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8-Prenylnaringenin

Item No. 17462

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CAS Number
68682-02-0
Synonyms
  • 8-PN
Molecular Formula
C20H20O5
Formula Weight
340.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 5 mg/mlEthanol: 2 mg/ml
λmax
294 nm
SMILES
O=C1CC(C2=CC=C(O)C=C2)OC3=C(C/C=C(C)/C)C(O)=CC(O)=C31
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
InChi Key
LPEPZZAVFJPLNZ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    8-Prenylnaringenin (8-PN) is a prenylflavonoid with potent estrogenic activity that can be isolated from hops.1,2 It inhibits both isoforms of the human estrogen receptor (ER; IC50s = 57 and 68 nM for ERα and ERβ, respectively).3 8-PN is effective in vivo, suppressing loss of bone mineral density in ovariectomized rats and blocking changes in tail skin temperature in a rat model of postmenopausal hot flashes.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Milligan, S., Kalita, J., Pocock, V., et al. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 123(2), 235-242 (2002).

    2. Hajirahimkhan, A., Simmler, C., Yuan, Y., et al. Evaluation of estrogenic activity of licorice species in comparison with hops used in botanicals for menopausal symptoms. PLoS One 8(7), e67947 (2013).

    3. Roelens, F., Heldring, N., Dhooge, W., et al. Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors α and β. J. Med. Chem. 49(25), 7357-7365 (2006).

    4. Keiler, A.M., Zierau, O., and Kretzschmar, G. Hop extracts and hop substances in treatment of menopausal complaints. Planta Med. 79(7), 576-579 (2013).