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Naringenin
Natural API
Naringenin.jpg
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Naringenin

Naringenin (CAS: 67604-48-2) is a natural dihydroflavonoid and the aglycone form of naringin. As a key bioactive compound in citrus fruits (e.g., grapefruit, oranges), it exhibits broad pharmacological activities, particularly in metabolic disorders, anti-inflammatory effects, and neuroprotection.

Product Name: Naringenin

IUPAC Name: (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

CAS No.​: 67604-48-2

Molecular Formula: C₁₅H₁₂O₅

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    Naringenin

    Basic information

    Product Name: Naringenin

    IUPAC Name: (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

    CAS No.​: 67604-48-2

    Molecular Formula: C₁₅H₁₂O₅

    Physicochemical Properties:

    Parameter

    Value/Description

    ​Appearance​

    Light yellow powder

    ​Melting Point​

    251-253°C

    ​Solubility​

    Poor in water (0.01 mg/mL), soluble in DMSO/ethanol

    ​logP​

    2.1 (moderate lipophilicity)

    ​pKa​

    7.1 (phenolic OH), 9.5 (enolic OH)

    Quality Standard: CP2020,JP,Customer Made

    Specification

    Test Items

    Standard

    Naringenin (CAS: 67604-48-2)

    98% by HPLC

    Loss on drying

    ≤5.0%

    Residue on ignition

    ≤2.0%

    Key Features

    index_10-7

    Natural Sources

    Citrus fruits (highest in grapefruit), tomatoes, and herbs (e.g., Scutellaria baicalensis).
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    Multifunctionalit

    Combines antioxidant, anti-inflammatory, metabolic regulation, and antifibrotic properties.
    index_10-7

    High Bioactivity

    More readily absorbed and target-specific compared to its glycoside form (naringin).

    Pharmacological Mechanisms

    1.Molecular Target Network

    Molecular Target Network

    2.Pharmacokinetics

    Absorption

    Oral bioavailability 15-20% (liposomal formulations increase to 50%).

    Distribution

    Widely distributed in liver, kidney, brain (BBB penetration ~5%).

    Metabolism

    Hepatic glucuronidation (UGT1A1/1A9), hydroxylation (CYP2C9/2C19).

    Excretion

    Primarily biliary (70%), urinary excretion <10%.

    Clinical Applications

    Indication​

    ​Mechanism​

    ​Clinical Stage​

    ​Type 2 Diabetes​

    Improves IR + inhibits glucose absorption

    Phase II Trials

    ​NAFLD​

    Lipid metabolism + antifibrotic effects

    Phase I Trials

    ​Menopausal Syndrome

    Selective ERβ agonism

    Preclinical

    Dosage and Administration

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    Metabolic Disorders

     100-300 mg/day (divided doses).
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    Antioxidant Supplement

    50-100 mg/day.
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    Maximum Tolerated Dose

    ≤500 mg single dose (healthy adults).

    Safety Evaluation

    1. Adverse Effects​

    ​System​

    ​Incidence​

    ​Manifestations​

    Gastrointestinal

    10%

    Mild diarrhea

    Endocrine

    <1%

    Estrogenic effects

    Hypersensitivity

    Rare

    Rash

    2. Drug Interactions​

    CYP3A4 Substrates​ (e.g., simvastatin): AUC may double.

    Anticoagulants​ (warfarin): Prolongs PT/INR (monitoring required).

    Research Progress Green max

    Novel Formulations​
    ​Nanoemulsions: 80% bioavailability (animal data).
    ​Transdermal Patches: For localized anti-inflammatory use (e.g., arthritis).

    New Indications​
    ​COVID-19: Inhibits 3CL protease (IC₅₀=25 μM).
    ​Parkinson’s Disease: Activates Parkin/PINK1 pathway (cell models).

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