DesMethyl Icaritin Tri-O-MethoxyMethyl Ether

Base Information

• Chemical Name: DesMethyl Icaritin Tri-O-MethoxyMethyl Ether
• CAS No.: 143724-76-9
• Molecular Formula: C26H30O9
• Molecular Weight: 486.511
• Mol file: 143724-76-9.mol

Synonyms:DesMethyl Icaritin Tri-O-MethoxyMethyl Ether;3,4',5,7-Tetrahydroxy-8-(3-Methyl-2-butenyl)flavone Tri-O-MethoxyMethyl Ether;4'-DesMethylicaritin Tri-O-MethoxyMethyl Ethe

Chemical Property of DesMethyl Icaritin Tri-O-MethoxyMethyl Ether

Chemical Property:

• PSA: 105.82000
• LogP: 4.62240
• Solubility.: Acetone, Chloroform, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Desmethyl Icaritin Tri-O-methoxymethyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected Icaritin metabolite.

Technology Process of DesMethyl Icaritin Tri-O-MethoxyMethyl Ether

There total 11 articles about DesMethyl Icaritin Tri-O-MethoxyMethyl Ether 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: 82.0%

5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol (143724-70-3) → 5-hydroxy-8-prenyl-3,4',7-tris-O-methoxymethylkaempferol (143724-76-9)

Guidance literature:

With N,N-diethylaniline; at 190 ℃; for 0.75h; Microwave irradiation; Inert atmosphere;

DOI:10.1002/ejoc.201403689

Reference yield: 24.0%

3,4',7-tris-O-methoxymethylkaempferol (143724-66-7) + prenyl bromide (870-63-3) → 5-hydroxy-8-prenyl-3,4',7-tris-O-methoxymethylkaempferol (143724-76-9) + 5-Hydroxy-3,7-bis-methoxymethoxy-2-(4-methoxymethoxy-phenyl)-6-(3-methyl-but-2-enyl)-chromen-4-one (143724-72-5) + 5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol (143724-70-3)

Guidance literature:

With potassium carbonate; In methanol; for 10h; Ambient temperature;

Reference yield:

2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone (118075-12-0) → 5-hydroxy-8-prenyl-3,4',7-tris-O-methoxymethylkaempferol (143724-76-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iodine / dimethyl sulfoxide / 24 h / Reflux

2.1: Oxone; sodium carbonate; sodium hydrogencarbonate / dichloromethane; acetone / 5 h / 0 °C

2.2: 0.5 h / 20 °C

3.1: hydrogenchloride / ethanol; water / 0.5 h / 20 °C

4.1: potassium carbonate / acetone / 0.5 h / 20 °C

4.2: 2 h / 20 °C

5.1: potassium carbonate / acetone / 1 h / 20 °C

5.2: 5 h / 50 °C

6.1: N,N-diethylaniline / 0.75 h / 190 °C / Microwave irradiation; Inert atmosphere

With hydrogenchloride; Oxone; iodine; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; N,N-diethylaniline; In ethanol; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1002/ejoc.201403689

upstream raw materials:

3,4',7-tris-O-methoxymethylkaempferol

prenyl bromide

kaempferol

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

Downstream raw materials:

8-prenylkaempferol

6,6-dimethyldihydropyran (2,3:7,8)-5,4'-dihydroxyflavonol

8-(3-hydroxy-3-methylbutyl)-5,7,4'-trihydroxyflavonol

8-prenyl-3,7,4'-trihydroxy-5-methoxyflavone

Refernces

• 1、 Fukai, Toshio,Nomura, Taro. "1H-NMR CHEMICAL SHIFT OF THE FLAVONOL 5-HYDROXY PROTON AS A CHARACTERIZATION OF 6- OR 8-ISOPRENOID SUBSTITUTION". . p. 1213 - 1225. Retrieved 2007/10/02.