Cyclopenta pyrene

FIGURE 10.11 UV-visible absorption spectrum of cyclopenta[ /]pyrene in cyclohexane (adapted from Karcher el al., 1985). This PAH does not fluoresce. 

Rogan, E., E. Cavalieri, A. Munhall, and S. Salmasi. 1983. Synergistic effect of the environmental contaminants cyclopenta(cd)pyrene and benzo[a]pyrene in mouse skin carcinogenicity. Pages 1035-1046 in M. Cooke and A.J. Dennis (eds.). Polynuclear Aromatic Hydrocarbons Mechanisms, Methods and Metabolism. Battelle Press, Columbus, OH. 

FIGURE 19.24 HPLC separation of a standard mixture of 16 EU-priority PAHs plus EPA-priority PAHs, benzo[e]pyrene and benzo[fc]chrysene. Na=naphthalene, Ac = acenaphthylene, E=fluorene, Pa=phenan-threne, A = anthracene, El = fluoranthene, P = pyrene, BcE = benzo[c]fluoranthene, CPP = cyclopenta[c,4] pyrene, BaA = benz[a]anthracene, Ch = chrysene, 5-MeCh = 5 methylchrysene, BeP = benzo[e]pyrene, BjE = benzo[/ ]fluoranthene, BbF = benzo[h]fluoranthene, BkE = benzo[l ]fluoranthene, BaP = benzo[a]pyrene, DBahA = dibenz[a,/j]anthracene, DBalP = dibenzo[a,l]pyrene, BghiP = benzo[g,/j,i]perylene, IP = indeno [l,2,3-c4]pyrene, DBaeP = dibenzo[a,e]pyrene, BbCh = benzo[h]chrisene, DBaiP = dibenzo[a,i]pyrene,... 

PAHs also generally have well-structured emission spectra (see Figs. 10.6-10.10) and relatively large fluorescence quantum yields. For example, in degassed n-heptane at room temperature, the fluorescence quantum yields are as follows fluoranthene, 0.35 benz[ ]anthracene, 0.23 chrysene, 0.18 BaP, 0.60 BeP, 0.11 and benzo[g/zi]perylene, 0.29 (Heinrich and Giisten,1980). Cyclopenta[crf]pyrene, however, does not fluoresce. 

Two human cell lines with good sensitivities have proven useful for laboratory and field studies MCL-5 (Crespi et al., 1991), and hlAlv2 (Penman et al., 1994). Durant and co-workers (1996) report specific activities determined with the hlAlv2 assay for standard (reference) samples of 67 PAHs and PACs. Fifty-five have been identified or are suspected to be present in ambient urban aerosols. The human cell potencies (relative to BaP = 1.00) of selected PAHs and PACs, along with their cancer potency equivalence factors (PEFs), are given in Tables 10.13 and 10.14. Dibenzo[a,/]pyrene (XXIX), cyclopenta[cd]pyrene... 

Cyclopenta[cd]pyrene (CPP, XXVIII) is a powerful human cell mutagen in strain hlAlv2, 7 times more potent than BaP (Durant et al., 1996 Hannigan et al., 1998), and a strong promutagen in both the Ames Salmonella typhimurium reversion assay (Eisenstadt and Gold, 1978) and the Salmonella typhimurium strain TM677 forward mutation assay (Kaden et al.., 1979) ... 

Hannigan et al. (1998) reported that most of the mutagenicity of the extract of the whole, composite sample of respirable ambient aerosols was in the whole aromatics fraction, 83 vs 17% in the aliphatic portion. Table 10.25 summarizes the results of this bioassay-directed chemical analysis for the aromatics. As seen in Table 10.26, six PAHs, cyclopenta[c[Pg.497]

II Anthanthrene, anthracene, benzola]pyrene, cyclopenta[ct/]pyrene, dibenzo[a,l]pyrene, dibenzol a,i]pyrene,... 

Temporal and spatial distributions across the air basin of the particle-phase primary pollutants BaP and cyclopenta[c<7]pyrene. as well as the vapor-phase secondary pollutant 3-nitrobiphenyl, are shown in Fig. 10.27 in order of increasing distance inland, i.e., in order of increasing transport time. The major 6 to 10 a.m. peaks of BaP and cy c I o p e n t a[ ec/ ] py r e n e at central Los Angeles and Azusa reflect the high density of motor vehicle emissions at this morning rush period. 

FIGURE 10.27 Spatial and temporal distributions of two reactive particle-associated PAHs, benzo[a]pyrene and cyclopenta[cd]pyrene, and the gas-phase atmospheric reaction product 3-nitrobiphenyl during transport of a heavily polluted air parcel across southern California, September 8-9, 1993 (adapted from Fraser et al., 1998). 

The rapid depletion of these reactive PAHs during transport of this polluted air parcel is dramatic. Thus, as seen in Table 10.31, their concentrations (averaged over all times) drop from 1.04 and 0.29 ng m 3 for cyclopenta[c<7]pyrene and BaP, respectively, at central Los Angeles to 0.03 ng m 3 for both PAHs at Claremont. 

The physical effect of dilution of the aerosols due to increased mixing depths during transport of the air parcel inland is factored out by taking the ratios of the concentrations at Claremont to those at central Los Angeles. As seen in Table 10.32, the ratios are 0.21 and 0.20 for the low-reactivity PAHs benzo[k](luoranthene and i nde no[ 1,2,3-cd ]pyrene (Class V, Table 10.30), reflecting dilution, whereas the ratios are 0.10 and 0.03 for reactive BaP and cyclopenta[cd ]pyrene (Class II), respectively, indicative of reactions in addition to dilution. 

Eisenstadt, E., and A. Gold, Cyclopenta[cz/]pyrene A Highly Mutagenic Polycyclic Aromatic Hydrocarbon, Proc. Natl. Acad. Sci. U.S.A., 75, 1667-1669 (1978). 

Sangaiah, R., and A. Gold, A Short and Convenient Synthesis of Cyclopenta[cd]pyrene and Its Oxygenated Derivatives, in Polynuclear Aromatic Hydrocarbons Mechanisms, Methods and Metabolism (M. Cooke and A. J. Dennis, Eds.), Eighth International Symposium on Polynuclear Aromatic Hydrocarbons, Bat-telle Press, Columbus, OH, 1985. 

---