CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Environmental Chemistry   
Environmental Chemistry
Journal Banner
  Environmental problems - Chemical approaches
blank image Search
blank image blank image
blank image
  Advanced Search

Journal Home
About the Journal
Editorial Structure
Online Early
Current Issue
Just Accepted
All Issues
Special Issues
Research Fronts
Virtual Issues
Sample Issue
For Authors
General Information
Submit Article
Author Instructions
Open Access
For Referees
Referee Guidelines
Review an Article
For Subscribers
Subscription Prices
Customer Service

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter logo LinkedIn


Article << Previous     |     Next >>   Contents Vol 7(5)

Investigation of an amoxicillin oxidative degradation product formed under controlled environmental conditions

Igal Gozlan A B, Adi Rotstein A B, Dror Avisar A C

A The Hydro-chemistry Laboratory, Department of Geography and Environmental Studies, Tel Aviv University, Tel Aviv, 69978, Israel.
B The Porter School of Environmental Studies, Tel Aviv University, Tel Aviv, 69978, Israel.
C Corresponding author. Email: droravi@post.tau.ac.il
PDF (635 KB) $25
 Export Citation

Environmental context. Although amoxicillin is a widely used antibiotic, it is yet to be detected in the aquatic environment. This study traces the production of the amoxicillin-S-oxide degradation product, and shows that it is consistently obtained only under sunlight irradiation. This is the first study to demonstrate the formation, under controlled environmental conditions, of this chemically stable product of amoxicillin.

Abstract. Amoxicillin (AMX) is a widely used penicillin-type antibiotic, and its presence in the environment has been widely investigated. The formation and structure of an oxidised degradation product (DP) of AMX are described in the present work. The experiments were carried out in buffer solution (pH 7.5) containing AMX at a concentration of 100 μg mL–1, with and without acid and in field secondary effluent. The DP, AMX-S-oxide (sulfoxide), was consistently obtained only under sunlight irradiation and was significantly augmented by the addition of humic acid (5 mg L–1) and mainly in field secondary effluent, which acts as a natural photo-sensitiser. The structure of the AMX-S-oxide DP was determined by an LC-MS technique using a mobile phase of deuterated and non-deuterated solvents. A 1H NMR spectrum was obtained for the pure compound isolated by preparative HPLC. Further confirmation of the AMX-S-oxide structure was achieved by comparison of its UV spectrum with those of the two oxidation products, AMX-S-oxide and hydroxylated AMX, obtained by the ozonolysis of AMX.

Keywords: AMX-S-oxide, antibiotic residues, LC-MS, NMR, secondary effluent.

Subscriber Login

Legal & Privacy | Contact Us | Help


© CSIRO 1996-2015