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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 ovicide for codling moth eggs and as a larvicide. Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood. It can also be used as a photocatalyst.
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 synthesis but with low yields.
The Asahina-Tanase method synthesizes some methoxylated xanthones, and xanthones with acid-sensitive substituents.
The Tanase method is used to synthesize polyhydroxyxanthones.
The Ullman method condenses a phenol with an O-chlorobenzene and cyclizes 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 xanthonoids. 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
Tetrahydroxanthones
Thioxanthone
Xanthene
References
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Xanthone - Wikipedia
Xanthone is an organic compound with the molecular formula C 13 H 8 O 2.It is a white solid. In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. [2] Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood. [3] It can also be used as a photocatalyst.
Xanthones, A Promising Anti-Inflammatory Scaffold: Structure, …
Xanthone derivatives have good compliance with the drug-likeness chemical properties. Many new drugs were developed from natural products and natural plants. Experimental data combined with bioinformatics predictive tools could be an efficient and economical way to discover new health products and new anti-inflammatory drugs. Despite some ...
Xanthone | C13H8O2 | CID 7020 - PubChem
Xanthone is the parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9. It has a role as an insecticide. ChEBI. Xanthone has been reported in Rhachidosorus mesosorus, Harungana madagascariensis, and other …
Xanthone Biosynthetic Pathway in Plants: A Review - PMC
Xanthone is a phenolic compound with a planar dibenzo-γ-pyron scaffold. It contains conjugated aromatic ring system that is composed of two rings; carbons 1–4 (ring A) and carbons 5–8 (ring B) and attached together through an oxygen atom and a carbonyl group (ring C) to form the basic skeleton of xanthone known as 9H-xanthen-9-one.
Xanthones: Biosynthesis and Trafficking in Plants, Fungi and …
Xanthone is an aromatic oxygenated heterocyclic molecule, with a dibenzo-γ-pirone scaffold, known as 9H-xanthen-9-one, with the molecular formula of C 13 H 8 O 2 . The number and class of rings A and B derive from the biosynthetic pathways in higher plants leading to the acetate-derived A-ring (carbons 1–4) and the shikimic acid pathway ...
Xanthone - an overview | ScienceDirect Topics
The xanthone skeleton (the word “xanthon” is derived from the Greek word xanthos, meaning yellow) is a planar, conjugated ring system composed of carbon 14 (aromatic ring A) and carbon 58 (aromatic ring B), combined through a carbonyl group and an oxygen atom (Fig. 3.9.3).The simplest member of the class, 9H-xanthen-9-one, is a symmetrical compound with a dibenzo-γ …
Xanthone - an overview | ScienceDirect Topics
The xanthone skeleton (the word “xanthon” is derived from the Greek word xanthos, meaning yellow) is a planar, conjugated ring system composed of carbons 1–4 (aromatic ring A) and carbons 5–8 (aromatic ring B), fused through a carbonyl group and an oxygen atom (Figure 11.1).
Naturally Occurring Xanthones and Their Biological Implications
06 Sep 2024 · Xanthones are chemical substances in higher plants, marine organisms, and lower microorganisms. The most prevalent naturally occurring sources of xanthones are those belonging to the families Caryophyllaceae, Guttiferae, and Gentianaceae. Structurally, xanthones (9H xanthan-9-one) are heterocyclic compounds with oxygen and a γ-pyrone component. …
Xanthones: Biosynthesis and Trafficking in Plants, Fungi and …
04 Feb 2023 · Xanthone is an aromatic oxygenated heterocyclic molecule, with a dibenzo-γ-pirone scaffold, known as 9H-xanthen-9-one, with the molecular formula of C 13 H 8 O 2 ().The number and class of rings A and B derive from the biosynthetic pathways in higher plants leading to the acetate-derived A-ring (carbons 1–4) and the shikimic acid pathway-derived B-ring …
Xanthones | Encyclopedia MDPI
23 Feb 2021 · Xanthone: A Privileged Scaffold . According the concept of Evans et al. the xanthone nucleus could be considered as a “privileged structure”, taking into account its binding to multiple, unrelated classes of protein receptors as high affinity ligands. Following, several authors associated the “xanthone” to the “privileged structure ...