title: Tris(dichloropropyl)phosphate, a mutagenic flame retardant: frequent cocurrence in human seminal plasma.
abstract: Negative-chemical-ionization mass spectral screening of extracts of human seminal plasma has revealed a presence of a Cl7 ion cluster at a mass-to-charge ratio (m/z) of 463 in a significant number of the samples examined (34 out of 123). Experiments with different gases used to generate the negative-chemical-ionization plasma indicated that the ion at m/z 463 was a chloride adduca of a Cl6 molecule with a mass of 428 daltons. Negative-chemical-ionization mass measurement with ions from the iodoform mass spectrum used as reference peaks gave a mass of 427.882 daltons; C9H15PCl6 has a molecular weight of 427.883. Extraction of polyurethane foam with toluene produced an extract that consistently gave a negative-chemical-ionization spectrum containing an intense Cl7ion at m/z463. The component producing ion was isolated, and its proton nuclear magnetic resonance spectrum confirmed that it was tris (1,3-dichloro-2-propyl)phosphate, a mutagenic flame retardant. The negative-chemical-ionization screening evidence suggests that this flame retardant or its isomer tris(2,3-dichloro-l-propyl)phosphate, or both, are absorbved into the body from formulations in which they are used as flame retardants. Remedial action seems indicated to reduce human exposure to these compunds.
mesh_terms: D004781:Environmental Exposure; D005411:Flame Retardants / Q000032:analysis*; D006801:Humans; D006843:Hydrocarbons, Chlorinated / Q000032:analysis; D008297:Male; D013058:Mass Spectrometry; D009153:Mutagens / Q000032:analysis*; D009943:Organophosphorus Compounds / Q000032:analysis*; D012661:Semen / Q000032:analysis*
chemical_list: D005411:Flame Retardants; D006843:Hydrocarbons, Chlorinated; D009153:Mutagens; D009943:Organophosphorus Compounds; C017779:tris(2,3-dichloropropyl)phosphate