859796
4-Imidazoleacrylic acid
99%
Synonym(s):
3-(4-Imidazolyl)acrylic acid, Urocanic acid
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About This Item
Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
203-258-4
Beilstein/REAXYS Number:
81405
MDL number:
Assay:
99%
Form:
powder
biological source
synthetic
assay
99%
form
powder
mp
226-228 °C (lit.)
functional group
carboxylic acid
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-OWOJBTEDSA-N
General description
4-Imidazoleacrylic acid also known as urocanic acid is a natural metabolite derived from histidine. It is majorly used as a UV chromophore with a strong absorption spectrum in the UV-B region in the range of 300-280 nm.
Application
4-Imidazoleacrylic acid can be used as a precursor for the synthesis of (±)-homohistidine, urocanic acid-modified chitosan, and N1-aryl(heteroaryl)alkyl-N2-[3-(1H-imidazol-4-yl)propyl]guanidines,.
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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Acylguanidines as bioisosteres of guanidines: N G-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists
Ghorai P, et al.
Journal of Medicinal Chemistry, 51(22), 7193-7204 (2008)
Efficient gene delivery by urocanic acid-modified chitosan
Kim TH, et al.
Journal of Controlled Release : Official Journal of the Controlled Release Society, 93(3), 389-402 (2003)
Harm C Arentsen et al.
The Journal of urology, 187(4), 1445-1449 (2012-02-22)
We determined the effect of protodynamic therapy against bladder cancer cells in vitro and in vivo. We investigated cis-urocanic acid in rat bladder cancer cell cultures and in an orthotopic rat urothelial carcinoma model to assess its safety and antiproliferative