Sophoraflavanone B

Base Information

• Chemical Name: Sophoraflavanone B
• CAS No.: 68682-02-0
• Molecular Formula: C20H20O5
• Molecular Weight: 340.376
• DSSTox Substance ID: DTXSID00333502
• Nikkaji Number: J936.413G
• Wikidata: Q82098820
• Pharos Ligand ID: PD5G17F5AT3K
• ChEMBL ID: CHEMBL460647
• Mol file: 68682-02-0.mol

Synonyms:8-isopentenylnaringenin

Chemical Property of Sophoraflavanone B

Chemical Property:

• PSA: 86.99000
• LogP: 4.01860
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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

rac8-Prenylnaringenin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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
• 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.

Technology Process of Sophoraflavanone B

There total 46 articles about Sophoraflavanone B 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: 93.0%

isoxanthohumol (521-48-2,70872-29-6) → 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one (68682-02-0)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; diethyl ether; for 12h; Heating;

DOI:10.1016/j.tet.2008.07.072

upstream raw materials:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

prenyl bromide

5,7,4'-trimethoxymethoxy-8-(3,3-dimethylallyl)-flavanone

desmethylxanthohumol

Downstream raw materials:

sophoraflavanone B

2-(4-acetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate

4',5,7-trihydroxy-8-prenylflavone

Refernces

• 1、 Osorio, Mauricio,Carvajal, Marcela,Vergara, Alejandra,Butassi, Estefania,Zacchino, Susana,Mascayano, Carolina,Montoya, Margarita,Mejías, Sophia,Martín, Marcelo Cortez-San,Vásquez-Martínez, Yesseny. "Prenylated flavonoids with potential antimicrobial activity: Synthesis, biological activity, and in silico study". . . Retrieved 2021/05/28.
• 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 2020/09/17.