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P3496

Sigma-Aldrich

(+/-)-8-Prenylnaringenin

Plant-derived estrogen receptor ligand

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About This Item

Empirical Formula (Hill Notation):
C20H20O5
Molecular Weight:
340.37
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.56

form

powder

storage temp.

−20°C

SMILES string

C\C(C)=C\Cc1c(O)cc(O)c2C(=O)CC(Oc12)c3ccc(O)cc3

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

Biochem/physiol Actions

8-Prenylnaringenin, a strong plant-derived estrogen receptor ligand, is a phytoestrogen that inhibits multidrug resistance-associated transporters, P-glycoprotein and MRP1. 8-Prenylnaringenin also inhibits EGF signaling at the level of phosphatidylinositol-3-OH kinase ((PI(3)K))activity.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Stephan Sehmisch et al.
Planta medica, 74(8), 794-801 (2008-06-10)
As the average age of society increases, identifying and preventing osteoporosis becomes more important. According to the results of the Women's Health Initiative study, substitution of estradiol is not recommended in hormone replacement therapy (HRT), although phytoestrogens might be a
Olga Wesołowska et al.
European journal of pharmacology, 644(1-3), 32-40 (2010-07-17)
Flavonoids with hydrophobic e.g. prenyl substituents might constitute the promising candidates for multidrug resistance (MDR) reversal agents. The interaction of 8-prenylnaringenin (8-isopentenylnaringenin), a potent phytoestrogen isolated from common hop (Humulus lupulus), with two multidrug resistance-associated ABC transporters of cancer cells
Elisa Brunelli et al.
The Journal of steroid biochemistry and molecular biology, 113(3-5), 163-170 (2008-12-24)
8-Prenylnaringenin (8PN), one of the strongest plant-derived oestrogen receptors (ERs) ligand, has been suggested to have potential cancer chemo-preventive activities and anti-angiogenic properties. Because published data suggest that ERs serve as nodal point that allows interactions between hormones and growth

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