Di-O-methylbergenin

Base Information

• Chemical Name: Di-O-methylbergenin
• CAS No.: 33815-57-5
• Molecular Formula: C16H20O9
• Molecular Weight: 356.329
• Mol file: 33815-57-5.mol

Synonyms:2.3-Dihydroxy-2-cyclopenten-1-on;2-hydroxytetronic acid;8,10-di-O-methylbergenin;3,4-Dihydroxy-5H-furan-2-on;dimethylbergenin;3,4-dihydroxy-5H-furan-2-one;tri-O-methylnorbergenin;

Chemical Property of Di-O-methylbergenin

Chemical Property:

• Melting Point: 194-196 °C
• Boiling Point: 532.9±50.0 °C(Predicted)
• PKA: 12.74±0.60(Predicted)
• PSA: 123.91000
• Density: 1.417±0.06 g/cm3(Predicted)
• LogP: -0.59460

Purity/Quality:

98%min ^*data from raw suppliers

Di-O-methylbergenin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Di-O-methylbergenin

There total 3 articles about Di-O-methylbergenin 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 11-O-(3',4',5'-trihydroxygalloyl)bergenin (82958-44-9) → 3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) + 3,4-dihydroxy-2-(hydroxymethyl)-8,9,10-trimethoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen6(10bH)-one (33815-57-5)

Guidance literature:

With trifluoroacetic acid; Yield given. Multistep reaction. Yields of byproduct given; 1) water, reflux, 30 h; 2) Et₂O, 4 deg C, 2.5 h;

DOI:10.1016/S0031-9422(00)82451-6

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + bergenin-4-O-gallate (82958-45-0) → 3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) + 3,4-dihydroxy-2-(hydroxymethyl)-8,9,10-trimethoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen6(10bH)-one (33815-57-5)

Guidance literature:

With trifluoroacetic acid; Yield given. Multistep reaction. Yields of byproduct given; 1) water, reflux, 30 h; 2) Et₂O, 4 deg C, 2.5 h;

DOI:10.1016/S0031-9422(00)82451-6

Reference yield:

methanol (67-56-1) + C61H66O31 (126132-67-0) → D-Glucose (2280-44-6) + 3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) + trimethyl octa-O-methylvaloneate (59252-29-8,118132-51-7,118964-21-9) + di-O-methylbergenin (33815-57-5)

Guidance literature:

With sodium methylate; for 1.5h; Product distribution; Ambient temperature; methanolysis;

DOI:10.1248/cpb.37.2940

upstream raw materials:

diazomethane

11-O-(3',4',5'-trihydroxygalloyl)bergenin

bergenin-4-O-gallate

methanol

Refernces

• 1、 Yoshida, Takashi,Seno, Kaoru,Takama, Yukiko,Okuda, Takuo. "BERGENIN DERIVAVTIVES FROM MALLOTUS JAPONICUS". . p. 1180 - 1182. Retrieved 2007/10/02.