Naringenin

Not to be confused with naringin.
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.865 Edit this at Wikidata
KEGG
UNII
  • 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 ☒N
    Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N ☒N
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
Properties
C15H12O5
Molar mass 272.256 g·mol−1
Melting point 251 °C (484 °F; 524 K)[1]
475 mg/L[citation needed]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

  1. ^ Naringenin at the Human Metabolome Database
  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.