| Identification | Back Directory | [Name]
(+/-)-8-PRENYLNARINGENIN | [CAS]
68682-02-0 | [Synonyms]
rac 8-Prenylnaringenin
(+/-)-8-PRENYLNARINGENIN
Naringenin 8-Prenyl Racemate
2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
(±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-butenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)- | [EINECS(EC#)]
245-096-7 | [Molecular Formula]
C20H20O5 | [MDL Number]
MFCD21364781 | [MOL File]
68682-02-0.mol | [Molecular Weight]
340.37 |
| Chemical Properties | Back Directory | [Melting point ]
183-184 °C | [Boiling point ]
597.6±50.0 °C(Predicted) | [density ]
1.314±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Light yellow powder | [pka]
7.70±0.40(Predicted) | [color ]
Off-White to Pale Yellow | [Stability:]
Light Sensitive | [Major Application]
food and beverages | [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 | [InChIKey]
LPEPZZAVFJPLNZ-SFHVURJKSA-N | [SMILES]
OC1=C(C(CC(C2=CC=C(O)C=C2)O3)=O)C3=C(CC=C(C)C)C(O)=C1 |
| Hazard Information | Back Directory | [Description]
(±)-8-Prenylnaringenin ((±)-8-PN) is a prenylflavonoid with potent estrogenic activity that can be isolated from hops. It inhibits both isoforms of the human estrogen receptor (ER; IC50s = 57 and 68 nM for ERα and ERβ, respectively). (±)-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. | [Uses]
8-Prenylnaringenin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding. | [Definition]
ChEBI: Rac 8-Prenylnaringenin is a member of flavanones. | [in vivo]
(±)-8-Prenylnaringenin (50 mg/kg; orally gavage; once daily; for 12 days) ameliorates impaired glucose homeostasis and islet dysfunction induced by STZ treatment. (±)-8-Prenylnaringenin increases the protein expression levels of ERα in the pancreas and liver and of fibroblast growth factor 21 in the liver[3]. | Animal Model: | Male C57BL/6J mice (Seven-week-old) injected with Streptozotocin (STZ)[3] | | Dosage: | 50 mg/kg | | Administration: | Orally gavage; once daily; for 12 days | | Result: | Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment. |
| [IC 50]
ERα: 57 nM (IC50); ERβ: 68 nM (IC50) | [References]
[1] S. MILLIGAN. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin.[J]. Reproduction, 2002, 123 2 1: 235-242. DOI: 10.1530/rep.0.1230235
[2] ATIEH HAJIRAHIMKHAN. Evaluation of estrogenic activity of licorice species in comparison with hops used in botanicals for menopausal symptoms.[J]. PLoS ONE, 2013: e67947. DOI: 10.1371/journal.pone.0067947
[3] FREDERIK ROELENS. Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β[J]. Journal of Medicinal Chemistry, 2006, 49 25: 7357-7365. DOI: 10.1021/jm060692n
[4] ANNEKATHRIN M KEILER Georg K Oliver Zierau. Hop extracts and hop substances in treatment of menopausal complaints.[J]. Planta medica, 2013, 79 7: 576-579. DOI: 10.1055/s-0032-1328330 |
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