Homocitric acid

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ImageFile=Homocitric acid.pngImageSize=200px
IUPACName=2-hydroxybutane-1,2,4-tricarboxylic acid
OtherNames= Homocitric acid
Homocitrate
Section1= Chembox Identifiers
CASNo=3562-74-1
PubChem=28371
SMILES=OC(=O)CCC(O)(CC(O)=O)C(O)=O
Section2= Chembox Properties
Formula=C₇H₁₀O₇
MolarMass=206.15 g/mol
Appearance=colorless solid
Density=
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BoilingPt=
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Section3= Chembox Hazards
MainHazards=
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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. [Douglas C. Rees "Great Metalloclusters in Enzymology" Annual Reviews of Biochemistry 2002, volume 71, pp. 221–46. DOI|10.1146/annurev.biochem.71.110601.135406] 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 group, which is implied with the term "homo." Unlike citric acid, homocitric acid is chiral. The acid exists in equilibrium with the lactone.

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