(±)-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.

Physicochemical Properties

Molecular Formula	C20H20O5
Molecular Weight	340.37
Exact Mass	340.131
CAS #	68682-02-0
PubChem CID	509245
Appearance	Typically exists as solid at room temperature
LogP	4.018
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	25
Complexity	504
Defined Atom Stereocenter Count	0
SMILES	CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC=C(C=C3)O)C
InChi Key	LPEPZZAVFJPLNZ-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3
Chemical Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-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)

Biological Activity

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]. Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops. Molecules. 2018 Mar 15;23(3):660. [2]. 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]. 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.
Additional Infomation	Rac 8-Prenylnaringenin is a member of flavanones. Sophoraflavanone B has been reported in Lespedeza cyrtobotrya, Artocarpus altilis, and other organisms with data available.

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 : PEG300 ：Tween 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). 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 : PEG300：Tween 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). 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.