5-O-(3-Methyl-2-butenyl) Kaempferol Tri-O-methoxymethyl Ether

Base Information

• Chemical Name: 5-O-(3-Methyl-2-butenyl) Kaempferol Tri-O-methoxymethyl Ether
• CAS No.: 143724-70-3
• Molecular Formula: C26H30O9
• Molecular Weight: 486.519
• DSSTox Substance ID: DTXSID40461818
• Mol file: 143724-70-3.mol

Synonyms:143724-70-3;5-O-(3-Methyl-2-butenyl) Kaempferol Tri-O-methoxymethyl Ether;3,7-bis(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]-5-(3-methylbut-2-enoxy)chromen-4-one;AGN-PC-006FPX;3,7-Bis(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]-5-[(3-methyl-2-butenyl)oxy]-4H-1-benzopyran-4-one;DTXSID40461818;FT-0671580;J-007866;5-O-(3-Methyl-2-butenyl)kaempferol tri-O-methoxymethyl ether;3,7-Bis(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-5-((3-methylbut-2-en-1-yl)oxy)-4H-chromen-4-one

Chemical Property of 5-O-(3-Methyl-2-butenyl) Kaempferol Tri-O-methoxymethyl Ether

Chemical Property:

• PSA: 94.82000
• LogP: 4.75310
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 486.18898253
• Heavy Atom Count: 35
• Complexity: 722

Purity/Quality:

97% ^*data from raw suppliers

5-O-(3-Methyl-2-butenyl)KaempferolTri-O-methoxymethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCOC1=CC(=CC2=C1C(=O)C(=C(O2)C3=CC=C(C=C3)OCOC)OCOC)OCOC)C
• Uses: Intermediate in the preparation of Icaritin metabolites.

Technology Process of 5-O-(3-Methyl-2-butenyl) Kaempferol Tri-O-methoxymethyl Ether

There total 11 articles about 5-O-(3-Methyl-2-butenyl) Kaempferol 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: 95.0%

3,4',7-tris-O-methoxymethylkaempferol (143724-66-7) + prenyl bromide (870-63-3) → 5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol (143724-70-3)

Guidance literature:

3,4',7-tris-O-methoxymethylkaempferol; With potassium carbonate; In acetone; at 20 ℃; for 1h;

prenyl bromide; In acetone; at 50 ℃; for 5h;

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:

kaempferol (520-18-3) → 5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol (143724-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / N,N-diisopropylethylamine / dimethylformamide / 20 °C

2: 75 percent / tetrabutylammonium hydroxide hydrate / CH₂Cl₂; toluene / 20 °C

With tetra(n-butyl)ammonium hydroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm040770b

upstream raw materials:

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

prenyl bromide

kaempferol

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

Downstream raw materials:

5-hydroxy-8-prenyl-3,4',7-tris-O-methoxymethylkaempferol

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

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

8-prenylkaempferol