XANTHONE (dibenzo-y-pyrone, or diphenylene ketone oxide), C H 0 in organic chemistry, a heterocyclic compound containing the ring system shown below.
Meyer, Ber., 1900, 33, p. 2580), and this latter compound condenses with hydroxylamine to form xanthone oxime.
8 6 CO 3 5 O // 3 Xanthone.
a-pyrone condenses with the benzene ring to form coumarin and isocoumarin; benzo-'y-pyrone constitutes the nucleus of several vegetable colouring matters (chrysin, fisetin, quercetin, &c., which are derivatives of flavone or phenyl benzo-y-pyrone); dibenzo--ypyrone is known as xanthone; related to this substance are fluorane (and fluorescein), fluorone, fluorime, pyronine, &c. The pyridine ring condenses with the benzene ring to form quinoline and isoquinoline; acridine and phenanthridine are dibenzo-pyridines; naphthalene gives rise to a-and /3-naphthoquinolines and the anthrapyridines; anthracene gives anthraquinoline; while two pyridine nuclei connected by an intermediate benzene nucleus give the phenanthrolines.
Baeyer has suggested that the nine carbon atom system of xanthone may act as a chromophore.
An alternative view, due to Green, is that the oxygen atom of the xanthone ring is tetravalent, a supposition which permits the formulation of these substances as ortho-quinonoids.
When heated in air for many hours it decomposes, yielding carbon dioxide, phenol and xanthone.
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