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.^[2] It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.^[2]

The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024.^[2] High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.^[2] Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs.^[2]

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.^[2]^[3]^[4]^[5]

^ Naringenin at the Human Metabolome Database
^ ^a ^b ^c ^d ^e ^f "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024.
^ Lohezic-Le Devehat, F.; Marigny, K.; Doucet, M.; Javaudin, L. (2002). "[Grapefruit juice and drugs: a hazardous combination?]". Therapie. 57 (5): 432–445. ISSN 0040-5957. PMID 12611197.
^ Singh, B. N. (September 1999). "Effects of food on clinical pharmacokinetics". Clinical Pharmacokinetics. 37 (3): 213–255. doi:10.2165/00003088-199937030-00003. ISSN 0312-5963. PMID 10511919.
^ Fuhr, U. (April 1998). "Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance". Drug Safety. 18 (4): 251–272. doi:10.2165/00002018-199818040-00002. ISSN 0114-5916. PMID 9565737.

[1] Naringenin at the Human Metabolome Database

[lpi-2] ^ ^a ^b ^c ^d ^e ^f "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024.

[3] Lohezic-Le Devehat, F.; Marigny, K.; Doucet, M.; Javaudin, L. (2002). "[Grapefruit juice and drugs: a hazardous combination?]". Therapie. 57 (5): 432–445. ISSN 0040-5957. PMID 12611197.

[4] Singh, B. N. (September 1999). "Effects of food on clinical pharmacokinetics". Clinical Pharmacokinetics. 37 (3): 213–255. doi:10.2165/00003088-199937030-00003. ISSN 0312-5963. PMID 10511919.

[5] Fuhr, U. (April 1998). "Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance". Drug Safety. 18 (4): 251–272. doi:10.2165/00002018-199818040-00002. ISSN 0114-5916. PMID 9565737.

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