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2-Hydroxyanthraquinone

Alias: 2-Hydroxyanthraquinone; β-Hydroxyanthraquinone; β Hydroxyanthraquinone; NSC 2595; NSC2595; NSC-2595; 2-hATQ; 2 hATQ; 2 Hydroxyanthraquinone; 2-hydroxy-9,10-Anthraquinone
Cat No.:V64459 Purity: ≥98%
2-Hydroxyanthraquinone is a naturally occurring compound with antitumor and immunosuppressive activities.
2-Hydroxyanthraquinone
2-Hydroxyanthraquinone Chemical Structure CAS No.: 605-32-3
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-Hydroxyanthraquinone is a natural product with antitumor and immunosuppressive activities.
2-Hydroxyanthraquinone (2-HAQ, 2-hydroxy-9,10-anthracenedione) is a monohydroxylated derivative of the anthraquinone scaffold. It has the molecular formula C14H8O3 and molecular weight 224.21 g/mol. The compound has been found in Spermacoce latifolia and exhibits antibacterial and estrogenic activities. It is active against B. subtilis and other bacteria. 2-Hydroxyanthraquinone is known for its potential biological activities, including antimicrobial and anticancer properties.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of 2-hydroxyanthraquinone include bacterial cells and estrogen receptors. As an antibacterial agent, it likely targets bacterial cell wall synthesis or membrane integrity. Its estrogenic activity suggests interaction with estrogen receptors. The compound also exhibits antitumor and immunosuppressive activity, suggesting additional cellular targets involved in cell proliferation and immune function.
ln Vitro
In vitro studies demonstrate that 2-hydroxyanthraquinone exhibits antibacterial activity against B. subtilis and other bacteria. The compound also shows antitumor and immunosuppressive activity. Its estrogenic activity has been reported. These diverse biological activities make 2-hydroxyanthraquinone a compound of interest for drug discovery and natural product research.
ln Vivo
In vivo activity data for 2-hydroxyanthraquinone are limited, as the compound is primarily studied in vitro. Its antibacterial and antitumor activities suggest potential in vivo effects, but specific in vivo studies have not been extensively reported. The compound's estrogenic activity may have physiological effects in vivo.
Enzyme Assay
Non-cellular assays for 2-hydroxyanthraquinone typically involve measuring its antibacterial activity using broth microdilution or agar diffusion methods. The compound is incubated with bacterial cultures, and the minimum inhibitory concentration (MIC) is determined. Estrogenic activity is assessed using receptor binding assays or reporter gene assays. These cell-free systems allow for characterization of the compound's biological activities.
Cell Assay
Cellular assays for 2-hydroxyanthraquinone are conducted using cancer cell lines to assess its antitumor activity. Cells are treated with the compound, and cell viability is measured using MTT or similar assays. Apoptosis is evaluated by flow cytometry with Annexin V/PI staining. Antibacterial activity is assessed using bacterial cell cultures. These studies demonstrate the compound's potential therapeutic effects.
Animal Protocol
In vivo animal experiments for 2-hydroxyanthraquinone are limited. The compound may be studied in tumor xenograft models to assess its antitumor activity. Antibacterial efficacy may be evaluated in infection models. However, specific in vivo studies have not been extensively reported in the available literature.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-hydroxyanthraquinone are not well-characterized. The compound has a molecular weight of 224.21 g/mol and is likely lipophilic based on its anthraquinone structure. Its absorption, distribution, metabolism, and excretion have not been extensively studied. The compound is typically stored at -20°C for long-term stability.
Toxicity/Toxicokinetics
Toxicological data for 2-hydroxyanthraquinone are limited. As a natural product, it is generally considered to have moderate toxicity. The compound's estrogenic activity suggests potential endocrine-disrupting effects. Standard laboratory safety precautions should be followed when handling the compound. Further toxicological studies are needed to establish its safety profile.
References

[1]. Antitumour and immunosuppressive activity of hydroxyanthraquinones and their glucosides. Folia Biol (Praha). 1977;23(2):99-109.

Additional Infomation
2-Hydroxyanthraquinone is a monohydroxyanthraquinone. It has been reported to exist in madder, ruby, and primrose, and there is relevant data available.
Other information includes 2-hydroxyanthraquinone's presence in Spermacoce latifolia and its antibacterial and estrogenic activities. It is known for its potential biological activities, including antimicrobial and anticancer properties. The compound has antitumor and immunosuppressive activity. It is also known as β-hydroxyanthraquinone and 9,10-anthracenedione, 2-hydroxy-. It is used as a research reagent for studying anthraquinone pharmacology and natural product chemistry.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H8O3
Molecular Weight
224.21
Exact Mass
224.047
Elemental Analysis
C, 75.00; H, 3.60; O, 21.41
CAS #
605-32-3
PubChem CID
11796
Appearance
Yellow to green yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
409.7±14.0 °C at 760 mmHg
Melting Point
314℃ (acetic acid )
Flash Point
215.7±16.6 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.695
LogP
3.37
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
17
Complexity
349
Defined Atom Stereocenter Count
0
SMILES
C1=CC=C2C(=C1)C(=O)C3=C(C=C(C=C3)O)C2=O
InChi Key
GCDBEYOJCZLKMC-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H
Chemical Name
2-hydroxyanthracene-9,10-dione
Synonyms
2-Hydroxyanthraquinone; β-Hydroxyanthraquinone; β Hydroxyanthraquinone; NSC 2595; NSC2595; NSC-2595; 2-hATQ; 2 hATQ; 2 Hydroxyanthraquinone; 2-hydroxy-9,10-Anthraquinone
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: 100 mg/mL (446.01 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.15 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 (11.15 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.4601 mL 22.3005 mL 44.6010 mL
5 mM 0.8920 mL 4.4601 mL 8.9202 mL
10 mM 0.4460 mL 2.2301 mL 4.4601 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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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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