GLPBio

2,4-Diacetylphloroglucinol

Catalog No.: GC14471Purity:>97.00%Synonyms: 5-Acetyl-2,4,6-trihydroxyacetophenone,DAPG,1,3-Diacetyl-2,4,6-trihydroxybenzene
COASDSData Sheet
El 2,4-diacetilfloroglucinol, producido por algunos aislados de la bacteria beneficiosa Pseudomonas fluorescens, es un potente antibiÓtico.

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2,4-Diacetylphloroglucinol
Cas No.: 2161-86-6
10mM (in 1mL DMSO)In Stock
$23.00
1
5mgIn Stock
$21.00
1
10mgIn Stock
$32.00
1
25mgIn Stock
$64.00
1
50mgIn Stock
$96.00
1
100mgIn Stock
$144.00
1
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Citas (Citations)

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    641, 529–536 (2025)
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    610, 366–372 (2022)
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    Cell
    187(9):2288-2304 (2024)
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    183(7):1867-1883 (2020)
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    35, 97–116 (2025)
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Descripción (Description)

2,4-Diacetylphloroglucinol is a polyketide antibiotic and secondary metabolite produced by various strains of fluorescent Pseudomonas[1]. 2,4-Diacetylphloroglucinol inhibits primary root growth and stimulates lateral root production in tomato seedlings by interacting with an auxin-dependent signaling pathway[2]. 2,4-Diacetylphloroglucinol interferes with the expression of genes involved in the biofilm formation of Bacillus subtilis, and suppresses the production of quorum-sensing autoinducers by Pectobacterium carotovorum[3]. 2,4-Diacetylphloroglucinol has been widely used in antibacterial research to disrupt the integrity of fungal cell membranes and affect fungal cellular respiration[4].

In vitro, 2,4-Diacetylphloroglucinol treatment for 48 hours markedly reduced the viability of VERO and LLC-PK1 cells, with IC50 values of 12μg/ml and 11μg/ml, respectively[5]. Treatment with 15μg/ml 2,4-Diacetylphloroglucinol for 28 hours impaired mitochondrial function, altered mitochondrial morphology and affected calcium homeostasis in Neurospora crassa[6].

In vivo, intrahippocampal injection of 20nmol (2μl) 2,4-Diacetylphloroglucinol decreased the soluble Aβ level and increased the levels of sAPPα and C83 in the brains of APPsw/PS1dE9 transgenic mouse model within two days[7].

References:

[1] Kim S H, Kwon Y S, Nguyen C C, et al. 2, 4-Diacetylphloroglucinol (DAPG) Enhances Induced Systemic Resistance Against Necrotrophic Pathogens Through the COI1-Mediated JA Signaling Pathway in Arabidopsis[J]. Journal of Plant Growth Regulation, 2025, 44(8): 4881-4890.

[2] Brazelton J N, Pfeufer E E, Sweat T A, et al. 2, 4-Diacetylphloroglucinol alters plant root development[J]. Molecular Plant-Microbe Interactions, 2008, 21(10): 1349-1358.

[3] Stepanov A A, Poshvina D V, Vasilchenko A S. 2, 4-Diacetylphloroglucinol modulates Candida albicans virulence[J]. Journal of Fungi, 2022, 8(10): 1018.

[4] Brucker R M, Baylor C M, Walters R L, et al. The identification of 2, 4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus[J]. Journal of chemical ecology, 2008, 34(1): 39-43.

[5] Bharate S B, Khan S I, Yunus N A M, et al. Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols[J]. Bioorganic & Medicinal Chemistry, 2007, 15(1): 87-96.

[6] Troppens D M, Chu M, Holcombe L J, et al. The bacterial secondary metabolite 2, 4-diacetylphloroglucinol impairs mitochondrial function and affects calcium homeostasis in Neurospora crassa[J]. Fungal Genetics and Biology, 2013, 56: 135-146.

[7] Jang B G, Choi B, Kim S, et al. 2, 4-Diacetylphloroglucinol reduces beta-Amyloid production and secretion by regulating Adam10 and intracellular trafficking in cellular and animal models of Alzheimer’s disease[J]. Cells, 2022, 11(16): 2585.

Protocolo (Protocol)

Cell experiment [1]:

Cell lines

 VERO cells

Preparation Method

 VERO cells were cultured in DMEM medium supplemented with 100μg/ml streptomycin, 100μg/ml penicillin and 10% fetal bovine serum at 37°C in an incubator with 5% CO2. VERO cells (2.5×104/well) were seeded in the 96-well plates and cultured overnight followed by treatment with different concentrations of 2,4-Diacetylphloroglucinol (0, 1, 5, 10, and 100μg/ml) for 48h. Cell death was measured.

Reaction Conditions

 0, 1, 5, 10, and 100μg/ml; 48h

Applications

 2,4-Diacetylphloroglucinol promoted cell death in VERO cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

 APPsw/PS1dE9 transgenic mice

Preparation Method

APPsw/PS1dE9 transgenic mice were housed individually in specific cages and placed in a ventilated cabinet, temperature was kept relatively constant at 22-25°C and humidity between 50 and 70%, and the lighting was controlled to be 12h light and 12h dark. The mice were anesthetized with isoflurane (2% induction, 1-1.5% for surgery and maintenance in a 65:35 mixture of N2O:O2) and secured in a stereotaxic frame. 20nmol 2,4-Diacetylphloroglucinol in a 2μl solution of 15% dimethylformamide and 85% 1× DPBS or the solution alone were injected into the hippocampus (2mm posterior; 1.25mm lateral; 2mm depth). Two days after the injection, the mice were sacrificed, and the brains were dissected and processed for immunoblot and ELISA analyses.

Dosage form

20nmol (2μl); once; intrahippocampal injection

Applications

2,4-Diacetylphloroglucinol treatment decreased the soluble Aβ level and increased the levels of sAPPα and C83 in the brains of mice.

References:

[1] Bharate S B, Khan S I, Yunus N A M, et al. Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols[J]. Bioorganic & Medicinal Chemistry, 2007, 15(1): 87-96.

[2] Jang B G, Choi B, Kim S, et al. 2, 4-Diacetylphloroglucinol reduces beta-Amyloid production and secretion by regulating Adam10 and intracellular trafficking in cellular and animal models of Alzheimer’s disease[J]. Cells, 2022, 11(16): 2585.

Documentos del producto (Product Documents)

Purity:>97.00%Appearance:A solid
COASDSData Sheet

Propiedades químicas (Chemical Properties)

N.º CAS
2161-86-6
Sinónimos
5-Acetyl-2,4,6-trihydroxyacetophenone,DAPG,1,3-Diacetyl-2,4,6-trihydroxybenzene
Nombre químico
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis-ethanone
SMILES
OC1=C(C(C)=O)C(O)=C(C(C)=O)C(O)=C1
Fórmula molecular
C10H10O5
Peso molecular
210.2
Solubilidad
≥ 11.55mg/mL in DMSO
Almacenamiento
Store at -20°C
Consejos generales
Seleccione un disolvente adecuado según los datos de solubilidad del producto. Una vez preparada, divida la solución madre en alícuotas para evitar ciclos repetidos de congelación y descongelación.
Utilice las soluciones madre en un plazo de 6 meses si se conservan a -80°C, o de 1 mes si se conservan a -20°C.
Para mejorar la solubilidad, caliente el tubo a 37°C y soníquelo durante un periodo adecuado.
Condiciones de envío
Las muestras de evaluación se envían con acumuladores de frío. Los demás tamaños se envían a temperatura ambiente o, previa solicitud, con acumuladores de frío.

Calculadoras (Calculators)Molaridad / Dilución / Peso molecular / Conversión de unidades / Formulación in vivo / Solubilidad

g/mol

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