6-Methylapigenin

6-Methylapigenin

Names
IUPAC name 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methylchromen-4-one
Identifiers
CAS Number	5526-57-8
3D model (JSmol)	Interactive image
PubChem CID	9965615
CompTox Dashboard (EPA)	DTXSID70433447
InChI InChI=1S/C16H12O5/c1-8-11(18)6-14-15(16(8)20)12(19)7-13(21-14)9-2-4-10(17)5-3-9/h2-7,17-18,20H,1H3
SMILES CC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
Properties
Chemical formula	C16H12O5
Molar mass	284.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

6-Methylapigenin is a naturally occurring flavonoid and a derivative of apigenin. It has activity at GABA_A receptors as a positive modulator.

Natural occurrence

6-Methylapigenin can be found in multiple plants, such as Valeriana officinalis, Valeriana jatamansi, and Picea neoveitchii.^[1]

Biological activity

6-Methylapigenin binds to the GABA_A receptor on the benzodiazepine binding site. This compound possesses anxiolytic effects. In a mouse model, it is also able to potentiate sleep induced by hesperidin, another flavonoid.^[2][3] However, since it does not have the chemical structure of benzodiazepines, it can therefore be classed as a nonbenzodiazepine.

References