1407510-65-9

Basic information

• Product Name: methyl 5-allyl-2,3-dihydroxybenzoate
• Synonyms: methyl 5-allyl-2,3-dihydroxybenzoate
• CAS NO: 1407510-65-9
• Molecular Weight: 208.214
• Mol File: 1407510-65-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 5-allyl-2,3-dihydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-allyl-2,3-dihydroxybenzoate(1407510-65-9)
• EPA Substance Registry System: methyl 5-allyl-2,3-dihydroxybenzoate(1407510-65-9)

Safety Data

• Hazardous Substances Data: 1407510-65-9(Hazardous Substances Data)

Upstream product

• 85614-43-3 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester 

Relevant articles and documents

Siderophore-mediated cargo delivery to the cytoplasm of escherichia coli and pseudomonas aeruginosa: Syntheses of monofunctionalized enterobactin scaffolds and evaluation of enterobactin-cargo conjugate uptake

The design and syntheses of monofunctionalized enterobactin (Ent, l- and d-isomers) scaffolds where one catecholate moiety of enterobactin houses an alkene, aldehyde, or carboxylic acid at the C5 position are described. These molecules are key precursors to a family of 10 enterobactin-cargo conjugates presented in this work, which were designed to probe the extent to which the Gram-negative ferric enterobactin uptake and processing machinery recognizes, transports, and utilizes derivatized enterobactin scaffolds. A series of growth recovery assays employing enterobactin-deficient E. coli ATCC 33475 (ent-) revealed that six conjugates based on l-Ent having relatively small cargos promoted E. coli growth under iron-limiting conditions whereas negligible-to-no growth recovery was observed for four conjugates with relatively large cargos. No growth recovery was observed for the enterobactin receptor-deficient strain of E. coli H1187 (fepA-) or the enterobactin esterase-deficient derivative of E. coli K-12 JW0576 (fes-), or when the d-isomer of enterobactin was employed. These results demonstrate that the E. coli ferric enterobactin transport machinery identifies and delivers select cargo-modified scaffolds to the E. coli cytoplasm. Pseudomonas aeruginosa PAO1 K648 (pvd-, pch-) exhibited greater promiscuity than that of E. coli for the uptake and utilization of the enterobactin-cargo conjugates, and growth promotion was observed for eight conjugates under iron-limiting conditions. Enterobactin may be utilized for delivering molecular cargos via its transport machinery to the cytoplasm of E. coli and P. aeruginosa thereby providing a means to overcome the Gram-negative outer membrane permeability barrier.