Article · Wikipedia archive · Last revised Aug 1, 2026

Epicocconone

Epicocconone is a long Stokes' shift fluorogenic natural product found in the fungus Epicoccum nigrum. Though weakly fluorescent in water 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 is 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 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.

Last revised
Aug 1, 2026
Read time
≈ 2 min
Length
477 w
Citations
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Source
Wikipedia ↗
Epicocconone
Chemical structure of epicocconone
source ↗
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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • 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
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).

Epicocconone is a long Stokes' shift fluorogenic natural product found in the fungus Epicoccum nigrum.1 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).2 Epicoconone is notable because it is 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.2 Additionally, this dye can be used as a sensitive total protein stain for 1D and 2D electrophoresis,3 quantitative determination of protein concentration,4 making it a powerful loading control for Western blots.5

Synthetic variant

In addition to the natural variant from the fungus, there are several synthetic analogs.6 With respect to protein staining properties there are few differences between natural and synthetic analogs.

Reaction

7

References

References

  1. Bell, P. J. L.; Karuso, P. (2003). "Epicocconone, A Novel Fluorescent Compound from the Fungus Epicoccum nigrum". Journal of the American Chemical Society. 125 (31): 9304–9305. Bibcode:2003JAChS.125.9304B. doi:10.1021/ja035496+. PMID 12889954.
  2. Choi, H. -Y.; Veal, D. A.; Karuso, P. (2005). "Epicocconone, A New Cell-Permeable Long Stokes' Shift Fluorescent Stain for Live Cell Imaging and Multiplexing". Journal of Fluorescence. 16 (4): 475–482. doi:10.1007/s10895-005-0010-7. PMID 16328703.
  3. MacKintosh, J. A.; Choi, H. Y.; Bae, S. H.; Veal, D. A.; Bell, P. J.; Ferrari, B. C.; Van Dyk, D. D.; Verrills, N. M.; Paik, Y. K.; Karuso, P (2003). "A fluorescent natural product for ultra sensitive detection of proteins in one-dimensional and two-dimensional gel electrophoresis". Proteomics. 3 (12): 2273–88. doi:10.1002/pmic.200300578. PMID 14673778.
  4. MacKintosh, J. A.; Veal, D. A.; Karuso, P. (2005). "Fluoroprofile, a fluorescence-based assay for rapid and sensitive quantitation of proteins in solution". Proteomics. 5 (18): 4673–4677. doi:10.1002/pmic.200500095. PMID 16267819.
  5. Moritz, C. P.; Marz, S. X.; Reiss, R; Schulenborg, T; Friauf, E (2014). "Epicocconone staining: A powerful loading control for Western blots". Proteomics. 14 (2–3): 162–8. doi:10.1002/pmic.201300089. PMID 24339236.
  6. Peixoto, P. A.; Boulangé, A; Ball, M; Naudin, B; Alle, T; Cosette, P; Karuso, P; Franck, X (2014). "Design and synthesis of epicocconone analogues with improved fluorescence properties". Journal of the American Chemical Society. 136 (43): 15248–56. Bibcode:2014JAChS.13615248P. doi:10.1021/ja506914p. PMID 25271695.
  7. Coghlan, Daniel R.; Mackintosh, James A.; Karuso, Peter (2005-05-17). "Mechanism of Reversible Fluorescent Staining of Protein with Epicocconone". Organic Letters. 7 (12). American Chemical Society (ACS): 2401–2404. doi:10.1021/ol050665b. ISSN 1523-7060. PMID 15932208.