Homocitric acid

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Homocitric acid
Homocitric acid.png
IUPAC name
2-Hydroxybutane-1,2,4-tricarboxylic acid
Other names
Homocitric acid
3562-74-1 YesY
ChemSpider 26392 N
Jmol-3D images Image
PubChem 28371
Molar mass 206.15 g·mol−1
Appearance Colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Homocitric acid is an organic compound with the formula HOC(CO2H)(CH2CO2H)(C2H4CO2H). This tricarboxylic acid occurs naturally as a component of the iron-molybdenum cofactor of certain nitrogenase proteins.[1] Biochemists often refer to this cofactor as homocitrate, which is the conjugate bases that predominate in neutral aqueous solutions of this species.

The molecule is related to citric acid by the addition of one methylene unit, hence the prefix "homo." Unlike citric acid, homocitric acid is chiral. The acid exists in equilibrium with the lactone.


See also[edit]


  1. ^ Rees, Douglas C. (2002). "Greatmetalloclustersinenzymology". Annual Review of Biochemistry 71: 221–46. doi:10.1146/annurev.biochem.71.110601.135406. PMID 12045096.