Coelenteramide

Coelenteramide
Names
IUPAC name
N-[2-benzyl-6-(4-oxocyclohexa-2,5-dien-1-ylidene)-1H-pyrazin-3-yl]-2-(4-hydroxyphenyl)acetamide
Other names
Coelenteramide
Identifiers
50611-86-4 N
ChemSpider [1].html 4484099[2] N
Jmol interactive 3D Image
PubChem 5326781
Properties
C25H21N3O3
Molar mass 411.45254
Density 1.26 g/cm3
Boiling point 678.298 °C (1,252.936 °F; 951.448 K) at 760 mmHg
Hazards
Flash point 364.022 °C (687.240 °F; 637.172 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Coelenteramide is the oxidized product, or oxyluciferin, of the bioluminescent reactions in many marine organisms that use coelenterazine. It was first isolated as a blue fluorescent protein from Aequorea victoria after the animals were stimulated to emit light.[3] Under basic conditions, the compound will break down further into coelenteramine and 4-hydroxyphenylacetic acid.

It is an aminopyrazine.[4]

References

  1. http://www.chemspider.com/Chemical-Structure.4484099.html (accessed 22:19, Jun 6, 2012)
  2. http://www.chemspider.com/Chemical-Structure.4484099.html (accessed 22:19, Jun 6, 2012)
  3. Shimomura O, Johnson FH (1975). "Chemical Nature of Bioluminescence Systems in Coelenterates". PNAS USA 72 (4): 1546–1549. doi:10.1073/pnas.72.4.1546. PMC 432574. PMID 236561.
  4. Discovery and Validation of a New Family of Antioxidants: The Aminopyrazine Derivatives. M. L. N. Dubuisson, J.-F. Rees and J. Marchand-Brynaert, Mini-Reviews in Medicinal Chemistry, 2004, 4, 159-165, doi:10.2174/1389557043403927


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