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1 Migration of Parabens, Bisphenols, Benzophenone-Type UV filters, Triclosan, and Triclocarban from Teethers and Its Implications for Infant Exposure Alexandros G. Asimakopoulos a,, Madhavan Elangovan a,, Kurunthachalam Kannan a,b* a Wadsworth Center, New York State Department of Health, and Department of Environmental Health Sciences, School of Public Health, State University of New York at Albany, Empire State Plaza, P.O. Box 509, Albany, New York , United States. b Biochemistry Department, Faculty of Science and Bioactive Natural Products Research Group, King Abdulaziz University, Jeddah, Saudi Arabia. *Corresponding author: K. Kannan Wadsworth Center Empire State Plaza, P.O. Box 509 Albany, NY Tel: Fax: kurunthachalam.kannan@health.ny.gov For submission to: Environmental Science & Technology These authors contributed equally. Number of pages: 12 Number of figures: 4 Number of tables: 7 Supporting Information S1
2 Fig. 1S. Migration trial with Milli-Q water. S2
3 Fig. 2S. Migration trial with methanol. S3
4 Fig. 3S. Differences between the median of the gel-filled teethers with the water-filled and solid teethers for MeP, EtP, PrP, and BuP. S4
5 % Total Exctracted Amount 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% Water Methanol Fig. 4S. Migration profiles of parabens, bisphenols, benzophenones and antimicrobial agents from baby teethers into water and methanol extracts; Values in Y-axis refers to % of the total extraction. Values in X-axis refer to methyl- [MeP], ethyl- [EtP], propyl- [PrP], butyl- [BuP], benzyl- [BezP] heptyl- [HeP] parabens, 4-hydroxy benzoic acid [4-HB], 3,4-dihydroxy benzoic acid [3,4-DHB], methyl-protocatechuic acid [OH-MeP] and ethyl-protocatechuic acid [OH-EtP], 2,2-bis(4-hydroxyphenyl)propane [BPA], 4,4 - (hexafluoroisopropylidene)-diphenol [BPAF], 4,4 -(1-phenylethylidene) bisphenol [BPAP], 4,4 -sulfonyldiphenol [BPS], 4,4 - dihydroxydiphenylmethane [BPF], 4,4 -(1,4-phenylenediisopropylidene) bisphenol [BPP], 4,4 -cyclo-hexylidenebisphenol [BPZ], 2,2-bis(4-hydroxyphenyl)butane [BPB], and 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene [BPM], 2-hydroxy-4 - methoxybenzophenone [BP-3], 2,4-dihydroxybenzophenone [BP-1], 2,2,4,4-tetrahydroxybenzophenone [BP-2], and 4- hydroxybenzophenone [4-OH-BP], triclosan [TCS], and triclocarban [TCC]. S5
6 Table S1. Tandem MS transitions of the target analytes and internal standards Compound Precursor ions (m/z) Product ions (m/z) BPA BPB BPS BPAF BPAP BPF BPZ BPP BPM C 12 -BPA C 12 -BPS C 12 -BPAF MeP EtP PrP BuP BezP HeP HB ,4-DHB OH-MeP OH-EtP TCS TCC C 6 -MeP C 6 -EtP C 6 -PrP C 6 -BuP D 4 -BzP D 4 -HeP C 6-4-HB C 6 -TCC BP BP BP BP OH-BP C 6 -BP S6
7 Table S2. Limits of Detection (LODs) and limits of quantification (LOQs) Target Chemicals LODs (ng/ml) LOQs (ng/ml) BPA BPAF BPAP BPS BPF BPP BPZ BPB BPM MeP EtP PrP BuP BezP HeP HB ,4-DHB OH-MeP OH-EtP BP BP BP BP OH-BP TCS TCC S7
8 Table S3. Reagent blank amounts (ng) Target Chemicals Mean (SD; N=9) ng Milli-Q water trial Mean (SD; N=9) ng Methanol trial BPA 0.42 (0.21) 0.68 (0.21) BPAF (0.010) (0.022) BPAP (0.042) (0.030) BPS 0.12 (0.064) 0.18 (0.18) BPF 0.74 (0.67) 0.46 (0.32) BPP - - BPZ (0.023) (0.033) BPB (0.017) (0.038) BPM (0.054) 0.12 (0.16) MeP 0.70 (0.82) 0.40 (0.40) EtP 0.14 (0.21) 0.11 (0.11) PrP 0.20 (0.88) 0.14 (0.067) BuP (0.008) (0.005) BezP - - HeP HB 3.20 (6.8) 1.91 (0.55) 3,4-DHB 0.47 (1.42) 0.36 (0.25) OH-MeP (0.064) (0.026) OH-EtP (0.016) (0.014) BP (0.13) 0.40 (0.23) BP (0.11) - BP (0.14) - BP (0.096) 0.14 (0.12) 4-OH-BP (0.075) 0.13 (0.14) TCS (0.12) (0.12) TCC (0.007) (0.010) S8
9 Table S4. Mean absolute and relative recoveries (N=7, 50 ng/ml) of the target analytes Compound (internal standard used for calculating the relative recoveries and quantification) Absolute recovery % from Milli-Q water/methanol solution Relative recovery % from Milli-Q water/methanol solution BPA ( 13 C 12 -BPA) 49.6/ /80.3 BPB ( 13 C 12 -BPA) 70.5/ /110.1 BPS ( 13 C 12 -BPS) 56.5/ /110.1 BPAF ( 13 C 12 -BPAF) 68.0/ /95.0 BPAP ( 13 C 12 -BPA) 149.5/ /75.7 BPF ( 13 C 12 -BPA) 61.8/ /74.3 BPZ ( 13 C 12 -BPAF) 67.0/ /75.8 BPP ( 13 C 12 -BPA) 33.0/ /68.9 BPM ( 13 C 12 -BPA) 75.8/ /82.4 MeP ( 13 C 6 -MeP) 94.6/ /75.2 EtP ( 13 C 6 -EtP) 104.1/ /72.4 PrP ( 13 C 6 -PrP) 100.5/ /76.9 BuP ( 13 C 6 -BuP) 110.8/ /78.6 BezP ( 2 D 4 -BezP) 120.8/ /81.7 HeP ( 2 D 4 -HeP) 113.0/ / HB ( 13 C 6-4-HB) 68.0/ /80.5 3,4-DHB ( 13 C 6-4-HB) 41.7/ /74.2 OH-MeP ( 13 C 6 -MeP) 81.6/ /98.0 OH-EtP ( 13 C 6 -EtP) 84.7/ /99.0 TCS ( 13 C 12 -TCC) 53.5/ /72.8 TCC ( 13 C 6 -TCC) 70.9/ /74.4 BP-1 ( 13 C 6 -BP-3) 51.1/ /129.5 BP-2 ( 13 C 6 -BP-3) 60.0/ /68.9 BP-3 ( 13 C 6 -BP-3) 68.2/ /73.0 BP-8 ( 13 C 6 -BP-3) 58.5/ / OH-BP ( 13 C 6 -BP3) 88.8/ /132.7 S9
10 Table S5. Amounts of methyl- (MeP), ethyl- (EtP), propyl- (PrP), butyl- (BuP), benzyl- (BzP) parabens, 4-hydroxy benzoic acid [4- HB], 3,4-dihydroxy benzoic acid [3,4-DHB], methyl-protocatechuic acid [OH-MeP], and ethyl-protocatechuic acid [OH-EtP] leached from baby teethers into water and methanol extracts. Parabens MeP EtP PrP BuP BezP Migration to water/methanol/total* W M T W M T W M T W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) Parabens HeP 4-HB 3,4-DHB OH-MeP OH-EtP Migration to water/methanol/total* W M T W M T W M T W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) *total (T): Sum of amounts from water and methanol migration trials; W=Water extract; M=methanol extract. S10
11 Table S6. Amounts of 2,2-bis(4-hydroxyphenyl)propane [BPA], 4,4 -(hexafluoroisopropylidene)-diphenol [BPAF], 4,4 -(1- phenylethylidene) bisphenol [BPAP], 4,4 -sulfonyldiphenol [BPS], 4,4 -dihydroxydiphenylmethane [BPF], 4,4 -(1,4- phenylenediisopropylidene) bisphenol [BPP], 4,4 -cyclo-hexylidenebisphenol [BPZ], 2,2-bis(4-hydroxyphenyl)butane [BPB], and 1,3- bis(2-(4-hydroxyphenyl)-2-propyl)benzene [BPM] leached from baby teethers into water and methanol extracts. Bisphenol derivatives BPA BPS BPF BPB Migration to water/methanol/total* W M T W M T W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) Bisphenol derivatives BPZ BPAP BPAF BPP BPM Migration to water/methanol/total* W M T W M T W M T W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) *total (T): Sum of amounts from water and methanol migration trials; W=Water extract; M=methanol extract. S11
12 Table S7. Amounts of 2-hydroxy-4-methoxybenzophenone [BP-3], 2,4-dihydroxybenzophenone [BP-1], 2,2-dihydroxy-4- methoxybenzophenone [BP-8], 2,2,4,4-tetrahydroxybenzophenone [BP-2], 4-hydroxybenzophenone [4-OH-BP], triclosan [TCS], and triclocarban [TCC] leached from baby teethers into water and methanol extracts. Benzophenones BP-3 BP-1 BP-2 BP-8 4-OH-BP Migration to water/methanol/total* W M T W M T W M T W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) Antimicrobials TCS TCC Migration to water/methanol/total* W M T W M T Detected samples (out of 59) Average (ng) Median (ng) Max. Detected (ng) Min. Detected (ng) *total (T): Sum of amounts from water and methanol migration trials; W=Water extract; M=methanol extract. S12
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