Supporting Information Cover Sheet
Occurrence and behavior of chiral anti-inflammatory drug naproxen in an aquatic environment
Toshinari Suzuki†*, Yuki Kosugi†, Mitsugu Hosaka†, Tetsuji Nishimura‡, and Dai Nakae†
†Division of Environmental Science, Tokyo Metropolitan Institute of Public Health, Hyakunin-cho,
3-24-1, Shinjuku-ku, Tokyo 169-0073, Japan
‡ Faculty of Pharmaceutical Sciences, Teikyo Heisei University, Nakano, 4-21-2, Nakano-ku, Tokyo
164-8530, Japan
Number of pages: 3
Number of text: 1
Number of figure: 2
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Text S1
Synthesis of DM-NAP
A 520 mg of (Rac)-NAP was desmethylated by 570 mg of boron bromide in 20 mL of
dichloromethane by stirring at room temperature in darkness for 12 h. The excess boron bromide was
hydrolyzed by adding 100 mL of water, and DM-NAP was extracted with 20 mL of dichloromethane.
The dichloromethane solution was dehydrated with sodium sulfate anhydride (Na2SO4) and
concentrated by rotary evaporator at 50°C. DM-NAP was recrystallized from dichloromethane at 4°C.
The yield of DM-NAP was 26%. DM-NAP was confirmed by GC/MS after trimethylsilylation by N,Obis(trimethylsilyl)trifluoroacetamide (BSTFA, Wako Pure Chemicals Co.). The purity of DM-NAP was
more than 95%, and its fragmentation (m/z) is as follows: 360 (molecular ion, 10%), 243 (40%), and 79
(base peak, 100%).
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Figures:
DM-naproxen
Relative intensity (%)
DM-naproxen
naproxen
naproxen
TIC
Retention time (min)
Figure S1. GC/MS chromatograms of naproxen and DM-naproxen after trimethylsilyl derivatization.
Concentration of (S)-naproxen (µg L-1)
1000
y = 105.69e -0.271x
R² = 0.9953
100
10
1
0
1
2
3
4
5
6
7
8
Irradiation time (h)
Figure S2. Photodegrdation of (S)-NAP in purified and Tama River water.
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