2 acetamidophenol

Phenacetin, acetaminophen, 2-acetamidophenol, coumarin, 7-hydroxy-comuarin (umbelliferone), flurbiprofen, dextromethorphan, dextrorphan, trazodone, thymol, bupropion, 6-hydroxy-bupropion, alprazolam, 1′-hydroxy-alprazolam, NADP⁺, isocitrate dehydrogenase, and DL-isocitrate were purchased from Sigma-Aldrich (St. Louis, MO, USA). Pronethalol was from Tocris (Minneapolis, MN, USA). Propofol was provided by Zeneca Pharmaceuticals (Wilmington, DE, USA). 4′-hydroxy-flurbiprofen, 2-fluoro-4-biphenyl-acetic acid, 4-hydroxy-propofol, chlorzoxazone, and 6-hydroxy-chlorzoxazone were purchased from Toronto Research Chemicals (Toronto, ON, Canada). S-Mephenytoin and 4-hydroxymephenytoin were purchased from Gentest (Corning, Corning, NY, USA). GW340416A, a chemical analogue of bupropion, was kindly provided by GlaxoSmithKline (Research Triangle Park, NC, USA). Omeprazole was purchased from BeanTown Chemical, Inc. (Hudson, NH, USA) and omeprazole sulfone was purchased from Cayman Chemical Company (Ann Arbor, MI, USA). Sodium hydroxide, potassium phosphate monobasic and potassium phosphate dibasic and EDTA were purchased from J.T. Baker (Center Valley, PA, USA). HPLC-grade acetonitrile and methanol were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Ultra-pure water was obtained using a Milli-Q^® Q-POD Millipore System (EMD Millipore, Burlington, MA, USA).

The 2-acetamido-phenol (2), 2-amino-3-nitrophenol (18), and N-(2-hydroxy-5-nitrophenyl)acetamide (5) were purchased from FluoroChem Ltd., Glossop, UK; N-(2-hydroxy-4-nitrophenyl)acetamide (8) was from Accela ChemBio Inc., San Diego, CA, USA. N-(2-hydroxy-3-nitrophenyl)acetamide (4) and N-(2-hydroxy-6-nitrophenyl)acetamide (7) were synthesized (see below). The 2-acetamido-phenol used for the incubation of microorganisms was purchased from Sigma-Merck, Taufkirchen, Germany. Solvents and reagents for synthesis were from Merck, if not stated otherwise. Sources of other chemicals are mentioned in the text. Glucosylated 5 was extracted Arabidopsis roots incubated with 5, as described below. Purchased, synthesized and identified isolated compounds were used as references.