8-Prenylnaringenin

Base Information

• Chemical Name: 8-Prenylnaringenin
• CAS No.: 53846-50-7
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376
• UNII: 5L872SZR8X
• DSSTox Substance ID: DTXSID60333083
• Nikkaji Number: J607.005A
• Wikipedia: 8-Prenylnaringenin
• Wikidata: Q4644281
• Pharos Ligand ID: PD5N6CVY35B6
• Metabolomics Workbench ID: 57369
• ChEMBL ID: CHEMBL376915
• Mol file: 53846-50-7.mol

Synonyms:8-prenyl-naringenin;8-prenylnaringenin

Chemical Property of 8-Prenylnaringenin

Chemical Property:

• Boiling Point: 597.6±50.0 °C(Predicted)
• PKA: 7.70±0.40(Predicted)
• PSA: 86.99000
• Density: 1.314±0.06 g/cm3(Predicted)
• LogP: 4.01860
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 340.13107373
• Heavy Atom Count: 25
• Complexity: 504

Purity/Quality:

98%Min ^*data from raw suppliers

(-)-8-Prenylnaringenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC=C(C=C3)O)C
• Isomeric SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
• Recent ClinicalTrials: Oral Bioavailability and Bioactivity of Prenylflavonoids From Hops
• Uses: (-)-8-Prenylnaringin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.

Technology Process of 8-Prenylnaringenin

There total 14 articles about 8-Prenylnaringenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Isoxanthohumol (70872-29-6) → sophoraflavanone B (53846-50-7,68682-02-0,72357-32-5)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; diethyl ether; at 65 - 72 ℃; for 20h; Inert atmosphere; Darkness;

DOI:10.3390/molecules22071092

Reference yield: 96.0%

C24H24O7 → sophoraflavanone B (53846-50-7,68682-02-0,72357-32-5)

Guidance literature:

With Pseudonomas sp. (Roche) lipase; In tetrahydrofuran; butan-1-ol; at 20 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Time;

DOI:10.1002/anie.201306500

Reference yield: 76.0%

2-(4-acetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate (1141487-32-2) → sophoraflavanone B (53846-50-7,68682-02-0,72357-32-5)

Guidance literature:

With methanol; ammonium acetate; at 50 - 55 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0031-1290756

upstream raw materials:

2-methyl-3-buten-2-ol

naringenin

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one

dimethylallyl diphosphate

Downstream raw materials:

8-dimethylallylsteppogenin

Refernces

• 1、 Stompor, Monika,Uram, ?ukasz,Podgórski, Rafa?. "In vitro effect of 8-prenylnaringenin and naringenin on fibroblasts and glioblastoma cells-cellular accumulation and cytotoxicity". . . Retrieved 2017.
• 2、 Riepl, Herbert,Urmann, Corinna. "Semi-Synthetic Approach Leading to 8-Prenylnaringenin and 6-Prenylnaringenin: Optimization of the Microwave-Assisted Demethylation of Xanthohumol Using Design of Experiments". . . Retrieved 2020.