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Xanthopurpurin (Purpuroxanthin)

Cat No.:V73241 Purity: ≥98%
Xanthopurpurin is an anthraquinone glycoside extracted from the rhizome of Rubia akane.
Xanthopurpurin (Purpuroxanthin)
Xanthopurpurin (Purpuroxanthin) Chemical Structure CAS No.: 518-83-2
Product category: MMP
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Xanthopurpurin is an anthraquinone glycoside extracted from the rhizome of Rubia akane. It mainly has a strong inhibitory effect on collagen-induced platelet aggregation.
Xanthopurpurin (Purpuroxanthin) is a dihydroxyanthraquinone that occurs naturally in plants of the Rubia genus, such as Rubia akane and Rubia cordifolia (Indian madder). It has a deep red to purple color and is known for its biological activities. It is of interest for its potential as a collagen-induced platelet aggregation inhibitor and for other biological properties.
Biological Activity I Assay Protocols (From Reference)
Targets
Collagen-induced platelet aggregation. Xanthopurpurin is an inhibitor of this process. It is not a traditional enzyme inhibitor but a small molecule that affects platelet function. It is isolated as an anthraquinone glycoside from the roots of Rubia plants.
ln Vitro
Xanthopurpurin, an anthraquinone glycoside isolated from the roots of Rubia akane, mainly shows strong inhibition of collagen-induced platelet aggregation. It has also demonstrated antimicrobial and anticancer properties in preliminary studies, though these are less well-characterized.
ln Vivo
The in vivo activity of Xanthopurpurin has not been extensively studied. As a natural product with anti-platelet aggregation activity in vitro, it has potential for in vivo applications in animal models of thrombosis, though its pharmacological properties (e.g., absorption, distribution, metabolism, and excretion) would need to be characterized first.
Enzyme Assay
For non-cellular enzyme assays, the effect of Xanthopurpurin can be tested on purified enzymes or target proteins. A general protocol for in vitro enzyme inhibition would involve incubating the enzyme with its substrate in the presence of varying concentrations of Xanthopurpurin. The enzymatic activity is measured using a chromogenic or fluorogenic substrate. For example, to assess its anti-platelet aggregation activity, a platelet aggregation assay is used (see below).
Cell Assay
For cell-based assays, the anti-platelet aggregation activity of Xanthopurpurin is typically measured using platelet-rich plasma (PRP). PRP is isolated from citrated whole blood. Platelet aggregation is induced by a specific agonist, such as collagen. Xanthopurpurin is added to the PRP at varying concentrations (e.g., 1-100 uM) before the agonist, and the aggregation response is monitored using a light transmission aggregometer. The extent of inhibition is calculated by comparing treated samples to a vehicle control.
Animal Protocol
For in vivo studies, Xanthopurpurin could be administered intravenously or orally to rodent models of thrombosis, such as the ferric chloride-induced carotid artery injury model or the pulmonary embolism model. Doses would need to be optimized. The primary endpoints would be the time to occlusion (in the ferric chloride model) or survival rate. The compound would likely need to be formulated using a suitable vehicle, such as DMSO, PEG, or a cyclodextrin-based solution.
ADME/Pharmacokinetics
Pharmacokinetic data for Xanthopurpurin are limited. A UPLC-ESI-Orbitrap MS method has been developed for the quantitative determination of Xanthopurpurin in rat plasma and used for a pharmacokinetic study, indicating that methods are available to assess its absorption and clearance. These studies would help determine key parameters such as Cmax, Tmax, t1/2, and AUC.
Toxicity/Toxicokinetics
Toxicological data for Xanthopurpurin are not widely reported. As a naturally occurring anthraquinone, there may be concerns about potential toxicity at high doses, as some anthraquinones can have genotoxic or cytotoxic properties. However, it is used as a research chemical, and standard laboratory safety precautions should be followed. It should not be ingested or applied to the skin without appropriate safety assessments.
References

[1]. Antiplatelet constituents of formosan Rubia akane. J Nat Prod. 1994 Feb;57(2):313-6.

Additional Infomation
Xanthine is a dihydroxyanthraquinone. It has the function of a metabolite. Xanthine has been reported in Artemisia argyi, Rubia cordifolia, and other organisms for which data are available. See also: Rubia cordifolia root (partial).
Xanthopurpurin is a natural product also known by its IUPAC name 1,3-dihydroxyanthracene-9,10-dione and the synonym purpuroxanthin. It is one of ten dihydroxyanthraquinone isomers and can be synthesized through the hydroxylation of anthraquinone. It is also used as a precursor for synthesizing other anthraquinone derivatives and as a natural dye. The compound is not an approved drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H8O4
Molecular Weight
240.21
Exact Mass
240.042
CAS #
518-83-2
PubChem CID
196978
Appearance
White to yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
514.5±30.0 °C at 760 mmHg
Melting Point
268 - 270 °C
Flash Point
279.0±21.1 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.733
LogP
3.98
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
378
Defined Atom Stereocenter Count
0
SMILES
C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=CC(=C3)O)O
InChi Key
WPWWKBNOXTZDQJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
Chemical Name
1,3-dihydroxyanthracene-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: 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)
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 4.1630 mL 20.8151 mL 41.6302 mL
5 mM 0.8326 mL 4.1630 mL 8.3260 mL
10 mM 0.4163 mL 2.0815 mL 4.1630 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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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)
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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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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