Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2018-01-23 18:47:33 UTC
Primary IDFDB001044
Secondary Accession Numbers
  • FDB030170
Chemical Information
FooDB NameL-Malic acid
DescriptionOccurs naturally in apples and various other fruits. Flavour enhancer, pH control agent. L-Malic acid is found in many foods, some of which are mulberry, black cabbage, european plum, and fig.
CAS Number97-67-6
Structure
Thumb
Synonyms
SynonymSource
(-)-L-Malic acidChEBI
(S)-(-)-Hydroxysuccinic acidChEBI
L-2-Hydroxybutanedioic acidChEBI
L-Apple acidChEBI
MalateChEBI
Malic acidChEBI
S-2-Hydroxybutanedioic acidChEBI
L-MalateKegg
(-)-L-MalateGenerator
(S)-(-)-HydroxysuccinateGenerator
L-2-HydroxybutanedioateGenerator
S-2-HydroxybutanedioateGenerator
(-)-(S)-MalateHMDB
(-)-(S)-Malic acidHMDB
(-)-HydroxysuccinateHMDB
(-)-Hydroxysuccinic acidHMDB
(-)-Malic acidHMDB
(2S)-2-HydroxybutanedioateHMDB
(2S)-2-Hydroxybutanedioic acidHMDB
(S)-Hydroxy-butanedioateHMDB
(S)-Hydroxy-butanedioic acidHMDB
(S)-HydroxybutanedioateHMDB
(S)-Hydroxybutanedioic acidHMDB
(S)-Malic acidHMDB
Apple acidHMDB
L-(-)-Malic acidHMDB
L-HydroxybutanedioateHMDB
L-Hydroxybutanedioic acidHMDB
L-HydroxysuccinateHMDB
L-Hydroxysuccinic acidHMDB
S-(-)-MalateHMDB
S-(-)-Malic acidHMDB
(S)-MalateHMDB
L-Malic acidChEBI
(-)-(s)-malatebiospider
(-)-(s)-malic acidbiospider
(-)-hydroxysuccinatebiospider
(-)-hydroxysuccinic acidbiospider
(-)-l-malic acidbiospider
(-)-malic acidbiospider
(S)-(-)-2-Hydroxysuccinic acidbiospider
(s)-(-)-hydroxysuccinatebiospider
(s)-(-)-hydroxysuccinic acidbiospider
(s)-hydroxy-butanedioatebiospider
(s)-hydroxy-butanedioic acidbiospider
(s)-hydroxybutanedioatebiospider
(s)-hydroxybutanedioic acidbiospider
(s)-malatebiospider
(s)-malic acidbiospider
Butanedioic acid, hydroxy-, (s)-biospider
FEMA 2655db_source
L-(-)-malic acidbiospider
L-apple acidbiospider
L-hydroxybutanedioatebiospider
L-hydroxybutanedioic acidbiospider
L-hydroxysuccinatebiospider
L-hydroxysuccinic acidbiospider
L-malatebiospider
Malic acid, (l)biospider
Malic acid, 8CI; L-formdb_source
Malic acid, l-biospider
S-(-)-malatebiospider
S-(-)-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(2S)-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-/m0/s1
InChI KeyBJEPYKJPYRNKOW-REOHCLBHSA-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
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 PointMp 104-105° (100°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa2 5.1DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -28.7 (c, 5.5 in Py) (>99.8% ee)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID193317
ChEMBL IDNot Available
KEGG Compound IDC00149
Pubchem Compound ID222656
Pubchem Substance IDNot Available
ChEBI ID15589
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00156
CRC / DFC (Dictionary of Food Compounds) IDDCG74-V:BQR68-X
EAFUS ID2098
Dr. Duke IDL-MALIC-ACID
BIGG ID34045
KNApSAcK IDC00001192
HET IDLMR
Flavornet IDNot Available
GoodScent IDrw1030861
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
Enzymes
NameGene NameUniProt ID
Fumarate hydratase, mitochondrialFHP07954
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
Pyruvate MetabolismSMP00060 map00620
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).