The Synthesis of Salicyl Glucuronide Derivatives

Authors

Emilio Arredondo, State University of IowaFollow
W. D. Paul, State University of IowaFollow
J. I. Routh, State University of IowaFollow

Document Type

Research

Abstract

The formation of glucuronides of salicylic acid as conjugated products in the body has been demonstrated for many years. Quick (1) in 1932 found salicyl diglucuronates in the urine of dogs fed salicylic acid, whereas, Kapp and Coburn (2) demonstrated the presence of both mono- and di-glucuronides of salicylic acid in human urine. Bray and coworkers (3) observed small amounts of ester linked glucuronides and ether linked glucuronides in the urine of rabbits fed salicylic acid. Recently, Smith et al. (4) using C¹⁴ carboxyl labeled salicyclic acid obtained evidence for the excretion of the two types of mono-glucuronides in human urine. One had an ester linkage between the carboxyl group of salicylic acid and a hydroxyl group of glucuronic acid. The other had an ether linkage between the hydroxyl groups of salicylic and glucuronic acids. To our knowledge, none of the salicyl glucuronides have been isolated in crystalline form. The present investigation was an attempt to synthesize both forms of salicyl-ß-d-glucuronide. Glucurone lactone was converted to the methyl ester (Goebel and Babers (5) which was then acetylated to the α- and ß-tetraacetyl methyl esters of glucuronic acid (6).

Publication Date

1954

Journal Title

Proceedings of the Iowa Academy of Science

Volume

61

Issue

1

First Page

217

Last Page

224

Copyright

©1954 Iowa Academy of Science, Inc.

Language

en

File Format

application/pdf

Recommended Citation

Arredondo, Emilio; Paul, W. D.; and Routh, J. I. (1954) "The Synthesis of Salicyl Glucuronide Derivatives," Proceedings of the Iowa Academy of Science, 61(1), 217-224.
Available at: https://scholarworks.uni.edu/pias/vol61/iss1/25