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Phloroglucide (2,3',4,5',6-pentahydroxybiphenyl)

Cat No.:V59143 Purity: ≥98%
Phloroglucide is a naturally occurring compound that can be extracted from ferns.
Phloroglucide (2,3',4,5',6-pentahydroxybiphenyl)
Phloroglucide (2,3',4,5',6-pentahydroxybiphenyl) Chemical Structure CAS No.: 491-45-2
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
Other Sizes
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Product Description
Phloroglucide is a naturally occurring compound that can be extracted from ferns.
Phloroglucide (2,3',4,5',6-pentahydroxybiphenyl) is a naturally occurring compound that can be extracted from ferns. It is a dimer of phloroglucinol and serves as a versatile and valuable chemical scaffold in organic synthesis and biomedical research. With a molecular formula of C₁₂H₁₀O₅ and a molecular weight of 234.20 g/mol, its structure features multiple phenolic hydroxyl groups. Phloroglucide is used as a fundamental building block for the synthesis of more complex organic molecules, including natural product analogs, pharmaceuticals, and novel polymers. It also acts as a potential corrosion inhibitor of aluminum when combined in hybrid flake composites.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary mechanism of action of Phloroglucide involves its antioxidant activity through the donation of hydrogen atoms to stabilize reactive oxygen species (ROS), thereby interrupting destructive radical chain reactions. This property is of significant interest in investigating cellular damage, aging, and various disease models. The compound's defined molecular framework also serves as a core structure in supramolecular chemistry and materials science for developing functional organic materials. Its phenolic hydroxyl groups are key to its radical-scavenging capabilities and its utility as a chemical scaffold.
ln Vitro
Phloroglucide has demonstrated anticancer activity in vitro by inducing apoptosis in cancer cell lines and suppressing tumor angiogenesis through inhibition of endothelial progenitor cell bioactivities. The compound's antioxidant properties have been characterized through its ability to scavenge reactive oxygen species. Its multiple phenolic hydroxyl groups make it a potent antioxidant, enabling studies into oxidative stress and the neutralization of free radicals. These in vitro activities support its potential as an anticancer and antioxidant agent for research applications, though specific potency data are not detailed in the available literature.
ln Vivo
In vivo studies of Phloroglucide have not been extensively reported in the available literature. The compound is primarily used as a research tool for studying antioxidant mechanisms and as a chemical scaffold rather than as a pharmacologically active agent in animal models. Its role as a naturally occurring compound suggests it may have physiological functions, but specific in vivo efficacy data in disease models are not available. Further research is needed to evaluate its potential therapeutic applications and in vivo pharmacokinetic properties.
Enzyme Assay
Typical in vitro assays for evaluating the antioxidant activity of Phloroglucide include DPPH and ABTS radical scavenging assays, where the compound is incubated with radical solutions at various concentrations and absorbance is measured at specific wavelengths. For studying its effects on angiogenesis, endothelial progenitor cell functional assays are employed, assessing cell proliferation, migration, and tube formation. The compound's ability to induce apoptosis can be evaluated using flow cytometry with Annexin V/PI staining in cancer cell lines. These cell-free systems provide insights into the compound's mechanism of action as an antioxidant and anticancer agent.
Cell Assay
Cellular assays for Phloroglucide typically involve treating cancer cell lines or endothelial cells with the compound at concentrations ranging from 1-100 µM for 24-48 hours. Cell viability is assessed using MTT or CCK-8 assays. Apoptosis is evaluated by Annexin V/PI staining and caspase activity measurements. For studying anti-angiogenic effects, endothelial progenitor cells are treated with the compound, and their bioactivities including proliferation, migration, and tube formation are assessed. Intracellular ROS levels can be measured using fluorescent probes such as DCFH-DA to evaluate the compound's antioxidant effects at the cellular level.
Animal Protocol
In vivo animal experiments for Phloroglucide are not detailed in the available literature. For antioxidant and anticancer compounds, typical animal studies involve xenograft mouse models where tumor-bearing mice are treated with the compound via oral gavage or intraperitoneal injection at doses ranging from 10-100 mg/kg. Tumor volume and body weight are monitored regularly, and endpoints include tumor growth inhibition, apoptosis markers, and angiogenesis assessment. Toxicological endpoints such as body weight, organ weights, and histopathology are also evaluated. However, such studies have not been reported for phloroglucide.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Phloroglucide are not available in the consulted sources. As a polyphenolic compound with a molecular weight of 234.20 g/mol, it would be expected to have moderate oral bioavailability, extensive metabolism via glucuronidation and sulfation, and rapid elimination. The compound's multiple hydroxyl groups suggest it may undergo significant first-pass metabolism. Distribution would likely be extensive due to its lipophilic nature, with potential accumulation in tissues. However, detailed ADME parameters have not been characterized in the literature.
Toxicity/Toxicokinetics
Toxicological data for Phloroglucide are not available in the consulted sources. Polyphenolic compounds generally have low acute toxicity but may exhibit cytotoxicity at high concentrations. The compound's antioxidant properties suggest it may have a protective role against oxidative stress-induced damage. However, comprehensive toxicity studies including genotoxicity, reproductive toxicity, and chronic toxicity would be required for therapeutic development. The compound is intended for research use only and is not approved for human or veterinary use.
References

[1]. Pharmaceutical Studies on Ferns. III. YAKUGAKU ZASSHI, 72(1), 153–154.

Additional Infomation
Phloroglucide is a naturally occurring compound that can be extracted from ferns and serves as a versatile chemical scaffold in organic synthesis and biomedical research. Its mechanism of action as an antioxidant primarily involves the donation of hydrogen atoms to stabilize reactive oxygen species. The compound is used as a fundamental building block for synthesizing natural product analogs, pharmaceuticals, and novel polymers. It is also a derivative of phloroglucinol, which is known as an antispasmodic. Phloroglucide is not approved for any clinical indication and is strictly a research compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H10O5
Molecular Weight
234.20
Exact Mass
234.053
CAS #
491-45-2
PubChem CID
248349
Appearance
Yellow to brown solid powder
Density
1.594g/cm3
Boiling Point
529.5ºC at 760 mmHg
Melting Point
216-218 ºC (water )
Flash Point
268.1ºC
Vapour Pressure
7.91E-12mmHg at 25°C
Index of Refraction
1.756
LogP
1.881
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Heavy Atom Count
17
Complexity
237
Defined Atom Stereocenter Count
0
SMILES
C1=C(C=C(C=C1O)O)C2=C(C=C(C=C2O)O)O
InChi Key
KICYRZIVKKYRFS-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10O5/c13-7-1-6(2-8(14)3-7)12-10(16)4-9(15)5-11(12)17/h1-5,13-17H
Chemical Name
2-(3,5-dihydroxyphenyl)benzene-1,3,5-triol
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 4.2699 mL 21.3493 mL 42.6985 mL
5 mM 0.8540 mL 4.2699 mL 8.5397 mL
10 mM 0.4270 mL 2.1349 mL 4.2699 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
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • 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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