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
ChEBI	CHEBI:184639
ChemSpider	8141208
PubChem CID	9965615
CompTox Dashboard (EPA)	DTXSID70433447
InChI Key: ZLGRXDWWYMFIGI-UHFFFAOYSA-N 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

1. PubChem. "6-Methylapigenin". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-04.
2. Fernández, Sebastián P.; Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel (2005-04-11). "Synergistic interaction between hesperidin, a natural flavonoid, and diazepam". European Journal of Pharmacology. 512 (2–3): 189–198. doi:10.1016/j.ejphar.2005.02.039. ISSN   0014-2999. PMID   15840404.
3. Marder, Mariel; Viola, Haydeé; Wasowski, Cristina; Fernández, Sebastián; Medina, Jorge H.; Paladini, Alejandro C. (2003). "6-methylapigenin and hesperidin: new valeriana flavonoids with activity on the CNS". Pharmacology, Biochemistry, and Behavior. 75 (3): 537–545. doi:10.1016/s0091-3057(03)00121-7. ISSN   0091-3057. PMID   12895671. S2CID   37559366.