859796
4-Imidazoleacrylic acid
99%
Synonym(s):
3-(4-Imidazolyl)acrylic acid, Urocanic acid
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All Photos(5)
About This Item
Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
Beilstein:
81405
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
biological source
synthetic
Assay
99%
form
powder
mp
226-228 °C (lit.)
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
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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,.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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)
Claudia L Kleinman et al.
Nucleic acids research, 45(10), 5757-5769 (2017-03-24)
LuxR-type transcription factors control diverse physiological functions necessary for bacterial adaptation to environmental changes. In the intracellular pathogen Brucella, the LuxR homolog VjbR has been shown to regulate the expression of virulence factors acting at early stages of the intracellular
A theoretical study of the low-lying excited states of trans-and cis-urocanic acid
Page CS, et al.
The Journal of Physical Chemistry A, 103(48), 9864-9871 (1999)
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