Firefly luciferin

Firefly luciferin
Names
	IUPAC name (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
	Other names D-(−)-Luciferin, beetle luciferin
Identifiers
CAS Number	2591-17-5;
3D model (JSmol)	Interactive image;
ChemSpider	4588411; 16735812 One of the other tautomeric representations;
ECHA InfoCard	100.018.166
EC Number	219-981-3;
PubChem CID	92934;
UNII	5TBB02N29K;
CompTox Dashboard (EPA)	DTXSID00894865 ;
	InChI InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1 Key: BJGNCJDXODQBOB-SSDOTTSWSA-N; One of the other tautomeric representations: InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,13H,4H2,(H,15,16)/b10-9+/t7-/m1/s1; InChI=1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1;
	SMILES O=C(O)[C@@H]1/N=C(\SC1)c2sc3cc(O)ccc3n2;
Properties
Chemical formula	C11H8N2O3S2
Molar mass	280.32 g·mol−1
UV-vis (λmax)	330 nm (neutral and somewhat acidic aqueous solutions)
Absorbance	ε330 = 18.2 mM−1 cm−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Firefly luciferin (also known as beetle luciferin) is the luciferin, or light-emitting compound, used for the firefly (Lampyridae), railroad worm (Phengodidae), starworm (Rhagophthalmidae), and click-beetle (Pyrophorini) bioluminescent systems. It is the substrate of luciferase (EC 1.13.12.7), which is responsible for the characteristic yellow light emission from many firefly species.

As with all other luciferins, oxygen is required to elicit light; however, it has also been found adenosine triphosphate (ATP) and magnesium are required for light emission.^[2]^[3]

^ ^a ^b "D-luciferin product information" (PDF). Sigma Aldrich.
^ McElroy WD (1947). "The Energy Source for Bioluminescence in an Isolated System". Proc Natl Acad Sci USA. 33 (11): 342–345. Bibcode:1947PNAS...33..342M. doi:10.1073/pnas.33.11.342. PMC 1079070. PMID 16588763.
^ Green A, McElroy WD (1956). "Function of adenosine triphosphate in the activation of luciferin". Arch Biochem Biophys. 64 (2): 257–271. doi:10.1016/0003-9861(56)90268-5. PMID 13363432.

[lamdaRef1-1] "D-luciferin product information" (PDF). Sigma Aldrich.

[2] McElroy WD (1947). "The Energy Source for Bioluminescence in an Isolated System". Proc Natl Acad Sci USA. 33 (11): 342–345. Bibcode:1947PNAS...33..342M. doi:10.1073/pnas.33.11.342. PMC 1079070. PMID 16588763.

[3] Green A, McElroy WD (1956). "Function of adenosine triphosphate in the activation of luciferin". Arch Biochem Biophys. 64 (2): 257–271. doi:10.1016/0003-9861(56)90268-5. PMID 13363432.

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