A prenylated flavonoid and phytoestrogen
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(−)-8-Prenylnaringenin

Item No. 37906

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CAS Number
53846-50-7
Synonyms
  • Flavaprenin
  • (−)-8-PN
  • (S)-8-Prenylnaringenin
  • Sophoraflavanone B
Molecular Formula
C20H20O5
Formula Weight
340.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly solubleEthanol: Slightly solubleMethanol: Soluble
SMILES
O=C1C2=C(O)C=C(O)C(C/C=C(C)\C)=C2O[C@H](C3=CC=C(C=C3)O)C1
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/t18-/m0/s1
InChi Key
LPEPZZAVFJPLNZ-SFHVURJKSA-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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    Product Description

    (−)-8-Prenylnaringenin is a prenylated flavonoid and phytoestrogen that has been found in H. lupulus and has estrogenic activity.1 It binds to recombinant human estrogen receptor α (ERα) and ERβ in cell-free assays and induces ER activation in a reporter assay using yeast expressing human ER in a concentration-dependent manner. (−)-8-Prenylnaringenin increases uterine vascular permeability in ovariectomized mice in a dose-dependent manner.

    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).