75886-05-4Relevant academic research and scientific papers
Xanthochymol and Isoxanthochymol, Two Novel Polyisoprenylated Benzophenones from Gracinia xanthochymus
Rao, A. V. Rama,Ventkatswamy, G.,Yemul, S. S.
, p. 627 - 633 (2007/10/02)
Two optically active polyprenylated benzophenone derivates, (+)-xanthochymol and (+)-isoxanthochymol have been isolated from the fruits of Gracinia xanthochymus (fam.: Guttiferae).Both these compounds possess the same molecular formula, C38H50O6, and have many common features.Xanthochymol has a free enolic hydroxyl group which forms a part of the chroman ring in isoxanthochymol.Chemical and spectral evidence clearly indicate that both these compounds are derived from maclurin (2,4,6,3',5'-pentahydroxybenzophenone) in which the acetate derived phloroglucinol ringbecomes the target of attack by five "active isoprene" groups.Although, a partial structure has been suggested, the final structure for (+)-isoxanthochymol (V) has been established by X-ray analysis.Spectral evidence including 13C NMR data leads to structure (VIII) for (+)-xanthochymol which has also been arrived at independently by Blount and Williams . (+)-Xanthochymol has been smoothly converted to (+)-isoxanthochymol by acid-catalysed reactions.Bronianone isolated earlier by Ollis et al., from G. hambroniana has the same basic skeleton as xanthochymol and can be represented as X instead of having a bicyclooctene system.
