Lupiwighteone

Base Information

• Chemical Name: Lupiwighteone
• CAS No.: 104691-86-3
• Molecular Formula: C20H18O5
• Molecular Weight: 338.36
• UNII: S5W46B3BUM
• DSSTox Substance ID: DTXSID601132953
• Nikkaji Number: J397.729C
• Wikidata: Q104392370
• Metabolomics Workbench ID: 22333
• ChEMBL ID: CHEMBL3616491
• Mol file: 104691-86-3.mol

Synonyms:lupiwighteone

Chemical Property of Lupiwighteone

Chemical Property:

• Vapor Pressure: 3.25E-14mmHg at 25°C
• Melting Point: 133-135℃
• Boiling Point: 583.5°C at 760 mmHg
• Flash Point: 211.8°C
• PSA: 90.90000
• Density: 1.351g/cm³
• LogP: 4.08550
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 338.11542367
• Heavy Atom Count: 25
• Complexity: 554

Purity/Quality:

99%, ^*data from raw suppliers

Lupiwighteone ^*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)C(=CO2)C3=CC=C(C=C3)O)C
• Uses: Lupiwighteone 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 Lupiwighteone

There total 20 articles about Lupiwighteone 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: 93.0%

4',7-bis(benzoyloxy)-5-acetoxy-8-(3-methyl-2-butenyl)isoflavone (210166-33-9) → lupiwighteone (104691-86-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 50 ℃; for 0.833333h;

Reference yield: 84.0%

4-(7-acetoxy-5-hydroxy-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)phenyl acetate (583037-96-1) → lupiwighteone (104691-86-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; methanol; at 20 - 60 ℃;

DOI:10.1016/S0040-4020(03)00579-9

Reference yield: 75.0%

5,7,4'-trimethoxymethoxy-8-C-prenylisoflavone → lupiwighteone (104691-86-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 0 - 50 ℃; for 6h;

DOI:10.1016/j.bmcl.2015.08.059

upstream raw materials:

4',7-bis(benzoyloxy)-5-acetoxy-8-(3-methyl-2-butenyl)isoflavone

4-(7-acetoxy-5-hydroxy-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)phenyl acetate

4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate

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

Downstream raw materials:

atalantoflavone

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.
• 2、 Sun, Hua,Li, Yashan,Zhang, Xiaoting,Lei, Yanan,Ding, Weina,Zhao, Xue,Wang, Haomeng,Song, Xiaotong,Yao, Qingwei,Zhang, Yongmin,Ma, Ying,Wang, Runling,Zhu, Tao,Yu, Peng. "Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones". . p. 4567 - 4571. Retrieved 2015/10/12.