Xanthone is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
molecular formula
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, such as paren ...
C
13H
8O
2. It is a white solid.
In 1939, xanthone was introduced as an
insecticide
Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
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, and a codling moth larva is often called an " apple worm". Along with ...
eggs and as a
larvicide. Xanthone is also used in the preparation of
xanthydrol, which is used in the determination of
urea
Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...
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 photocatalyst, the excited state of which "repeatedly interacts with the reaction partners forming reaction intermediates and regenerates itself after each ...
.
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
Polyphenols () are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as ...
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 a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. It is a white solid with a low melting point and ros ...
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
substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule.
The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...
s.
*The Tanase method is used to synthesize polyhydroxyxanthones.
*The
Ullman method condenses a
phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
with an ''O''-
chlorobenzene and
cyclizes the resulting
diphenylether
Diphenyl ether is the organic compound with the formula (carbon, C6hydrogen, H5)2oxygen, O. It is a colorless, low-melting solid. This compound, the simplest diaryl ether, has a variety of niche applications.
Synthesis and reactions
Diphenyl e ...
.
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.
Source
The rind of partially ripe mangos ...
or
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 foliose lichen, leafy lichen in the 1940s. The compound is known ...
. 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
The Clusiaceae or Guttiferae Juss. (1789) (''nom. alt. et cons.'' = alternative and valid name) are a family (biology), fami ...
s. Over 200 natural xanthones have been identified. Many are phytochemicals found in plants in the families
Bonnetiaceae
Bonnetiaceae is a family of flowering plants, consisting of 3 genera and 38 species. The family is Neotropical, with the exception of the genus '' Ploiarium'', which is found in Malesia. It is sister to the family Clusiaceae
The Clusiaceae or ...
,
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 ...
. They are also found in some species of the genus
''Iris''. Some xanthones are found in the
pericarp
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.
Fruitlike structures may develop directly from the seed itself rather th ...
of the
mangosteen
Mangosteen (''Garcinia mangostana''), also known as the purple mangosteen, is a tropical evergreen tree with edible fruit native to Island Southeast Asia, from the Malay Peninsula to Borneo. It has been cultivated extensively in tropical Asia ...
fruit (''
Garcinia
''Garcinia'' is a genus of flowering plants in the family (biology), family Clusiaceae native to the Sundaland bioregion of Asia, America, Australia, tropical and southern Africa, and Polynesia.
The number of species is disputed; Plants of the W ...
mangostana'') as well as in the bark and timber of ''
Mesua thwaitesii''.
See also
*
Tetrahydroxanthones
*
Thioxanthone
*
Xanthene
Xanthene (9''H''-xanthene, 10''H''-9-oxaanthracene) is the organic compound with the formula CH2 6H4sub>2O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are u ...
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