(±)-8-Prenylnaringenin
Based on 1 Customer Validation
(±)-8-Prenylnaringenin, a natural prenylated flavonoid, is a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally active selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that inhibits ERα and ERβ with IC50s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anticancer effects, and can be used for osteoporosis research.
For research use only. We do not sell to patients.
- Purity: 99.97%
- CAS No.: 68682-02-0
- Formula: C20H20O5
- Molecular Weight:340.37
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Storage:
-20°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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ERα 57 nM (IC50) |
ERβ 68 nM (IC50) |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| COS-7 | IC50 |
16.23 μM
Compound: 8-PN
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Inhibition of human recombinant PDE5A1 expressed in COS7 cells
Inhibition of human recombinant PDE5A1 expressed in COS7 cells
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[PMID: 18778098] |
| HSC-2 | CC50 |
0.13 mM
Compound: 20
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Cytotoxicity against human HSC2 cells
Cytotoxicity against human HSC2 cells
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[PMID: 11170668] |
| RAW264.7 | IC50 |
20.4 μM
Compound: 8
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Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation after 20 hrs
Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation after 20 hrs
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[PMID: 16643064] |
| RAW264.7 | IC50 |
26.3 μM
Compound: 15
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Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide production after 24 hrs by Griess method
Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide production after 24 hrs by Griess method
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[PMID: 26073007] |
| RAW264.7 | IC50 |
41.6 μM
Compound: 8
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Cytotoxicity against mouse RAW264.7 cells by MTT assay
Cytotoxicity against mouse RAW264.7 cells by MTT assay
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[PMID: 16643064] |
In rabbit bone marrow cells, (±)-8-Prenylnaringenin inhibits the formation and induces apoptosis of Osteoclasts to a greater extent than naringenin. (±)-8-Prenylnaringenin is applied to the MC3T3-E1 osteoblast cell line, where it enhances differentiation and maturation, and also inhibits the differentiation of the RAW264.7 osteoclast cell line. (±)-8-Prenylnaringenin inhibits the expression of receptor activator of nuclear factor-κB ligand (RANKL), and leads to increased expression of osteoprotegerin[1].
A significant, dose-dependent inhibition of proliferation is observed in PC-3 human prostate cancer cells and UO.31 human renal carcinoma cells after exposure to (±)-8-Prenylnaringenin. In MCF-10A, a human breast cancer cell line, (±)-8-Prenylnaringenin modulats the metabolic pathways of estradiol conversion into cancer-promoting metabolites, and thereby inhibits malignant transformation[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male C57BL/6J mice (Seven-week-old) injected with Streptozotocin (STZ)[3]
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Dosage:50 mg/kg
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Administration:Orally gavage; once daily; for 12 days
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Result:Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment.
Chemical Information
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CAS No. 68682-02-0
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Appearance Solid
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Molecular Weight 340.37
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Formula C20H20O5
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Color White to off-white
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SMILES
O=C1CC(OC2=C(C(O)=CC(O)=C21)C/C=C(C)\C)C3=CC=C(C=C3)O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
-20°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Solvent & Solubility
DMSO : 100 mg/mL (293.80 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (276 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Kateřina Štulíková, et al. Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops. Molecules. 2018 Mar 15;23(3):660. [Content Brief]
[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. [Content Brief]
[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. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.9380 mL | 14.6899 mL | 29.3798 mL | 73.4495 mL |
| 5 mM | 0.5876 mL | 2.9380 mL | 5.8760 mL | 14.6899 mL | |
| 10 mM | 0.2938 mL | 1.4690 mL | 2.9380 mL | 7.3449 mL | |
| 15 mM | 0.1959 mL | 0.9793 mL | 1.9587 mL | 4.8966 mL | |
| 20 mM | 0.1469 mL | 0.7345 mL | 1.4690 mL | 3.6725 mL | |
| 25 mM | 0.1175 mL | 0.5876 mL | 1.1752 mL | 2.9380 mL | |
| 30 mM | 0.0979 mL | 0.4897 mL | 0.9793 mL | 2.4483 mL | |
| 40 mM | 0.0734 mL | 0.3672 mL | 0.7345 mL | 1.8362 mL | |
| 50 mM | 0.0588 mL | 0.2938 mL | 0.5876 mL | 1.4690 mL | |
| 60 mM | 0.0490 mL | 0.2448 mL | 0.4897 mL | 1.2242 mL | |
| 80 mM | 0.0367 mL | 0.1836 mL | 0.3672 mL | 0.9181 mL | |
| 100 mM | 0.0294 mL | 0.1469 mL | 0.2938 mL | 0.7345 mL |
(±)-8-Prenylnaringenin Related Classifications
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