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Hemiphloin

Cat No.:V59055 Purity: ≥98%
Hemiphloin is a naturally occurring flavonoid.
Hemiphloin
Hemiphloin Chemical Structure CAS No.: 71963-94-5
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Hemiphloin is a naturally occurring flavonoid.
Hemiphloin is a natural flavonoid compound. It has a molecular formula of C₂₁H₂₂O₁₀ and a molecular weight of 434.39 g/mol. Studies have shown it to have anti-inflammatory activity and is a therapeutic candidate for inflammatory skin diseases. It enhances insulin-stimulated glucose uptake in L6 myotubes and inhibits α-amylase (IC₅₀ 46.42 µM). It has defined antioxidant capacity (DPPH IC₅₀ 264.44 mM; superoxide IC₅₀ 360.03 µM).
Biological Activity I Assay Protocols (From Reference)
Targets
Hemiphloin targets multiple pathways. It enhances insulin-stimulated glucose uptake in L6 myotubes, suggesting it may target insulin signaling pathways. It inhibits α-amylase (IC₅₀ 46.42 µM), indicating it may be useful for managing postprandial blood glucose levels. It shows anti-inflammatory activities in LPS-induced J774 cells by decreasing LPS-induced NO productions and iNOS and COX-2 expressions. It also inhibits LPS-induced TNF-α, IL-1β, and IL-6 gene expressions.
ln Vitro
In vitro, Hemiphloin enhances insulin-stimulated glucose uptake in L6 myotubes. It inhibits α-amylase with an IC₅₀ of 46.42 µM. It has defined antioxidant capacity (DPPH IC₅₀ 264.44 mM; superoxide IC₅₀ 360.03 µM). It shows anti-inflammatory activities in LPS-induced J774 cells by decreasing LPS-induced NO productions and iNOS and COX-2 expressions. It inhibits LPS-induced TNF-α, IL-1β, and IL-6 gene expressions.
ln Vivo
In vivo, Hemiphloin has been studied for its effects against atopic dermatitis-like skin inflammation. It showed anti-inflammatory activities and is a therapeutic candidate for inflammatory skin diseases. Its ability to enhance insulin-stimulated glucose uptake and inhibit α-amylase suggests potential for managing diabetes. However, specific in vivo efficacy data are not detailed in the available literature.
Enzyme Assay
Typical in vitro assays for Hemiphloin include α-amylase inhibition assays, where the enzyme is incubated with starch substrate and various concentrations of the compound, and activity is measured by the reduction of DNS reagent. Antioxidant assays include DPPH and superoxide radical scavenging assays. Anti-inflammatory assays measure NO production in LPS-stimulated J774 macrophages by Griess assay. Glucose uptake is measured in L6 myotubes using 2-deoxyglucose uptake assays.
Cell Assay
Cellular assays for Hemiphloin typically involve treating L6 myotubes or J774 macrophages with the compound at concentrations ranging from 1-100 µM for 24-48 hours. Glucose uptake is measured using radiolabeled or fluorescent glucose analogs. Inflammatory markers such as NO, iNOS, COX-2, TNF-α, IL-1β, and IL-6 are measured by Griess assay, ELISA, or Western blot. ROS levels are measured using fluorescent probes. These cell-based systems allow for detailed analysis of the compound's mechanism of action.
Animal Protocol
In vivo animal experiments for Hemiphloin are not detailed in the available literature. For atopic dermatitis studies, typical animal models involve inducing skin inflammation in mice and applying the compound topically. Skin inflammation, histological changes, and inflammatory markers are assessed. For diabetes studies, diabetic mouse models are used, and blood glucose levels are measured. However, such studies have not been reported for this specific compound.
ADME/Pharmacokinetics
Pharmacokinetic data for Hemiphloin are limited. As a flavonoid with a molecular weight of 434.39 g/mol, it would be expected to have moderate oral bioavailability. Flavonoids are typically metabolized by conjugation reactions. However, detailed ADME parameters are not available in the consulted sources.
Toxicity/Toxicokinetics
Toxicological data for Hemiphloin are limited. As a natural flavonoid, it is generally considered to have low toxicity. However, comprehensive toxicological studies have not been reported. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Schoepfin A, B, C: three new chalcone C-glycosides from Schoepfia chinensis. Nat Prod Res. 2008 May 10;22(7):623-7.

Additional Infomation
Hemiflavonoids are flavonoid compounds belonging to the C-glycoside class. They have been reported to exist in custard apples, broad beans, and other organisms with relevant data.
Hemiphloin is a natural flavonoid with anti-inflammatory, antioxidant, anti-diabetic, and anti-α-amylase activities. It enhances insulin-stimulated glucose uptake and is a therapeutic candidate for inflammatory skin diseases. It is a research compound for studying diabetes, inflammation, and oxidative stress. It is not approved for any clinical indication.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H22O10
Molecular Weight
434.393
Exact Mass
434.121
CAS #
71963-94-5
PubChem CID
160711
Appearance
Typically exists as solid at room temperature
LogP
-0.1
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
3
Heavy Atom Count
31
Complexity
638
Defined Atom Stereocenter Count
6
SMILES
C1[C@H](OC2=C(C1=O)C(=C(C(=C2)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C4=CC=C(C=C4)O
InChi Key
QKPKGDDHOGIEOO-JVVVWQBKSA-N
InChi Code
InChI=1S/C21H22O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-4,6,12,14,17,19-23,25-29H,5,7H2/t12-,14+,17+,19-,20+,21-/m0/s1
Chemical Name
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one
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 2.3021 mL 11.5104 mL 23.0208 mL
5 mM 0.4604 mL 2.3021 mL 4.6042 mL
10 mM 0.2302 mL 1.1510 mL 2.3021 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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