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Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid

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Abstract

The conversion of caryophyllene upon contact with Al2O3 and SiO2 impregnated with sulfuric acid was carried out, and the components of the resulting mixtures were identified. Having in hands such “standard” mixtures greatly facilitates identification of components of sesquiterpene fractions of essential oils and other mixtures of natural origin. The catalytic activity of silica gel impregnated with sulfuric acid (H+-SiO2) in the acid-catalyzed isomerization of caryophyllene is significantly higher than that for H+-Al2O3 and is comparable with the activity of concentrated sulfuric acid.

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References

  1. A. V. Tkachev, Chem. Nat. Compd. (Engl. Transl.), 1987, 23: 393.

    Article  Google Scholar 

  2. I. G. Collado, J. R. Hanson, A. J. Macias-Sanchez, Nat. Prod. Rep., 1998, 15: 187.

    Article  CAS  Google Scholar 

  3. M. G. Sarpietro, A. Di Sotto, M. L. Accolla, F. Castelli, Thermochim. Acta, 2015, 600: 28.

    Article  CAS  Google Scholar 

  4. R. Medeiros, G. F. Passos, C. E. Vitor, J. Koepp, T. L. Mazzuco, L. F. Pianowski, M. M. Campos, J. B. Calixto, Br. J. Pharmacol., 2007, 151: 618.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. L. Langhasova, V. Hanusova, J. Rezek, B. Stohanslova, M. Ambroz, V. Kralova, T. Vanek, J. Dong Lou, Zh. Li Yun, J. Yang, L. Skalova, Ind. Crops Prod., 2014, 59: 20.

    Article  CAS  Google Scholar 

  6. A.-L. Klauke, I. Racz, B. Pradier, A. Markert, A. M. Zimmer, J. Gertsch, A. Zimmer, Eur. Neuropsychopharmacol., 2014, 24: 608.

    Article  CAS  PubMed  Google Scholar 

  7. J. Gertsch, M. Leonti, S. Raduner, I. Racz, J.-Zh. Chen, X.-Q. Xie, K.-H. Altmann, M. Karsak, A. Zimmer, Proc. Natl. Acad. Sci. USA, 2008, 105: 9099.

    Article  PubMed  Google Scholar 

  8. G.-Q. Zheng, P. M. Kenney, L. K. Lam, J. Nat. Prod., 1992, 55: 999.

    Article  CAS  PubMed  Google Scholar 

  9. K. Fidyt, A. Fiedorowicz, L. Strządała, A. Szumny, Cancer Med., 2016, 5: 3007.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. W. A. König, N. Bülow, Y. Saritas, Flavour Fragrance J., 1999, 14: 367.

    Article  Google Scholar 

  11. V. A. Basiuk, Russ. Chem. Rev., 1995, 64: 1003.

    Article  Google Scholar 

  12. A. K. Banerjee, M. S. Laya, W. J. Vera, Russ. Chem. Rev., 2001, 70: 971.

    Article  CAS  Google Scholar 

  13. J. M. Riego, Z. Sedin, J. M. Zaldivar, N. C. Marziano, C. Tortato, Tetrahedron Lett., 1996, 37: 513.

    Article  CAS  Google Scholar 

  14. N. C. Marziano, C. Tortato, L. Ronchin, F. Martini, C. Bianchi, Catal. Lett., 1999, 58: 81.

    Article  CAS  Google Scholar 

  15. N. C. Marziano, C. Tortato, L. Ronchin, C. Bianchi, Catal. Lett., 2000, 64: 15.

    Article  CAS  Google Scholar 

  16. A. V. Tkachev, V. I. Mamatyuk, Zh. V. Dubovenko, J. Org. Chem. USSR, 1990, 26: 1469.

    Google Scholar 

  17. V. P. Gatilova, D. V. Korchagina, I. Yu. Bagryanskaya, Yu. V. Gatilov, Zh. V. Dubovenko, V. A. Barkhash, V. A. Koptyug, J. Org. Chem. USSR, 1985, 21: 5.

    Google Scholar 

  18. V. Lamare, A. Archelas, R. Faure, M. Cesario, C. Pascard, R. Furstoss, Tetrahedron, 1989, 45: 3761.

    Article  CAS  Google Scholar 

  19. L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, M. Noltemeyer, J. Am. Chem. Soc., 1995, 117: 9180.

    Article  CAS  Google Scholar 

  20. K. Tanaka, Y. Matsubara, Nippon Kagaku Kaishi, 1976, 1883.

  21. S. Shankar, R. M. Coates, J. Org. Chem., 1998, 63: 9177.

    Article  CAS  Google Scholar 

  22. A. V. Tkachev, Yu. V. Gatilov, I. K. Korobeinicheva, Zh. V. Dubovenko, V. A. Pentegova, Chem. Nat. Compd., 1983, 19: 154.

    Article  Google Scholar 

  23. T. M. Homenko, D. V. Korchagina, Yu. V. Gatilov, I. Yu. Bagryanskaya, A. V. Tkachev, A. I. Vjalkov, O. B. Kun, V. L. Salenko, Zh. V. Dubovenko, V. A. Barkhash, J. Org. Chem. USSR, 1990, 26: 1839.

    Google Scholar 

  24. V. P. Gatilova, D. V. Korchagina, T. V. Rybalova, Yu. V. Gatilov, Zh. V. Dubovenko, V. A. Barkhash, J. Org. Chem. USSR, 1989, 25: 285.

    Google Scholar 

  25. A. V. Tkachev, Issledovaniye letuchikh veshchestv rasteniy [Investigation of Volatile Substances of Plants], Offset, Novosibirsk, 2008, 969 pp. (in Russian).

  26. H. Iwabuchi, M. Yoshikura, W. Kamisako, Chem. Pharm. Bull., 1988, 36: 2447.

    Article  CAS  PubMed  Google Scholar 

  27. G. A. Nisnevich, V. I. Makalskii, D. V. Korchagina, Yu. V. Gatilov, I. Yu. Bagryanskaya, V. A. Barkhash, Russ. J. Org. Chem., 1994, 30: 165.

    Google Scholar 

  28. I. G. Collado, J. R. Hanson, R. Hernandez-Galan, P. B. Hitchcock, A. J. Macias-Sanchez, J. C. Racero, Tetrahedron, 1998, 54: 1615.

    Article  CAS  Google Scholar 

  29. G. Ramis, P. F. Rossi, G. Busca, V. Lorenzelli, A. L. Ginestra, P. Patrono, Langmuir, 1989, 5: 917.

    Article  CAS  Google Scholar 

  30. L. R. Pizzio, C. V. Caceres, M. N. Blanco, Appl. Catal., A, 1998, 167: 283.

    Article  CAS  Google Scholar 

  31. G. Busca, G. Ramis, V. Lorenzelli, P. F. Rossi, A. L. Ginestra, P. Patrono, Langmuir, 1989, 5: 911.

    Article  CAS  Google Scholar 

  32. C. M. Fougret, W. F. Holderich, Appl. Catal., A, 2001, 207: 295.

    Article  CAS  Google Scholar 

  33. E. P. Romanenko, A. V. Tkachev, Chem. Sustain. Dev., 2007, 571.

  34. W. Parker, R. A. Raphael, J. S. Roberts, J. Chem. Soc. C, 1969, 2634.

  35. K. Yoshihara, Y. Hirose, Bull. Chem. Soc. Jpn., 1975, 48: 2078.

    Article  CAS  Google Scholar 

  36. G. Charlot, Les metodes de la chemie analytique: analyse quantitative minrale, Masson etcie, Paris, 1961, 1024 p.

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Correspondence to A. V. Tkachev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1051–1058, June, 2018.

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Romanenko, E.P., Tkachev, A.V. Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid. Russ Chem Bull 67, 1051–1058 (2018). https://doi.org/10.1007/s11172-018-2179-3

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  • DOI: https://doi.org/10.1007/s11172-018-2179-3

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