Record Information
Version2.0
Creation Date2012-05-31 13:56:40 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB02329
Identification
Name:Oxalic acid
DescriptionOxalic acid is a 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. (Wikipedia)
Structure
Thumb
Synonyms:
  • Ammonium oxalate
  • Ammonium oxalic acid
  • Ethane-1,2-dioate
  • Ethane-1,2-dioic acid
  • Ethanedioate
  • Ethanedioate dihydrate
  • Ethanedioic acid
  • Ethanedioic acid dihydrate
  • Ethanedioic acid dihydric acid
  • Ethanedionate
  • Ethanedionic acid
  • Kyselina stavelova
  • Oxaalzuur
  • Oxalate
  • Oxalate 2-Hydrate
  • Oxalate anhydrous
  • Oxalate diammonium salt
  • Oxalate dihydrate
  • Oxalic acid
  • Oxalic acid 2-Hydrate
  • Oxalic acid 2-Hydric acid
  • Oxalic acid anhydrous
  • Oxalic acid diammonium salt
  • Oxalic acid dihydrate
  • Oxalic acid dihydric acid
Chemical Formula:C2H2O4
Weight:Average: 90.0349
Monoisotopic: 89.995308552
InChI Key:MUBZPKHOEPUJKR-UHFFFAOYSA-N
InChI:InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)
CAS number:144-62-7
IUPAC Name:oxalic acid
Traditional IUPAC Name:oxalic acid
SMILES:OC(=O)C(O)=O
Chemical Taxonomy
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
Physical Properties
State:Solid
Charge:-2
Melting point:189.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:220 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Chloroalkane and chloroalkene degradation ec00625
  • Glyoxylate and dicarboxylate metabolism ec00630
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0900000000-eaa92cf80964dd7d345aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9500000000-e5db327eab9e8a2f149eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00sl-3910000000-75af6e42d4cc12d798f4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-8aef9a64d926571c2de0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-eaa92cf80964dd7d345aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-b9206a3a54b5be6f07d9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9500000000-e5db327eab9e8a2f149eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00sl-3910000000-75af6e42d4cc12d798f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-3cee49bf06349fbe625eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-f5e8094c68372ab25a63View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9510000000-28b0e365a156d2091afdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-cb3d53cc3c40c1cbbba7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-9000000000-53a009b344e3920ffca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-2bafb6c472ab1030cd0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-8aef9a64d926571c2de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d1ff7c94a720b1eecaf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-21d33d1d99d80526ee71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ac27102ff43446c313d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-fe58eaea122c39178fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-3850c6a7016e2874d55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-32ac4118fe0eb9a5abb2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-538465f019815d5e1b4aView in MoNA
References
References:
  • Amoroso A, Pirulli D, Florian F, Puzzer D, Boniotto M, Crovella S, Zezlina S, Spano A, Mazzola G, Savoldi S, Ferrettini C, Berutti S, Petrarulo M, Marangella M: AGXT gene mutations and their influence on clinical heterogeneity of type 1 primary hyperoxaluria. J Am Soc Nephrol. 2001 Oct;12(10):2072-9. Pubmed: 11562405
  • Astarcioglu I, Karademir S, Gulay H, Bora S, Astarcioglu H, Kavukcu S, Turkmen M, Soylu A: Primary hyperoxaluria: simultaneous combined liver and kidney transplantation from a living related donor. Liver Transpl. 2003 Apr;9(4):433-6. Pubmed: 12682898
  • de O G Mendonca C, Martini LA, Baxmann AC, Nishiura JL, Cuppari L, Sigulem DM, Heilberg IP: Effects of an oxalate load on urinary oxalate excretion in calcium stone formers. J Ren Nutr. 2003 Jan;13(1):39-46. Pubmed: 12563622
  • de Water R, Noordermeer C, van der Kwast TH, Nizze H, Boeve ER, Kok DJ, Schroder FH: Calcium oxalate nephrolithiasis: effect of renal crystal deposition on the cellular composition of the renal interstitium. Am J Kidney Dis. 1999 Apr;33(4):761-71. Pubmed: 10196021
  • Huang MY, Chaturvedi LS, Koul S, Koul HK: Oxalate stimulates IL-6 production in HK-2 cells, a line of human renal proximal tubular epithelial cells. Kidney Int. 2005 Aug;68(2):497-503. Pubmed: 16014026
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kwak C, Jeong BC, Kim HK, Kim EC, Chox MS, Kim HH: Molecular epidemiology of fecal Oxalobacter formigenes in healthy adults living in Seoul, Korea. J Endourol. 2003 May;17(4):239-43. Pubmed: 12816588
  • Massey LK, Palmer RG, Horner HT: Oxalate content of soybean seeds (Glycine max: Leguminosae), soyfoods, and other edible legumes. J Agric Food Chem. 2001 Sep;49(9):4262-6. Pubmed: 11559120
  • Mizusawa Y, Parnham AP, Falk MC, Burke JR, Nicol D, Yamanaka J, Lynch SV, Strong RW: Potential for bilateral nephrectomy to reduce oxalate release after combined liver and kidney transplantation for primary hyperoxaluria type 1. Clin Transplant. 1997 Oct;11(5 Pt 1):361-5. Pubmed: 9361924
  • Motoyoshil Y, Hattori M, Chikamoto H, Nakakura H, Furue T, Miyakawa S, Kohno M, Ito K, Kai K, Nakajima I, Fuchinoue S, Teraoka S, Akiba T, Kitayama H, Wada N, Ogawa Y: [Sequential combined liver-kidney transplantation for a one-year-old boy with infantile primary hyperoxaluria type 1] Nippon Jinzo Gakkai Shi. 2006;48(1):22-8. Pubmed: 16480063
  • Mydlik M, Derzsiova K, Pribylincova V, Reznicek J: [Urinary oxalic acid excretion in chronic kidney failure and after kidney transplantation] Vnitr Lek. 1996 Dec;42(12):813-7. Pubmed: 9072879
  • Nakagawa Y, Abram V, Parks JH, Lau HS, Kawooya JK, Coe FL: Urine glycoprotein crystal growth inhibitors. Evidence for a molecular abnormality in calcium oxalate nephrolithiasis. J Clin Invest. 1985 Oct;76(4):1455-62. Pubmed: 4056037
  • Pecorella I, McCartney AC, Lucas S, Michaels L, Ciardi A, Di Tondo U, Garner A: Histological study of oxalosis in the eye and adnexa of AIDS patients. Histopathology. 1995 Nov;27(5):431-8. Pubmed: 8575733
  • Petrarulo M, Vitale C, Facchini P, Marangella M: Biochemical approach to diagnosis and differentiation of primary hyperoxalurias: an update. J Nephrol. 1998 Mar-Apr;11 Suppl 1:23-8. Pubmed: 9604805
  • Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309. Pubmed: 12768081
  • Robertson WG: Renal stones in the tropics. Semin Nephrol. 2003 Jan;23(1):77-87. Pubmed: 12563603
  • Selvam R, Kalaiselvi P: A novel basic protein from human kidney which inhibits calcium oxalate crystal growth. BJU Int. 2000 Jul;86(1):7-13. Pubmed: 10886075
  • Shapiro R, Weismann I, Mandel H, Eisenstein B, Ben-Ari Z, Bar-Nathan N, Zehavi I, Dinari G, Mor E: Primary hyperoxaluria type 1: improved outcome with timely liver transplantation: a single-center report of 36 children. Transplantation. 2001 Aug 15;72(3):428-32. Pubmed: 11502971
  • Singh S, Tai C, Ganz G, Yeung CK, Magil A, Rosenberg F, Applegarth D, Levin A: Steroid-responsive pleuropericarditis and livedo reticularis in an unusual case of adult-onset primary hyperoxaluria. Am J Kidney Dis. 1999 Apr;33(4):e5. Pubmed: 10196036
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • van Woerden CS, Groothof JW, Wanders RJ, Waterham HR, Wijburg FR: [From gene to disease; primary hyperoxaluria type I caused by mutations in the AGXT gene] Ned Tijdschr Geneeskd. 2006 Jul 29;150(30):1669-72. Pubmed: 16922352
  • Vicanova J, Boelsma E, Mommaas AM, Kempenaar JA, Forslind B, Pallon J, Egelrud T, Koerten HK, Ponec M: Normalization of epidermal calcium distribution profile in reconstructed human epidermis is related to improvement of terminal differentiation and stratum corneum barrier formation. J Invest Dermatol. 1998 Jul;111(1):97-106. Pubmed: 9665394
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16995
HMDB IDHMDB02329
Pubchem Compound ID971
Kegg IDC00209
ChemSpider ID946
WikipediaOxalic acid
BioCyc IDOXALATE
EcoCyc IDOXALATE
Ligand ExpoOXL

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of the CoA moiety from formyl-CoA to oxalate
Gene Name:
frc
Uniprot ID:
P69902
Molecular weight:
45828
Reactions
Formyl-CoA + oxalate = formate + oxalyl-CoA.