A bacterial metabolite with diverse biological activities
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Isomer(s)
33094Curvulinic Acid
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2,4-Diacetylphloroglucinol

Item No. 16345

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis-ethanone
CAS Number
2161-86-6
Synonyms
  • 5-Acetyl-2,4,6-trihydroxyacetophenone
  • DAPG
  • 1,3-Diacetyl-2,4,6-trihydroxybenzene
Molecular Formula
C10H10O5
Formula Weight
210.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 15 mg/mlEthanol: 25 mg/ml
λmax
269, 329 nm
SMILES
OC1=C(C(C)=O)C(O)=C(C(C)=O)C(O)=C1
InChi Code
InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3
InChi Key
PIFFQYJYNWXNGE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2,4-Diacetylphloroglucinol is a bacterial metabolite originally isolated from P. fluorescens that has diverse biological activities.1 It is active against B. subtillis, E. faecalis, S. aureus, and S. lividans (MICs = 5, 50, 5, and 5 µg/ml, respectively). 2,4-Diacetylphloroglucinol is also active against the plant pathogenic fungi F. oxysporum, P. debaryanum, and R. solani (MICs = 16, 64, and 32-64 µg/ml, respectively). It reduces the growth of corn, flax, tobacco, and tomato seedlings (MICs = 16-32, 32, 8, and 16 µg/ml, respectively) and suppresses T. basicola-induced black root rot on tobacco plants. It also inhibits cell growth in A549 lung, MDA-MB-231 breast, and HeLa cervical cancer cells (IC50s = 52, 94, and 141 nM, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Keel, C., Ursula, S., Maurhofer, M., et al. Suppression of root diseases by Pseudomonas fluorescens CHA0: Importance of the bacterial seconday metabolite 2,4-diacetylphloroglucinol. Mol. Plant Microbe Interact. 5(1), 4-13 (1995).

    2. Veena, V.K., Popavath, R.N., Kennedy, K., et al. In vitro antiproliferative, pro-apoptotic, antimetastatic and anti-inflammatory potential of 2,4-diacetylphloroglucinol (DAPG) by Pseudomonas aeruginosa strain FP10. Apoptosis 20(10), 1281-1295 (2015).