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

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Sabita Rana et al.
The American journal of pathology, 178(6), 2783-2791 (2011-06-07)
Exposure to UVB radiation before antigen delivery at an unirradiated site inhibits functional immunological responses. Mice treated dorsally with suberythemal low-dose UVB and immunized with ova in abdominal skin generated ova-specific CD8 T cells with a significantly decreased activation, expansion...
Synthesis of (?)-homohistidine
Pirrung MC and Pei T
The Journal of Organic Chemistry, 65(7), 2229-2230 (2000)
Peter D Godfrey et al.
The Journal of chemical physics, 137(6), 064306-064306 (2012-08-18)
The microwave spectra of the two conformers each, of the 1H and 3H tautomers of 4-vinylimidazole, have been measured in the 48-72 GHz spectral region. The 4-vinylimidazole was generated in situ by the facile decarboxylation of urocanic acid at its...

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