Xanthone is an organic compound with the molecular formula C13H8O2. It is a white solid.
In 1939, xanthone was introduced as an insecticide and it currently finds uses as Insecticide for codling moth eggs and as a larvicide.[Steiner, L. F. and S. A. Summerland. 1943. Xanthone as an ovicide and larvicide for the codling moth. Journal of Economic Entomology 36, 435-439.] Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood.
Synthesis
Xanthone can be prepared by the heating of phenyl salicylate:
Six methods have been reported for synthesizing xanthone derivatives:
-
The Michael-Kostanecki method uses an equimolar mix of a polyphenol and an O-hydroxybenzoic acid, which are heated with a dehydrating agent.
-
The Friedel-Crafts method has a benzophenone intermediate.
-
The Robinson-Nishikawa method is a variant of the Hoesch reaction synthesis but with low yields.
-
The Asahina-Tanase method synthesizes some xanthones, and xanthones with acid-sensitive .
-
The Tanase method is used to synthesize polyhydroxyxanthones.
-
The Ullmann reaction condenses a phenol with an O-chlorobenzene and cyclic compound the resulting diphenylether.
Xanthone derivatives
Xanthone forms the core of a variety of natural products, such as
mangostin or
lichexanthone. These compounds are sometimes referred to as
xanthones or
. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families
Bonnetiaceae,
Clusiaceae, and
Podostemaceae.
They are also found in some species of the genus
Iris.
Some xanthones are found in the
pericarp of the
mangosteen fruit (
Garcinia mangostana) as well as in the bark and timber of
Mesua thwaitesii.
See also
