Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2018-01-23 19:01:20 UTC
Primary IDFDB008115
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Malic acid
Description(R)-Malic acid, also known as (r)-malic acid, 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 (R)-Malic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (R)-Malic acid has been detected, but not quantified in, herbs and spices. This could make (R)-malic acid a potential biomarker for the consumption of these foods.
CAS Number636-61-3
Structure
Thumb
Synonyms
SynonymSource
(+)-D-Malic acidChEBI
(R)-2-Hydroxybutanedioic acidChEBI
2-HYDROXY-succinIC ACIDChEBI
D-Malic acidChEBI
D-MalateKegg
(+)-D-MalateGenerator
(R)-2-HydroxybutanedioateGenerator
2-HYDROXY-succinateGenerator
(R)-MalateGenerator
(R)-Hydroxybutanedioic acidHMDB
D-(+)-Malic acidHMDB
D-Hydroxybutanedioic acidHMDB
Hydroxy-(R)-butanedioic acidHMDB
R-Malic acidHMDB
(r)-hydroxybutanedioic acidbiospider
(r)-malatebiospider
Butanedioic acid, hydroxy-, (r)-biospider
D-(+)-malic acidbiospider
D-hydroxybutanedioic acidbiospider
D-malatebiospider
D-malic acidbiospider
Malic acid, 8CI; D-formdb_source
R-malic acidbiospider
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
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O5
IUPAC name(2R)-2-hydroxybutanedioic acid
InChI IdentifierInChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
InChI KeyBJEPYKJPYRNKOW-UWTATZPHSA-N
Isomeric SMILESO[C@H](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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 35.83%; H 4.51%; O 59.66%DFC
Melting PointMp 101° (97-99°)DFC
Boiling PointNot Available
Experimental Water Solubility364 mg/mL at 20 oCBEILSTEIN
Experimental logP-1.26HANSCH,C ET AL. (1995)
Experimental pKapKa1 5.26 (25°, H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +28.4 (c, 5.5 in Py) (>99.8% ee)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0930000000-53a536e3bc82b8e91612JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9610000000-883e07f52319a029b9f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0930000000-53a536e3bc82b8e91612JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9610000000-883e07f52319a029b9f9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-add08efe51cfe6d9243cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0159-3900000000-b601107a03ca7060bc56JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000000-3b7d14a7ed7bb42627e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bj-9300000000-20f68e610aeba32d1947JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-044292489a383c81ae1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00m0-8900000000-9da4062d3c439ed2f7ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-9200000000-c4d019ab4961e5b1a1aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-bc073c2d0e1a2f8a82e3JSpectraViewer
ChemSpider ID83793
ChEMBL IDCHEMBL225986
KEGG Compound IDC00497
Pubchem Compound ID92824
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31518
CRC / DFC (Dictionary of Food Compounds) IDDCG74-V:DCG75-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDMR
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference