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U6883

Sigma-Aldrich

cis-Urocanic acid

≥98% (HPLC), solid (fluffy)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C6H6N2O2
Numéro CAS:
7699-35-6
Poids moléculaire :
138.12
Numéro MDL:
MFCD11045310
Code UNSPSC :
12352106
ID de substance PubChem :
329827646
Nomenclature NACRES :
NA.77

product name

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

Pureté

≥98% (HPLC)

Forme

solid (fluffy)

Conditions de stockage

protect from light

Couleur

white

Solubilité

H2O: >10 mg/mL

Température de stockage

−20°C

Chaîne 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-

Clé InChI

LOIYMIARKYCTBW-UPHRSURJSA-N

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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
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
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