(+/-)-8-PRENYLNARINGENIN

Product Name: (+/-)-8-PRENYLNARINGENIN
CAS No.: 68682-02-0
Chemical Name: (+/-)-8-PRENYLNARINGENIN
Synonyms: rac 8-Prenylnaringenin;(±)-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)-
CBNumber: CB6504166
Molecular Formula: C20H20O5
Formula Weight: 340.37
MOL File: 68682-02-0.mol

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(+/-)-8-PRENYLNARINGENIN Property

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

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Safety

Safety Statements: 22-24/25
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Precautionary statements: P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 75119
Product name: 8-Prenylnaringenin
Purity: analyticalstandard
Packaging: 5mg
Price: $729
Updated: 2022/05/15

TCI Chemical

Product number: P2132
Product name: 8-Prenylnaringenin
Packaging: 5MG
Price: $252
Updated: 2025/07/31

Cayman Chemical

Product number: 17462
Product name: (±)-8-Prenylnaringenin
Purity: ≥98%
Packaging: 1mg
Price: $51
Updated: 2024/03/01

Cayman Chemical

Product number: 17462
Product name: (±)-8-Prenylnaringenin
Purity: ≥98%
Packaging: 5mg
Price: $178
Updated: 2024/03/01

Cayman Chemical

Product number: 17462
Product name: (±)-8-Prenylnaringenin
Purity: ≥98%
Packaging: 10mg
Price: $330
Updated: 2024/03/01

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(+/-)-8-PRENYLNARINGENIN Chemical Properties,Usage,Production

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

(+/-)-8-PRENYLNARINGENIN Preparation Products And Raw materials

Raw materials

Preparation Products

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(+/-)-8-PRENYLNARINGENIN Suppliers

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View Lastest Price from (+/-)-8-PRENYLNARINGENIN manufacturers

Career Henan Chemical Co

Product: (+/-)-8-PRENYLNARINGENIN 68682-02-0
Price: US $1.00/g
Min. Order: 1g
Purity: ≥98%
Supply Ability: g/kg/T
Release date: 2019-12-24

68682-02-0, (+/-)-8-PRENYLNARINGENINRelated Search:

ISOXANTHOHUMOL

(±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-butenyl)-4H-1-benzopyran-4-one

2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

rac 8-Prenylnaringenin

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-

Naringenin 8-Prenyl Racemate

(+/-)-8-PRENYLNARINGENIN

(±)-8-Prenylnaringenin

68682-02-0

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