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4-Imidazoleacrylic acid (CAS 104-98-3)

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Alternate Names:
3-(4-Imidazolyl)acrylic acid; Urocanic acid
CAS Number:
104-98-3
Purity:
≥98%
Molecular Weight:
138.12
Molecular Formula:
C6H6N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Imidazoleacrylic acid is a chemical compound utilized in various research applications that focus on biochemical and enzymatic studies. It is particularly relevant in the study of the metabolism of histidine, as 4-Imidazoleacrylic acid is an intermediate in the catabolic pathway of this amino acid. Researchers investigate its role in enzymatic reactions where it may serve as a substrate or inhibitor, providing insights into enzyme mechanisms and specificity. The compound is also relevant in the field of microbiology where it is used to examine the metabolic pathways of bacteria that can degrade imidazole-containing compounds. Additionally, 4-Imidazoleacrylic acid is employed in the synthesis of more complex molecules, serving as a building block in organic synthesis and chemical biology studies, due to its reactive functional groups and stable imidazole ring. This compound aids in understanding the chemical ecology of natural systems where imidazole derivatives might play a role.


4-Imidazoleacrylic acid (CAS 104-98-3) References

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  2. RNA cleavage by a DNA enzyme with extended chemical functionality.  |  Santoro, SW., et al. 2000. J Am Chem Soc. 122: 2433-9. PMID: 11543272
  3. A TD-DFT study of the photochemistry of urocanic acid in biologically relevant ionic, rotameric, and protomeric forms.  |  Danielsson, J., et al. 2001. J Am Chem Soc. 123: 9817-21. PMID: 11583543
  4. Nitrogen K-edge XANES - an overview of reference compounds used to identify unknown organic nitrogen in environmental samples.  |  Leinweber, P., et al. 2007. J Synchrotron Radiat. 14: 500-11. PMID: 17960033
  5. Urocanic acid analogues and the suppression of the delayed type hypersensitivity response to Herpes simplex virus.  |  Norval, M., et al. 1989. Photochem Photobiol. 49: 633-9. PMID: 2547218
  6. High throughput screening of photocatalytic conversion of pharmaceutical contaminants in water.  |  Romão, J., et al. 2017. Environ Pollut. 220: 1199-1207. PMID: 27839992
  7. pH-controllable cell-penetrating polypeptide that exhibits cancer targeting.  |  Lee, D., et al. 2017. Acta Biomater. 57: 187-196. PMID: 28528116
  8. Volatile and bioactive compounds in opercula from Muricidae molluscs supports their use in ceremonial incense and traditional medicines.  |  Nongmaithem, BD., et al. 2017. Sci Rep. 7: 17404. PMID: 29234065
  9. Development of an analytical method for urocanic acid isomers in fish based on reactive extraction cleanup and chaotropic chromatography techniques.  |  Zhong, JJ., et al. 2018. J Chromatogr A. 1548: 44-50. PMID: 29567364
  10. Bioinspired Metal-Organic Framework Catalysts for Selective Methane Oxidation to Methanol.  |  Baek, J., et al. 2018. J Am Chem Soc. 140: 18208-18216. PMID: 30525562
  11. Recent Advances in the Design and Sensing Applications of Hemin/Coordination Polymer-Based Nanocomposites.  |  Alsharabasy, AM., et al. 2021. Adv Mater. 33: e2003883. PMID: 33217074
  12. Role of Microbial Metabolites of Histidine in the Development of Colitis.  |  Wu, J., et al. 2022. Mol Nutr Food Res. 66: e2101175. PMID: 35585003
  13. Development and evaluation of a HILIC-MS method for the determination of amino acid and non-amino acid impurities in histidine.  |  Xu, Q. and Tadjimukhamedov, FK. 2022. J Pharm Biomed Anal. 219: 114936. PMID: 35853262
  14. Convenient synthesis of alkyl esters of urocanic acid.  |  Honda, K. and Nishijima, Y. 1981. J Pharm Sci. 70: 98-9. PMID: 7229940
  15. Investigating the red shift between in vitro and in vivo urocanic acid photoisomerization action spectra.  |  Jones, CD., et al. 1996. Photochem Photobiol. 63: 302-5. PMID: 8881334

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Imidazoleacrylic acid, 5 g

sc-214246
5 g
$65.00

4-Imidazoleacrylic acid, 25 g

sc-214246A
25 g
$280.00

4-Imidazoleacrylic acid, 100 g

sc-214246B
100 g
$880.00