Coelenterazine

June 25, 2018
I create light underwater.
What molecule am I?

Coelenterazine is a luciferin—the most prevalent bioluminescent molecule in sea life. It exists in many marine species, from protozoa to fish. Luciferase enzymes cause coelenterazine to oxidize, which triggers the luminescence.

In the mid-1970s, coelenterazine was discovered independently by two research teams: Milton J. Cormier et al. at the University of Georgia (Athens) and Osamu Shimamura and Frank Johnson at Princeton University (NJ). In both cases, the species investigated were in the phylum cnidaria: Renilla reniformis (sea pansy) and Aequorea victoria (crystal jelly). Shimamura was one of the recipients of the 2008 Nobel Prize in Chemistry.

Luciferins previously presented in Molecule of the Week were lucifer yellow (October 29, 2012) and firefly luciferin (October 26, 2015). Both were featured in anticipation of Halloween.

MOTW update

Capsaicin was the Molecule of the Week for August 18, 2008. It is what makes chili peppers and other spicy foods “hot”. It is also used medicinally for treating pain and itching, but it has unpleasant side effects. Now, chemists at Miguel Hernández University of Elche (Spain) and the University of Eastern Piedmont (Italy) report capsaicin derivatives that do capsaicin’s job, then hydrolyze in the body to prevent subsequent unpleasantness.

Coelenterazine fast facts

CAS Reg. No. 55779-48-1
Molar mass 423.46 g/mol
Empirical formula C26H21N3O3
Appearance Orange-yellow crystals
Melting point 170–181 ºC (dec.)*
Water solubility 68 mg/L (est.)

*Depending on conditions.

Coelenterazine hazard information

GHS classification**: hazardous to the aquatic environment, long-term hazard (category 4)
H413—May cause long-lasting harmful effects to aquatic life

**Globally Harmonized System of Classification and Labeling of Chemicals. 

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