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U6883

Sigma-Aldrich

cis-Urocanic acid

≥98% (HPLC), solid (fluffy)

Sinónimos:

cis-3-(1H-imidazol-4-yl)-2-propenoic acid, cis-UCA

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About This Item

Fórmula empírica (notación de Hill):
C6H6N2O2
Número de CAS:
7699-35-6
Peso molecular:
138.12
Número MDL:
MFCD11045310
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
329827646
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nombre del producto

cis-Urocanic acid, ≥98% (HPLC), solid (fluffy)

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

solid (fluffy)

condiciones de almacenamiento

protect from light

color

white

solubilidad

H2O: >10 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

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-

Clave InChI

LOIYMIARKYCTBW-UPHRSURJSA-N

Aplicación

cis-Urocanic acid (cis-UCA) has been used:
  • to study its protective effects on autoimmune encephalomyelitis[1]
  • in sample preparation to study the distribution of skin chemical components by line illumination Raman microscopy technique in Line-focus illumination mode[2]
  • as a standard to study the levels of cis-UCA and to check its effect on immune response in multiple sclerosis patients[3]

Acciones bioquímicas o fisiológicas

cis-Urocanic acid (cis-UCA) affects the immune cells of the body and is excreted in the urine due to photoisomerization.[3] 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.[4]
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.

Nota de preparación

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000395429
0000284529
0000284529
0000284534
0000395429

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1-Vinylimidazole ≥99%

Sigma-Aldrich

235466

1-Vinylimidazole

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
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
High-speed line-focus Raman microscopy with spectral decomposition of mouse skin
Ilchenko O, et al.
Vibrational Spectroscopy, 83, 180-190 (2016)
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
Amy A Irving et al.
BMC neuroscience, 18(1), 8-8 (2017-01-07)
Ultraviolet B irradiation confers strong resistance against experimental autoimmune encephalomyelitis, a model of multiple sclerosis. This protection by ultraviolet B is independent of vitamin D production but causes isomerization of urocanic acid, a naturally occurring immunosuppressant. To determine whether UCA
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