Skip to Content
Merck
All Photos(5)

Documents

859796

Sigma-Aldrich

4-Imidazoleacrylic acid

99%

Synonym(s):

3-(4-Imidazolyl)acrylic acid, Urocanic acid

Sign Into View Organizational & Contract Pricing
All Photos(5)

About This Item

Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
104-98-3
Molecular Weight:
138.12
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

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 Code

11 - Combustible Solids

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)

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of (?)-homohistidine
Pirrung MC and Pei T
The Journal of Organic Chemistry, 65(7), 2229-2230 (2000)
Anne J Keurentjes et al.
Frontiers in public health, 9, 602933-602933 (2021-03-23)
Introduction: Non-melanoma skin cancer (NMSC) incidence is increasing, and occupational solar exposure contributes greatly to the overall lifetime ultraviolet radiation (UVR) dose. This is reflected in an excess risk of NMSC showing up to three-fold increase in outdoor workers. Risk
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service