AFCDB: Oxalic acid (FDB003357)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:46 UTC

Update date

2020-04-21 18:03:34 UTC

Primary ID

FDB003357

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

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.

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 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 26.68%; H 2.24%; O 71.08%	DFC
Melting Point	Mp 101.5° (dihydrate)	DFC
Boiling Point	Not Available
Experimental Water Solubility	220 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa2 3.85 (25°,H2O)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d18.54 1.65	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-538465f019815d5e1b4a	2014-09-20	View Spectrum
GC-MS	Oxalic acid, 2 TMS, GC-MS Spectrum	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	Oxalic acid, 2 TMS, GC-MS Spectrum	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	Oxalic acid, 2 TMS, GC-MS Spectrum	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-8aef9a64d926571c2de0	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-eaa92cf80964dd7d345a	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-b9206a3a54b5be6f07d9	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-9500000000-e5db327eab9e8a2f149e	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-00sl-3910000000-75af6e42d4cc12d798f4	Spectrum
GC-MS	Oxalic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-3cee49bf06349fbe625e	Spectrum
Predicted GC-MS	Oxalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9000000000-f5e8094c68372ab25a63	Spectrum
Predicted GC-MS	Oxalic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-9510000000-28b0e365a156d2091afd	Spectrum
Predicted GC-MS	Oxalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-cb3d53cc3c40c1cbbba7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0uk9-9000000000-53a009b344e3920ffca1	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-2bafb6c472ab1030cd0f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9000000000-8aef9a64d926571c2de0	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d1ff7c94a720b1eecaf2	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-21d33d1d99d80526ee71	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ac27102ff43446c313d3	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fe58eaea122c39178fbe	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-3850c6a7016e2874d55b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-32ac4118fe0eb9a5abb2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-43de084d66dd1bebdeac	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-159ed524013577f6f801	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-8e2d2f7a8acc88f00195	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-d7b47276d03e46ce72a2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a1e091bb1f5fa6e9cbc7	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB03902

HMDB ID

HMDB02329

CRC / DFC (Dictionary of Food Compounds) ID

CWF22-Y:CWF22-Y

EAFUS ID

Not Available

Dr. Duke ID

OXALATE|12-DICARBONIC-ACID|OXALIC-ACID

BIGG ID

34265

KNApSAcK ID

C00001198

HET ID

OXD

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Oxalic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
central nervous system paralytic	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
fatal			DUKE
hemostatic			DUKE
irritant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
renotoxic	50909	A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.	DUKE
varroacide			DUKE

Enzymes

Name	Gene Name	UniProt ID
Proto-oncogene tyrosine-protein kinase Src	SRC	P12931

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Oxalic acid (FDB003357)

Structure for FDB003357 (Oxalic acid)