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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
Yellow to brown solid
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
Source
Originated from plants: Rubiaceae Hedyotis diffusa Willd.
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), 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: ~5 mg/mL (~21.0 mM; with ultrasonication and warming by heating to 60°C)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.5 mg/mL (2.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (5.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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.

 (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.

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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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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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