An Improved Synthesis of the Antimicrobial Thymol- and Carvacrol-β-D-Glucopyranosides

Title:An Improved Synthesis of the Antimicrobial Thymol- and Carvacrol-β-D-Glucopyranosides

Volume: 13 Issue: 5

Author(s): Melanie Walker, Ashlee Robison and William R. Collins

Affiliation:

Keywords: Campylobacter, carvacrol, carvacrol-β-D-glucopyranoside, foodborne pathogen, gut bacteria, phase-transfer reactions, thymol, thymol-β-D-glucopyranoside.

Abstract: Thymol (1) and Carvacrol (2) are monoterpenoid natural products that display in vitro antimicrobial activity against Campylobacter jejuni and coli, food-borne pathogens found in animal distal guts/avian crops that commonly contaminate meat and poultry during processing. Recently, it has been shown that thymol-β-D-glucopyranoside (3), a glucosylated variant of the free monoterpenoid, also induces Campylobacter reductions within collected gut contents. Unfortunately, commercial sources of 3 are prohibitively expensive for large-scale use, and syntheses of glucosylated variants of either thymol or carvacrol are low yielding. Herein we report on an improved synthesis of both 3 as well as carvacrol-β- D-glucopyranoside (4). This synthesis utilizes phase transfer catalysis glycosylation conditions in lieu of the previously reported, low-yielding and expensive Koenigs-Knorr reactions.

Cite this article as:

Walker Melanie, Robison Ashlee and Collins R. William, An Improved Synthesis of the Antimicrobial Thymol- and Carvacrol-β-D-Glucopyranosides, Letters in Organic Chemistry 2016; 13 (5) . https://dx.doi.org/10.2174/1570178613666160524160916