Synthesis and PMR and Mass Spectra of Potential Metabolites and Other Derivatives of Bis(2-ethylhexyl) Phthalate

Carter, James E.; Petersen, Robert V.; Roll, David B.

doi:10.1002/jps.2600660422

Cited by 10 publications

(2 citation statements)

References 6 publications

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“…Glucose 6-phosphate, glucose 6-phosphate dehydrogenase and β-nicotinamide adenine dinucleotide phosphate (β-NADP + ) were obtained from Oriental Yeast Co., Ltd. (Tokyo, Japan). 4-hydroxyphthalate (DMP-4OH) and dimethyl 3-hydroxyphthalate (DMP-3OH) were synthesized according to the method reported by Carter et al 16) Other chemicals used were of the highest quality commercially available. Preparation of Rat Liver Microsomes ---Male Sprague-Dawley rats (5 weeks of age) were purchased from Clea Japan Inc. (Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

Novel Estrogenic Microsomal Metabolites from Phthalate Esters

Okamoto

Okajima

Toda

et al. 2004

JOURNAL OF HEALTH SCIENCE

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Many researchers have found evidence of the estrogenic effects of phthalate esters (PEs), but the disruption mechanism is not fully elucidated. Once PEs are hydroxylated at the ring 4-position, the resulting compounds exhibit unequivocal binding affinity for human estrogen receptors. In this study, we first succeeded to demonstrate the generation of potent estrogenic metabolite from PEs. We used rat liver microsomes and dimethyl phthalate (DMP) as a representative for the metabolism of PEs. Among the metabolites detected by HPLC, one of them was consistent with an authentic compound, 4-hydroxylated DMP (DMP-4OH) on their HPLC profiles. Together with the UV (max = 257 nm) and MS (m/z 210) data, the metabolite was concluded to be DMP-4OH. We propose that this ring-hydroxylated metabolite could be a key active species in the endocrine disrupting processes of PEs.

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Section: Methodsmentioning

confidence: 99%

Novel Estrogenic Microsomal Metabolites from Phthalate Esters

Okamoto

Okajima

Toda

et al. 2004

JOURNAL OF HEALTH SCIENCE

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“…They are metabolized mainly by hydrolysis to monoalkyl phthalates and phthalic acid (50,54,(66)(67)(68)(69). These compounds are easily extracted from biological samples (blood, tissue) with solvents.…”

Section: Metabolism Of Phthalic Esters; Mass Spectra Of Derivatives Omentioning

confidence: 99%