3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one

Base Information

• Chemical Name: 3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS No.: 51225-30-0
• Molecular Formula: C20H18O5
• Molecular Weight: 338.36
• Mol file: 51225-30-0.mol

Synonyms:Erythrinin B;5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one;6-prenylgenistein;5,7,4'-Trihydroxy-6-prenylisoflavone;6-isopentenylgenistein;6-dimethylallylgenistein;Wighteone;6-prenyl-5,7,4'-trihydroxyisoflavone;

Chemical Property of 3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one

Chemical Property:

• Vapor Pressure: 2.47E-14mmHg at 25°C
• Melting Point: 227 °C(Solv: methanol (67-56-1))
• Boiling Point: 586.1°C at 760 mmHg
• PKA: 7.03±0.20(Predicted)
• Flash Point: 212.8°C
• PSA: 90.90000
• Density: 1.351g/cm³
• LogP: 4.08550

Purity/Quality:

99% ^*data from raw suppliers

Wighteone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Wighteone is a natural product derivative of Genistein (G350000). Genistein exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol.

Technology Process of 3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one

There total 29 articles about 3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one 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: 91.0%

Wighteon-7,4'-diacetat (65388-05-8) → erythrinin B (51225-30-0)

Guidance literature:

With potassium carbonate; In methanol; at 40 ℃; for 2h;

DOI:10.1002/adsc.200600454

Reference yield: 72.0%

7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone (887149-31-7) → erythrinin B (51225-30-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; methanol; at 25 ℃; for 0.333333h;

DOI:10.1016/j.tet.2006.06.066

Reference yield:

C22H18O7 → erythrinin B (51225-30-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / Eu(fod)3 / CHCl₃ / 18 h / 85 °C / sealed tube

2: 86 percent / (1,3-dimesitylimidazolidin-2-yl)(PCy₃)benzylidene-RuCl₂ / benzene / 72 h / 20 °C / sealed tube

3: 91 percent / K₂CO₃ / methanol / 2 h / 40 °C

With potassium carbonate; Eu(fod)3; In methanol; chloroform; benzene; 1: Claisen rearrangement;

DOI:10.1002/adsc.200600454

upstream raw materials:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

dimethylallyl diphosphate

7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone

Wighteon-7,4'-diacetat

Downstream raw materials:

5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone

alpinumisoflavone

erythrinin C

6-(2,3-Dihydroxy-3-methyl-butyl)-5,7-dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-one

Refernces

• 1、 Wang, Ruishan,Chen, Ridao,Li, Jianhua,Liu, Xiao,Xie, Kebo,Chen, Dawei,Yin, Yunze,Tao, Xiaoyu,Xie, Dan,Zou, Jianhua,Yang, Lin,Dai, Jungui. "Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata". . p. 35815 - 35825. Retrieved 2015/02/19.
• 2、 Hossain, Mohammad M.,Kawamura, Yasuhiko,Yamashita, Kazuyo,Tsukayama, Masao. "Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents". . p. 8625 - 8635. Retrieved 2007/10/03.