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MedKoo Cat#: 598850 | Name: Epicocconone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Epicocconone is a fluorescent compound from the fungus epicoccumnigrum.

Chemical Structure

Epicocconone
Epicocconone
CAS#371163-96-1

Theoretical Analysis

MedKoo Cat#: 598850

Name: Epicocconone

CAS#: 371163-96-1

Chemical Formula: C23H22O7

Exact Mass: 410.1366

Molecular Weight: 410.42

Elemental Analysis: C, 67.31; H, 5.40; O, 27.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Epicocconone; Deep purple; Lightning fast; LavaPurple; Lightning Fast Protein Gel Stain;
IUPAC/Chemical Name
(6S,9aS)-3-((1Z,4E,6E,8E)-1-hydroxy-3-oxodeca-1,4,6,8-tetraen-1-yl)-6-(hydroxymethyl)-9a-methyl-5,6-dihydro-2H-furo[3,2-g]isochromene-2,9(9aH)-dione
InChi Key
JKMBMIMLVFMXRW-LYYFRFARSA-N
InChi Code
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
SMILES Code
O=C(O1)C(/C(O)=C/C(/C=C/C=C/C=C/C)=O)=C2[C@@]1(C)C(C3=CO[C@H](CO)CC3=C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 410.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Peixoto PA, Boulangé A, Ball M, Naudin B, Alle T, Cosette P, Karuso P, Franck X. Design and synthesis of epicocconone analogues with improved fluorescence properties. J Am Chem Soc. 2014 Oct 29;136(43):15248-56. doi: 10.1021/ja506914p. Epub 2014 Oct 16. PubMed PMID: 25271695. 2: Moritz CP, Marz SX, Reiss R, Schulenborg T, Friauf E. Epicocconone staining: a powerful loading control for Western blots. Proteomics. 2014 Feb;14(2-3):162-8. doi: 10.1002/pmic.201300089. Erratum in: Proteomics. 2014 Jun;14(11):1444. PubMed PMID: 24339236. 3: Randrianjatovo I, Girbal-Neuhauser E, Marcato-Romain CE. Epicocconone, a sensitive and specific fluorescent dye for in situ quantification of extracellular proteins within bacterial biofilms. Appl Microbiol Biotechnol. 2015 Jun;99(11):4835-44. doi: 10.1007/s00253-015-6570-9. Epub 2015 Apr 26. PubMed PMID: 25913004. 4: Syzgantseva OA, Tognetti V, Boulangé A, Peixoto PA, Leleu S, Franck X, Joubert L. Evaluating charge transfer in epicocconone analogues: toward a targeted design of fluorophores. J Phys Chem A. 2014 Jan 30;118(4):757-64. doi: 10.1021/jp410407u. Epub 2014 Jan 21. PubMed PMID: 24446675. 5: Chatterjee S, Karuso P, Boulangé A, Franck X, Datta A. Excited state dynamics of brightly fluorescent second generation epicocconone analogues. J Phys Chem B. 2015 May 21;119(20):6295-303. doi: 10.1021/acs.jpcb.5b02190. Epub 2015 May 6. PubMed PMID: 25902354. 6: Syzgantseva OA, Tognetti V, Joubert L, Boulangé A, Peixoto PA, Leleu S, Franck X. Electronic excitations in epicocconone analogues: TDDFT methodological assessment guided by experiment. J Phys Chem A. 2012 Aug 23;116(33):8634-43. doi: 10.1021/jp305269y. Epub 2012 Aug 10. PubMed PMID: 22882017. 7: Chatterjee S, Burai TN, Karuso P, Datta A. Ultrafast dynamics of epicocconone, a second generation fluorescent protein stain. J Phys Chem A. 2011 Sep 15;115(36):10154-8. doi: 10.1021/jp205634g. Epub 2011 Aug 23. PubMed PMID: 21827198. 8: Choi HY, Veal DA, Karuso P. Epicocconone, a new cell-permeable long Stokes' shift fluorescent stain for live cell imaging and multiplexing. J Fluoresc. 2006 Jul;16(4):475-82. Epub 2005 Dec 3. PubMed PMID: 16328703. 9: Boulangé A, Peixoto PA, Franck X. Diastereoselective IBX oxidative dearomatization of phenols by remote induction: towards the epicocconone core framework. Chemistry. 2011 Sep 5;17(37):10241-5. doi: 10.1002/chem.201101681. Epub 2011 Aug 2. PubMed PMID: 21809405. 10: Bell PJ, Karuso P. Epicocconone, a novel fluorescent compound from the fungus epicoccumnigrum. J Am Chem Soc. 2003 Aug 6;125(31):9304-5. PubMed PMID: 12889954. 11: Nabavi Zadeh PS, Mallak KA, Carlsson N, Åkerman B. A fluorescence spectroscopy assay for real-time monitoring of enzyme immobilization into mesoporous silica particles. Anal Biochem. 2015 May 1;476:51-8. doi: 10.1016/j.ab.2015.02.005. Epub 2015 Feb 11. PubMed PMID: 25681112. 12: Coghlan DR, Mackintosh JA, Karuso P. Mechanism of reversible fluorescent staining of protein with epicocconone. Org Lett. 2005 Jun 9;7(12):2401-4. PubMed PMID: 15932208. 13: Panda D, Khatua S, Datta A. Enhanced fluorescence of epicocconone in surfactant assemblies as a consequence of depth-dependent microviscosity. J Phys Chem B. 2007 Feb 22;111(7):1648-56. Epub 2007 Jan 31. PubMed PMID: 17263570. 14: Tognetti V, Boulangé A, Peixoto PA, Franck X, Joubert L. A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid. J Mol Model. 2014 Aug;20(8):2342. doi: 10.1007/s00894-014-2342-1. Epub 2014 Jul 20. PubMed PMID: 25038631. 15: Chatterjee S, Karuso P, Boulangé A, Peixoto PA, Franck X, Datta A. The role of different structural motifs in the ultrafast dynamics of second generation protein stains. J Phys Chem B. 2013 Dec 5;117(48):14951-9. doi: 10.1021/jp4092927. Epub 2013 Nov 20. PubMed PMID: 24168431. 16: Mackintosh JA, Choi HY, Bae SH, Veal DA, Bell PJ, Ferrari BC, Van Dyk DD, Verrills NM, Paik YK, Karuso P. A fluorescent natural product for ultra sensitive detection of proteins in one-dimensional and two-dimensional gel electrophoresis. Proteomics. 2003 Dec;3(12):2273-88. PubMed PMID: 14673778. 17: Mackintosh JA, Veal DA, Karuso P. Fluoroprofile, a fluorescence-based assay for rapid and sensitive quantitation of proteins in solution. Proteomics. 2005 Dec;5(18):4673-7. PubMed PMID: 16267819. 18: Sundaram RK, Balasubramaniyan N, Sundaram P. Protein stains and applications. Methods Mol Biol. 2012;869:451-64. doi: 10.1007/978-1-61779-821-4_39. PubMed PMID: 22585510. 19: Karuso P, Crawford AS, Veal DA, Scott GB, Choi HY. Real-time fluorescence monitoring of tryptic digestion in proteomics. J Proteome Res. 2008 Jan;7(1):361-6. Epub 2007 Dec 1. PubMed PMID: 18052032. 20: Cleemann F, Karuso P. Fluorescence anisotropy assay for the traceless kinetic analysis of protein digestion. Anal Chem. 2008 Jun 1;80(11):4170-4. doi: 10.1021/ac7025783. Epub 2008 Apr 24. PubMed PMID: 18433148.