Chromone

Chromone

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 number	491-38-3^Y
PubChem	10286
ChEMBL	CHEMBL13311^N
Jmol-3D images	Image 1
SMILES C1=CC=C2C(=C1)C(=O)C=CO2
Properties
Molecular formula	C₉H₆O₂
Molar mass	146.14 g mol⁻¹
Basicity (pK_b)	-2.0
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

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

Roger Altounyan studied chromones and eventually found disodium cromoglicate.^[2] This drug was found to inhibit antigen challenge as well as stress induced symptoms. Cromoglicate is used as a mast cell stabilizer in allergic rhinitis, asthma and allergic conjunctivitis. Comparatively free of side-effects, unfortunately its short half-life limited its value.
Nedocromil sodium was found to have a somewhat longer half-life.

^ 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

Types of phenylpropanoids

Phenylpropanoids	Hydroxycinnamic acids \| Chromones (Furanochromones) \| Cinnamaldehydes \| Monolignols \| Coumarins \| Flavonoids \| Phenylpropenes \| Stilbenoids \| Lignans \| Lignins \| Suberins