Abstract
Bisphenol A (BPA) is metabolized by a Gram-negative aerobic bacterium via a novel pathway involving oxidative skeletal rearrangement of the BPA. Oxidation of the aliphatic methyl group of BPA leads to coproduction of the methyl-hyroxylated 2,2-bis(4-hydroxyphenyl)-1-propanol and a skeletally rearranged triol 1,2-bis(4-hydroxyphenyl)-2-propanol. The major route of metabolism (> 80%) is through the rearrangement. The 1,2-bis(4-hydroxyphenyl)-2-propanol is dehydrated to 4,4'-dihydroxy-alpha-methylstilbene, which is rapidly cleaved by oxidation to 4-hydroxybenzaldehyde and 4-hydroxyacetophenone. 4-Hydroxybenzaldehyde is oxidized to 4-hydroxybenzoic acid. Both 4-hydroxybenzoic acid and 4-hydroxyacetophenone are mineralized. The minor product of BPA hydroxylation, 2,2-bis(4-hydroxyphenyl)-1-propanol, is further oxidized to form both 2,2-bis(4-hydroxyphenyl)propanoic acid and a skeletally rearranged tetraol, 2,3-bis(4-hydroxyphenyl)-1,2-propanediol. As is the case in the hydroxylation of BPA, the major product is skeletally rearranged. 2,3-Bis(4-hydroxyphenyl)-1,2-propanediol is slowly transformed to 4-hydroxyphenacyl alcohol.
Highlights
Bisphenol A (BPA)is metabolized by a Gram-negative t h e benzylic methyl group to 4-hydroxybenzyl alcohol before aerobic bacterium via a novel pathway involving oxida- further oxidation to 3,4-dihydroxybenzoic acid(8)
Oxidation otfhe A Gram-negative aerobic bacterium, designated straiMn V1, aliphatic methyl group ofBPA leads to coproduction of that is capableof growth onBPA as the sole source of carbon (9)
The methyl-hydroxylated 2,2-bis(4-hydroxyphenyl)-l- was studied to determine the biochemical pathway by which propanol and a skeletally rearranged triol 1,2-bis(4-hy- BPA is degraded
Summary
(Received for publication, May 28, 1993, and in revised form, November 23, 1993). From General Electric Corporate Research & Development, Schenectady, New York 12301-0008. Bisphenol A (BPA)is metabolized by a Gram-negative t h e benzylic methyl group to 4-hydroxybenzyl alcohol before aerobic bacterium via a novel pathway involving oxida- further oxidation to 3,4-dihydroxybenzoic acid(8). The methyl-hydroxylated 2,2-bis(4-hydroxyphenyl)-l- was studied to determine the biochemical pathway by which propanol and a skeletally rearranged triol 1,2-bis(4-hy- BPA is degraded. HPLC gradients and flow rates were varied over the course of the investigation as indicated.Aromatic compounds were detectedby monitoring column effluent at 275 nm, and W spectra were obtained from analysis of the effluent by the Waters 990 photodiode array detector. Let detection;TMS, tetramethylsilane; BSTFA, bis(trimethylsily1)triflu- HPLC-MS wasrun without adding acids to the eluants and at reduced oroacetamide;GCNS, gas chromatography-massspectrometry. NMR spectra were obtained from a Varian XL200 (200 MHz for lH) noic acid catalyzed condensation of phenol with diethyl ketomalonate.
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