859796

Sigma-Aldrich

4-Imidazoleacrylic acid

99%

Synonym(s):
3-(4-Imidazolyl)acrylic acid, Urocanic acid
Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
Beilstein/REAXYS Number:
81405
EC Number:
MDL number:
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,.

Packaging

5, 25, 100 g in poly bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)
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)
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)
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...

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