Aerosol samples (PM2.5) collected in Nanjing China between July 2004 and January 2005 contained mean maleic acid
concentrations of 1.89-31.6 ng/cu m during daytime and 1.18-18.1 ng/cu during nightime(3). Aerosol samples collected in Tokyo Japan in
1992 contained malic acid concentrations of 21-33 ng/cu m(4).
(1) Kawamura K, Ikushima K; Environ Sci Technol 27: 2227-35 (1993) (2) Rogge WF et al; Atmos Environ 27A: 1309-30 (1993) (3) Wang G, Kawamura K; Environ
Sci Technol 39: 7430-38 (2005) (4) Sempere R, Kawamura K; Atmos Environ 28: 449-59 (1994)
HSDB
RURAL/REMOTE: Fine aerosol samples collected at the Great Smoky Mountain National Park, Tennessee between July 15 to August 25, 1995
contained malic acid in 9 of 21 daytime samples (2.5-38.5 ng/cu m) and 2 of 10 nighttime samples (4.7-14 ng/cu m)(1). Arctic aerosol
samples collected from Alert, Canada during 1987-1988 contained a mean malic acid concentration of 0.026 ng/cu m with a range of
<0.003-0.14 ng/cu m(2); elevated diacid levels occurred during extended sunlight times, as opposed to dark periods, suggesting the
presence of the diacids (such as malic acid) was due to photooxidation generation from other atmospheric compounds(2). Aerosol samples
collected at a forest area in Hungary between June 4 and July 10, 2003 contained a mean malic acid concentration of 40 ng/cu m (range of
16.5-78 ng/cu m)(3).
(1) Yu LE et al; Environ Sci Technol 39: 707-15 (2005) (2) Kawamura K et al; Atmos Environ 30: 1709-22 (1996) (3) Kourtchev I et al; Environ Sci Technol 43: 4665-
71 (2009)
HSDB
13.2.14 Food Survey Values
Malic acid has been found in apples and many other fruits and plants(1). An analysis of Caribbean cassava vegetables found a 0.2%
constituent of malic acid(2). Malic acid was detected in six wild edible mushroom species (Amanita caesarea, Boletus edulis, Gyroporus
castaneus, Lactarius delicious, Suillus collinitus and Xerocomus chrysenteron)(3). Malic acid occurs in fruits and edible plants such as apricot,
mango, rose, plum, elderberry, strawberry, pineapple, papaya, orange, tangerine, potato, grape, soybean, grapefruit, lettuce, onion, celery,
oats, cauliflower, cabbage, brussel sprouts, carrot, olive, sunflower, tomato, ginseng, poppy, pea, raspberry, sage, and corn(4).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 1060 (2013) (2) Dougan J et al; J Sci Food Agric 34: 874-84 (1983) (3)
Valentao P et al; J Agric Food Chem 53: 3626-3630 (2005) (4) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical.
Malic acid. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Mar 18, 2015: http://www.ars-grin.gov/duke/
HSDB
Reported food use categories for malic acid include baked goods, frozen dairy, nonalcoholic beverages and soft candy(1). Malic acid occurs
in maple sap, apple, melon, papaya, beer, grape wine, cocoa, sake, kiwifruit and chicory root(1).
(1) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 3rd Edition, Volumes 1-2. Boca Raton, FL: CRC Press, p 1050 (1994-1995)
HSDB
13.2.15 Plant Concentrations
Malic acid occurs in apples and many other fruits and plants(1). An analysis of Caribbean cassava vegetables found a 0.2% constituent of
malic acid(2). Malic acid was detected in six wild edible mushroom species (Amanita caesarea, Boletus edulis, Gyroporus castaneus, Lactarius
delicious, Suillus collinitus and Xerocomus chrysenteron)(3). Malic acid has been identified as occurring in tobacco(4). Malic acid was
detected in pumpkin(5) and pomegrante fruit(6).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 1060 (2013) (2) Dougan J et al; J Sci Food Agric 34: 874-84 (1983) (3)
Valentao P et al; J Agric Food Chem 53: 3626-30 (2005) (4) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke, 2nd ed. Boca
Raton, FL: CRC Press, p. 1774 (2013) (5) Nawirska-Olszariska A et al; Food Chem 148: 415-19 (2014) (6) Mayuoni-Kirshinbaum L, Porat R; J Sci Food Agric 94: 21-
7 (2014)
HSDB
The top forty plants containing malic acid(1).
Genus species Family Common name Part Concn (ppm)
Hibiscus sabdariffa L. Malvaceae Indian Sorrel Flower; Leaf; Stem 65,000; 12,500; 6,000
Rosa canina Rosaceae Dogbrier Fruit 62,200
Sorbus aucubaria Rosaceae Rowan berry Fruit 39,000
Mangifera indica Anacardiaceae Mango Fruit 36,600
Ficus carica Moraceae Fig Fruit; Leaf 30,200; 23,400
Genus species Family Common name Part Concn (ppm)
Prunus armeniaca Rosaceae Apricot Fruit 22,000
Sambucus nigra Adoxaceae European Elderberry Fruit 19,000
Fagopyrum esculentum Polygonaceae Buckwheat Leaf 15,100
Prunus domestica Rosaceae Plum Fruit 15,000
Tamarindus indica Fabaceae Tamarind Leaf; Fruit 15,000; 10,000
Hippophae rhamnoides Elaeagnaceae Buckthorn Fruit 15,000-29,000
Fragaria spp Rosaceae Strawberry Fruit 8,000
Ribes uva-crispa Grossulariaceae Gooseberry Fruit 7,300
Calendula officinlis Asteraceae Pot-Marigold Flower 6,400
Genipa americana Rubiaceae Genipap Fruit 6,300
Averrhoa carambola Oxalidaceae Star Fruit Fruit 1-12,100
Portulaca oleracea Portulacaeae Purslane Plant 5,100
Ananas comosus Bromeliaceae Pineapple Fruit 4,700
Carica papaya Caricaceae Papaya Latex exudate 4,400
Musa x paradisiaca Musaceae Banana Fruit 3,730
Ribes rubrum Grossulariaceae Red Currant Fruit 2,600
Datura stramonium Solanaceae Jimsonweed Plant 2,120
Citrus reticulata Rutaceae Tangerine Fruit 2,100
Citrus aurantiifolia Rutaceae Lime Fruit 2,000
Citrus sinensis Rutaceae Orange Fruit 2,000
Vitis vinifera Vitaceae European Grape Fruit 2,000
Passiflora edulis Passifloraceae Passionfruit Fruit 1,200-3,800
Opuntia ficus-indica Cactaceae Prickly Pear Fruit 1,700
Physalis ixocarpa Solanaceae Tomatillo Fruit 1,500
Solanum tuberosum Solanaceae Potato Tuber 1,120
Citrus mitis Rutaceae Calamansi Fruit Juice 0-2,000
Glycine max Fabaceae Soybean Seed 1,000
Citrus paradisi Rutaceae Grapefruit Fruit 600
Lactuca sativa Asteraceae Lettuce Leaf 600
(1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Malic acid. Washington, DC: US Dept Agric, Agric Res Service.
Available from, as of Mar 17, 2015: http://www.ars-grin.gov/duke/
HSDB
13.2.16 Other Environmental Concentrations
Malic acid has been identified as a component of tobacco smoke(1).

(1) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke, 2nd ed., Boca Raton, FL: CRC Press, p. 1774 (2013)
HSDB
13.2.17 Probable Routes of Human Exposure
According to the 2012 TSCA Inventory Update Reporting data, 2 reporting facilities estimate the number of persons reasonably likely to be
exposed during the manufacturing, processing, or use of malic acid in the United States may be as low as 25-49 workers and as high as 100-
499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).
(1) US EPA; Chemical Data Reporting (CDR). Non-confidential 2012 Chemical Data Reporting information on chemical production and use in the United States.
Available from, as of Mar 17, 2015: http://www.epa.gov/cdr/pubs/guidance/cdr_factsheets.html
HSDB
NIOSH (NOES Survey 1981-1983) has statistically estimated that 80,674 workers (51,609 of these were female) were potentially exposed to
malic acid in the US(1). Occupational exposure to malic acid may occur through inhalation and dermal contact with this compound at
workplaces where malic acid is produced or used. Monitoring data indicate that the general population may be exposed to malic via
inhalation of ambient air and tobacco smoke, ingestion of food and beverages, and dermal contact with consumer products containing
malic acid(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by
2-digit standard industrial classification (SIC). Available from, as of Mar 17, 2015: http://www.cdc.gov/noes/
HSDB
14 Literature
14.1 NLM Curated PubMed Citations
PubChem
14.2 Springer Nature References
Springer Nature
14.3 Thieme References
Thieme Chemistry
14.4 Wiley References
Wiley
14.5 Depositor Provided PubMed Citations
PubChem
14.6 Synthesis References

Weiss, J. M.; Downs, C. R. Preliminary study on the formation of malic acid. Journal of the American Chemical Society (1922), 44 1118-25.
14.7 Metabolite References
14.8 Chemical Co-Occurrences in Literature
PubChem
14.9 Chemical-Gene Co-Occurrences in Literature
PubChem
14.10 Chemical-Disease Co-Occurrences in Literature
PubChem
15 Patents
15.1 Depositor-Supplied Patent Identifiers
PubChem
Link to all deposited patent identifiers
PubChem
15.2 WIPO PATENTSCOPE

Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=BJEPYKJPYRNKOW-UHFFFAOYSA-N
PATENTSCOPE (WIPO)
16 Biomolecular Interactions and Pathways
16.1 Protein Bound 3-D Structures

View 20 proteins in NCBI Structure
PubChem
16.2 Pathways
PubChem
16.3 Drug-Gene Interactions
Drug Gene Interaction database (DGIdb)
17 Biological Test Results
17.1 BioAssay Results
PubChem
18 Classification
18.1 Ontologies
18.1.1 MeSH Tree
MeSH
18.1.2 ChEBI Ontology
ChEBI
18.1.3 KEGG: Risk Category of Japanese OTC Drugs
KEGG
18.1.4 KEGG: Additive
KEGG
18.1.5 WIPO IPC
WIPO
18.1.6 EPA Safer Choice
EPA Safer Choice
18.1.7 ChemIDplus
ChemIDplus
18.1.8 Guide to PHARMACOLOGY Target Classification
IUPHAR/BPS Guide to PHARMACOLOGY
18.1.9 ChEMBL Target Tree
ChEMBL
18.1.10 UN GHS Classification
UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
18.1.11 EPA CPDat Classification
EPA Chemical and Products Database (CPDat)
19 Information Sources
FILTER BY SOURCE ALL SOURCES
1. ChEBI
Malic acid
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6650
ChEBI Ontology
http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
2. DrugBank
LICENSE
Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
https://www.drugbank.ca/legal/terms_of_use
Malic acid
http://www.drugbank.ca/drugs/DB12751
3. Human Metabolome Database (HMDB)

LICENSE
HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission
of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download
significant portions of the database cite the HMDB paper in any resulting publications.
http://www.hmdb.ca/citing
Malic acid
http://www.hmdb.ca/metabolites/HMDB0000744
4. ChemIDplus
LICENSE
https://www.nlm.nih.gov/copyright.html
Malic acid [NF]

https://chem.nlm.nih.gov/chemidplus/sid/0006915157
Poly(malate)
https://chem.nlm.nih.gov/chemidplus/sid/0078644425
ChemIDplus Chemical Information Classification

https://chem.sis.nlm.nih.gov/chemidplus/
5. DTP/NCI
DL-malic acid
https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=25941
6. EPA Chemicals under the TSCA

LICENSE
https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources
Butanedioic acid, 2-hydroxy-

https://www.epa.gov/chemicals-under-tsca
7. EPA DSSTox
LICENSE
Malic acid
https://comptox.epa.gov/dashboard/DTXSID0027640
8. European Chemicals Agency (ECHA)

LICENSE
Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations
provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in
part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such
acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under
the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
https://echa.europa.eu/web/guest/legal-notice
p p g g
DL-malic acid
https://echa.europa.eu/substance-information/-/substanceinfo/100.009.560
Malic acid
calcium malate
Malic acid
https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/12646
DL-malic acid
Calcium malate
9. HSDB
MALIC ACID
https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1202
10. ClinicalTrials.gov
LICENSE
The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the
copyright of third parties; you should consult these entities for any additional terms of use.
https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
https://clinicaltrials.gov/
11. Drug Gene Interaction database (DGIdb)

LICENSE
http://www.dgidb.org/downloads
http://www.dgidb.org/drugs/MALIC ACID
12. EPA Chemical and Products Database (CPDat)

LICENSE
dl-malic acid
https://comptox.epa.gov/dashboard/DTXSID0027640#exposure
EPA CPDat Classification
https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat
13. EU Food Improvement Agents

MALIC ACID
https://eur-lex.europa.eu/legal-content/EN/ALL/?uri=CELEX%3A32012R0231
14. EPA Safer Choice

LICENSE
Malic acid
https://www.epa.gov/saferchoice/safer-ingredients
EPA Safer Chemical Ingredients Classification
https://www.epa.gov/saferchoice
15. European Medicines Agency (EMA)

LICENSE
Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
https://www.ema.europa.eu/en/about-us/legal-notice
Soybean oil, Medium-chain triglycerides, Olive oil, Fish oil, Acetyl-cysteine, Alanine, Arginine /Glycine, Histidine, Isoleucin, Leucine, Lysine acetate,
Methionine, Phenylalanine, Proline, Serine/ Threonine, Tryptophan, Tyrosine, Valine, glucose, calcium chloride, Sodium glycerophosphate /Magnesium
sulphate, potassium chloride, Sodium acetate, Zinc sulphate, Malic acid(P/0133/2017)
https://www.ema.europa.eu/en/medicines/human/paediatric-investigation-plans/emea-002067-pip02-17
16. FAO/WHO Food Additive Evaluations (JECFA)

DL-MALIC ACID
http://apps.who.int/food-additives-contaminants-jecfa-database/chemical.aspx?chemID=5163
17. EU Clinical Trials Register

https://www.clinicaltrialsregister.eu/
18. NITE-CMC
DL-Malic acid - FY2011
https://www.nite.go.jp/chem/english/ghs/11-mhlw-0119e.html
19. FDA Center for Food Safety and Applied Nutrition (CFSAN)
LICENSE
Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be
republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the
source is appreciated but not required.
https://www.fda.gov/about-fda/about-website/website-policies#linking
MALIC ACID
https://www.accessdata.fda.gov/scripts/fdcc/?set=FoodSubstances&id=MALICACID
20. NIST Mass Spectrometry Data Center

DL-Malic acid
http://www.nist.gov/srd/nist1a.cfm
21. MassBank of North America (MoNA)

LICENSE
The content of the MoNA database is licensed under CC BY 4.0.
https://mona.fiehnlab.ucdavis.edu/documentation/license
DL-Malic acid
http://mona.fiehnlab.ucdavis.edu/spectra/browse?inchikey=BJEPYKJPYRNKOW-UHFFFAOYSA-N
22. SpectraBase
https://spectrabase.com/spectrum/KcEgSxo5UMc
https://spectrabase.com/spectrum/3MUUIdnsjH0
https://spectrabase.com/spectrum/DBIqVkZKsdH
https://spectrabase.com/spectrum/CcemTa9JuRx
https://spectrabase.com/spectrum/D1COTYNfktD
https://spectrabase.com/spectrum/Anz4RFKwMau
https://spectrabase.com/spectrum/4kDzZmhgqrE
https://spectrabase.com/spectrum/GGnqCRkxPuM
https://spectrabase.com/spectrum/3Y5SaVhSTlW
https://spectrabase.com/spectrum/3OA3cTDMV29
https://spectrabase.com/spectrum/I9qWWHC0otk
https://spectrabase.com/spectrum/2bzps6RrFCZ
23. Springer Nature
24. Thieme Chemistry

LICENSE
The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
https://creativecommons.org/licenses/by-nc-nd/4.0/
25. Wikipedia
DL-malic acid
https://en.wikipedia.org/wiki/Malic_acid
26. Wiley
https://pubchem.ncbi.nlm.nih.gov/substance/?source=wiley&sourceid=127271
27. PubChem
https://pubchem.ncbi.nlm.nih.gov
28. MeSH
malic acid
https://www.ncbi.nlm.nih.gov/mesh/67030298
MeSH Tree
http://www.nlm.nih.gov/mesh/meshhome.html
29. KEGG
Risk category of Japanese OTC drugs

http://www.genome.jp/kegg-bin/get_htext?br08312.keg
Pharmaceutical additives in Japan
http://www.genome.jp/kegg-bin/get_htext?br08316.keg
30. WIPO
International Patent Classification
http://www.wipo.int/classifications/ipc/
31. UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)

GHS Classification Tree
http://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
32. ChEMBL
Target Tree
https://www.ebi.ac.uk/chembl/target/browser
33. IUPHAR/BPS Guide to PHARMACOLOGY

Target Classification
http://www.guidetopharmacology.org/
34. PATENTSCOPE (WIPO)

SID 403029844
https://pubchem.ncbi.nlm.nih.gov/substance/403029844
35. NCBI
https://www.ncbi.nlm.nih.gov/projects/linkout

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10/4/2020 Malic acid | C4H6O5 - PubChem

COVID-19 is an emerging, rapidly evolving situation.

PubChem CID: 525

Find Similar Structures

Laboratory Chemical Safety Summary (LCSS) Datasheet

Molecular Formula: C4H6O5

Molecular Weight: 134.09 g/mol

Human Metabolome Database (HMDB)

2 Names and Identifiers

3 Chemical and Physical Properties

7 Drug and Medication Information

8 Food Additives and Ingredients

9 Pharmacology and Biochemistry

10 Use and Manufacturing

12 Safety and Hazards

16 Biomolecular Interactions and Pathways

17 Biological Test Results

Ball and Stick

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2.1.3 InChI Key

2.1.4 Canonical SMILES

2.2 Molecular Formula

EU Food Improvement Agents; PubChem

2.3 Other Identifiers

DTP/NCI; European Chemicals Agency (ECHA)

European Chemicals Agency (ECHA)

2.3.2 Related CAS

676-46-0 (di-hydrochloride salt)

2.3.3 Deprecated CAS

41308-42-3, 617-48-1, 623158-98-5, 879715-44-3, 1334703-48-8

2.3.4 European Community (EC) Number

230-022-8, 210-514-9, 202-601-5

EU Food Improvement Agents

European Chemicals Agency (ECHA)

European Chemicals Agency (ECHA)

European Chemicals Agency (ECHA)

2.3.5 NSC Number

2.3.6 DSSTox Substance ID

2.4.1 MeSH Entry Terms

calcium (hydroxy-1-malate) hexahydrate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name Property Value Reference

XLogP3 -1.3 Computed by XLogP3 3.0 (PubChem release 2019.06.18)

Rotatable Bond Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Heavy Atom Count 9 Computed by PubChem

Formal Charge 0 Computed by PubChem

Complexity 129 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Isotope Atom Count 0 Computed by PubChem

Defined Atom Stereocenter Count 0 Computed by PubChem

Undefined Atom Stereocenter Count 1 Computed by PubChem

Defined Bond Stereocenter Count 0 Computed by PubChem

Undefined Bond Stereocenter Count 0 Computed by PubChem

Covalently-Bonded Unit Count 1 Computed by PubChem

Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04)