6-Hydroxyflavone

6-Hydroxyflavone
Names


IUPAC name 6-Hydroxyflavone
Systematic IUPAC name 6-Hydroxy-2-phenyl-4H-1-benzopyran-4-one
Other names 6-Monohydroxyflavone; 6-Hydroxy-2-phenyl-4-benzopyrone
Identifiers
CAS Number	6665-83-4^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL138649^Y
ChemSpider	65233^Y
ECHA InfoCard	100.027.005
EC Number	229-704-8
KEGG	C14137^Y
PubChem CID	72279
UNII	148S6Z78H6^Y
CompTox Dashboard (EPA)	DTXSID8022327
InChI InChI=1S/C15H10O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-9,16H^Y Key: GPZYYYGYCRFPBU-UHFFFAOYSA-N^Y
SMILES C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=CC(=C3)O O=C\1c3c(O/C(=C/1)c2ccccc2)ccc(O)c3
Properties
Chemical formula	C₁₅H₁₀O₃
Molar mass	238.242 g·mol⁻¹
Melting point	234 to 236 °C (453 to 457 °F; 507 to 509 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

6-Hydroxyflavone is a flavone, a type of chemical compound. It is one of the noncompetitive inhibitors of cytochrome P450 2C9. It is reported in Crocus and leaves of Barleria prionitis Linn. (a common Acanthaceae from India).^[1] 6-Hydroxyflavone shows anxiolytic activity in a mouse model.^[2] Compared to the full agonist diazepam, 6-hydroxyflavone was approximately 200 times less potent.^[2]

References

^ M Daniel (2006). Medicinal Plants: Chemistry and Properties. Science Publishers. p. 78. ISBN 978-1-57808-395-4.
^ ^a ^b Ren, Lihuan; Wang, Feng; Xu, Zhiwen; Chan, Wing Man; Zhao, Cunyou; Xue, Hong (2010), "GABAA receptor subtype selectivity underlying anxiolytic effect of 6-hydroxyflavone", Biochemical Pharmacology, 79 (9): 1337–1344, doi:10.1016/j.bcp.2009.12.024, PMID 20067772

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide