Bisphenol A, a building block, is widely used as a monomer for the production of epoxy resins and polycarbonate plastics. These plastics are safe and convenient and used in many food and drink packaging applications, while the resins are inert materials, commonly used as lacquers to coat metal products such as food cans, bottle tops and water supply pipes. More information on this compound can be found at the Bisphenol A website from the Bisphenol A Global Industry Group and the Bisphenol A page at the Hormone Disrupting Compounds site.
Bisphenol A is metabolized by a Gram-negative aerobic bacterium (strain MV1) via a novel pathway involving oxidative skeletal rearrangement. The metabolism involves two primary pathways: a minor pathway, in which Bisphenol A is first oxidized to a triol, and a major pathway, in which Bisphenol A is metabolized to form the intermediates 4-hydroxybenzoate and 4-hydroxyacetophenone that are converted to carbon dioxide and biomass (Spivack et al., 1994).
The following is a text-format Bisphenol A pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (12k) format.
Bisphenol A <-- from the Tetrabromobisphenol A Pathway
Gram - aerobic bacterium strain MV1
|
|
|
+-------------+-------------+
| |
bisphenol A | | bisphenol A
hydroxylase B | | hydroxylase A
| |
v v
1,2-bis(4-Hydroxyphenyl) 2,2-bis(4-Hydroxyphenyl)
-2-propanol 1-propanol----------------------+
| | |
1,2-bis(4-Hydroxy | | | 2,2-bis(4-Hydroxy-
-phenyl)-2-pro- | | A | phenyl)-1-propanol
panol dehydratase | | | hydroxylase
| | |
v v v
4,4'-Dihydroxy-alpha 2,2-bis(4-Hydroxyphenyl) 2,3-bis(4-Hydroxyphenyl)
-methylstilbene 1-propanoate -1,2-propanediol
| |
4,4'-dihydroxy- | | 2,3-bis(4-hydroxyphenyl)
alpha-methylstil- | | -1,2-propanediol
bene dioxygenase | | dioxygenase
| |
+---------+---------+ +-------------+-------------+
| | | |
| | | |
| | | |
v v v v
4-Hydroxy- 4-Hydroxy- 4-Hydroxy- 4-Hydroxyphenacyl
benzaldehyde acetophenone benzoate<-------------------alcohol
| | | 2,4'-dihydroxy-
| | | acetophenone
| | | dioxygenase
| | |
v v v
to the to the to the
Toluene Pathway 4-Hydroxyacetophenone Vanillin Pathway
Pathway
Page Author(s): Prasad Kotharu
June 13, 2008 Contact Us
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