Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings--as the above formula shows. Phenanthrene has five resonance structures, given below. Image File history File links Phenanthrene. ... Polycyclic aromatic hydrocarbons (PAHs) are chemical compounds that consist of fused aromatic rings and do not contain heteroatoms or carry substituents. ... Benzene, also known as C6H6, PhH, and benzol, is an organic chemical compound which is a colorless and flammable liquid with a pleasant, sweet smell. ... Resonance structures are diagrammatic tools in organic chemistry to symbolize resonant bonds between atoms in molecules. ...
Reactions of phenanthrene typically occur at the 9 and 10 positions.
Phenanthrene did not yield positive results in sister chromatid exchange and chromosome aberration assays in mammalian cell cultures (Popescu et al., 1977) or in cell transformation assays in several types of mammalian cells (5-40 ug/mL) (Marquardt and Heidelberger, 1972; Kakunaga, 1973; Evans and DiPaolo, 1975; Pienta et al., 1977).
The relatively weak mutagenic and tumorigenic activity of phenanthrene diol epoxides is inconsistent with the "bay region theory" of PAH carcinogenesis.
Phenanthrene epoxides have a relatively small molecular size (relative to other more active PAH epoxides such as chrysene diol epoxides) and as a result may have a lower affinity for DNA or may be transported less efficiently into the mammalian nucleus (Wood et al., 1979).
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