A major epidermal chromophore
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Product Categories

Product Type

Biochemicals

Research Area

Immunology & Inflammation
Adaptive Immunity

trans-Urocanic Acid

Item No. 16228

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(1H-imidazol-5-yl)-2E-propenoic acid
CAS Number
3465-72-3
Molecular Formula
C6H6N2O2
Formula Weight
138.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 15 mg/mlPBS (pH 7.2): 0.3 mg/ml
λmax
286 nm
SMILES
OC(/C=C/C1=CN=CN1)=O
InChi Code
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-OWOJBTEDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $41

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    5 g

    $148

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    Product Description

    trans-Urocanic acid is a major epidermal chromophore for the immunosuppressive effects of UV radiation that is produced in mammalian stratum corneum by the action of histidine ammonialyase on L-histidine.1 It contributes to the acidification of the surface of the stratum corneum, and its function has been proposed as that of an endogenous sunscreen, endowing a low-level of protection (SPF ~ 1.5) against UV-induced DNA damage and excessive keratinocyte apoptosis.1 Upon UVB exposure, trans-urocanic acid is converted to the cis isomer, which is known to activate regulatory T cells.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gibbs, N.K., and Norval, M. Urocanic acid in the skin: A mixed blessing? J. Invest. Dermatol. 131(1), 14-17 (2011).

    2. Schwartz, T. Mechanisms of UV-induced immunosuppression. Keio J. Med. 54(4), 165-171 (2005).