13089-97-9

Basic information

• Product Name: Benzoic acid, 3,5-bis(acetyloxy)-4-methoxy-, methyl ester
• CAS NO: 13089-97-9
• Molecular Formula: C13H14O7
• Molecular Weight: 282.25
• Mol File: 13089-97-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3,5-bis(acetyloxy)-4-methoxy-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3,5-bis(acetyloxy)-4-methoxy-, methyl ester(13089-97-9)
• EPA Substance Registry System: Benzoic acid, 3,5-bis(acetyloxy)-4-methoxy-, methyl ester(13089-97-9)

Safety Data

• Hazardous Substances Data: 13089-97-9(Hazardous Substances Data)

Upstream product

• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 99-24-1 methyl galloate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 29970-29-4 3,5-diacetoxy-4-hydroxy-benzoic acid 
• 83553-80-4 3,5-Di-O-acetylgallussaeuremethylester 

Downstream Products

• 54186-41-3 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 24093-82-1 3,5-bis(benzyloxy)-4-methoxybenzyl chloride 
• 54186-42-4 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 54186-43-5 N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 
• 79043-20-2 (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline 
• 1240795-78-1 (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one 
• 76661-04-6 Acetic acid 2,4-diacetoxy-6-acetoxymethyl-3-methoxy-phenyl ester 
• 76661-05-7 3-Hydroxy-5-hydroxymethyl-2-methoxy-[1,4]benzoquinone 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 63542-40-5 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol 
• 4319-02-2 4-O-methylgallic acid 

Relevant articles and documents

Synthesis, crystal structure, and growth inhibition of human hepatoma cell (HepG2) of polyphenolic compounds based on gallates

Seven compounds (1-7) based on gallate were synthesized and characterized by elemental analysis, 1H NMR, and MS spectra. 2-(3,5-Dibenzyloxy-4- methoxy)phenyl-2-propanol (6) was a new compound. Methyl 3,5-dihydroxy-4- methoxybenzoate (3), methyl 3,5-dibenzyloxy-4-methoxybenzoate (4), 3,5-dibenzyloxy-4-methoxybenzyl alcohol (5), and compound 6 were structurally determined by single-crystal X-ray diffraction for the first time. Crystallography data for 3: space group P21212 1; a = 4.0750(8) A, b = 7.5880(15) A, c = 29.802(6) A; V = 921.5(3) A3 Z = 4. 4: space group P-1; a = 10.068(2) A b = 10.499(2) A, c = 11.388(2) A; α = 76.84(3)°, β= 66.79(3)°, γ = 64.10(3)°; V = 993.0(3) A3, Z = 2. 5: space group P-1; a = 8.1410(16) A, b = 8.7590(18) A, c = 12.879(3) A; α = 91.66(3)°, β= 94.69(3)°, γ = 91.73(3)°; V = 914.4(3) A3; Z = 2. 6: space group P21/c; a = 5.8100(12) A, b = 15.778(3) A, c = 23.237(5) A; β= 96.09(3)°; V = 2118.1(7) A3; Z = 4. All of the seven compounds were evaluated for the inhibition of growth of human hepatoma (HepG2) cells. Comparison with the positive-control 5-fluorouracil (IC50 51.6 μmol/L), 5 showed stronger cytotoxic activity with an IC50 around 15.3 μmol/L, while IC50 value of 3 was 90.3 μmol/L. The effect of slight structural variations in this series of compounds was found to cause a marked change in their activity against HepG2 cells.

Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin

A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.

Selective hydroxy group protection of gallic acid

An efficient procedure allowing selective differentiation of the 4-hydroxy group of methyl gallate was reported.