Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2020-04-21 18:03:34 UTC
Primary IDFDB003357
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOxalic acid
DescriptionPresent in many plants and vegetables. Toxin from rhubarb, especies the leaves but also present in the stems A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent. -- Pubchem; Bodily oxalic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 80% of kidney stones are formed from calcium oxalate. Some Aspergillus species produce oxalic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. There is some preliminary evidence that the administration of probiotics can affect oxalic acid excretion rates (and presumably oxalic acid levels as well.) -- Wikipedia; Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions. It usually binds as a bidentate ligand forming a 5-membered MO2C2 ring. An illustrative complex is potassium ferrioxalate, K3[Fe(C2O4)3]. The drug Oxaliplatin exhibits improved water solubility relative to older platinum-based drugs, avoiding the dose-limiting side-effect of nephrotoxicity. Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.; Oxalic acid (IUPAC name: ethanedioic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). Because of the joining of two carboxyl groups, this is one of the strongest organic acids. It is also a reducing agent. The anions of oxalic acid as well as its salts and esters are known as oxalates. -- Wikipedia; Oxalic acid is an important reagent in lanthanide chemistry. Hydrated lanthanide oxalates form readily in strongly acid solution in a densely crystalline easily filtered form, largely free from contamination by non-lanthanide elements. Lanthanide oxalates figure importantly in commercial processing of lanthanides, and are used to recover lanthanides from solution after separation. Upon ignition, lanthanide oxalates are converted to the oxides, which are the most common form in which the lanthanides are marketed.; Oxalic acid is the chemical compound with the formula H2C2O4. This dicarboxylic acid is better described with the formula HOOCCOOH. It is a relatively strong organic acid, being about 3,000 times as strong as acetic acid. The di-anion, known as oxalate, is also a reducing agent as well as a ligand in coordination chemistry. Many metal ions form insoluble precipitates with oxalate, a prominent example being calcium oxalate, which is the primary constituent of the most common kind of kidney stones. Oxalic acid is found in many foods, some of which are lettuce, chinese chives, red beetroot, and cherry tomato.
CAS Number144-62-7
Structure
Thumb
Synonyms
SynonymSource
EthandisaeureChEBI
Ethane-1,2-dioic acidChEBI
Ethanedioic acidChEBI
H2OxChEBI
HOOCCOOHChEBI
OxalsaeureChEBI
Ethane-1,2-dioateGenerator
EthanedioateGenerator
OxalateGenerator
Ammonium oxalateHMDB
Ethanedioic acid dihydrateHMDB
EthanedionateHMDB
Ethanedionic acidHMDB
Kyselina stavelovaHMDB
OxaalzuurHMDB
Oxalic acid 2-hydrateHMDB
Oxalic acid anhydrousHMDB
Oxalic acid diammonium saltHMDB
Oxalic acid dihydrateHMDB
Acid, oxalicHMDB
Aluminum oxalateHMDB
Chromium (3+) oxalate (3:2)HMDB
Dipotassium oxalateHMDB
Iron oxalateHMDB
Magnesium oxalateHMDB
Magnesium oxalate (1:1)HMDB
Oxalate, dilithiumHMDB
Oxalate, disodiumHMDB
Oxalate, monohydrogen monopotassiumHMDB
Oxalate, monopotassiumHMDB
Oxalate, potassiumHMDB
Chromium oxalateHMDB
Dilithium oxalateHMDB
Manganese (2+) oxalate (1:1)HMDB
Monosodium oxalateHMDB
Oxalate, chromiumHMDB
Oxalate, dipotassiumHMDB
Oxalate, magnesiumHMDB
Oxalate, monosodiumHMDB
Oxalate, potassium chromiumHMDB
Oxalate, sodiumHMDB
Potassium oxalateHMDB
Potassium oxalate (2:1)HMDB
Diammonium oxalateHMDB
Disodium oxalateHMDB
Oxalate, aluminumHMDB
Oxalate, diammoniumHMDB
Oxalate, ferricHMDB
Oxalate, monoammoniumHMDB
Potassium chromium oxalateHMDB
Chromium (2+) oxalateHMDB
Ferric oxalateHMDB
Iron (2+) oxalate (1:1)HMDB
Iron (3+) oxalateHMDB
Monoammonium oxalateHMDB
Monohydrogen monopotassium oxalateHMDB
Monopotassium oxalateHMDB
Oxalate, ironHMDB
Sodium oxalateHMDB
Oxalic acidKEGG
2duabiospider
2hwgbiospider
553-91-3 (DILITHIUM)biospider
Acido ossalicobiospider
Acidum oxalicumbiospider
Acidum Oxalicum-Injeel Forte Liq (D6-D200)biospider
Aktisalbiospider
Ammonium oxalate;Ethane-1,2-dioatebiospider
Aquisalbiospider
Clover aciddb_source
Ethanedioic acid (9CI)biospider
Ethanedioic acid, 9CIdb_source
H2oxbiospider
Hooccoohbiospider
Magnesium permanganatebiospider
Oxagelbiospider
Oxalate standard for icbiospider
Oxalic acid (8CI)biospider
Oxalic acid 2-Hydratebiospider
Oxalic Acid, Cadmium Salt (1:1)biospider
Oxalicum 5dh-30chbiospider
Oxalicum acidumbiospider
OXDbiospider
Oxiric acidbiospider
OXLbiospider
Ultraplast Activate S 52biospider
Predicted Properties
PropertyValueSource
Water Solubility65.7 g/LALOGPS
logP-0.51ALOGPS
logP-0.26ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)1.36ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.44 m³·mol⁻¹ChemAxon
Polarizability6.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC2H2O4
IUPAC nameoxalic acid
InChI IdentifierInChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
InChI KeyMUBZPKHOEPUJKR-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C(O)=O
Average Molecular Weight90.0349
Monoisotopic Molecular Weight89.995308552
Classification
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 26.68%; H 2.24%; O 71.08%DFC
Melting PointMp 101.5° (dihydrate)DFC
Boiling PointNot Available
Experimental Water Solubility220 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKapKa2 3.85 (25°,H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd18.54 1.65DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0900000000-eaa92cf80964dd7d345aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9500000000-e5db327eab9e8a2f149eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00sl-3910000000-75af6e42d4cc12d798f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8aef9a64d926571c2de0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-eaa92cf80964dd7d345aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9500000000-e5db327eab9e8a2f149eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00sl-3910000000-75af6e42d4cc12d798f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-3cee49bf06349fbe625eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-f5e8094c68372ab25a63JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9510000000-28b0e365a156d2091afdJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-cb3d53cc3c40c1cbbba7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-9000000000-53a009b344e3920ffca1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-2bafb6c472ab1030cd0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-8aef9a64d926571c2de0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d1ff7c94a720b1eecaf2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-21d33d1d99d80526ee71JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ac27102ff43446c313d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-fe58eaea122c39178fbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-3850c6a7016e2874d55bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-32ac4118fe0eb9a5abb2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-538465f019815d5e1b4aJSpectraViewer | MoNA
ChemSpider ID946
ChEMBL IDCHEMBL146755
KEGG Compound IDC00209
Pubchem Compound ID971
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB03902
HMDB IDHMDB02329
CRC / DFC (Dictionary of Food Compounds) IDCWF22-Y:CWF22-Y
EAFUS IDNot Available
Dr. Duke IDOXALATE|12-DICARBONIC-ACID|OXALIC-ACID
BIGG ID34265
KNApSAcK IDC00001198
HET IDOXD
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOxalic 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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
central nervous system paralytic35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
fatalDUKE
hemostaticDUKE
irritantDUKE
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
renotoxic50909 A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.DUKE
varroacideDUKE
Enzymes
NameGene NameUniProt ID
Proto-oncogene tyrosine-protein kinase SrcSRCP12931
PathwaysNot 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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.