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(+/-)-8-PRENYLNARINGENIN

(+/-)-8-PRENYLNARINGENIN Structure
(+/-)-8-PRENYLNARINGENIN structure
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
Molecular Weight:
340.37
MDL Number:
MFCD21364781
MOL File:
68682-02-0.mol
MSDS File:
SDS
Last updated:2026-01-13 11:24:11
Product description Number Pack Size Price
8-Prenylnaringenin analyticalstandard 75119 5mg $729
8-Prenylnaringenin P2132 5MG $252
(±)-8-Prenylnaringenin ≥98% 17462 1mg $51
(±)-8-Prenylnaringenin ≥98% 17462 5mg $178
(±)-8-Prenylnaringenin ≥98% 17462 10mg $330
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(+/-)-8-PRENYLNARINGENIN Properties

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)
pka 7.70±0.40(Predicted)
form Light yellow powder
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
UNSPSC Code 85151701
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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
Storage Class 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral

(+/-)-8-PRENYLNARINGENIN price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 75119 8-Prenylnaringenin analyticalstandard 68682-02-0 5mg $729 2022-05-15 Buy
TCI Chemical P2132 8-Prenylnaringenin 68682-02-0 5MG $252 2025-07-31 Buy
Cayman Chemical 17462 (±)-8-Prenylnaringenin ≥98% 68682-02-0 1mg $51 2024-03-01 Buy
Cayman Chemical 17462 (±)-8-Prenylnaringenin ≥98% 68682-02-0 5mg $178 2024-03-01 Buy
Cayman Chemical 17462 (±)-8-Prenylnaringenin ≥98% 68682-02-0 10mg $330 2024-03-01 Buy
Product number Packaging Price Buy
75119 5mg $729 Buy
P2132 5MG $252 Buy
17462 1mg $51 Buy
17462 5mg $178 Buy
17462 10mg $330 Buy

(+/-)-8-PRENYLNARINGENIN Chemical Properties,Uses,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

Licoflavone C

(+/-)-8-PRENYLNARINGENIN Suppliers

Global( 31)Suppliers
Supplier Tel Email Country ProdList Advantage
career henan chemical co 		+86-0371-86658258 +8613203830695 factory@coreychem.com China 29795 58
Antai Fine Chemical Technology Co.,Limited 		18503026267 info@antaichem.com CHINA 9636 58
Finetech Industry Limited 		+86-27-8746-5837 +8619945049750 info@finetechnology-ind.com China 9629 58
Aladdin Scientific 		tp@aladdinsci.com United States 57505 58
DAYANG CHEM (HANGZHOU) CO.,LTD 		+86-88938639 +86-17705817739 info@dycnchem.com China 53899 58
J & K SCIENTIFIC LTD. 18210857532; 18210857532 jkinfo@jkchemical.com China 96815 76
Chemsky (shanghai) International Co.,Ltd 021-50135380 shchemsky@sina.com China 15402 60
Finetech Industry Limited 027-87465837 19945049750 sales@finetechnology-ind.com China 9636 58
Shanghai EFE Biological Technology Co., Ltd. 021-65675885 18964387627 info@efebio.com China 9803 58
Shanghai YuanYe Biotechnology Co., Ltd. 021-61312847; 18021002903 3008007409@qq.com China 71826 60
Supplier Advantage
career henan chemical co 		58
Antai Fine Chemical Technology Co.,Limited 		58
Finetech Industry Limited 		58
Aladdin Scientific 		58
DAYANG CHEM (HANGZHOU) CO.,LTD 		58
J & K SCIENTIFIC LTD. 76
Chemsky (shanghai) International Co.,Ltd 60
Finetech Industry Limited 58
Shanghai EFE Biological Technology Co., Ltd. 58
Shanghai YuanYe Biotechnology Co., Ltd. 60

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(+/-)-8-PRENYLNARINGENIN pictures 2019-12-25 (+/-)-8-PRENYLNARINGENIN
68682-02-0
 US $1.00 / g 1g ≥98% g/kg/T Career Henan Chemical Co

68682-02-0((+/-)-8-PRENYLNARINGENIN)Related 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 Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals