Structure via PubChem · Public domain (PubChem)
naringenin
Sign in to saveAlso 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 Ų
- 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
- Subclass of
- flavanone
- Mass
- 272.068
Show 7 more facts
- found in taxon
- Dioscorea alata
- 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
- subject has role
- estrogen antagonist
- different from
- naringin
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- 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.
Excerpted from Wikipedia’s “naringenin” article, available under the CC BY-SA 4.0 licence.