U6883

cis-Urocanic acid

≥98% (HPLC), solid (fluffy)

• Synonym(s): cis-3-(1H-imidazol-4-yl)-2-propenoic acid, cis-UCA
• Empirical Formula (Hill Notation): C₆H₆N₂O₂
• CAS Number: 7699-35-6
• Molecular Weight: 138.12
• MDL number: MFCD11045310
• UNSPSC Code: 12352106
• PubChem Substance ID: 329827646
• NACRES: NA.77

Properties

• product name: cis-Urocanic acid, ≥98% (HPLC), solid (fluffy)
• Assay: ≥98% (HPLC)
• form: solid (fluffy)
• storage condition: protect from light
• color: white
• solubility: H₂O: >10 mg/mL
• storage temp.: −20°C
• SMILES string: OC(=O)\C=C/c1c[nH]cn1
• InChI: 1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
• InChI key: LOIYMIARKYCTBW-UPHRSURJSA-N

Description

Application

cis-Urocanic acid (cis-UCA) has been used:

• to study its protective effects on autoimmune encephalomyelitis
• in sample preparation to study the distribution of skin chemical components by line illumination Raman microscopy technique in Line-focus illumination mode
• as a standard to study the levels of cis-UCA and to check its effect on immune response in multiple sclerosis patients

Biochem/physiol Actions

cis-Urocanic acid (cis-UCA) affects the immune cells of the body and is excreted in the urine due to photoisomerization. It inhibits tumor immunity through photocarcinogenesis in mice. cis-Urocanic acid has been studied to prevent UV-radiation-induced DNA damage leading to skin cancer.

cis-Urocanic acid, a 5-HT agonist, is a product of UV isomerization of trans-urocanic acid in skin, which leads to immunosuppression via activation of 5-HT_2A receptor.

Preparation Note

cis-Urocanic acid is soluble in water at a concentration that is greater than 10 mg/ml.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves