Homocitric acid

Homocitric acid
Names
	Preferred IUPAC name 2-Hydroxybutane-1,2,4-tricarboxylic acid
	Other names Homocitric acid; Homocitrate
Identifiers
CAS Number	3562-74-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17852 ;
ChemSpider	26392 ;
KEGG	C01251 ;
PubChem CID	28371;
UNII	5883XD8HH4 ;
CompTox Dashboard (EPA)	DTXSID10331413 ;
	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;
	SMILES O=C(O)CC(O)(C(=O)O)CCC(=O)O;
Properties
Chemical formula	C7H10O7
Molar mass	206.150 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). verify (what is ?) 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.

References

^ Rees, Douglas C. (2002). "Great Metalloclusters in Enzymology" (PDF). Annual Review of Biochemistry. 71: 221–46. doi:10.1146/annurev.biochem.71.110601.135406. PMID 12045096.

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[1] Rees, Douglas C. (2002). "Great Metalloclusters in Enzymology" (PDF). Annual Review of Biochemistry. 71: 221–46. doi:10.1146/annurev.biochem.71.110601.135406. PMID 12045096.

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Names

Preferred IUPAC name 2-Hydroxybutane-1,2,4-tricarboxylic acid
Other names Homocitric acid Homocitrate
Identifiers
CAS Number	3562-74-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17852^N
ChemSpider	26392^N
KEGG	C01251^N
PubChem CID	28371
UNII	5883XD8HH4^Y
CompTox Dashboard (EPA)	DTXSID10331413
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)^N Key: XKJVEVRQMLKSMO-UHFFFAOYSA-N^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
SMILES O=C(O)CC(O)(C(=O)O)CCC(=O)O
Properties
Chemical formula	C₇H₁₀O₇
Molar mass	206.150 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). N verify (what is ^YN ?) Infobox references

Homocitric acid

See also

References