Synonym
cis-Urocanic acid; (Z)-Imidazole-4-acrylic acid; cis-UCA;
IUPAC/Chemical Name
(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid
InChi Key
LOIYMIARKYCTBW-UPHRSURJSA-N
InChi Code
1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
SMILES Code
O=C(O)/C=C\C1=CN=CN1
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
138.13
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Korhonen E, Piippo N, Hytti M, Kaarniranta K, Kauppinen A. Cis-urocanic acid improves cell viability and suppresses inflammasome activation in human retinal pigment epithelial cells. Biochem Pharmacol. 2023 Oct;216:115790. doi: 10.1016/j.bcp.2023.115790. Epub 2023 Sep 6. PMID: 37683842.
2: Gruner S, Oesterwitz H, Stoppe H, Henke W, Eckert R, Sönnichsen N. Cis- urocanic acid as a mediator of ultraviolet-light-induced immunosuppression. Semin Hematol. 1992 Apr;29(2):102-7. PMID: 1594941.
3: Yeh CY, Su SH, Tan YF, Tsai TF, Liang PH, Kelel M, Weng HJ, Hsiao YP, Lu CH, Tsai CH, Lee CH, Clausen BE, Liu FT, Lee YL. PD-L1 Enhanced by cis-Urocanic Acid on Langerhans Cells Inhibits Vγ4+ γδT17 Cells in Imiquimod-Induced Skin Inflammation. J Invest Dermatol. 2023 Aug;143(8):1449-1460. doi: 10.1016/j.jid.2023.02.018. Epub 2023 Mar 1. PMID: 36868499.
4: Norval M, El-Ghorr AA. Studies to determine the immunomodulating effects of cis-urocanic acid. Methods. 2002 Sep;28(1):63-70. doi: 10.1016/s1046-2023(02)00210-4. PMID: 12231189.
5: Jauhonen HM, Laihia J, Oksala O, Viiri J, Sironen R, Alajuuma P, Kaarniranta K, Leino L. Topical cis-urocanic acid prevents ocular surface irritation in both IgE -independent and -mediated rat model. Graefes Arch Clin Exp Ophthalmol. 2017 Dec;255(12):2357-2362. doi: 10.1007/s00417-017-3781-z. Epub 2017 Aug 24. PMID: 28840310.
6: Albert E, Walker J, Thiesen A, Churchill T, Madsen K. cis-Urocanic acid attenuates acute dextran sodium sulphate-induced intestinal inflammation. PLoS One. 2010 Oct 27;5(10):e13676. doi: 10.1371/journal.pone.0013676. PMID: 21060867; PMCID: PMC2965142.
