Xanthone is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

O ₆H₄sub>2CO. It is a white solid. In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for

codling moth The codling moth (''Cydia pomonella'') is a member of the Lepidopteran family Tortricidae. They are major pests to agricultural crops, mainly fruits such as apples and pears. Because the larvae are not able to feed on leaves, they are highly d ...

eggs and as a

larvicide A larvicide (alternatively larvacide) is an insecticide that is specifically targeted against the larval life stage of an insect. Their most common use is against mosquitoes. Larvicides may be contact poisons, stomach poisons, growth regulators, o ...

. Xanthone is also used in the preparation of

xanthydrol Xanthydrol is an organic chemical compound. Its formula is C13 H10 O2. Its total molecular weight is 198.221 g/ mol. Xanthydrol is used to test the levels of urea in the bloodstream. Synthesis Xanthydrol can be produced by the reduction of xan ...

, which is used in the determination of

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

levels in the blood. It can also be used as a

photocatalyst In chemistry, photocatalysis is the acceleration of a photoreaction in the presence of a catalyst. In catalyzed photolysis, light is absorbed by an adsorbed substrate. In photogenerated catalysis, the photocatalytic activity depends on the abil ...

Synthesis

Xanthone can be prepared by the heating of

phenyl salicylate Phenyl salicylate, or salol, is the organic compound with the formula C6H5O2C6H4OH. It is a white solid. It is occasionally used in sunscreens and as an antiseptic. Production and reactions The title compound was synthesized first in 1883 by th ...

Six methods have been reported for synthesizing xanthone derivatives: *The Michael-Kostanecki method uses an equimolar mix of a

polyphenol Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some o ...

and an ''O''-

hydroxybenzoic acid Hydroxybenzoic acid may refer to several related chemical compounds: * 2-Hydroxybenzoic acid (salicylic acid, ''o''-hydroxybenzoic acid) * 3-Hydroxybenzoic acid (''m''-hydroxybenzoic acid) * 4-Hydroxybenzoic acid (''p''-hydroxybenzoic acid) See ...

, which are heated with a dehydrating agent. *The Friedel-Crafts method has a

benzophenone Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylket ...

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 Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...

with an ''O''-

chlorobenzene Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorob ...

and cyclizes the resulting

diphenylether Diphenyl ether is the organic compound with the formula ( C6 H5)2 O. It is a colorless solid. This, the simplest diaryl ether, has a variety of niche applications. Synthesis and reactions Diphenyl ether and many of its properties were first rep ...

Xanthone derivatives

Xanthone forms the core of a variety of natural products, such as

mangostin Mangostin is a natural xanthonoid, a type of organic compound isolated from various parts of the mangosteen tree (''Garcinia mangostana''). It is a yellow crystalline solid with a xanthone core structure. Mangostin and a variety of other xanthono ...

lichexanthone Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in ma ...

. These compounds are sometimes referred to as ''xanthones'' or

xanthonoid A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids. Xanthonoid biosynthesis in cell cultures of '' Hypericum androsaemum'' involves the presence of a benzoph ...

s. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families Bonnetiaceae,

Clusiaceae The Clusiaceae or Guttiferae Juss. (1789) (''nom. alt. et cons.'' = alternative and valid name) are a family (biology), family of plants including 13 genera and ca 750 species. Several former members of Clusiacae are now placed in Calophyllaceae ...

, and

Podostemaceae Podostemaceae (riverweed family), a family in the order Malpighiales, comprise about 50 genera and species of more or less thalloid aquatic herbs. Distribution and habitat They are found mostly in tropical and subtropical areas worldwide. Ma ...

. They are also found in some species of the genus ''Iris''. Some xanthones are found in the

pericarp Fruit anatomy is the plant anatomy of the internal structure of fruit. Fruits are the mature ovary or ovaries of one or more flowers. They are found in three main anatomical categories: aggregate fruits, multiple fruits, and simple fruits. Aggr ...

of the

mangosteen Mangosteen (''Garcinia mangostana''), also known as the purple mangosteen, is a tropical evergreen tree with edible fruit native to tropical lands surrounding the Indian Ocean. Its origin is uncertain due to widespread prehistoric cultivation. ...

fruit (''

Garcinia ''Garcinia'' is a genus of flowering plants in the family Clusiaceae native to Asia, America, Australia, tropical and southern Africa, and Polynesia. The number of species is disputed; Plants of the World Online (POWO) recognise up to 400. Common ...

mangostana'') as well as in the bark and timber of ''

Mesua thwaitesii ''Mesua thwaitesii'', is a plant species in the family Calophyllaceae. It is endemic to Sri Lanka, where Sinhalese people called "Diya Nā - දිය නා". The plant is highly valuable as a medicinal plant within the country. Chemistry Timb ...

''. #Bone fide agents include AH 7614 & TUG-1387.

References

{{Reflist, refs= {{cite book , editor-last1=Khan , editor-first1=M.T.H. , editor-last2=Ather , editor-first2=A. , title=Lead Molecules from Natural Products: Discovery and New Trends , chapter=Xanthones as therapeutic agents: chemistry and pharmacology , last1=Diderot , first1=Noungoue Tchamo , last2=Silvere , first2=Ngouela , last3=Etienne , first3=Tsamo , publisher=Elsevier Science , series=Advances in Phytomedicine , year=2006 , isbn=978-0-08-045933-2 , chapter-url=https://books.google.com/books?id=CvfvjJ9TZs0C&pg=PA285 , pages=284–285 Insecticides

Synthesis

Xanthone derivatives

See also

References