JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 3 (2018): Journal of the Chilean Chemical Society
Original Research Papers

ABSOLUTE CONFIGURATION OF 18-ACETOXY-CIS-CLERODA-3,13E-DIEN-15-OIC ACID

Iván Brito
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Jorge Bórquez
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Diego Robledo
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Mario J. Simirgiotis
Instituto de Farmacia, Facultad de Ciencias, Universidad Austral de Chile
Alejandro Cárdenas
Departamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta
Published September 12, 2018
How to Cite
Brito, I., Bórquez, J., Robledo, D., Simirgiotis, M. J., & Cárdenas, A. (2018). ABSOLUTE CONFIGURATION OF 18-ACETOXY-CIS-CLERODA-3,13E-DIEN-15-OIC ACID. Journal of the Chilean Chemical Society, 63(3). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/769

Abstract

In this paper we report the absolute configuration which has been determined from the refinement of the Flack parameter, x = 0.05(5), which indicate that the correct configuration had been assigned against 1353 (99%) CuKα Bijvoet pairs. On this basis the absolute configuration was assigned as C5R, C8S, C9R and C10S. The structure of 18-acetoxy-cis-cleroda-3,13E-dien-15-oic acid consists of a clerodane skeleton and the corresponding methyl groups are α-oriented (C8, C9) while C5 is β-oriented. The acidic lateral chain is β-oriented and the double bond between C13 and C14 has E isomeric. The ciclohexene, cyclohexane rings are cis fused, and in an sofa and chair conformation respectively. In the crystal the molecules are linked by one intermolecular OH⋅⋅⋅O hydrogen bond forming 1D-dimensional chain with distance donor-acceptor of 2.060(6)Å with graph-set notation C1 1 (15).

References

  1. M. Montes, T. Wilkomirsky. Medicina Tradicional Chilena, Universidad de Concepción, Concepción, p. 193, (1985).
  2. A. Urzua, R. Torres, M. Muñoz, Y. Palacios. Journal of Ethnopharmacology, 45, 71, (1995).
  3. H.Vogel, M. González, F. Faini, I. Razmilic, J. Rodriguez, J.S. Martin and F. Urbina Journal of Ethnopharmacology 97, 97-100, (2005).
  4. F. Faini, R. Torres, J.M. Rodilla, C. Labbe,C. Delporte and F. Jaña. J. Braz. Chem. Soc. 22, 2344, (2011).
  5. G. Schmeda-Hirschmann, C. Quispe and B. González. Molecules. 20, 913, (2015).
  6. G.E. Wickens. Vegetation and ethnobotany of the Atacama Desert and adjacent Andes northern Chile. Opera Bot., 121, 291, (1993).
  7. N. Monterrey. Hierbas Medicinales Andinas 2a Región. Ministerio de Educación, Antofagasta, p. 35, (1996).
  8. A. Urzua, F. Jara, E. Tojo, M. Wilkens, L. Mendoza, M.M. Rezende. Journal of Ethnopharmacology 297, 103, (2006).
  9. G. Morales, P. Sierra, L.A. Loyola, J. Bórquez. Phytochemistry. 55, 863, (2000).
  10. J. Bórquez, A. Mancilla, S. Pedreros, L.A. Loyola, G. Morales, O. Wittke, I. Brito. Bol. Soc. Chil. Quím., 40, 157, (1995).
  11. E. Tojo, M.E. Rial, A. Urzua, L. Mendoza. Phytochemistry, 52, 1531, (1999).
  12. J. Bórquez, A. Ardiles, L.A. Loyola, L.M. Peña-Rodriguez, G.M. Molina- Salinas, J. Vallejos, G. Isidro, I.G. Collado, M.J. Simirgiotis. Molecules, 19, 3898, (2014).
  13. J. Bórquez, C. Echiburú-Chau, P. Winterhalter, J. Vallejos, G. Jerz, M.J. Simirgiotis.. Journal of Science of Food and Agriculture, 96, 2832, (2016).
  14. J. Borquez, E.J. Kennelly and M.J. Simirgiotis. Food Research International 52, 288, (2013).
  15. I. Brito, J. Borquez, M. Simirgiotis, A. Cardenas and M. Lopez-Rodriguez. Acta Crystallographica Section E-Structure Reports Online. E68, o32. (2012).
  16. I. Brito, J. Bórquez, M.J. Simirgiotis, M. Neves-Vieira, G. Jerz, P. Winterhalter, M. Bolte, A. Cárdenas. Zeitschrift für Kristallographie- New Crystal Structures, 229, 399, (2014).
  17. I. Brito, M.J. Simirgiotis, R. Muñoz, J. Benites, L. Pasten, J. Bórquez, A Cárdenas. Zeitschrift für Kristallographie-New Crystal Structures, 232, 13, (2017).
  18. Simirgiotis. Saudi Pharmaceutical Journal 25, 1032, (2017).
  19. H.D. Flack. Acta Cryst. A39, 876, (1983).
  20. G. M. Sheldrick, Acta Cryst. 112, A64, (2008).
  21. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, J. Appl. Cryst., 42, 339, (2009).
  22. D.Cremer, J.A. Pople. J.Am.Chem.Soc. 97, 1354, (1975).
  23. J. Bernstein, R.E. Davis, L. Shimoni, N.-L. Chang. Angew. Chem. Int. Ed. Engl. 34, 1555, (1995).

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