Chromone (or 1,4-benzopyrone) is a derivative of
benzopyran
4H-1-Benzopyran is an organic compound with the formula . It is one of two isomers of benzopyran, the other being 2H-1-Benzopyran, 2H-1-benzopyran, which is more prevalent. It can be viewed as the fusion of a benzene ring to a heterocyclic pyra ...
with a substituted
keto group on the
pyran
In chemistry, pyran is a six-membered heterocyclic, non-aromatic ring, consisting of five carbon atoms and one oxygen atom and containing two double bonds. The molecular formula is C5H6O. There are two isomers of pyran that differ by the location ...
ring. It is an isomer of
coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , forming a second six-me ...
.
Derivatives of chromone are collectively known as ''chromones''. Most, though not all, chromones are also
phenylpropanoid
The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...
s.
Examples
*
6,7-dimethoxy-2,3-dihydrochromone has been isolated from ''
Sarcolobus globosus''.
*
Eucryphin, a chromone rhamnoside, can be isolated from the bark of ''
Eucryphia cordifolia
''Eucryphia cordifolia'', the ulmo, is a species of tree in the family Cunoniaceae. It is found in Chile and Argentina. It is threatened by logging and habitat loss. The natural habitat is along the Andes Range from 38 to 43°S, and up to 700 ...
''.
*
Cromolyn
Cromoglicic acid (International Nonproprietary Name, INN)—also referred to as cromolyn (United States Adopted Name, USAN), cromoglycate (former British Approved Name, BAN), or cromoglicate—is traditionally described as a mast cell stabilizer ...
(disodium cromoglicate) was found to inhibit antigen challenge as well as stress induced symptoms.
[HOWELL, J.B. & ALTOUNYAN, R.E. (1967). A double-blind trial of disodium cromoglycate in the treatment of allergic bronchial asthma. Lancet, 2, 539–542]
Abstract
/ref> Cromoglicate is used as a mast cell stabilizer
Mast cell stabilizers are medications used to prevent or treat certain allergic disorders. They block mast cell degranulation, stabilizing the cell and thereby preventing the release of histamine and related mediators. One suspected pharmacody ...
in allergic rhinitis
Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. It is classified as a type I hypersensitivity reaction. Signs a ...
, asthma
Asthma is a common long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wh ...
and allergic conjunctivitis
Allergic conjunctivitis (AC) is Allergic Inflammation, inflammation of the conjunctiva (the membrane covering the white part of the eye) due to allergy. Although allergens differ among patients, the most common cause is hay fever. Symptoms consist ...
.
* Nedocromil
Nedocromil sodium is a medication considered a mast cell stabilizer which acts to prevent wheezing, shortness of breath, and other breathing problems caused by asthma. It is administered by an inhaler under the brand name Tilade, and as an eye dr ...
sodium was found to have a somewhat longer half-life than cromolyn; however, production was discontinued in the US in 2008.
* Xanthone
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 use ...
with a second aromatic ring.
See also
* Coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , forming a second six-me ...
– a structural isomer
* Furanochromones
References
External links
* – "4-chromone"
*
Synthesis at organic-chemistry.org
{{Phenylpropanoid