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859796

Sigma-Aldrich

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:
104-98-3
Molecular Weight:
138.12
Beilstein/REAXYS Number:
81405
EC Number:
203-258-4
MDL number:
MFCD00005203
UNSPSC Code:
12352005
PubChem Substance ID:
24888491
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,.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
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)
Lisa Eisenbeiss et al.
The Analyst, 145(20), 6586-6599 (2020-08-14)
Hair analysis has become an integral part in forensic toxicological laboratories for e.g. assessment of drug or alcohol abstinence. However, hair samples can be manipulated by cosmetic treatments, altering drug concentrations which eventually leads to false negative hair test results.
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