For research use only. Not for therapeutic Use.
<em>trans</em>-Urocanic acid is a major epidermal chromophore for the immunosuppressive effects of UV radiation that is produced in mammalian stratum corneum by the action of histidine ammonialyase on L-histidine. It contributes to the acidification of the surface of the stratum corneum, and its function has been proposed as that of an endogenous sunscreen, endowing a low-level of protection (SPF ~ 1.5) against UV-induced DNA damage and excessive keratinocyte apoptosis. Upon UVB exposure, <em>trans</em>-urocanic acid is converted to the <em>cis</em> isomer, which is known to activate regulatory T cells.
| Catalog Number | R065042 |
| CAS Number | 3465-72-3 |
| Synonyms | 3-(1H-imidazol-5-yl)-2E-propenoic acid |
| Molecular Formula | C6H6N2O2 |
| Purity | ≥95% |
| Target | Endogenous Metabolite |
| Storage | -20°C |
| IUPAC Name | (E)-3-(1H-imidazol-5-yl)prop-2-enoic acid |
| InChI | InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+ |
| InChIKey | LOIYMIARKYCTBW-OWOJBTEDSA-N |
| SMILES | C1=C(NC=N1)C=CC(=O)O |
| Reference | 1.Gibbs, N.K., and Norval, M. Urocanic acid in the skin: a mixed blessing? Journal of Investigative Dermatology 131(1), 14-17 (2011). |
