Skip to main content
SpringerLink
Log in

Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C2=C3 and C6=C7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C2=C3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.

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. Grayson, D.H., Nat. Prod. Rep., 1998, vol. 15, no. 5, p. 439.

    Article  CAS  Google Scholar 

  2. Wagner, K.-H. and Elmadfa, I., Ann. Nutr. Metab., 2003, vol. 47, nos. 3–4, p. 95.

    Article  CAS  Google Scholar 

  3. Crowell, P.L., J. Nutr., 1999, vol. 129, p. 775.

    Google Scholar 

  4. Mills, J.J., Chari, R.S., Boyer, I.J., Gould, M.N., and Jirtle, R.L., Cancer Res., 1995, vol. 55, p. 979.

    CAS  Google Scholar 

  5. Carnesecchi, S., Schneider, Y., Ceraline, J., Duranton, B., Gosse, F., Seller, N., and Raul, F., J. Pharm. Exp. Ther., 2001, vol. 298, p. 197.

    CAS  Google Scholar 

  6. Elgendy, E.M., Boll. Chim. Farm., 1997, vol. 136, p. 532.

    CAS  Google Scholar 

  7. Elgendy, E.M., Chim. Pharm J., 1998, vol. 50, p. 225.

    CAS  Google Scholar 

  8. Méou, A., Garcia, M.-A., and Brun, P., J. Mol. Catal. A: Chem., 1999, vol. 138, nos. 2–3, p. 221.

    Article  Google Scholar 

  9. Elgendy, E.M., Boll. Chim. Farm., 2004, vol. 143, p. 337.

    CAS  Google Scholar 

  10. Geraghty, N.W.A., Photochemistry, Dunkin, I., Ed., London: Royal Soc. Chem., 2005, vol. 35, p. 116.

    Chapter  Google Scholar 

  11. Richter, S., Gatto, B., Fabris, D., Takao, K.-i., Kobayashi, S., and Palumbo, S.M., Nucleic Acids Res., 2003, vol. 31, no. 17, p. 5149.

    Article  CAS  Google Scholar 

  12. Yarovaya, O.I., Korchagina, D.V., Salomatina, O.V., Polovinka, M.P., and Barkhash, V.A., Mendeleev Commun., 2003, p. 27.

  13. Yarovaya, O.I., Korchagina, D.V., Gatilov, Yu.V., and Barkhash, V.A., Russ. J. Org. Chem., 2002, vol. 38, no. 6, p. 810.

    Article  CAS  Google Scholar 

  14. Asthana, A., Larson, R. A., Marley, K.A., and Tuveson. R.W., Photochem. Photobiol., 1992, vol. 56, no. 2, p. 211.

    Article  CAS  Google Scholar 

  15. Tisserand, R.B. and Balacs, T., Essential oil Safety: A Guide for Health Care Professionals, Edinburgh: Churchill Livingstone, 1995, p. 147.

    Google Scholar 

  16. Schaneberg, B.T. and Khan, I.A., J. Agric. Food Chem., 2002, vol. 50, no. 6, p. 1345.

    Article  CAS  Google Scholar 

  17. Reis-Vasco, E.M.C., Coelho, J.A.P., and Palavra, A.M.F., Flavor Fragrance J., 1999, vol. 14, no. 3, p. 156.

    Article  CAS  Google Scholar 

  18. Barnes, J., Anderson, L.A., and Phillipson, J.D., Herbal Medicines, London: Pharmaceutical, 2002, 2nd ed., p. 207.

    Google Scholar 

  19. French, L.G., Chem. Educator, 2002, vol. 1, no. 5, p. 270.

    Article  Google Scholar 

  20. Khojasteh-Bakht, S.C., Chen, W., Koenigs, L.L., Peter, R.M., and Nelson, S.D., Drug Metab. Dispos., 1999, vol. 27, no. 5, p. 574.

    CAS  Google Scholar 

  21. Ngo, K.-S., Cheung, K.-K., and Brown, G.D., J. Chem. Res., Synop., 1998, p. 80.

  22. Epe, B., Häring, M., Ramaiah, D., Stopper, H., Abou-Elzahab, M.M., Adam, W., and Saha-Möller, C.R., Carcinogenesis, 1993, vol. 14, no. 11, p. 2271.

    Article  CAS  Google Scholar 

  23. Elgendy, E.M., Chim. Pharm. J., 2000, vol. 52, p. 227.

    CAS  Google Scholar 

  24. Kochevar, I.E. and Dumn, D.A., Photochemistry and the Nucleic Acids, Morrison, H., Ed., (Bioorganic Photochemistry, vol. 1), New York: Wiley, 1990, p. 273.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Specific Education, Mansoura University, Mansoura, Egypt

    E. M. Elgendy

  2. Faculty of Educational’s Girls, Ministry of Education, Jeddah, Saudi Arabia

    S. A. Khayyat

Authors
  1. E. M. Elgendy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Khayyat
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. M. Elgendy.

Additional information

Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 825–833.

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Elgendy, E.M., Khayyat, S.A. Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene. Russ J Org Chem 44, 814–822 (2008). https://doi.org/10.1134/S1070428008060067

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008060067

Keywords

Search

Navigation