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cis-Urocanic acid

SIGMA/U6883 - ≥98% (HPLC), solid (fluffy)

Synonym: cis-3-(1H-imidazol-4-yl)-2-propenoic acid; cis-UCA

CAS Number: 7699-35-6
Empirical Formula (Hill Notation): C6H6N2O2
Molecular Weight: 138.12
MDL Number: MFCD11045310
Linear Formula: C6H6N2O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-U6883-10MG 10 mg
 $284.00
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45-U6883-50MG 50 mg
 $1140.00
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assay ≥98% (HPLC)
color white
form solid (fluffy)
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
Quality Level 100 
SMILES string OC(=O)C=C/c1c[nH]cn1
solubility H2O: >10 mg/mL
storage condition protect from light
storage temp. −20°C
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.
Biochem/physiol Actions: 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-HT2A receptor.
Packaging: 10, 50 mg in glass bottle
Preparation Note: cis-Urocanic acid is soluble in water at a concentration that is greater than 10 mg/ml.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 12352106

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