U6883
cis-Urocanic acid
≥98% (HPLC), solid (fluffy)
Synonym(s):
cis-3-(1H-imidazol-4-yl)-2-propenoic acid, cis-UCA
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About This Item
Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
cis-Urocanic acid, ≥98% (HPLC), solid (fluffy)
SMILES string
OC(=O)\C=C/c1c[nH]cn1
InChI key
LOIYMIARKYCTBW-UPHRSURJSA-N
InChI
1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
assay
≥98% (HPLC)
form
solid (fluffy)
storage condition
protect from light
color
white
solubility
H2O: >10 mg/mL
storage temp.
−20°C
Quality Level
Related Categories
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-HT2A receptor.
Preparation Note
cis-Urocanic acid is soluble in water at a concentration that is greater than 10 mg/ml.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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S Beissert et al.
Journal of immunology (Baltimore, Md. : 1950), 167(11), 6232-6238 (2001-11-21)
UV radiation induces skin cancer primarily by its DNA-damaging properties, but also by its capacity to suppress the immune system. The photoisomer of urocanic acid (UCA), cis-UCA, is an important mediator of UV-induced immunosuppression and is involved in the inhibition
Jorge Correale et al.
Journal of neuroimmunology, 261(1-2), 134-140 (2013-06-27)
The role of cis-urocanic acid (UCA) as a UV-mediated immunomodulator in MS patients was investigated. Plasma levels of cis-UCA were significantly lower in MS patients compared to controls. Stimulation of MBP- and MOG-specific T cells in the presence of cis-UCA
High-speed line-focus Raman microscopy with spectral decomposition of mouse skin
Ilchenko O, et al.
Vibrational Spectroscopy, 83, 180-190 (2016)
Hanna-Mari Jauhonen et al.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie, 255(12), 2357-2362 (2017-08-26)
Our purpose was to investigate the effect of locally administered cis-urocanic (cis-UCA) in two experimental models of allergic conjunctivitis. The compound 48/80 (C48/80)-induced ocular irritation model (IgE-independent) and the ovalbumin (OA)-induced ocular allergy model (IgE-mediated) were used to test and
Evgeny Berdyshev et al.
The Journal of allergy and clinical immunology, 147(1), 361-367 (2020-07-03)
The nonlesional skin of children with atopic dermatitis (AD) with peanut allergy (PA) is associated with increased transepidermal water loss; low urocanic acid (UCA) and pyrrolidone carboxylic acid (PCA), both of which are filaggrin breakdown products; and a reduced ratio
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