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2,4-Diacetylphloroglucinol

Cat No.:V49492 Purity: ≥98%
2,4-Diacetylphloroglucinol is generated by some isolates of beneficial bacteria like Pseudomonas fluorescens and is an effective antibiotic.
2,4-Diacetylphloroglucinol
2,4-Diacetylphloroglucinol Chemical Structure CAS No.: 2161-86-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
2,4-Diacetylphloroglucinol is generated by some isolates of beneficial bacteria like Pseudomonas fluorescens and is an effective antibiotic. 2,4-Diacetylphloroglucinol has activivty against many organisms like plants, fungi, viruses, bacteria, and nematodes.
2,4-Diacetylphloroglucinol (CAS 2161-86-6), also known as DAPG, is a natural phenol and polyketide antibiotic produced by certain bacteria, particularly Pseudomonas fluorescens. It has a molecular weight of 210.19 g/mol and formula C10H10O5. The compound exhibits broad-spectrum antimicrobial activity and is used for its biocontrol properties against plant pathogens. It displays antiviral activity and inhibitory effects on bacteria, fungi, and plants.
Biological Activity I Assay Protocols (From Reference)
Targets
2,4-Diacetylphloroglucinol targets microbial pathogens through its antimicrobial activity. The compound exerts its antimicrobial effects by disrupting cellular membranes and inhibiting the growth of pathogens. It is a polyketide antibiotic produced by Pseudomonas fluorescens strain CHAO, where it functions as a pathogen suppressor. The compound displays broad-spectrum toxicity against bacteria, fungi, and plants. It is used for biocontrol of soilborne diseases in agriculture.
ln Vitro
2,4-Diacetylphloroglucinol exhibits broad-spectrum antimicrobial activity against bacteria, fungi, and plants. It is a potent antibiotic and antifungal agent produced by Pseudomonas species. The compound displays antiviral activity. It acts as a pathogen suppressor and shows inhibitory effects on microbial growth. The compound's antimicrobial mechanism involves disrupting cellular membranes and inhibiting pathogen growth. It is used for biocontrol of soilborne diseases in agriculture.
ln Vivo
In vivo, 2,4-diacetylphloroglucinol is produced by Pseudomonas fluorescens in the rhizosphere, where it provides biocontrol against plant pathogens. The compound has been studied for its effectiveness in protecting crops from soilborne diseases. It exhibits broad-spectrum antimicrobial activity in vivo, inhibiting the growth of various plant pathogens. The compound is not used as a therapeutic agent for humans but is studied for its agricultural applications.
Enzyme Assay
In vitro antimicrobial assays for 2,4-diacetylphloroglucinol typically involve testing the compound against various bacterial and fungal pathogens using disc diffusion or broth microdilution methods. The compound is dissolved in appropriate solvents (ethanol or DMSO) and serially diluted in growth media. The minimum inhibitory concentration (MIC) is determined by measuring the lowest concentration that inhibits visible growth. Antiviral activity is assessed using cell-based assays with appropriate virus models. The compound's activity is compared to standard antibiotics.
Cell Assay
In vitro cellular assays for 2,4-diacetylphloroglucinol are primarily conducted in the context of its antimicrobial activity. Bacterial or fungal cells are treated with the compound at concentrations ranging from 0.1 to 100 μg/mL. Cell viability is assessed by colony counting or optical density measurements. The compound's effects on cell membrane integrity can be assessed using fluorescent dyes or by measuring leakage of cellular contents. The compound is dissolved in DMSO or ethanol and diluted in culture media.
Animal Protocol
In vivo animal studies for 2,4-diacetylphloroglucinol are not typically performed, as the compound is used for agricultural biocontrol rather than as a therapeutic agent for humans. Studies are typically conducted in plant systems to evaluate the compound's effectiveness in protecting crops from pathogens. The compound is applied to soil or plants, and disease incidence is monitored. The compound is not intended for human therapeutic use.
ADME/Pharmacokinetics
2,4-Diacetylphloroglucinol has a molecular weight of 210.19 g/mol and formula C10H10O5. The compound is a solid at room temperature and should be stored frozen at -20°C. It is soluble in organic solvents such as DMSO and ethanol. Detailed PK parameters are not applicable for this compound, as it is used for agricultural applications rather than as a therapeutic agent.
Toxicity/Toxicokinetics
Toxicity data for 2,4-diacetylphloroglucinol indicate that it has broad-spectrum toxicity against bacteria, fungi, and plants. The compound is intended for research and agricultural use only and is not approved for human therapeutic applications. Appropriate safety precautions should be taken when handling. The compound's antimicrobial activity suggests potential toxicity to microbial systems, which is the basis for its biocontrol applications.
References

[1]. Toxicity of 2,4-diacetylphloroglucinol (DAPG) to plant-parasitic and bacterial-feeding nematodes. J Nematol. 2009 Dec;41(4):274-80.

Additional Infomation
2,4-Dacetyl-Resorcinol is a phloroglucinol derivative in which two hydrogen atoms on the resorcinol ring are replaced by acetyl groups. It is both a bacterial metabolite and an antifungal agent. It is a diketone, aromatic ketone, methyl ketone, and phloroglucinol. Functionally, it is related to resorcinol. It is the conjugate acid of 2,4-Dacetyl-Resorcinol (1-). 2,4-Dacetyl-Resorcinol has been reported in Pseudomonas, Pseudomonas fluorescens, and Pseudomonas putida, with relevant data available.
2,4-Diacetylphloroglucinol (CAS 2161-86-6) is a natural phenol and polyketide antibiotic produced by Pseudomonas fluorescens. It has a molecular weight of 210.19 g/mol and formula C10H10O5. The compound exhibits broad-spectrum antimicrobial activity and is used for biocontrol of plant pathogens. It displays antiviral activity and inhibitory effects on bacteria, fungi, and plants. The compound is also known as DAPG. It is not approved for human therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H10O5
Molecular Weight
210.1834
Exact Mass
210.053
CAS #
2161-86-6
PubChem CID
16547
Appearance
Off-white to light yellow solid powder
Density
1.422g/cm3
Boiling Point
374.7ºC at 760mmHg
Melting Point
164ºC
Flash Point
194.6ºC
Vapour Pressure
3.81E-06mmHg at 25°C
Index of Refraction
1.62
LogP
1.208
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Heavy Atom Count
15
Complexity
249
Defined Atom Stereocenter Count
0
InChi Key
PIFFQYJYNWXNGE-UHFFFAOYSA-N
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
Chemical Name
1-(3-acetyl-2,4,6-trihydroxyphenyl)ethanone
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~475.78 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.89 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7578 mL 23.7891 mL 47.5783 mL
5 mM 0.9516 mL 4.7578 mL 9.5157 mL
10 mM 0.4758 mL 2.3789 mL 4.7578 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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