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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

product name

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

Análisis

≥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
  • 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

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. 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.

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
Karolina Bossak-Ahmad et al.
International journal of molecular sciences, 21(17) (2020-09-02)
The tripeptide NH2-Gly-His-Lys-COOH (GHK), cis-urocanic acid (cis-UCA) and Cu(II) ions are physiological constituents of the human body and they co-occur (e.g., in the skin and the plasma). While GHK is known as Cu(II)-binding molecule, we found that urocanic acid also
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