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Licochalcone A
Natural API
Licochalcone A.jpg
licorice.jpg

Licochalcone A

Licochalcone A (CAS: 58749-22-7) is a chalcone compound isolated from the roots of Glycyrrhiza glabra (Leguminosae family). As a unique bioactive constituent of licorice, its α,β-unsaturated ketone structure confers remarkable antibacterial, anti-inflammatory, and antitumor activities. Recognized by the EU as a cosmetic functional ingredient (INCI: Licochalcone A) and documented in China's Encyclopedia of Traditional Chinese Medicine for medicinal value.

Product Name: Licochalcone A

IUPAC Name: (E)-1-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

CAS No.​: 58749-22-7

Molecular Formula: C₂₁H₂₂O₄

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    Licochalcone A

    Basic information

    Product Name: Licochalcone A

    IUPAC Name: (E)-1-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

    CAS No.​: 58749-22-7

    Molecular Formula: C₂₁H₂₂O₄

    Physicochemical Properties:

    Parameter

    Value/Description

    ​Appearance​

    Yellow powder

    ​Melting Point​

    168-171°C

    ​Solubility​

    Water solubility 0.03 mg/mL, soluble in ethanol/DMSO

    ​logP​

    3.8 (high lipophilicity)

    ​UV Characteristics​

    λmax=370 nm (ε=18,200)

    Quality Standard: CP2020,JP,Customer Made

    Specification

    Test Items

    Standard

    Licochalcone A (CAS: 58749-22-7)

    98% by HPLC

    Loss on drying

    ≤5.0%

    Residue on ignition

    ≤2.0%

    Key Features

    index_10-7

    Structural Specificity

    C2 isopentenyl modification enhances membrane penetration
    index_10-7

    Multi-Target Action

    Simultaneously modulates NF-κB, MAPK, and Nrf2 pathways.
    index_10-7

    Versatility

    From acne treatment to anti-aging skincare applications.

    Pharmacological Mechanisms

    1. Molecular Target Network

    Microbial targeting

    Disrupt bacterial membrane potential (ΔΨ↓80%)

    Inhibit β-ketoacyl-ACP synthase (FabF)

    Inflammation regulation

    Block IKKβ phosphorylation

    Down-regulate TNF-α/IL-1β

    Oxidative stress

    Activate Nrf2/ARE pathway

    2. Pharmacokinetics

    AAbsorption

    Oral bioavailability 8-12% (nanoemulsion↑to 35%).

    Distribution

    Skin concentration 20× plasma levels (topical).

    Metabolism

    Hepatic CYP1A2-mediated hydroxylation (4'-O-methylation).

    Excretion

    Primarily fecal (90% clearance in 72h).

    Clinical Applications​

    Indications & Protocols​

    Field​

    ​Formulation​

    ​Evidence​

    ​Acne Treatment​

    0.5% gel (topical)

    65%↓ inflammatory lesions*

    ​Rosacea​

    1% microemulsion serum

    Erythema index↓48%

    ​Oral Ulcers​

    2% oral patch

    Healing time↓40%

    *Randomized double-blind trial (n=120)

    Special Populations​

    ​Pregnancy: Avoid high systemic doses (weak estrogenic activity in vitro).

     ​Pediatrics: ≥12 years for topical use.

    Dosage and Administration

    Formulations​

    Topicals: 0.1-1% gels/creams/microemulsions

    Oral Capsules: 50 mg/capsule (research use)

    Injection: 10 mg/mL (preclinical)

    Dosing Guidelines​

    ​Use​

    ​Dose​

    ​Duration​

    Acne vulgaris

    0.5% gel bid

    4-8 weeks

    Photoaging

    1% serum qd

    Long-term

    Cancer adjuvant

    50 mg po tid

    Clinical trials

    Safety Evaluation

    Adverse Reactions​

    ​System​

    ​Incidence​

    ​Manifestations​

    Skin irritation

    3%

    Transient erythema

    Gastrointestinal

    <1%

    Oral nausea

    Photosensitivity

    Rare

    UV-exposed pruritus

    Contraindications & Interactions​

    Absolute CI:
    Hypersensitivity to chalcones.
    Concomitant photosensitizing drugs (e.g., tetracyclines).

    Cautions:CYP1A2 substrates (e.g., theophylline): Metabolism inhibition risk.

    Research Progress Green max

    Novel Formulations​

    ​Nanocrystals: 15× enhanced skin penetration.

    ​Thermosensitive Gel: For oral mucosa sustained release (Patent WO2022156778).

    New Indications​

    ​Atopic Dermatitis: Inhibits IL-31 signaling (↓60% itching in animals).

    ​Melanoma: Blocks BRAF/MEK pathway (preclinical promise).

    licorice

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