Naringenin

Naringenin
Names
	IUPAC name (2S)-4′,5,7-Trihydroxyflavan-4-one
	Systematic IUPAC name (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
	Other names Naringetol; Salipurol; Salipurpol
Identifiers
CAS Number	480-41-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50202 ;
ChEMBL	ChEMBL9352 ;
ChemSpider	388383 ;
DrugBank	DB03467 ;
ECHA InfoCard	100.006.865
KEGG	C00509 ;
PubChem CID	439246;
UNII	HN5425SBF2 ;
CompTox Dashboard (EPA)	DTXSID1022392 ;
	InChI InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N ;
	SMILES O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O;
Properties
Chemical formula	C15H12O5
Molar mass	272.256 g·mol−1
Melting point	251 °C (484 °F; 524 K)
Solubility in water	475 mg/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.

The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs.

Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications.