77376-71-7

Basic information

• Product Name: Benzoic acid, 2,6-dihydroxy-4-(phenylmethoxy)-, methyl ester
• CAS NO: 77376-71-7
• Molecular Formula: C15H14O5
• Molecular Weight: 274.273
• Mol File: 77376-71-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2,6-dihydroxy-4-(phenylmethoxy)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2,6-dihydroxy-4-(phenylmethoxy)-, methyl ester(77376-71-7)
• EPA Substance Registry System: Benzoic acid, 2,6-dihydroxy-4-(phenylmethoxy)-, methyl ester(77376-71-7)

Safety Data

• Hazardous Substances Data: 77376-71-7(Hazardous Substances Data)

Upstream product

• 3147-39-5 methyl 2,4,6-trihydroxybenzoate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 93652-78-9 4-(benzyloxy)-2,6-dimethoxybenzoic acid methyl ester 
• 185038-85-1 methyl 4-(benzyloxy)-2-hydroxy-6-methoxybenzoate 
• 185038-90-8 (R)-3,4,5,6,7,8,9,10-Octahydro-12-benzyloxy-14-methoxy-3-methyl-5,5-(prop-1,3-ylenedithio)-1H-2-benzoxacyclododecin-1-one 
• 185038-91-9 (S)-3,4,5,6,7,8,9,10-Octahydro-12-benzyloxy-14-methoxy-3-methyl-5,5-(prop-1,3-ylenedithio)-1H-2-benzoxacyclododecin-1-one 
• 185038-88-4 4-Benzyloxy-2-{5-[2-((S)-2-hydroxy-propyl)-[1,3]dithian-2-yl]-pentyl}-6-methoxy-benzoic acid methyl ester 
• 185038-89-5 (S)-4-Benzyloxy-2-methoxy-6-{5-[2-(2-hydroxypropyl)-1,3-dithian-2-yl]pentyl}benzoic acid 
• 185038-86-2 4-Benzyloxy-2-methoxy-6-trifluoromethanesulfonyloxy-benzoic acid methyl ester 
• 32885-81-7 (3S)-lasiodiplodin 
• 77376-72-8 methyl 4-benzyloxy-6-hydroxy-2-<4-(2-methoxy-6-methyltetrahydropyran-2-yl)butoxy>benzoate 
• 77376-73-9 4-benzyloxy-6-hydroxy-2-(9-hydroxy-5-oxodecyloxy)benzoic acid lactone 

Relevant articles and documents

DPPH (=2,2-diphenyl-1-picrylhydrazyl=2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl) radical-scavenging reaction of protocatechuic acid esters (=3,4-dihydroxybenzoates) in alcohols: Formation of bis-alcohol adduct

Protocatechuic acid esters (=3,4-dihydroxybenzoates) scavenge ca. 5 equiv. of radical in alcoholic solvents, whereas they consume only 2 equiv. of radical in nonalcoholic solvents. While the high radical-scavenging activity of protocatechuic acid esters in alcoholic solvents as compared to that in nonalcoholic solvents is due to a nucleophilic addition of an alcohol molecule at C(2) of an intermediate o-quinone structure, thus regenerating a catechol (=benzene-l,2-diol) structure, it is still unclear why protocatechuic acid esters scavenge more than 4 equiv. of radical (C(2) refers to the protocatechuic acid numbering). Therefore, to elucidate the oxidation mechanism beyond the formation of the C(2) alcohol adduct, 3,4-dihydroxy-2-methoxybenzoic acid methyl ester (4), the C(2) MeOH adduct, which is an oxidation product of methyl protocatechuate (1) in MeOH, was oxidized by the DPPH radical (=2,2-diphenyl-1-picrylhydrazyl) or o-chloranil (=3,4,5,6-tetrachlorocyclohexa- 3,5-diene-1,2-dione) in CD3-OD/(D6)acetone 3:1). The oxidation mixtures were directly analyzed by NMR. Oxidation with both the DPPH radical and o-chloranil produced a C(2),C(6) bis-methanol adduct (7), which could scavenge additional 2 equiv. of radical. Calculations of LUMO electron densities of o-quinones corroborated the regioselective nucleophilic addition of alcohol molecules with o-quinones. Our results strongly suggest that the regeneration of a catechol structure via a nucleophilic addition of an alcohol molecule with a o-quinone is a key reaction for the high radical-scavenging activity of protocatechuic acid esters in alcoholic solvents.