Homocitric acid

Homocitric acid
IUPAC name 2-Hydroxybutane-1,2,4-tricarboxylic acid
Other names Homocitric acid Homocitrate
Identifiers
CAS number	3562-74-1
PubChem	28371
ChemSpider	26392
Jmol-3D images	Image 1
SMILES O=C(O)CC(O)(C(=O)O)CCC(=O)O
InChI InChI=1S/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13) Key: XKJVEVRQMLKSMO-UHFFFAOYSA-N InChI=1/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13) Key: XKJVEVRQMLKSMO-UHFFFAOYAL
Properties
Molecular formula	C7H10O7
Molar mass	206.15 g mol−1
Appearance	Colorless solid
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. 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

• Homoisocitric acid