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68682-02-0

68682-02-0 Structure

68682-02-0 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332
[Precautionary statements ]

P280-P301+P312+P330-P302+P352+P312-P304+P340+P312
[Safety Statements ]

22-24/25
[WGK Germany ]

3
Hazard InformationBack 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)
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