Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2019-11-26 02:55:50 UTC
Primary IDFDB001044
Secondary Accession Numbers
  • FDB030170
Chemical Information
FooDB NameL-Malic acid
DescriptionL-Malic acid, also known as malate or L-apple 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. L-Malic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Malic acid exists in all eukaryotes, ranging from yeast to humans. L-Malic acid, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, colorectal cancer, eosinophilic esophagitis, and missing teeth; L-malic acid has also been linked to the inborn metabolic disorder 2-ketoglutarate dehydrogenase complex deficiency.
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
(2S)-2-Hydroxysuccinic acidHMDB
(2S)-Malic acidHMDB
(S)-2-Hydroxysuccinic acidHMDB
2-Hydroxybutanedioic acidHMDB
2-Hydroxyethane-1,2-dicarboxylic acidHMDB
2-Hydroxysuccinic acidHMDB
Deoxytetraric acidHMDB
Hydroxybutanedioic acidHMDB
Hydroxysuccinic acidHMDB
Monohydroxybutanedioic acidHMDB
alpha-Hydroxysuccinic acidHMDB
α-Hydroxysuccinic acidHMDB
(-)-(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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd82020-02-03View Spectrum
GC-MSL-Malic acid, 3 TMS, GC-MS Spectrumsplash10-000t-0940000000-142d6f5fc2efbf0d5109Spectrum
GC-MSL-Malic acid, 3 TMS, GC-MS Spectrumsplash10-0002-0920000000-505483ce10ee3c4c9d20Spectrum
GC-MSL-Malic acid, 3 TMS, GC-MS Spectrumsplash10-00di-9710000000-8f263d045d715ae9fe2bSpectrum
GC-MSL-Malic acid, non-derivatized, GC-MS Spectrumsplash10-000t-0940000000-142d6f5fc2efbf0d5109Spectrum
GC-MSL-Malic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-505483ce10ee3c4c9d20Spectrum
GC-MSL-Malic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9710000000-8f263d045d715ae9fe2bSpectrum
GC-MSL-Malic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-fadd80af55894555ea72Spectrum
Predicted GC-MSL-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efSpectrum
Predicted GC-MSL-Malic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4Spectrum
Predicted GC-MSL-Malic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Malic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-acd7d0159b8bb70b80fd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0096-9000000000-7359292556d9d393d8f42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0097-9000000000-a111335688b3219c1fc12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00lr-0942120000-9504700a82dcf5dc3adb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-45e58d8a75d957cc5c412012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4ec56105367de7bf00272012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-1decf12f117200e0f28d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-4900000000-86fd329658581c81c0ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9100000000-82ffef2aa053f77cdbc52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-424bd54bc81a9db65a552012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a916941735427ee3c48d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-1decf12f117200e0f28d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-4900000000-86fd329658581c81c0ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9100000000-82ffef2aa053f77cdbc52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-424bd54bc81a9db65a552017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a916941735427ee3c48d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-afdfdad3edeeb90cb3e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-01b9-4900000000-01b3a756de8f5a3ae6de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01b9-4900000000-5fc3f0befc374a6fcdd62021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015af2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb765232016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed9272016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a1892016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eae2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).