Glyoxylic acid

Glyoxylic acid
Names
	Preferred IUPAC name Oxoacetic acid
	Systematic IUPAC name Oxoethanoic acid
	Other names Glyoxylic acid; 2-Oxoacetic acid; Formylformic acid
Identifiers
CAS Number	298-12-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	741891
ChEBI	CHEBI:16891 ;
ChEMBL	ChEMBL1162545 ;
ChemSpider	740 ;
DrugBank	DB04343 ;
ECHA InfoCard	100.005.508
EC Number	206-058-5;
Gmelin Reference	25752
KEGG	C00048 ;
PubChem CID	760;
UNII	JQ39C92HH6 ;
CompTox Dashboard (EPA)	DTXSID5021594 ;
	InChI InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Key: HHLFWLYXYJOTON-UHFFFAOYSA-N ; InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Key: HHLFWLYXYJOTON-UHFFFAOYAU;
	SMILES C(=O)C(=O)O;
Properties
Chemical formula	C2H2O3
Molar mass	74.035 g·mol−1
Density	1.384 g/mL
Melting point	80 °C (176 °F; 353 K)
Boiling point	111 °C (232 °F; 384 K)
Acidity (pKa)	3.18, 3.32
Related compounds
Other anions	glyoxylate
Related carboxylic acids	formic acid; acetic acid; glycolic acid; oxalic acid; propionic acid; pyruvic acid
Related compounds	acetaldehyde; glyoxal; glycolaldehyde
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C₂ carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

^ ^a ^b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.
^ pKa Data Compiled by R. Williams, "Archived copy" (PDF). Archived from the original (PDF) on 2010-06-02. Retrieved 2010-06-02.{{cite web}}: CS1 maint: archived copy as title (link).
^ Merck Index, 11th Edition, 4394

Names


Preferred IUPAC name Oxoacetic acid^[1]
Systematic IUPAC name Oxoethanoic acid
Other names Glyoxylic acid^[1] 2-Oxoacetic acid Formylformic acid
Identifiers
CAS Number	298-12-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	741891
ChEBI	CHEBI:16891^Y
ChEMBL	ChEMBL1162545^Y
ChemSpider	740^Y
DrugBank	DB04343^Y
ECHA InfoCard	100.005.508
EC Number	206-058-5
Gmelin Reference	25752
KEGG	C00048^Y
PubChem CID	760
UNII	JQ39C92HH6^Y
CompTox Dashboard (EPA)	DTXSID5021594
InChI InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)^Y Key: HHLFWLYXYJOTON-UHFFFAOYSA-N^Y InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Key: HHLFWLYXYJOTON-UHFFFAOYAU
SMILES C(=O)C(=O)O
Properties
Chemical formula	C₂H₂O₃
Molar mass	74.035 g·mol⁻¹
Density	1.384 g/mL
Melting point	80 °C (176 °F; 353 K)^[4]
Boiling point	111 °C (232 °F; 384 K)
Acidity (pK_a)	3.18,^[2] 3.32 ^[3]
Related compounds
Other anions	glyoxylate
Related carboxylic acids	formic acid acetic acid glycolic acid oxalic acid propionic acid pyruvic acid
Related compounds	acetaldehyde glyoxal glycolaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references