Malic acid (CHEM017272)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:08:18 UTC
Update Date2016-10-28 10:02:52 UTC
Accession NumberCHEM017272
Identification
Common NameMalic acid
ClassSmall Molecule
DescriptionA 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC4H6O5
Average Molecular Mass134.087 g/mol
Monoisotopic Mass134.022 g/mol
CAS Registry Number6915-15-7
IUPAC Name2-hydroxybutanedioic acid
Traditional Namemalic acid
SMILESOC(CC(O)=O)C(O)=O
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
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0951000000-1d993823fa816ba3cfb1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0930000000-6a116527910d172eb561Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0951000000-1d993823fa816ba3cfb1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03e9-3900000000-6112a756a8c8c7c7cd50Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9100000000-b3efe8bce2f89afcff34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00ec-9300000000-c0aaa5301dcac30685dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb76523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a189Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eaeSpectrum
MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd8Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12751
HMDB IDHMDB0000744
FooDB IDFDB008114
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDRS-Malate
METLIN ID118
PDB IDNot Available
Wikipedia LinkMalic_acid
Chemspider ID510
ChEBI ID6650
PubChem Compound ID525
Kegg Compound IDC03668
YMDB IDNot Available
ECMDB IDECMDB00156
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15767321
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17896933
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19743855
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22411507
7. Weiss, J. M.; Downs, C. R. Preliminary study on the formation of malic acid. Journal of the American Chemical Society (1922), 44 1118-25.
8. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.
9. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.
10. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
11. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
12. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
13. 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. Hem SL: Elimination of aluminum adjuvants. Vaccine. 2002 May 31;20 Suppl 3:S40-3.
15. Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29.
16. Anneroth G, Nordenram G, Bengtsson S: Effect of saliva stimulants (Hybrin and malic acid) on cervical root surfaces in vitro. Scand J Dent Res. 1980 Jun;88(3):214-8.
17. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.