Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism.
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.
Spivack
J
J
General Electric Corporate Research & Development, Schenectady, New York 12301-0008.
Leib
T K
TK
Lobos
J H
JH
D000433:1-Propanol / Q000378:metabolism; D001559:Benzhydryl Compounds; D001665:Binding Sites; D001673:Biodegradation, Environmental; D006089:Gram-Negative Anaerobic Bacteria / Q000378:metabolism*; D006900:Hydroxylation; D010084:Oxidation-Reduction; D010636:Phenols / Q000378:metabolism*; D020005:Propanols; D013267:Stilbenes / Q000378:metabolism*; D000098826:Bisphenol A Compounds
D000433:1-Propanol; D001559:Benzhydryl Compounds; D010636:Phenols; D020005:Propanols; D013267:Stilbenes; C006780:bisphenol A; D000098826:Bisphenol A Compounds