Chromone

Last updated
Chromone
Chromone.svg
Names
IUPAC name
Chromen-4-one
Preferred IUPAC name
4H-1-Benzopyran-4-one
Other names
4-Chromone; 1,4-Benzopyrone; 4H-Chromen-4-one; Benzo-gamma-pyrone; 1-Benzopyran-4-one; 4H-Benzo(b)pyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.035 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H X mark.svgN
    Key: OTAFHZMPRISVEM-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
    Key: OTAFHZMPRISVEM-UHFFFAOYAY
  • O=C1C=COc2ccccc12
Properties
C9H6O2
Molar mass 146.145 g·mol−1
Acidity (pKa)-2.0 (of conjugate acid)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Chromone (or 1,4-benzopyrone) is a derivative of benzopyran with a substituted keto group on the pyran ring. It is an isomer of coumarin.

Contents

Derivatives of chromone are collectively known as chromones. Most, though not all, chromones are also phenylpropanoids.

Examples

See also

Related Research Articles

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Coumarin Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C
9
H
6
O
2
. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone.

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Cromoglicic acid

Cromoglicic acid (INN) — also referred to as cromolyn (USAN), cromoglycate, or cromoglicate — is traditionally described as a mast cell stabilizer, and is commonly marketed as the sodium salt sodium cromoglicate or cromolyn sodium. This drug prevents the release of inflammatory chemicals such as histamine from mast cells.

Benzofuran Heterocyclic compound consisting of fused benzene and furan rings

Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

Ketotifen

Ketotifen, sold under the brand name Zaditor among others, is a second-generation noncompetitive H1-antihistamine and mast cell stabilizer. It is most commonly sold as a salt with fumaric acid, ketotifen fumarate, and is available in two forms. In its ophthalmic form, it is used to treat allergic conjunctivitis. In its oral form, it is used to prevent asthma attacks or anaphylaxis, as well as various mast cell, allergic-type disorders.

Cyclooctatetraene Chemical compound

1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as [8]annulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy.

Umbelliferone Chemical compound

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

Pechmann condensation

The Pechmann condensation is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a β-carbonyl group. The condensation is performed under acidic conditions. The mechanism involves an esterification/transesterification followed by attack of the activated carbonyl ortho to the oxygen to generate the new ring. The final step is a dehydration, as seen following an aldol condensation. It was discovered by the German chemist Hans von Pechmann .

Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered ring containing one oxygen atom and a ketone functional group. There are two isomers denoted as 2-pyrone and 4-pyrone. The 2-pyrone structure is found in nature as part of the coumarin ring system. 4-Pyrone is found in some natural chemical compounds such as chromone, maltol and kojic acid.

Nedocromil

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Conduritol or 1,2,3,4-cyclohexenetetrol is any of the organic compounds with chemical formula C6H10O4, that can be seen as derivatives of cyclohexene with four hydroxyl groups (OH) replacing hydrogen atoms on the four carbon atoms not adjacent to the double bond. They are therefore cyclic polyols or cyclitols.

Benzopyrone may refer to either of two ketone derivatives of benzopyran which constitute the core skeleton of many flavonoid compounds:

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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 meters (2300 ft) above sea level. It is a very elegant tree with a thick trunk and wide crown and can become over 12 m (39 ft) high. It blooms in February and March, depending on latitude and altitude. The fruit is a capsule about 1.5 cm (0.6 in) length.

Bergapten Chemical compound

Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.

Taxifolin Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

Leucodelphinidin Chemical compound

Leucodelphinidin is a colorless chemical compound related to leucoanthocyanidins. It can be found in Acacia auriculiformis, in the bark of Karada and in the kino (gum) from Eucalyptus pilularis.

Azaleatin Chemical compound

Azaleatin is a chemical compound. It is an O-methylated flavonol, a type of flavonoid. It was first isolated from the flowers of Rhododendron mucronatum in 1956 and has since been recorded in forty-four other Rhododendron species, in Plumbago capensis, in Ceratostigma willmottiana and in Carya pecan. It has been also been found in the leaves of Eucryphia.

Eugenitin Chemical compound

Eugenitin is a chromone derivative, a type of phenolic compound found in cloves. It has also been isolated from the fungal species Cylindrocarpon sp. C.M.I. 127996.

Proxicromil Chemical compound

Proxicromil is a detergent-like, lipophilic oral medication developed in the late 1970s that was not admitted on the market because of its possible carcinogenic effects. It suppresses allergic reactions by binding to FcεRI receptor in mast cells, thereby inhibiting production of histamines. It is absorbed through the gastrointestinal tract and is proven hepatotoxic for dogs as a result of its accumulation in the biliary canaliculus.

References

  1. Eucryphin, a new chromone rhamnoside from the bark of Eucryphia cordifolia. R. Tschesche, S. Delhvi, S. Sepulveda and E. Breitmaier, Phytochemistry, Volume 18, Issue 5, 1979, pages 867–869, doi : 10.1016/0031-9422(79)80032-1
  2. 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