Chromone
| 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 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
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.
Derivatives of chromone are collectively known as chromones. Most, though not all, chromones are also phenylpropanoids.
Examples
- 6,7-dimethoxy-2,3-dihydrochromone has been isolated from Sarcolobus globosus.
- Altechromone A can be isolated from fungi such as Alternaria sp.[1]
- Eucryphin, a chromone rhamnoside, can be isolated from the bark of Eucryphia cordifolia.[2]
- Cromolyn (disodium cromoglicate) was found to inhibit antigen challenge as well as stress induced symptoms.[3] Cromoglicate is used as a mast cell stabilizer in allergic rhinitis, asthma and allergic conjunctivitis.
- Nedocromil sodium was found to have a somewhat longer half-life than cromolyn; however, production was discontinued in the US in 2008.
- Xanthone with a second aromatic ring.
See also
- Coumarin – a structural isomer
- Furanochromones
References
- ^ Königs, P.; Rinker, B.; Maus, L.; Nieger, M.; Rheinheimer, J.; Waldvogel, S. R. (2010-12-27). "Structural Revision and Synthesis of Altechromone A". Journal of Natural Products. 73 (12): 2064–2066. doi:10.1021/np1005604. ISSN 0163-3864.
- ^ 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
- ^ 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
External links
- CID 10286 from PubChem – "4-chromone"
- Chromones at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
- Synthesis at organic-chemistry.org