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

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

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 5 , 2016

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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.

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

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Article Details

VOLUME: 13
ISSUE: 5
Year: 2016
Page: [338 - 342]
Pages: 5
DOI: 10.2174/1570178613666160524160916
Price: $58

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