ContaminantDB: Oxalic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-06-09 20:08:59 UTC

Update Date

2026-05-14 17:57:25 UTC

Accession Number

CHEM000741

Identification

Common Name

Oxalic acid

Class

Small Molecule

Description

Oxalic acid is a dicarboxylic acid. It is a colorless crystalline solid that dissolves in water to give colorless, acidic solutions. In terms of acid strength, it is much stronger than acetic acid. Oxalic acid, because of its di-acid structure can also act as a chelating agent for metal cations. About 25% of produced oxalic acid is used as a mordant in dyeing processes. It is also used in bleaches, especially for pulpwood. Oxalic acid's main applications include cleaning (it is also found in baking powder) or bleaching, especially for the removal of rust. Oxalic acid is found in a number of common foods with members of the spinach family being particularly high in oxalates. Beat leaves, parsley, chives and cassava are quite rich in oxalate. Rhubarb leaves contain about 0.5% oxalic acid and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Bacteria naturally produce oxalates from the oxidation of carbohydrates. At least two pathways exist for the enzyme-mediated formation of oxalate in humans. In one pathway, oxaloacetate (part of the citric acid cycle) can be hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase. Oxalic acid can also be generated from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol. Oxalate is a competitive inhibitor of lactate dehydrogenase (LDH). LDH catalyses the conversion of pyruvate to lactic acid oxidizing the coenzyme NADH to NAD+ and H+ concurrently. As cancer cells preferentially use aerobic glycolysis, inhibition of LDH has been shown to inhibit tumor formation and growth. However, oxalic acid is not particularly safe and is considered a mild toxin. In particular, it is a well-known uremic toxin. In humans, ingested oxalic acid has an oral lowest-published-lethal-dose of 600 mg/kg. It has been reported that the lethal oral dose is 15 to 30 grams. The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin
Reducing Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ethandisaeure	ChEBI
Ethane-1,2-dioic acid	ChEBI
Ethanedioic acid	ChEBI
H2Ox	ChEBI
HOOCCOOH	ChEBI
Oxalsaeure	ChEBI
Ethane-1,2-dioate	Generator
Ethanedioate	Generator
Oxalate	Generator
Ammonium oxalate	HMDB
Ethanedioic acid dihydrate	HMDB
Ethanedionate	HMDB
Ethanedionic acid	HMDB
Kyselina stavelova	HMDB
Oxaalzuur	HMDB
Oxalic acid 2-hydrate	HMDB
Oxalic acid anhydrous	HMDB
Oxalic acid diammonium salt	HMDB
Oxalic acid dihydrate	HMDB
Acid, oxalic	HMDB
Aluminum oxalate	HMDB
Chromium (3+) oxalate (3:2)	HMDB
Dipotassium oxalate	HMDB
Iron oxalate	HMDB
Magnesium oxalate	HMDB
Magnesium oxalate (1:1)	HMDB
Oxalate, dilithium	HMDB
Oxalate, disodium	HMDB
Oxalate, monohydrogen monopotassium	HMDB
Oxalate, monopotassium	HMDB
Oxalate, potassium	HMDB
Chromium oxalate	HMDB
Dilithium oxalate	HMDB
Manganese (2+) oxalate (1:1)	HMDB
Monosodium oxalate	HMDB
Oxalate, chromium	HMDB
Oxalate, dipotassium	HMDB
Oxalate, magnesium	HMDB
Oxalate, monosodium	HMDB
Oxalate, potassium chromium	HMDB
Oxalate, sodium	HMDB
Potassium oxalate	HMDB
Potassium oxalate (2:1)	HMDB
Diammonium oxalate	HMDB
Disodium oxalate	HMDB
Oxalate, aluminum	HMDB
Oxalate, diammonium	HMDB
Oxalate, ferric	HMDB
Oxalate, monoammonium	HMDB
Potassium chromium oxalate	HMDB
Chromium (2+) oxalate	HMDB
Ferric oxalate	HMDB
Iron (2+) oxalate (1:1)	HMDB
Iron (3+) oxalate	HMDB
Monoammonium oxalate	HMDB
Monohydrogen monopotassium oxalate	HMDB
Monopotassium oxalate	HMDB
Oxalate, iron	HMDB
Sodium oxalate	HMDB
Oxalic acid	KEGG

Chemical Formula

C₂H₂O₄

Average Molecular Mass

90.035 g/mol

Monoisotopic Mass

89.995 g/mol

CAS Registry Number

144-62-7

IUPAC Name

oxalic acid

Traditional Name

oxalic acid

SMILES

OC(=O)C(O)=O

InChI Identifier

InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)

InChI Key

MUBZPKHOEPUJKR-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:16995 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Bladder
Epidermis
Eye Lens
Fibroblasts
Intestine
Kidney
Liver
Pancreas
Testes

Pathways

Name	SMPDB Link	KEGG Link
Primary Hyperoxaluria Type I	SMP00352	Not Available
Primary hyperoxaluria II, PH2	SMP00558	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystals

Experimental Properties

Property	Value
Melting Point	189.5°C
Boiling Point	Not Available
Solubility	220 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	65.7 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.26	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.44 m³·mol⁻¹	ChemAxon
Polarizability	6.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-8aef9a64d926571c2de0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-3cee49bf06349fbe625e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9000000000-f5e8094c68372ab25a63	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9510000000-28b0e365a156d2091afd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-cb3d53cc3c40c1cbbba7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0uk9-9000000000-53a009b344e3920ffca1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-2bafb6c472ab1030cd0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9000000000-8aef9a64d926571c2de0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d1ff7c94a720b1eecaf2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-21d33d1d99d80526ee71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ac27102ff43446c313d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fe58eaea122c39178fbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-3850c6a7016e2874d55b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-32ac4118fe0eb9a5abb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-43de084d66dd1bebdeac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-159ed524013577f6f801	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-8e2d2f7a8acc88f00195	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-d7b47276d03e46ce72a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a1e091bb1f5fa6e9cbc7	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-538465f019815d5e1b4a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The affinity of divalent metal ions is sometimes reflected in their tendency to form insoluble precipitates. Thus in the body, oxalic acid also combines with metals ions such as Ca2+, Fe2+, and Mg2+ to deposit crystals of the corresponding oxalates, which irritate the gut and kidneys. (2) Therefore the toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite that can also cause acute kidney failure.

Metabolism

Oxalic acid is not metabolized but excreted in the urine.

Toxicity Values

Not Available

Lethal Dose

Oral LDLo (lowest published lethal dose) of 600 mg/kg. It has been reported that the lethal oral dose is 15 to 30 grams.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (21)

Uses/Sources

Oxalic acid and oxalates are abundantly present in many plants, most notably fat hen (lamb's quarters), sorrel, and Oxalis species. The root and/or leaves of rhubarb and buckwheat are listed being high in oxalic acid.[8] Other edible plants that contain significant concentrations of oxalic acid include—in decreasing order—star fruit (carambola), black pepper, parsley, poppy seed, amaranth, spinach, chard, beets, cocoa, chocolate, most nuts, most berries, and beans. (23)

Minimum Risk Level

Not Available

Health Effects

Because it binds vital nutrients such as calcium, long-term consumption of foods high in oxalic acid can be problematic. Healthy individuals can safely consume such foods in moderation, but those with kidney disorders, gout, rheumatoid arthritis, or certain forms of chronic vulvar pain (vulvodynia) are typically advised to avoid foods high in oxalic acid or oxalates. The calcium oxalate precipitate (better known as kidney stones) obstruct the kidney tubules. Conversely, calcium supplements taken along with foods high in oxalic acid can cause calcium oxalate to precipitate out in the gut and drastically reduce the levels of oxalate absorbed by the body (by 97% in some cases.) Chronically high levels of oxalic acid are associated with at least 2 inborn errors of metabolism including: Type I primary hyperoxaluria and Primary hyperoxaluria. Oxalate stones in primary hyperoxaluria tend to be severe, resulting in relatively early kidney damage (before age 20), which impairs the excretion of oxalate leading to a further acceleration in accumulation of oxalate in the body. After the development of renal failure patients may develop oxalate deposits in the bones, joints and bone marrow. Severe cases may develop haematological problems such as anaemia and thrombocytopaenia. The deposition of oxalate in the body is sometimes called "oxalosis" to be distinguished from "oxaluria" which refers to oxalate in the urine.

Symptoms

Oxalic acid poisoning symptoms include weakness, burning in the mouth, death from cardiovascular collapse, on the respiratory system, throat – burning in the throat, abdominal pain, nausea, vomiting, diarrhea, convulsions, and coma.

Treatment

Acute Exposure: If oxalic acid is swallowed, immediately give the person water or milk, unless instructed otherwise by a health care provider. DO NOT give water or milk if the person is having symptoms (such as vomiting, convulsions, or a decreased level of alertness) that make it hard to swallow. If acute exposure occurs to the eyes, irrigate opened eyes for several minutes under running water. Chronic exposure: in some patients with primary hyperoxaluria type 1, pyridoxine treatment (vitamin B6) may decrease oxalate excretion and prevent kidney stone formation.

Concentrations

Not Available

External Links

DrugBank ID

DB03902

HMDB ID

HMDB0002329

FooDB ID

FDB031074

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB02329

References

Synthesis Reference

Giuseppe Messina, Giovanni M. Sechi, Loreno Lorenzoni, Giovanni Chessa, “Method of preparation of oxalic acid esters and amides.” U.S. Patent US4981963, issued July, 1971.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15587083

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22735334

3. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.

4. 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.

5. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309.

6. 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.

7. 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.

8. 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.

9. 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.