FComEx: Oxalic acid (PC000696)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:01 UTC

Update date

2017-01-19 02:36:33 UTC

FoodComEx ID

PC000696

FoodDB Record

FDB003357

Chemical Information

Name

Oxalic acid

Description

Present 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 Number

144-62-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2dua	biospider
2hwg	biospider
553-91-3 (DILITHIUM)	biospider
Acido ossalico	biospider
Acidum oxalicum	biospider
Acidum Oxalicum-Injeel Forte Liq (D6-D200)	biospider
Aktisal	biospider
Ammonium oxalate;Ethane-1,2-dioate	biospider
Aquisal	biospider
Clover acid	db_source
Ethandisaeure	ChEBI
Ethane-1,2-dioate	Generator
Ethane-1,2-dioic acid	biospider
Ethanedioate	biospider
Ethanedioic acid	ChEBI
Ethanedioic acid (9CI)	biospider
Ethanedioic acid dihydrate	biospider
Ethanedioic acid, 9CI	db_source
Ethanedionate	biospider
Ethanedionic acid	biospider
H2ox	biospider
Hooccooh	biospider
Kyselina stavelova	HMDB
Magnesium permanganate	biospider
Oxaalzuur	biospider
Oxagel	biospider
Oxalate	Generator
Oxalate standard for ic	biospider
Oxalic acid (8CI)	biospider
Oxalic acid 2-Hydrate	biospider
Oxalic acid anhydrous	biospider
Oxalic acid diammonium salt	biospider
Oxalic acid dihydrate	biospider
Oxalic Acid, Cadmium Salt (1:1)	biospider
Oxalicum 5dh-30ch	biospider
Oxalicum acidum	biospider
Oxalsaeure	ChEBI
OXD	biospider
Oxiric acid	biospider
OXL	biospider
Ultraplast Activate S 52	biospider

Chemical Formula

C2H2O4

IUPAC name

oxalic acid

InChI Identifier

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

InChI Key

MUBZPKHOEPUJKR-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C(O)=O

Average Molecular Weight

90.0349

Monoisotopic Molecular Weight

89.995308552

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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	Not Available
Experimental Water Solubility	220 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 101.5° (dihydrate)	DFC

Foods of Origin