Chromone

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
CAS Number	491-38-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:72013  N
ChEMBL	ChEMBL13311  N
ChemSpider	9866  N
ECHA InfoCard	100.007.035
PubChem CID	10286
UNII	20C556MJ76  Y
CompTox Dashboard (EPA)	DTXSID40197680
InChI InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H N Key: OTAFHZMPRISVEM-UHFFFAOYSA-N N InChI=1/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H Key: OTAFHZMPRISVEM-UHFFFAOYAY
SMILES O=C1C=COc2ccccc12
Properties
Chemical formula	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). N  verify  (what is  YN ?) 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

1. 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.
2. 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
3. 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