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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:72013 ;
ChEMBL	ChEMBL13311 ;
ChemSpider	9866 ;
ECHA InfoCard	100.007.035
PubChem CID	10286;
UNII	20C556MJ76 ;
CompTox Dashboard (EPA)	DTXSID40197680 ;
	InChI InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H Key: OTAFHZMPRISVEM-UHFFFAOYSA-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).

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.

^ 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

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:72013
ChEMBL	ChEMBL13311
ChemSpider	9866
ECHA InfoCard	100.007.035
PubChem CID	10286
UNII	20C556MJ76
CompTox Dashboard (EPA)	DTXSID40197680
InChI InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H Key: OTAFHZMPRISVEM-UHFFFAOYSA-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 (pK_a)	-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).