Skip to main content
SpringerLink
Log in

Synthesis of 5-(hydroxy-, chloro-, bromomethyl)furan-2-enones Based on Fructose and their Antioxidant Activity

  • Published:
Chemistry of Natural Compounds Aims and scope

New enones were synthesized from 5-hydroxymethylfurfurol (5-HMF) and its derivatives using Wittig reactions of various phosphoranes. The synthesized enones were observed to affect free-radical oxidation in model systems, in particular, to suppress generation of reactive oxygen species.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. Besson, P. Gallezot, and C. Pinel, Chem. Rev., 114, 1827 (2014).

    Article  CAS  Google Scholar 

  2. C. Moreau, M. N. Belgacem, and A. Gandini, Top. Catal., 27, 11 (2004).

    Article  CAS  Google Scholar 

  3. V. M. Chernyshev, O. A. Kravchenko, and V. P. Ananikov, Russ. Chem. Rev., 86 (5), 357 (2017).

    Article  CAS  Google Scholar 

  4. J. Lewkowski, ARKIVOC, 2001, 17 (2001).

    Article  Google Scholar 

  5. W. Fan, Ch. Verrier, Y. Queneau, and F. Popowycz, Curr. Org. Synth., 16, 583 (2019).

    Article  CAS  Google Scholar 

  6. H. Van Bekkum, “Studies on Selective Carbohydrate Oxidation,” in: Carbohydrates as Organic Raw Materials, F. W. Lichtenthaler (ed.), VCH, Weinheim, 1991, 289 pp.

    Google Scholar 

  7. L. V. Romashov, Candidate Dissertation, Zelinsky Inst. Org. Chem., RAS, 2017, 52 pp.

    Google Scholar 

  8. H. Zhao, J. E. Holladay, H. Brown, and Z. C. Zhang, Science, 316 (5831), 1597 (2007).

    Article  CAS  Google Scholar 

  9. I. M. Sakhautdinov, R. N. Malikova, G. F. Sakhautdinova, and A. G. Mustafin, Chem. Nat. Compd., 56, 341 (2020).

    Article  CAS  Google Scholar 

  10. T. Chhabra, As. Bahuguna, S. S. Dhankhar, C. M. Nagaraja, and V. Krishnan, Green Chem., 21, 6012 (2019).

    Article  CAS  Google Scholar 

  11. T. M. Kohl, B. Bizet, P. Kevan, C. Sellwood, J. Tsanaktsidis, and C. H. Hornung, React. Chem. Eng., 2, 541 (2017).

    Article  CAS  Google Scholar 

  12. I. V. Petrova, V. A. Kataev, S. A. Meshcheryakova, K. V. Nikolaeva, D. A. Munasipova, and R. R. Farkhutdinov, Med. Vestn. Bashkortostana, 8, 64 (2013).

    Google Scholar 

  13. I. V. Petrova, V. A. Kataev, S. A. Meshcheryakova, K. V. Nikolaeva, D. A. Munasipova, and R. R. Farkhutdinov, Med. Vestn. Bashkortostana, 8, 163 (2013).

    Google Scholar 

Download references

Acknowledgment

The work was performed according to the plan of scientific research at Ufa Institute of Chemistry, UFRC, RAS, on the topic Creation of Materials with Given Functional Properties of Electrical Conductivity, Anticorrosion, and Biological Activity (State Reg. No. AAAA-A19-119020890014-7) and in the framework of a State Task for Scientific Research and Development at BSMU, Ministry of Health of Russia, on the topic Oxidative Stress: Early Diagnosis, Methods of Prevention and Correction (State Reg. No. AAAA-A19-119121000021-4). The spectral part of the research used equipment at the Khimiya CCU, UfIC, RAS.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 69 Prosp. Oktyabrya, Ufa, Republic of Bashkortostan, 450054, Russia

    G. F. Sakhautdinova, R. N. Malikova, I. M. Sakhautdinov & A. G. Mustafin

  2. Bashkir State Medical University, Ministry of Health of Russia, 3 Lenina St., Republic of Bashkortostan, Ufa, 450008, Russia

    Yu. L. Bortsova, K. S. Mochalov, E. M. Muratov & E. F. Galimova

Authors
  1. G. F. Sakhautdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. N. Malikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. L. Bortsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. S. Mochalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. M. Muratov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. F. Galimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. I. M. Sakhautdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. A. G. Mustafin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. N. Malikova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2021, pp. 743–747.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sakhautdinova, G.F., Malikova, R.N., Bortsova, Y.L. et al. Synthesis of 5-(hydroxy-, chloro-, bromomethyl)furan-2-enones Based on Fructose and their Antioxidant Activity. Chem Nat Compd 57, 869–874 (2021). https://doi.org/10.1007/s10600-021-03500-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-021-03500-0

Keywords

Search

Navigation