(+/-)-8-PRENYLNARINGENIN manufacturers
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| | (+/-)-8-PRENYLNARINGENIN Basic information |
| Product Name: | (+/-)-8-PRENYLNARINGENIN | | Synonyms: | (±)-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;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;rac 8-Prenylnaringenin | | CAS: | 68682-02-0 | | MF: | C20H20O5 | | MW: | 340.37 | | EINECS: | 245-096-7 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 68682-02-0.mol |  |
| | (+/-)-8-PRENYLNARINGENIN Chemical 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) | | 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 |
| 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 Usage And Synthesis |
| 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 |
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