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(+/-)-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

Canada 1 China 25 India 1 Switzerland 1 United States 2 USA 1 Global 31
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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

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  • 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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