Electrochemical synthesis of coenzymes Q n by oxidation of tetramethoxy precursors

  • Maria Antonietta Sabatino
  • Giuseppe Filardo
  • Alessandro Galia
  • Onofrio Scialdone
Original Paper


The electrochemical oxidation of tetramethoxy precursors (2) to coenzymes Q n (1) at a carbon anode was investigated both in a bench-scale batch electrochemical reactor and in a continuous recirculation reaction system equipped with a parallel-plate electrochemical divided cell. High faradic efficiency (>60%) and excellent selectivity (>90%) in coenzymes Q n were obtained in CH3CN or CH3CN/CH2Cl2 + 0.15 M Bu4NBF4 under potentiostatic or amperostatic alimentation.


Electrosynthesis Coenzymes Qn Anodic oxidation Ubiquinones 



This work was financially supported by the Università di Palermo and by the Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR). Antonina Natoli is gratefully acknowledged for her support.


  1. 1.
    Steckhan E (2002) Electrochemistry. In: Ullmann’s encyclopedia of industrial chemistry, 7th edn. Wiley-VCH, Weinheim, Electronic releaseGoogle Scholar
  2. 2.
    Scialdone O, Belfiore C, Filardo G, Galia A, Sabatino MA, Silvestri G (2005) Electrochim Acta 51:598CrossRefGoogle Scholar
  3. 3.
    Putter H (2001) In: Lund H, Hammerich O (eds) Organic electrochemistry, 4th edn. Marcel Dekker, New York, p 1259Google Scholar
  4. 4.
    Scialdone O, Galia A, Belfiore C, Filardo G, Silvestri G (2004) Ind Eng Chem Res 43:5006CrossRefGoogle Scholar
  5. 5.
    Sabatino MA, Galia A, Filardo G, Scialdone O (2007) Electrochem Commun 9:1355CrossRefGoogle Scholar
  6. 6.
    Filardo G, Galia A, Sabatino MA, Scialdone O (2007) Italian Patent RM2007 A000067Google Scholar
  7. 7.
    Sinatra ST (2001) In: Kanagan VE, Quinn PJ (eds) Coenzyme Q: molecular mechanism in health and disease. CRC Press, Boca Raton, FLGoogle Scholar
  8. 8.
    Shepherd JA, Poon WW, Myles DC, Clarke CF (1996) Tetrahedron Lett 37:2395CrossRefGoogle Scholar
  9. 9.
    Sasaki K, Watanabe M, Suda Y, Ishizuka A, Noparatnaraporn N (2005) J Biosci Bioeng 100:481CrossRefGoogle Scholar
  10. 10.
    Van Liemt WBS, Steggerda WF, Esmeijer R, Lugtenburg J (1994) Recl Trav Chim Pays-Bas 113:153Google Scholar
  11. 11.
    Lipshutz BH, Bulow G, Fernandez-Lazaro F, Kim SK, Lowe RF, Mollard P, Stevens KL (1999) J Am Chem Soc 121:11664CrossRefGoogle Scholar
  12. 12.
    Min JH, Lee JS, Yang JD, Koo S (2003) J Org Chem 68:7925CrossRefGoogle Scholar
  13. 13.
    West D (2003) United States Patent 6506915Google Scholar
  14. 14.
    Lipshutz BH, Mollard P, Pfeiffer SS, Chrisman W (2002) J Am Chem Soc 124:14282CrossRefGoogle Scholar
  15. 15.
    Lipshutz BH, Lower A, Berl B, Schein K, Wetterich F (2005) Org Lett 78:4095CrossRefGoogle Scholar
  16. 16.
    Negishi E, Liou SY, Xu C, Huo S (2002) Org Lett 4:261CrossRefGoogle Scholar
  17. 17.
    Sigma-Aldrich Catalog (2006) Sigma-Aldrich, St. Louis, p 682Google Scholar
  18. 18.
    Wheeler JW, Chung RH (1969) J Org Chem 34:1148Google Scholar
  19. 19.
    Scialdone O, Filardo G, Galia A, Mantione D, Silvestri G (1999) Acta Chem Scand 53:800CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Maria Antonietta Sabatino
    • 1
  • Giuseppe Filardo
    • 1
  • Alessandro Galia
    • 1
  • Onofrio Scialdone
    • 1
  1. 1.Dipartimento di Ingegneria Chimica dei Processi e dei MaterialiUniversità di PalermoPalermoItaly

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