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8-Prenylnaringenin (Synonyms: Flavaprenin,8-PN)

Catalog No.GC17119

estrogen receptor inhibitor

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8-Prenylnaringenin Chemical Structure

Cas No.: 53846-50-7

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1mg
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5mg
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10mg
$392.00
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25mg
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

IC50: 57 and 68 nM for ERα and ERβ, respectively

8-Prenylnaringenin is an estrogen receptor inhibitor.

The two estrogen receptors ERα and ERβ belong to the nuclear receptor superfamily and are ligand-regulated transcription factors accounting for mediating the physiological effects of the steroid hormone 17α-estradiol. ER is an established target for the development of synthetic ligands for therapeutic applications.

In vitro: Previous study identified 8-prenylnaringenin as a potent phytoestrogen in hops, which had an activity greater than other known plant estrogens. The estrogenic activity of 8-prenylnaringenin was reflected in its relative binding affinity to estrogen receptors from rat uteri. In addition, the presence of 8-prenylnaringenin in hops might explane the accounts of menstrual disturbances in female hop workers [1].

In vivo: Previous animal data demonstrated that 8-prenylnaringenin treatment could result in AMPK signaling pathway activation, therefore suppressing lipogenesis. The consumption of 8-prenylnaringenin was able to prevent body weight gain and improve plasma lipid profile, with significant improvement of insulin resistance and glucose tolerance. Moreove, it was found that 8-prenylnaringenin-enriched diet could ameliorate diabetic-associated metabolic disturbances via regulating glucose and lipid pathways [2].

Clinical trial: So far, no clinical study has been conducted.

References:
[1] Milligan SR, Kalita JC, Heyerick A, Rong H, De Cooman L, De Keukeleire D. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab. 1999 Jun;84(6):2249-52.
[2] Costa R et al.  Xanthohumol and 8-prenylnaringenin ameliorate diabetic-related metabolic dysfunctions in mice. J Nutr Biochem. 2017 Apr 6;45:39-47.

Chemical Properties

Cas No. 53846-50-7 SDF
Synonyms Flavaprenin,8-PN
Chemical Name (2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
Canonical SMILES O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C(C/C=C(C)/C)C(O)=CC(O)=C31
Formula C20H20O5 M.Wt 340.4
Solubility DMF: 10 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 5 mg/ml,Ethanol: 2 mg/ml Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.9377 mL 14.6886 mL 29.3772 mL
5 mM 0.5875 mL 2.9377 mL 5.8754 mL
10 mM 0.2938 mL 1.4689 mL 2.9377 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 38 reference(s) in Google Scholar.)

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