For research use only, not for therapeutic use.
cis-Urocanic acid (Cat No.:I017482) is an endogenous compound and an isomer of urocanic acid. It is a photoreceptor and is primarily found in the skin, where it plays a role in UV radiation protection and immunomodulation. Upon exposure to UVB radiation, cis-urocanic acid can undergo a photoisomerization reaction to its trans form, leading to the activation of various immune responses and inflammation. It has been implicated in the regulation of immune tolerance, skin pigmentation, and the development of certain skin disorders. Understanding the role of cis-urocanic acid in skin physiology and its interactions with UV radiation can provide insights into skin health and potential therapeutic interventions.
| Catalog Number | I017482 |
| CAS Number | 7699-35-6 |
| Molecular Formula | C₆H₆N₂O₂ |
| Purity | ≥95% |
| IUPAC Name | (Z)-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-UPHRSURJSA-N |
| SMILES | C1=C(NC=N1)/C=C\C(=O)O |
| Reference | [1]. Walterscheid JP, et al. Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor. Proc Natl Acad Sci U S A. 2006 Nov 14;103(46):17420-5.<br>[2]. Viiri J, et al. Cis-urocanic acid suppresses UV-B-induced interleukin-6 and -8 secretion and cytotoxicity in human corneal and conjunctival epithelial cells in vitro. Mol Vis. 2009 Sep 8;15:1799-805. |
