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Malic acid (FDB008114)

Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2019-11-26 03:02:07 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd82015-03-01View Spectrum
GC-MSMaslic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-d3afa3ad5c227740eae3Spectrum
GC-MSMaslic acid, 3 TMS, GC-MS Spectrumsplash10-001i-0951000000-1d993823fa816ba3cfb1Spectrum
GC-MSMaslic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0930000000-6a116527910d172eb561Spectrum
GC-MSMaslic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-d3afa3ad5c227740eae3Spectrum
GC-MSMaslic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0951000000-1d993823fa816ba3cfb1Spectrum
Predicted GC-MSMaslic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efSpectrum
Predicted GC-MSMaslic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03e9-3900000000-6112a756a8c8c7c7cd502012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9100000000-b3efe8bce2f89afcff342012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00ec-9300000000-c0aaa5301dcac30685db2012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015af2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb765232017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed9272017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a1892017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eae2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH 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).