Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2018-05-29 00:42:16 UTC
Primary IDFDB008114
Secondary Accession Numbers
  • FDB007218
Chemical Information
FooDB NameMalic acid
DescriptionMainly used as an acidifier in a wide range of food, such as fruit drinks, jams, sweet and sour sauces, boiled sweets, chewing gum. Occasionally used as a metal ion chelator in wine or in hard water. Flavour enhancer Malic acid is the active ingredient in many sour or tart foods. Malic acid is found mostly in unripe fruits. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. Malic acid is found in many foods, some of which are garden rhubarb, sour cherry, white lupine, and coconut.
CAS Number6915-15-7
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxybutanedioic acidChEBI
2-Hydroxyethane-1,2-dicarboxylic acidChEBI
2-Hydroxysuccinic acidChEBI
alpha-Hydroxysuccinic acidChEBI
AepfelsaeureChEBI
Apple acidChEBI
DL-Malic acidChEBI
e296ChEBI
H2MalChEBI
Hydroxybutanedioic acidChEBI
Hydroxysuccinic acidChEBI
MalateKegg
2-HydroxybutanedioateGenerator
2-Hydroxyethane-1,2-dicarboxylateGenerator
2-HydroxysuccinateGenerator
a-HydroxysuccinateGenerator
a-Hydroxysuccinic acidGenerator
alpha-HydroxysuccinateGenerator
Α-hydroxysuccinateGenerator
Α-hydroxysuccinic acidGenerator
DL-MalateGenerator
HydroxybutanedioateGenerator
HydroxysuccinateGenerator
DeoxytetrarateHMDB
Deoxytetraric acidHMDB
Musashi-NO-ringosanHMDB
Pomalus acidHMDB
R,S-MalateHMDB
R,S-Malic acidHMDB
R,SMalateHMDB
R,SMalic acidHMDB
Malic acid, disodium saltHMDB
Malic acid, disodium salt, (R)-isomerHMDB
Malic acid, disodium salt, (S)-isomerHMDB
Malic acid, monopotassium salt, (+-)-isomerHMDB
Malic acid, (R)-isomerHMDB
Malic acid, calcium salt, (1:1), (S)-isomerHMDB
Malic acid, magnesium salt (2:1)HMDB
Calcium (hydroxy-1-malate) hexahydrateHMDB
Malic acid, potassium salt, (R)-isomerHMDB
Malic acid, sodium salt, (+-)-isomerHMDB
2-Hydroxydicarboxylic acidbiospider
Butanedioic acid, 2-hydroxy-biospider
Butanedioic acid, hydroxy-biospider
E296db_source
Hydroxy succinic acidbiospider
Hydroxyethane-1,2-dicarboxylic acidbiospider
Succinic acid, hydroxy-biospider
α-hydroxysuccinateGenerator
α-hydroxysuccinic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
logP-0.87ALOGPS
logP-1.1ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O5
IUPAC name2-hydroxybutanedioic acid
InChI IdentifierInChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
InChI KeyBJEPYKJPYRNKOW-UHFFFAOYSA-N
Isomeric SMILESOC(CC(O)=O)C(O)=O
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
Classification
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 35.83%; H 4.51%; O 59.66%DFC
Melting Point131-133 oC
Boiling PointNot Available
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.26HANSCH,C ET AL. (1995)
Experimental pKa3.4
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0930000000-6a116527910d172eb561View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03e9-3900000000-6112a756a8c8c7c7cd50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9100000000-b3efe8bce2f89afcff34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00ec-9300000000-c0aaa5301dcac30685dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb76523View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a189View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eaeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd8View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID510
ChEMBL IDCHEMBL1455497
KEGG Compound IDC03668
Pubchem Compound ID525
Pubchem Substance IDNot Available
ChEBI ID6650
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00744
CRC / DFC (Dictionary of Food Compounds) IDDCG74-V:DCG74-V
EAFUS ID2097
Dr. Duke IDMALIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMalic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti fibromyalgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
bruchiphobeDUKE
hemopoieticDUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
mycobactericideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sialogogueDUKE
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128 map00010
Malate-Aspartate ShuttleSMP00129 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).