Epicocconone

Epicocconone
Names
	Preferred IUPAC name (6S,9aS)-6-(Hydroxymethyl)-3-[(1Z,4E,6E,8E)-1-hydroxy-3-oxodeca-1,4,6,8-tetraen-1-yl]-9a-methyl-5,6-dihydro-2H-furo[3,2-g][2]benzopyran-2,9(9aH)-dione
	Other names Deep Purple ; Lava Purple ; Lightning Fast
Identifiers
CAS Number	371163-96-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51226;
ChemSpider	8398759;
PubChem CID	56464320;
UNII	6QLH9631R8 ;
	InChI InChI=1S/C23H22O7/c1-3-4-5-6-7-8-15(25)11-19(26)20-18-10-14-9-16(12-24)29-13-17(14)21(27)23(18,2)30-22(20)28/h3-8,10-11,13,16,24,26H,9,12H2,1-2H3/b4-3+,6-5+,8-7+,19-11-/t16-,23-/m0/s1 Key: JKMBMIMLVFMXRW-LYYFRFARSA-N; InChI=1/C23H22O7/c1-3-4-5-6-7-8-15(25)11-19(26)20-18-10-14-9-16(12-24)29-13-17(14)21(27)23(18,2)30-22(20)28/h3-8,10-11,13,16,24,26H,9,12H2,1-2H3/b4-3+,6-5+,8-7+,19-11-/t16-,23-/m0/s1 Key: JKMBMIMLVFMXRW-LYYFRFARBG;
	SMILES C/C=C/C=C/C=C/C(=O)/C=C(/C1=C2C=C3C[C@H](OC=C3C(=O)[C@]2(OC1=O)C)CO)\O;
Properties
Chemical formula	C23H22O7
Molar mass	410.422 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Epicocconone is a long Stokes' shift fluorogenic natural product found in the fungus Epicoccum nigrum. Though weakly fluorescent in water (green emission, 520 nm) it reacts covalently yet reversibly with primary amines such as those in proteins to yield a product with a strong orange-red emission (610 nm). Epicoconone is notable because it the first covalent/reversible/turn-on fluorophore to be discovered and is a natural product with a new fluorescent scaffold. It is also cell membrane permeable, unlike many other fluorophores, and subsequently can be used in in vivo (live cell) applications. Additionally, this dye can be used as a sensitive total protein stain for 1D and 2D electrophoresis, quantitative determination of protein concentration, making it a powerful loading control for Western blots.