naringenin

Also known as (S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one, (-)-(2S)-naringenin, naringetol, pelargidanon, salipurpol, (2S)-Naringenin, Naringenine

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

Chemical data

Formula: C15H12O5
Molecular weight: 272.25 g/mol
IUPAC name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES: C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
XLogP: 2.4
Polar surface area: 87 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

5,355 papers

Naringenin: A potential flavonoid phytochemical for cancer therapy.Life sciences · 2022
Naringenin Nanoformulations for Neurodegenerative Diseases.Current pharmaceutical biotechnology · 2024
Naringenin: its chemistry and roles in neuroprotection.Nutritional neuroscience · 2024
Naringenin: A flavanone with anti-inflammatory and anti-infective properties.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
Naringenin alleviates nonalcoholic steatohepatitis in middle-aged Apoe(-/-)mice: role of SIRT1.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2021

via PubMed

Wikidata facts

Mass: 272.068

Show 4 more facts

chemical formula: C₁₅H₁₂O₅
Commons category: Naringenin
canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
isomeric SMILES: C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

Sources (5)

via Wikidata · CC0

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Article

5 sections

Contents

Structure
Sources and bioavailability
Biosynthesis and metabolism
Metabolic fate after dietary intake
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.