(±)-8-Prenylnaringenin

Name: (±)-8-Prenylnaringenin
Brand: MedChemExpress
SKU: HY-126109
Rating: 4.5 (1 reviews)

Cat. No.: HY-126109 Purity: 99.97%: Data Sheet
COA

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Handling Instructions
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(±)-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.

(±)-8-Prenylnaringenin Chemical Structure

CAS No. : 68682-02-0

Size	Stock	Quantity
1 mg	In-stock	Estimated Time of Arrival: December 31
5 mg	Get quote
10 mg	Get quote

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Based on 1 publication(s) in Google Scholar

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Estrogen receptor ERα ERβ ERRα ERRβ ERRγ

Biological Activity
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target^[2]

ERα

57 nM (IC₅₀)

ERβ

68 nM (IC₅₀)

Cellular Effect

Cell Line	Type	Value	Description	References
COS-7	IC₅₀	16.23 μM Compound: 8-PN	Inhibition of human recombinant PDE5A1 expressed in COS7 cells Inhibition of human recombinant PDE5A1 expressed in COS7 cells	[PMID: 18778098]
HSC-2	CC₅₀	0.13 mM Compound: 20	Cytotoxicity against human HSC2 cells Cytotoxicity against human HSC2 cells	[PMID: 11170668]
RAW264.7	IC₅₀	20.4 μM Compound: 8	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	[PMID: 16643064]
RAW264.7	IC₅₀	26.3 μM Compound: 15	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	[PMID: 26073007]
RAW264.7	IC₅₀	41.6 μM Compound: 8	Cytotoxicity against mouse RAW264.7 cells by MTT assay Cytotoxicity against mouse RAW264.7 cells by MTT assay	[PMID: 16643064]

In Vitro

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.

In Vivo

(±)-8-Prenylnaringenin (50 mg/kg; orally gavage; once daily; for 12 days) ameliorates impaired glucose homeostasis and islet dysfunction induced by STZ treatment. (±)-8-Prenylnaringenin increases the protein expression levels of ERα in the pancreas and liver and of fibroblast growth factor 21 in the liver^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Male C57BL/6J mice (Seven-week-old) injected with Streptozotocin (STZ)^[3]
Dosage:	50 mg/kg
Administration:	Orally gavage; once daily; for 12 days
Result:	Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment.

Molecular Weight

340.37

Formula

C₂₀H₂₀O₅

CAS No.

68682-02-0

Appearance

Solid

Color

White to off-white

SMILES

O=C1CC(OC2=C(C(O)=CC(O)=C21)C/C=C(C)\C)C3=CC=C(C=C3)O

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

-20°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

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)

Preparing
Stock Solutions

Concentration Solvent Mass	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

View the 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.

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This equation is commonly abbreviated as: C₁V₁ = C₂V₂

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

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Working solution concentration: mg/mL

Purity & Documentation

Purity: 99.97%

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Data Sheet (276 KB) SDS (393 KB)

COA (250 KB) HNMR (108 KB) LCMS (94 KB)

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

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