Chromone

Chromone

Names
IUPAC name Chromen-4-one
Other names 4-Chromone; 1,4-Benzopyrone; 4H-Chromen-4-one; Benzo-gamma-pyrone; 4H-1-Benzopyran-4-one; 1-Benzopyran-4-one; 4H-Benzo(b)pyran-4-one
Identifiers
CAS Registry Number	491-38-3 Y
ChEBI	CHEBI:72013 N
ChEMBL	ChEMBL13311 N
ChemSpider	9866 N
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
Jmol-3D images	Image
PubChem	10286
SMILES C1=CC=C2C(=C1)C(=O)C=CO2
Properties
Molecular formula	C9H6O2
Molar mass	146.14 g·mol−1
Acidity (pKa)	-2.0 (of conjugate acid)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.

• Eucryphin, a chromone rhamnoside, can be isolated from the bark of Eucryphia cordifolia.^[1]

• Cromolyn (disodium cromoglicate) was found to inhibit antigen challenge as well as stress induced symptoms.^[2] 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.

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

See also

• Furanochromones
• Coumarin - a structural isomer

External links

• PubChem 10286 - "4-chromone"
• Chromones at the US National Library of Medicine Medical Subject Headings (MeSH)
• Synthesis at organic-chemistry.org