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Emodinanthrone

Cat No.:V50870 Purity: ≥98%
Emodinanthrone is an anthraquinone compound, the precursor of emodin, and has antibiotic activity.
Emodinanthrone
Emodinanthrone Chemical Structure CAS No.: 491-60-1
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Emodinanthrone is an anthraquinone compound, the precursor of emodin, and has antibiotic activity. Emodinanthrone inhibits respiration-driven solute transport in E. coli membrane vesicles at micromolar concentrations.
Emodinanthrone, also known as emodin anthrone or 1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one, is a natural anthracenone belonging to the class of anthraquinone derivatives. It is a precursor of emodin (a well-known anthraquinone) and has been reported to possess antibiotic activity. Emodinanthrone is a research tool used to study its biological activities, which include laxative effects, antimicrobial action, and potential anticancer properties. It plays a key role in the biotransformation of emodin in vivo.
Biological Activity I Assay Protocols (From Reference)
Targets
Emodinanthrone targets bacterial transport systems. It has been shown to inhibit respiration-driven solute transport at micromolar concentrations in membrane vesicles of Escherichia coli. This suggests that its antibiotic activity may be related to the disruption of energy-dependent transport processes in bacteria. Its role as a precursor to emodin also links it to the biological activities of emodin, which include anti-inflammatory, antioxidant, and anticancer effects.
ln Vitro
The AknX oxygenase test was conducted using Rhein as a substitute substrate [1].
In vitro, emodinanthrone exhibits antibiotic activity. It inhibits respiration-driven solute transport in E. coli membrane vesicles at micromolar concentrations. This activity is consistent with its role as an anthraquinone precursor. Its potential anticancer properties have also been associated with this compound. As a natural product, it is used to study the biological activities of anthracenones and their derivatives.
ln Vivo
In vivo, emodinanthrone is a precursor of emodin, and it contributes to the biotransformation and therapeutic effects of emodin in vivo. Its biological activities, including laxative and antimicrobial effects, are related to its metabolism to emodin. Specific in vivo studies on emodinanthrone itself are limited, as its primary role is as a metabolic intermediate.
Enzyme Assay
The biological activities of emodinanthrone are assessed using various in vitro assays. Its antibiotic activity is evaluated using standard antimicrobial susceptibility tests, such as the broth microdilution method, to determine its minimum inhibitory concentration (MIC) against bacterial strains. Its effect on solute transport can be assessed using membrane vesicle assays, where the uptake of radiolabeled substrates is measured.
Cell Assay
The cellular activity of emodinanthrone is evaluated in bacterial cell cultures. Bacteria are treated with the compound, and its effect on cell growth and viability is measured. Its effect on respiration-driven solute transport can be assessed by measuring the uptake of substrates in the presence of an energy source. Its potential anticancer activity can be evaluated in cancer cell lines using standard cytotoxicity assays.
Animal Protocol
In animal studies, emodinanthrone is not typically administered directly, as it is primarily a metabolic intermediate. However, its role in the biotransformation of emodin is studied by administering emodin and measuring the levels of emodinanthrone and other metabolites. Its in vivo effects are largely attributed to its conversion to emodin.
ADME/Pharmacokinetics
Emodinanthrone has a molecular weight of 256.25 g/mol and a chemical formula of C15H12O4. It is a solid with a purity of 98%. It is a natural product belonging to the class of anthracenes. Its solubility and stability are characteristic of anthraquinone derivatives. Detailed pharmacokinetic parameters are not extensively documented in the provided sources.
Toxicity/Toxicokinetics
Formal toxicology data for emodinanthrone is limited, as it is a research compound. As a natural product, it is generally considered to have a low toxicity profile, but formal toxicology studies have not been conducted. Its use is limited to research applications.
References

[1]. Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus. J Bacteriol. 2002 Nov;184(22):6115-22.

[2]. Inhibition of electron transfer and uncoupling effects by emodin and emodinanthrone in Escherichia coli. Antimicrob Agents Chemother. 1986 Jul;30(1):147-51.

[3]. Triterpenoid saponins from Berneuxia thebetica. Phytochemistry. 1998 Aug;48(8):1411-4.

Additional Infomation
Emodin anthrone belongs to the anthrone class of compounds, with the chemical formula anthraquinone-9(10H)-anthrone, containing a methyl group at position 6 and hydroxyl groups at positions 1, 3, and 8. It is an intermediate precursor in the synthesis of hypericin and also a fungal metabolite. It is an anthrone compound belonging to the phenolic class. Emodin anthrone has been reported to exist in peony (Paeonia emodi), sorrel (Rumex acetosa), and rhamnus prinoides, and relevant data are available for reference.
Emodinanthrone (CAS: 491-60-1) is a natural anthracenone and a precursor of the bioactive compound emodin. Its antibiotic activity, demonstrated by its ability to inhibit respiration-driven solute transport in E. coli, makes it a valuable research tool for studying bacterial transport mechanisms and the biological activities of anthraquinone derivatives. It is available from various commercial suppliers for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H12O4
Molecular Weight
256.25338
Exact Mass
256.074
CAS #
491-60-1
PubChem CID
122635
Appearance
Light yellow to yellow solid powder
Density
1.471 g/cm3
Boiling Point
556.2ºC at 760 mmHg
Melting Point
254-258 °C(dec.)
Vapour Pressure
5.6E-13mmHg at 25°C
Index of Refraction
1.723
LogP
2.247
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Heavy Atom Count
19
Complexity
369
Defined Atom Stereocenter Count
0
InChi Key
LAJSXCAVRQXZIO-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3
Chemical Name
1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ~16.67 mg/mL (~65.05 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9024 mL 19.5122 mL 39.0244 mL
5 mM 0.7805 mL 3.9024 mL 7.8049 mL
10 mM 0.3902 mL 1.9512 mL 3.9024 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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