Metabolism of the epoxy resin component 2,2-bis[4-(2,3-epoxypropoxy)phenyl]propane, the diglycidyl ether of bisphenol a (DGEBPA) in the mouse.; Part II. Identification of metabolites in urine and faeces following a single oral dose of¹⁴C-DGEBPA

Abstract

1. The major metabolic transformation of orally ingested 14C-DGEBPA is by hydrolytic ring-opening of the two epoxide rings to form diols. This metabolite (the bis-diol of DGEBPA) is excreted in both free and conjugated forms and is further metabolized to various carboxylic acids, including two containing a methylsulphonyl moiety. 2. The product of oxidative dealkylation either of DGEBPA (with concomitant formation of glycidaldehyde) or of the bis-diol of DGEBPA (with concomitant formation of glyceraldehyde) is excreted in both free and conjugated forms in amounts representing 5% of the dose. 3. The high activity of epoxide hydratase towards DGEBPA suggests that glyceraldehyde and not glycidaldehyde is formed in vivo. 4. Hepatic epoxide hydratase activity towards DGEBPA measured in vitro decreased in the order rabbit greater than mouse greater than rat. 5. Two discrete epoxide hydratases are present in large amounts in the mouse. One is membrane-bound in the liver microsomal fraction and the other is a "soluble' enzyme located in the liver cytosol. This cytosolic enzyme was present in only very small amounts in the rat.

Widespread Occurrence and Distribution of Bisphenol A Diglycidyl Ether (BADGE) and its Derivatives in Human Urine from the United States and China

“…In addition to the direct intake of BADGE·2H 2 O from foods, in vivo metabolism of BADGE and other precursors can contribute to the formation of BADGE·2H 2 O in human bodies. 15,16,19,20 The proportion of BADGE·-H 2 O·HCl is relatively low, especially in urine from China, indicating a lower level of chloride derivatives of BADGEs in human urine. Creatinine also was determined in urine samples from the U.S. and China.…”

Urinary bisphenol A and plasma hormone concentrations in male workers exposed to bisphenol A diglycidyl ether and mixed organic solvents

“…15 According to the study, bisphenol A was one of the minor metabolites, and the amount was reported to be small. 16 The experiment by Climie et al used radiolabelled BADGE, so the results of their study seemed to be generally reliable.…”

“…In this study, we could not analyse major metabolites of BADGE, for example, bis-diol of BADGE, 15 because their standard reagents were not available. Thus, we could not directly confirm exposure to BADGE in the sprayers.…”

Bisphenol A Diglycidyl Ether Induces Adipogenic Differentiation of Multipotent Stromal Stem Cells through a Peroxisome Proliferator–Activated Receptor Gamma-Independent Mechanism

“…Both migrate from containers into foods, and are routinely ingested (Cabado et al 2008; Cao et al 2009). Studies of BADGE metabolism suggest that it is not a significant source of BPA (Climie et al 1981) although BPA leaches from some BADGE-containing dental sealants (Joskow et al 2006; Olea et al 1996). …”