Log in

Synthesis of the betulin dipropionate from the upper birch bark

  • Low-Molecular-Weight Compounds
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

A one-step synthesis of the betulin dipropionate directly from the birch bark without a separate stage of the betulin preparation is described in this paper. Extracts with different content of the betulin dipropionate were shown to form depending on the conditions of acylation of the upper birch bark with propionic acid. The product with the maximum content of the betulin dipropionate was prepared from the starting fraction of 2–5 mm of the upper birch bark and the fraction of 10–20 mm that was preliminarily activated with superheated water vapor. The upper bark extract was analyzed by gas chromatography. The structure of betulin dipropionate was confirmed by element analysis, 1H NMR, 13C NMR, and FTIR spectroscopy.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Vasilenko, Yu.K., Semenchenko, V.F., and Frolova, L.M., Eksp. Klin. Farmakol., 1993, vol. 56, no. 4, pp. 53–55.

    PubMed  CAS  Google Scholar 

  2. Tolstikov, A.G., Flekhter, O.B., Shul’ts, E.E., and Baltina, L.A., Khim. Interesah Ustoich. Razvit., 2005, no. 13, pp. 1–30.

  3. Flekhter, O.B., Boreko, E.I., and Nigmatulina, L.R., Khim.-Farm. Zh., 2004, vol. 38, no. 3, pp. 31–34.

    Google Scholar 

  4. Matsuda, H., Ishikado, A., and Nishida, N., Bioorg. Med. Chem. Letts., 1998, vol. 8, pp. 2939–2944.

    Article  CAS  Google Scholar 

  5. Flekhter, O.B., Boreko, E.I., and Nigmatulina, L.R., Khim.-Farm. Zh., 2004, vol. 38, no. 7, pp. 10–14.

    Google Scholar 

  6. Symon, A.V., Veselova, N.N., and Kaplun, A.P., Russ. J. Bioorg. Chem., 2005, vol. 31, no. 3, pp. 320–325.

    Article  CAS  Google Scholar 

  7. Hajduch, M. and Sarek, J., US Patent No. 7041701, 2006.

  8. Maurya, S.K., Devi, S., Pandey, V.B., and Khosa, R.I., Fitoterapia, 1989, vol. 60, no. 5, pp. 468–469.

    CAS  Google Scholar 

  9. Fulda, S., Scaffidi, C., and Susin, S.A., J. Biol. Chem., 1998, vol. 8, no. 51, pp. 33942–33948.

    Article  Google Scholar 

  10. Nemilov, V.E., Nachinkin, O.I., and Tsarev, G.I., in Fiziko-khimiya polimerov: Sb. Nauch. Tr. (Physical Chemistry of Polymers: Collected Scientific Papers), Tver, 1996, issue 2, pp. 124–127.

  11. Shelevich, I.S., Rybina, A.V., Galkin, F.Z., and Talipov, R.F., in Khimiya i tekhnologiya rastitel’nykh veshchestv: mater. Vseros. konf. (Chemistry and Technology of Plant Substances: Proc. All-Russia Conf.), Syktyvkar, 2006, p. 453.

  12. Barton, D. and Ollis, U.D., Obshchaya organicheskaya khimiya (General Organic Chemistry), Moscow, 1983, vol. 4.

  13. Kislitsyn, A.N. and Trofimov, A.N., RF Patent No. 2150473, 2000.

  14. Kobubshi, K. and Kensetsu, H., JP Patent No. 2001288222, 2001.

  15. Kuznetsova, S.A., Kuznetsov, B.N., Red’kina, E.S., Sokolenko, V.A., and Skvortsova, G.P., RF Patent No. 2324700, 2008.

  16. Kuznetsova, S.A., Skurydina, E.S., Kuznetsov, B.N., and Skvortsova, G.P., RF Patent No. 2415148, 2011.

  17. Kuznetsova, S.A., Vasil’eva, N.Yu., Kalacheva, G.S., Titova, N.M., Red’kina, E.S., and Skvortsova, G.P., Zh. Sib. Feder. Univ., Khimiya, 2008, vol. 1, no. 2, pp. 151–165.

    Google Scholar 

  18. Kuznetsova, S.A., Kuznetsov, B.N., Skvortsova, G.P., Skurydina, E.S., and Kalacheva, G.S., Zh. Sib. Feder. Univ., Khimiya, 2010, vol. 3, no. 2, pp. 174–182.

    Google Scholar 

  19. Kuznetsova, S.A., Kuznetsov, B.N., Skvortsova, G.P., Vasil’eva, N.Yu., Skurydina, E.S., and Kalacheva, G.S., Khim. Interesah Ustoich. Razvit., 2010, vol. 18, no. 3, pp. 313–320.

    CAS  Google Scholar 

  20. Kuznetsov, B.N., Kuznetsova, S.A., Levdanskii, V.A., Sudakova, I.G., and Veselova, O.F., Khim. Interesah Ustoich. Razvit., 2005, vol. 13, no. 3, pp. 391–400.

    CAS  Google Scholar 

  21. Kuznetsova, S.A., Titova, N.M., Kalacheva, G.S., and Zaibel’, I.A., Vestn. Krasnoyarsk. Gos. Univ., Estestv. Nauki, 2005, no. 2, pp. 113–118.

  22. Kuznetsova, S.A., Kuznetsov, B.N., Veselova, O.F., Kukina, T.P., Kalacheva, G.S., Skvortsova, G.P., and Red’kina, E.S., Khim. Rastit. Syr’ya, 2008, no. 1, pp. 45–49.

  23. Kuznetsova, S.A., Skvortsova, G.P., Kalacheva, G.S., Zaibel’, I.A., and Khanchich, O.A., Khim. Rastit. Syr’ya, 2010, no. 1, pp. 137–141.

  24. Kravitis, Ya.A., Khim. Drev., 1987, no. 7, pp. 3–21.

  25. Kuznetsova, S.A., Aleksandrova, N.B., and Kuznetsova, B.N., Khim. Interesah Ustoich. Razvit., 2001, vol. 9, no. 5, pp. 655–665.

    CAS  Google Scholar 

  26. Komarov, V.L., Prakticheskii kurs anatomii rastenii (A Practical Course in Plant Anatomy), Moscow, 1941.

  27. Kuznetsov, B.N., Levdanskii, V.A., Es’kina, A.P., and Polezhaeva, N.I., Khim. Rastit. Syr’ya, 1998, no. 1, pp. 5–9.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. A. Kuznetsova.

Additional information

Original Russian Text © S.A. Kuznetsova, G.P. Skvortsova, Yu.N. Malyar, V.A. Sokolenko, B.N. Kuznetsov, 2011, published in Khimija Rastitel’nogo Syr’ja, 2011, No. 4, pp. 77–82.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kuznetsova, S.A., Skvortsova, G.P., Malyar, Y.N. et al. Synthesis of the betulin dipropionate from the upper birch bark. Russ J Bioorg Chem 38, 743–748 (2012). https://doi.org/10.1134/S1068162012070126

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162012070126

Keywords

Navigation