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SYNTHESIS AND MUTAGENIC PROPERTIES OF 4,4'-DIAMINO-PARA-TERPHENYL AND 4,4'-DIAMINO-PARA-QUATERPHENYL
Citation:
WANG, J., H. S. FREEMAN, AND L. D. CLAXTON. SYNTHESIS AND MUTAGENIC PROPERTIES OF 4,4'-DIAMINO-PARA-TERPHENYL AND 4,4'-DIAMINO-PARA-QUATERPHENYL. Coloration Technology. Blackwell Publishing, Malden, MA, 123(1):34-38, (2007).
Impact/Purpose:
This study was an effort to examine some potential replacements for specific benzidine analogs for their genotoxic potential.<
Description:
DBPs in drinking water can be controlled by the type of treatment and by knowing andd controlling major sources of DBP toxicant precursors and toxicants that "evade" treatment processes. Efforts are being directed at one category at a time. The initial precursor categories to be considered are pharmaceuticals, municipal sludge, and dyes/pigments. Because studies in Japan, Brazil, Germany, and the US have identified that dyes can contribute extreme levels of toxicants to source waters and because this is a "relatively narrow" class, dyes were the first category chosen. Initial efforts are (1) examining source and drinking waters from Brazil and the identified azo dyes and (2) making efforts to design, synthesize, and evaluate replacement dyes. Goals for the development of replacement dyes and pigments are making ones that are (1) environmental and health effects friendly and (2) retain good straining properties for commercial use. The results will also be useful to those involved in the PMN (premanufacturing notice) process and those involved in the Safe Pesticides/Safe Products (SP2) programs.
What is the impact to the field and the Agency?
Because this study showed that 4,4'-diamino jJara-terphenyl (DATP) is more mutagenic than benzidine, inserting one phenyl moiety into the biphenyl ring linkage enhances rather than reduces the mutagenicity of the prototype compound. However, inserting a second ring to give 4,4'-diamino para-quaterphenyl (DAQP) leads to a nonmutagenic diamine in Salmonella TA98 and TA100. Thus the absence of mutagenicity makes this diamine a potential candidate for the synthesis of organic dyes and pigments.. The study aids in identifying benzidine replacements that are potentially useful to the dye industry but are less likely to cause human health effects. This structure-activity study also aids in the development of computational toxicology methods for predicting the genotoxicity of similar compounds.