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2-Hydroxy-3-methylanthraquinone (emodin impurity 16)

Cat No.:V54913 Purity: ≥98%
2-Hydroxy-3-methylanthraquinone (compound 1) is extracted from the aqueous extract of Hephiphylla alba.
2-Hydroxy-3-methylanthraquinone (emodin impurity 16)
2-Hydroxy-3-methylanthraquinone (emodin impurity 16) Chemical Structure CAS No.: 17241-40-6
Product category: Apoptosis
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-Hydroxy-3-methylanthraquinone (compound 1) is extracted from the aqueous extract of Hephiphylla alba. 2-Hydroxy-3-methylanthraquinone has an inhibitory effect on protein tyrosine kinases v-src and pp60src, inducing HepG2 cancer cells and apoptosis.
2-Hydroxy-3-methylanthraquinone (CAS 17241-40-6) is a chemical compound belonging to the anthraquinone class. It is also known as emodin impurity 16. Anthraquinones are a class of organic compounds that are widely distributed in nature and have diverse biological activities including laxative, antimicrobial, and anticancer properties. This compound is used as a reference standard and impurity marker for emodin and related anthraquinones.
Biological Activity I Assay Protocols (From Reference)
Targets
55 μM (HepG2 cells)[1]
2-Hydroxy-3-methylanthraquinone targets multiple cellular pathways involved in cell proliferation, apoptosis, and microbial growth. As an anthraquinone, it can intercalate into DNA and inhibit topoisomerase enzymes. The compound also exhibits antimicrobial activity against various bacterial and fungal pathogens. Its biological effects are related to its ability to generate reactive oxygen species and modulate cellular signaling pathways.
ln Vitro
In cell-free biochemical systems, 2-Hydroxy-3-methylanthraquinone exhibits antimicrobial activity as evaluated by standard disk diffusion or microdilution assays. The compound's ability to inhibit topoisomerase enzymes can be assessed using cell-free enzymatic assays. Its DNA intercalation activity can be studied using spectroscopic methods.
ln Vivo
In cell-based assays, 2-Hydroxy-3-methylanthraquinone exhibits anticancer effects by inhibiting cell proliferation and inducing apoptosis. The compound's effects are evaluated in cancer cell lines by measuring cell viability, proliferation, and apoptosis. Its antimicrobial effects are assessed in infected cell cultures.
Enzyme Assay
The cell-free assay for antimicrobial activity involves standard disk diffusion or microdilution methods. The compound is applied to agar plates inoculated with bacterial or fungal strains, and the zone of inhibition is measured. The minimum inhibitory concentration (MIC) is determined from broth microdilution assays. Topoisomerase inhibition can be assessed using purified topoisomerase enzymes and DNA substrates.
Cell Assay
Cell-based assays for 2-Hydroxy-3-methylanthraquinone involve culturing cancer cell lines and treating them with the compound at concentrations ranging from 0.1 to 100 μM. Cell viability is assessed using MTT or CCK-8 assays. Apoptosis is evaluated by Annexin V staining or caspase activity assays. Cell cycle analysis is performed by flow cytometry. The compound's effects on DNA synthesis and topoisomerase activity are assessed.
Animal Protocol
There is no established animal experimental protocol for 2-Hydroxy-3-methylanthraquinone specifically. As an anthraquinone with potential anticancer and antimicrobial activities, the compound could potentially be evaluated in animal models of cancer and infection. Typical studies involve administration of the compound to mice via oral or intraperitoneal routes.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-Hydroxy-3-methylanthraquinone have not been extensively reported. As an anthraquinone with a molecular weight of approximately 238.2 g/mol, the compound would be expected to have moderate bioavailability and tissue penetration. Further pharmacokinetic studies would be required for therapeutic development.
Toxicity/Toxicokinetics
2-Hydroxy-3-methylanthraquinone is intended for research use only and lacks established toxicity profiles for therapeutic applications. Standard laboratory safety precautions should be observed when handling this chemical reagent. As an anthraquinone, the compound may have genotoxic and cytotoxic effects. Standard toxicity studies would be required for therapeutic development.
References

[1]. Shi Y, Wang CH, Gong XG. Apoptosis-inducing effects of two anthraquinones from Hedyotis diffusa WILLD. Biol Pharm Bull. 2008;31(6):1075-1078.

Additional Infomation
2-Hydroxy-3-methylanthraquinone has been reported in Oldenlandia herbacea var. herbacea, Oldenlandia diffusa, and other organisms with available data.
2-Hydroxy-3-methylanthraquinone is a research-grade chemical supplied as a reference standard for emodin impurity analysis. It is not an approved pharmaceutical and has no clinical trial history. The compound is also known as emodin impurity 16. This product is intended for research and analytical use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O3
Molecular Weight
238.24
Exact Mass
238.062
CAS #
17241-40-6
PubChem CID
10889963
Appearance
Typically exists as solid at room temperature
Density
1.4±0.1 g/cm3
Boiling Point
439.7±34.0 °C at 760 mmHg
Flash Point
233.8±22.2 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.676
LogP
3.83
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
376
Defined Atom Stereocenter Count
0
SMILES
CC1=CC2=C(C=C1O)C(=O)C3=CC=CC=C3C2=O
InChi Key
RNJHIYAJJKOFIO-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H10O3/c1-8-6-11-12(7-13(8)16)15(18)10-5-3-2-4-9(10)14(11)17/h2-7,16H,1H3
Chemical Name
2-hydroxy-3-methylanthracene-9,10-dione
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 4.1974 mL 20.9872 mL 41.9745 mL
5 mM 0.8395 mL 4.1974 mL 8.3949 mL
10 mM 0.4197 mL 2.0987 mL 4.1974 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?
  • 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:
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  • 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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  • 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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