20189-90-6

Basic information

• Product Name: Benzoic acid, 3,4,5-tris(acetyloxy)-, methyl ester
• CAS NO: 20189-90-6
• Molecular Formula: C14H14O8
• Molecular Weight: 310.26
• Mol File: 20189-90-6.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3,4,5-tris(acetyloxy)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3,4,5-tris(acetyloxy)-, methyl ester(20189-90-6)
• EPA Substance Registry System: Benzoic acid, 3,4,5-tris(acetyloxy)-, methyl ester(20189-90-6)

Safety Data

• Hazardous Substances Data: 20189-90-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 852052-01-8 1-O-galloyl-6-O-luteoyl-α-D-glucose 
• 108-24-7 acetic anhydride 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 445434-08-2 4-geranoyl-3-acetoxy-5-hydroxysinapic acid methyl ester 
• 439944-31-7 4-geranoyl-3,5-diacetoxybenzoic acid methyl ester 
• 79043-20-2 (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 520-31-0 tricetin 
• 70475-59-1 3,4,5-triacetoxybenzoyl chloride 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 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 

Relevant articles and documents

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).

PHYTOCHEMICAL ANTIBIOTIC CONJUGATES AS INHIBITORS OF LACTOBACILLALES BACTERIA

The present application relates to treatments for bacterial infections. For example, the application relates to the use a gallic acid-sulfamethoxazole conjugate for treatment of a Lactobacillales bacterial infection or a disease, disorder or condition arising from a Lactobacillales bacterial infection.

Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri

Bioassay-guided fractionation of boiled aqueous extracts from the whole plant of Phyllanthus niruri led to the isolation of 1-O-galloyl-6-O-luteoyl- α-D-glucose (1), with IC50 values of 4.7 μg/mL against Babesia gibsoni and 1.4 μg/mL against Plasmodium falciparum in vitro. The known compounds β-glucogallin (2), quercetin 3-O-β-D-glucopyranosyl- (2→1)-O-β-D-xylopyranoside (3), β-sitosterol, and gallic acid were also isolated. Structures of these compounds were elucidated on the basis of their chemical and spectroscopic data.

Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.

Novel chemoselective de-esterification of esters of polyacetoxy aromatic acids by lipases

Candida cylindracea lipase (CCL) and porcine pancreatic lipase (PPL) have been used for deacetylation of peracetates of methyl and ethyl esters of six different polyphenolic acids in organic solvents. Exclusive de-esterification of the ester groups derived from the phenolic hydroxy and aliphatic acid over the ester group of the aromatic acid and aliphatic alcohol has been achieved affording the corresponding esters of phenolic acids in as high yields as 90-97%. The results have been corroborated with the mechanism of lipase action.