JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 3 (2016): Journal of the Chilean Chemical Society
Original Research Papers

CRYSTAL STRUCTURE OF 3,4-DIHYDROXY-5-GERANYL-BENZOIC ACID

Iván Brito
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Mario J. Simirgiotis
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Maria Avendaño
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Alejandra Bravo
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Jorge Borquez
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Alejandro Cárdenas
Departamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta
Published September 10, 2016
Keywords
  • New phenolic structure,
  • Benzoic acid derivative,
  • Flavonoids,
  • Chilean plants,
  • Heliotropium,
  • NMR,
  • X-ray diffraction
  • ...More
    Less
How to Cite
Brito, I., Simirgiotis, M. J., Avendaño, M., Bravo, A., Borquez, J., & Cárdenas, A. (2016). CRYSTAL STRUCTURE OF 3,4-DIHYDROXY-5-GERANYL-BENZOIC ACID. Journal of the Chilean Chemical Society, 61(3). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/94

Abstract

The crystal structure of the aromatic compound 3,4-dihydroxy-5-geranyl-benzoic acid (5) is reported for the first time. This compound was isolated from the resinous exudate of Manto Negro (Heliotropium taltalense I. M. Johnst), an endemic species growing in The Atacama Desert using a combination of High speed counter current chromatography (HSCCC) and permeation through Sephadex LH-20. The structure was elucidated by spectroscopic means and confirmed by X-ray crystal-structure analysis. All OH groups are involved in hydrogen bonding with the average H⋅⋅⋅O distance of 2.760(3) Å and O-H⋅⋅⋅O angles in the range 125-159°, so in the crystal packing the molecules are associated by three strong intermolecular hydrogen bonds forming ring with graph-set motif R2²(14) R2²(6). 

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