Skip to main content
Log in

Synthesis and Characterization of 3-Hydroxy-2-(5'-Hydroxypentyl)-4H-Pyran-4-one and Study of Its Complexation with Iron(III)

  • PHYSICAL CHEMISTRY OF SOLUTIONS
  • Published:
Russian Journal of Inorganic Chemistry Aims and scope Submit manuscript

Abstract

With the special focus to obtain a new tridentate ligand able to coordinate Fe(III), 3-hydroxy-2-(5'-hydroxypentyl)-4H-pyran-4-one (5-H) has been synthesized. Iron/ligand solution chemistry has been investigated in aqueous solution by ESI-MS and cyclic voltammetric measurements. The physiologic predominant specie is the tris-chelate complex as Job test attested. The electrode potential of the [FeIII(5)3]/[FeII(5)3] couple was evaluated to be –0.54 V vs. SCE, pH 7.4.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. T. A. Ivanova, O. A. Turanova, I. F. Gil’mutdinov, L. V. Mingalieva, and I. V. Ovchinnikov, et al., Russ. J. Inorg. Chem. 64, 520 (2019). https://doi.org/10.1134/S0036023619040119

    Article  CAS  Google Scholar 

  2. O. R. Simonova, S. V. Zaitseva, D. V. Tyurin, et al., Russ. J. Inorg. Chem. 63, 1164 (2018). https://doi.org/10.1134/S003602361809019X

    Article  CAS  Google Scholar 

  3. E. N. Frolova, T. A. Ivanova, O. A. Turanova, et al., Russ. J. Inorg. Chem. 63, 1012 (2018). https://doi.org/10.1134/S0036023618080077

    Article  CAS  Google Scholar 

  4. A. G. Starikov, A. A. Starikova, M. G. Chegerev, and V. I. Minkin, Russ. J. Coord. Chem. 45, 105 (2019).https://doi.org/10.1134/S1070328419020088

    Article  CAS  Google Scholar 

  5. P. Bourosh, I. Bulhac, O. Covaci, et al., Russ. J. Coord. Chem. 44, 507 (2018).https://doi.org/10.1134/S1070328418080018

    Article  CAS  Google Scholar 

  6. A. Kolnagou, M. Kleanthous, and G. J. Kontoghiorghes, Eur. J. Haematol. 85, 430 (2010). https://doi.org/10.1111/j.1600-0609.2010.01499.x

    Article  CAS  PubMed  Google Scholar 

  7. G. M. Brittenham, New Eng. J. Med. 364, 146 (2011). https://doi.org/10.1056/NEJMct1004810

    Article  CAS  PubMed  Google Scholar 

  8. J. Emerit, C. Beaumont, and F. Trivin, Biomed. Pharm. 55, 333 (2001). https://doi.org/10.1016/S0753-3322(01)00068-3

    Article  CAS  Google Scholar 

  9. B. Halliwell, Amer. J. Med. 91, S14 (1991). https://doi.org/10.1016/0002-9343(91)90279-7

    Article  Google Scholar 

  10. J. Prousek, Pure and Appl. Chem. 79, 2325 (2007). https://doi.org/10.1351/pac200779122325

    Article  CAS  Google Scholar 

  11. S. J. Dixon and B. R. Stockwell, Nat. Chem. Biol. 10, 9 (2013). https://doi.org/10.1038/nchembio.1416

    Article  CAS  Google Scholar 

  12. L. Zecca, M. B. H. Youdim, P. Riederer, et al., Nat. Rev. Neurosc. 5, 863 (2004). https://doi.org/10.1038/nrn1537

    Article  CAS  Google Scholar 

  13. M. Muñoz, J. A. García-Erce, and Á. F. Remacha, J. Clin. Pathol. 64, 287 (2011). https://doi.org/10.1136/jcp.2010.086991

    Article  CAS  PubMed  Google Scholar 

  14. W. H. Koppenol and R. H. Hider, Free Rad. Bio. Med. 133, 3 (2019). https://doi.org/10.1016/j.freeradbiomed.2018.09.022

    Article  CAS  Google Scholar 

  15. H. C. Hatcher, R. N. Singh, F. M. Torti, and S. V. Torti, Fut. Med. Chem. 1, 1643 (2009). https://doi.org/10.4155/fmc.09.121

    Article  CAS  Google Scholar 

  16. T. B. Chaston and D. R. Richardson, Am. J. Hemataol. 73, 200 (2003). https://doi.org/10.1002/ajh.10348

    Article  CAS  Google Scholar 

  17. K. H. Thompson, C. A. Barta, and C. Orvig, Chem. Soc. Rev. 35, 545 (2006). https://doi.org/10.1039/b416256k

    Article  CAS  PubMed  Google Scholar 

  18. V. M. Nurchi, G. Crisponi, J. I. Lachowicz, M. de G. Jaraquemada-Pelaez, C. Bretti, M. Peana, S. Medici, and M. A. Zoroddu, J. Inorg. Biochem. 189, 103 (2018).https://doi.org/10.1016/j.jinorgbio.2010.01.007

    Article  CAS  PubMed  Google Scholar 

  19. V. Ramanathan and R. Levine, J. Org. Chem. 27, 1216 (1962). https://doi.org/10.1021/jo01051a022

    Article  CAS  Google Scholar 

  20. M. Robert Leanna, T. J. Sowin, and H. E. Morton, Tetrahedron Lett. 33, 5029 (1992). https://doi.org/10.1016/S0040-4039(00)61180-2

    Article  Google Scholar 

  21. P. D. Weeks, T. M. Brennan, D. P. Brannegan, D. E. Kuhla, M. L. Elliott, H. A. Watson, B. Wlodecki, and R. Breitenbachet al., J. Org. Chem. 45, 1109 (1980). https://doi.org/10.1021/jo01294a037

    Article  CAS  Google Scholar 

  22. I. A. Antipova, S. A. Mukha, and S. A. Medvedeva, Russ. Chem. Bull. 53, 780 (2004). https://doi.org/10.1023/B:RUCB.0000037841.67079.2b

    Article  CAS  Google Scholar 

  23. Werner. Likussar, and D. F. Boltz, Anal. Chem. 43, 1265 (1971). https://doi.org/10.1021/ac60304a021

  24. M. Merkofer, R. Kissner, R. Hider, and W. Koppenol, Helvet. Chim. Acta 87, 3021 (2004). https://doi.org/10.1002/hlca.200490272

    Article  CAS  Google Scholar 

  25. S. Chaves, S. Canário, M. P. Carrasco, et al., J. Inorg. Biochem. 114, 38 (2012). https://doi.org/10.1016/j.jinorgbio.2012.04.019

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors acknowledge Prof. Marco Ferrali for his stimulating idea.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to M. Corsini or S. Fusi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Corsini, M., Fusi, S. Synthesis and Characterization of 3-Hydroxy-2-(5'-Hydroxypentyl)-4H-Pyran-4-one and Study of Its Complexation with Iron(III). Russ. J. Inorg. Chem. 64, 1836–1840 (2019). https://doi.org/10.1134/S003602361914002X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S003602361914002X

Keywords:

Navigation