(±)-8-Prenylnaringenin (racemic 8-prenylnaringenin)

Cat No.:V18319 Purity: ≥98%
(±)-8-Prenylnaringenin is a natural prenylated flavonoid and a potent phytoestrogen.
(±)-8-Prenylnaringenin (racemic 8-prenylnaringenin) Chemical Structure CAS No.: 68682-02-0
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
(±)-8-Prenylnaringenin is a natural prenylated flavonoid and a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally bioactive selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that can inhibit ERα and ERβ with IC50s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anti-neoplastic activities and may be used in osteoporosis research.
Biological Activity I Assay Protocols (From Reference)
Targets
ERα 57 nM (IC50) ERβ 68 nM (IC50)
ln Vitro
(±)-8-Prenylnaringenin caused osteoclast apoptosis more often than osteoclast development in rabbit bone marrow cells. (±)-8-Prenylnaringenin inhibits the differentiation of RAW264.7 osteoclast cell line, but can increase the differentiation and maturation of MC3T3-E1 osteoblast cell line. Osteoprotegerin is expressed more when (±)-8-prenylnaringenin inhibits the expression of receptor activator of nuclear factor-κB ligand (RANKL) [1]. After being exposed to (±)-8-Prenylnaringenin, PC-3 human prostate cancer cells and UO.31 human renal cancer cells showed significant dose-dependent suppression of growth. (±)-8-Prenylnaringenin inhibits malignant transformation in the human breast cancer cell line MCF-10A by regulating the metabolic pathway that transforms estradiol into compounds that promote cancer [1].
ln Vivo
(±)-8-Prenylnaringenin (50 mg/kg; oral gavage; once daily; for 12 days) ameliorates islet dysfunction and poor glucose homeostasis brought on by STZ therapy. The protein expression levels of ERα in the liver and pancreas, as well as fibroblast growth factor 21 in the liver, are increased by (±)-8-prenylnaringenin [3].
Animal Protocol
Animal/Disease Models: Male C57BL/6J mice (Sevenweeks old) injected with Streptozotocin (STZ)[3]
Doses: 50 mg/kg
Route of Administration: Orally gavage; one time/day; for 12 days
Experimental Results: Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment.
References
[1]. Kateřina Štulíková, et al. Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops. Molecules. 2018 Mar 15;23(3):660.
[2]. Frederik Roelens, et al. Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta. J Med Chem. 2006 Dec 14;49(25):7357-65.
[3]. Song Park, et al. Naringenin and Phytoestrogen 8-Prenylnaringenin Protect against Islet Dysfunction and Inhibit Apoptotic Signaling in Insulin-Deficient Diabetic Mice. Molecules. 2022 Jun 30;27(13):4227.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H20O5
Molecular Weight
340.37
CAS #
68682-02-0
SMILES
OC1C2C(=O)CC(C3C=CC(O)=CC=3)OC=2C(C/C=C(\C)/C)=C(O)C=1
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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 2.9380 mL 14.6899 mL 29.3798 mL
5 mM 0.5876 mL 2.9380 mL 5.8760 mL
10 mM 0.2938 mL 1.4690 mL 2.9380 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?
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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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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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