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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:
7699-35-6
Molecular Weight:
138.12
UNSPSC Code:
12352106
PubChem Substance ID:
329827646
NACRES:
NA.77
MDL number:
MFCD11045310
Assay:
≥98% (HPLC)
Form:
solid (fluffy)
Storage condition:
protect from light
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Product Name

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

Quality Segment

100

assay

≥98% (HPLC)

form

solid (fluffy)

storage condition

protect from light

color

white

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

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-

InChI key

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

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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