Urocanic acid


Urocanic acid is an intermediate in the catabolism of L-histidine.

Metabolism

It is formed from L-histidine through the action of histidine ammonialyase by elimination of ammonium.
In the liver, urocanic acid is transformed by urocanate hydratase to 4-imidazolone-5-propionic acid and subsequently to glutamic acid.

Clinical significance

Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as urocanic aciduria.
An important role for the onset of atopic dermatitis and asthma has been attributed to Filaggrin, a skin precursor of urocanic acid.

Function

Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against UVB-induced DNA damage. Urocanic acid is found predominantly in the stratum corneum of the skin and it is likely that most of it is derived from filaggrin catabolism. When exposed to UVB irradiation, trans-urocanic acid is converted in vitro and in vivo to the cis isomer. The cis form is known to activate regulatory T cells.
Some studies attribute filaggrin an important role in keeping the skin surface slightly acidic, through a breaking down mechanism to form histidine and subsequently trans-urocanic acid, however others have shown that the filaggrin–histidine–urocanic acid cascade is not essential for skin acidification.

History

Urocanic acid was first isolated in 1874 by the chemist Max Jaffé from the urine of a dog, hence the name.