Chiral perspective evaluations: Enantioselective hydrolysis of 6PPD and 6PPD-quinone in water and enantioselective toxicity to Gobiocypris rarus and Oncorhynchus mykiss

As a ubiquitous tire antidegradant, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) is persistently released into the environment. It is highly toxic to aquatic organisms, and its transformation product 6PPD-quinone (6PPD-Q), is "very highly toxic" to Oncorhynchus kisutch at a median lethal concentration (LC50) of 50, 162-201 ng/mL), and it had no enantioselective difference. 6PPD-Q was "very highly toxic" (LC50, 1.66-4.31 ng/mL) to Oncorhynchus mykiss, which is of commercial importance, and the toxicities of rac-6PPD-Q and S-6PPD-Q were 1.9 and 2.6 times higher than R-6PPD-Q. Furthermore, the formation concentrations of S-6PPD-Q and R-6PPD-Q in 6PPD water solutions were higher than the LC50 values of O. kisutch and O. mykiss, and the toxicity of 6PPD-Q was highly species-specific, which should raise concern. These results provide important information for environmental risk assessments of 6PPD and 6PPD-Q, especially from the perspective of enantiomers.