Absolute Configuration and 1H NMR Characterization of Rosmaridiphenol Diacetate

Marcelo A. Muñoz†, Nury Perez-Hernandez‡, Mariano W. Pertino§, Guillermo Schmeda-Hirschmann§, and Pedro Joseph-Nathan*

^† Instituto de Ciencias Químicas, Facultad de Ciencias, Universidad Austral de Chile, Casilla 567, Valdivia, Chile

^‡ Programa Institucional de Biomedicina Molecular, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, México, D. F., 07320 México

^§ Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile

Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 México

J. Nat. Prod., Article ASAP

DOI: 10.1021/np200951y

Publication Date (Web): March 16, 2012

The correction of patented structure 1 of rosmaridiphenol, an antioxidant isolated from rosemary, Rosmarinus officinalis, was made recently. The correct structure is proposed as 11,12-dihydroxy-8,11,13-icetexatrien-1-one (2a) based on 2D NMR data. In order to further support the structure, this work reports the single-crystal X-ray analysis, the complete ¹H NMR assignment by full spin–spin simulation, and the absolute configuration of the diacetate 2b derived via vibrational circular dicroism measurements in comparison with density functional theory calculated data.

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