Pinocembrin racemate (DL0108)

Alias: DL-0108; DL0108; DL 0108; Pinocembrin
Cat No.:V7595 Purity: ≥98%
Pinocembrin (DL-0108), the racemate of Pinocembrin, is a potent androgen receptor ligand with the potential for the treatment of acute stroke.
Pinocembrin racemate (DL0108) Chemical Structure CAS No.: 68745-38-0
Product category: Free Fatty Acid Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
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1g
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Pinocembrin (DL-0108), the racemate of Pinocembrin, is a potent androgen receptor ligand with the potential for the treatment of acute stroke. Pinocembrin [(+)-Pinocoembrin; Dihydrochrysin; Galangin flavanone] is a naturally occurring flavonoid that is present in fingerroot, propolis, damiana, and honey. It has strong antimicrobial, anti-inflammatory, and gastrointestinal protective properties. It is a potent anti-allergic agent that functions as a competitive inhibitor of histidine decarboxylase.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Pinocembrin (5,7-dihydroxyflavanone) is one of the main flavonoids that have been isolated and purified using different chromatographic techniques from a variety of plants, primarily from Sparattosperma leucanthum, Eucalyptus, Populus, and Pinus heartwood, among other diverse flora. Numerous pharmacological properties, such as antimicrobial, anti-inflammatory, antioxidant, and anticancer properties, have been thoroughly studied[1]. In primary cortical neurons exposed to oxygen-glucose deprivation/reoxygenation (OGD/R), pinocembrin has been demonstrated to increase neuronal viability, decrease lactate dehydrogenase release, inhibit the production of NO and ROS, increase glutathione levels, and downregulate the expression of neuronal NO synthase (nNOS) and iNOS[2].
ln Vivo
Pinocembrin has a broad therapeutic time window for its neuroprotective effects against cerebral ischemia injury, which may be related to its antiexcitotoxic properties[1]. It can control apoptosis, modify mitochondrial function, shield the blood-brain barrier, and lower reactive oxygen species (ROS). Astrocytic end-feet edema, neuronal apoptosis, deformation of endothelial cells and capillaries, and brain swelling may all be ameliorated by pinocembrin (10 mg/kg, i.v.). Pinocembrin inhibits ER stress and apoptosis in MCAO rats by lowering the expression of caspase-12 and C/EBP homologous protein (CHOP)/GADD153 through the PERK-elF2α-ATF4 signaling pathway. In mice, the lethal dose of intravenous pinocembrin (LD50) exceeds 700 mg/kg.
Cell Assay
SH-SY5Y cells are cultured at 37°C in a humidified environment with 5% CO2 in DMEM supplemented with 10% FBS, 100 units/mL penicillin, and 100 µg/mL streptomycin. Trypsinization is used to pass cells every three to five days. Subsequently, a 96-well plate is seeded with 1 × 104 cells per well, and the plate is incubated for 24 hours at 37 °C in a humidified atmosphere that contains 5% CO2. After one of the compounds is pretreated for one hour, the entire medium is replaced with fresh medium containing 1% FBS. Either 30 nM staurosporine or 2.0 µg/mL tunicamycin is then added. Assays for nuclear staining are conducted 24 hours after the initial incubation. Cell death is evaluated.
Animal Protocol
male Sprague-Dawley rats
22.5 or 67.5 mg/kg
i.v.
References

[1]. Biomed Res Int . 2013:2013:379850.

[2]. Mol Neurobiol . 2016 Apr;53(3):1794-1801.

[3]. J Pharm Biomed Anal . 2009 Jul 12;49(5):1277-81.

[4]. J Agric Food Chem . 2008 Oct 8;56(19):8944-53.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H12O4
Molecular Weight
256.25
Exact Mass
256.07
Elemental Analysis
C, 70.31; H, 4.72; O, 24.97
CAS #
68745-38-0
Related CAS #
68745-38-0
Appearance
Solid powder
SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
InChi Key
URFCJEUYXNAHFI-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
Chemical Name
5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms
DL-0108; DL0108; DL 0108; Pinocembrin
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 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 3.9024 mL 19.5122 mL 39.0244 mL
5 mM 0.7805 mL 3.9024 mL 7.8049 mL
10 mM 0.3902 mL 1.9512 mL 3.9024 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.

Biological Data
  • Chemical structure of pinocembrin. Mol Neurobiol . 2016 Apr;53(3):1794-1801.
  • Potential therapeutic applications of pinocembrin. In the central nervous system (CNS), pinocembrin is a drug candidate for ischemic stroke, but it also exerts protection against Alzheimer’s disease (AD) and Parkinson’s disease (PD). Mol Neurobiol . 2016 Apr;53(3):1794-1801.
  • Chemical structure and natural sources of pinocembrin. Biomed Res Int . 2013:2013:379850.
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