Dibenzo pyrenes

Benzo [rst]pentaphen 1,2 7,8-Dibenzo-pyren (3,4 9,10-Dibenzo-pyren)... 

C jHitNiOS S-Qxo-5-thia-1.2-diiiza-5.S-di hydro-3.4 9.10-dibenzo-pyren (Anthra> cninon-thiozanthan-azin) 27 1597. 

Two of the most carcinogenic compounds known dibenzo[a,l]pyrene, a polycyclic aromatic hydrocarbon (PAH) and aflatoxin Bi, a fungal metabolite. 

Dibenzo [a, l pyrene Dibenzo [a, l pyrene-11,12-diol-13,14-epoxide... 

The normal pathway toward excretion of foreign molecules like aflatoxin Bi and dibenzo [a,/]pyrene, however, also involves nucleophilic substitution reactions of their epoxides. 

Methods for the synthesis of the biologically active dihydrodiol and diol epoxide metabolites of both carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons are reviewed. Four general synthetic routes to the trans-dihydrodiol precursors of the bay region anti and syn diol epoxide derivatives have been developed. Syntheses of the oxidized metabolites of the following hydrocarbons via these methods are described benzo(a)pyrene, benz(a)anthracene, benzo-(e)pyrene, dibenz(a,h)anthracene, triphenylene, phen-anthrene, anthracene, chrysene, benzo(c)phenanthrene, dibenzo(a,i)pyrene, dibenzo(a,h)pyrene, 7-methyl-benz(a)anthracene, 7,12-dimethylbenz(a)anthracene, 3-methylcholanthrene, 5-methylchrysene, fluoranthene, benzo(b)fluoranthene, benzo(j)fluoranthene, benzo(k)-fluoranthene, and dibenzo(a,e)fluoranthene. 

These hexacyclic hydrocarbons are generally recognized as two of the most potent unsubstituted carcinogenic PAH (38). The 3,4-dihydro-diol of dibenzo(a,i)pyrene (17) and the 1,2-dihydrodiol of dibenzo-(a,h) pyrene (lg) have been synthesized from 4-oxo-l,2,3,4-tetra-hydrodibenzo(a,i)pyrene and 1-oxo-l,2,3,4-tetrahydrodibenzo(a,h)py-rene, respectively, by Method I. (69). Treatment of these dihydro-diols with m-chloroperbenzoic acid gave the corresponding anti diol epoxides (66). 

Dibenzo[jatQ pyrene DBaiP strong care. 

This list includes BP, 7,12-dimethylbenz[a]anthracene, 3-methylchol-anthrene, dibenzo[a,i]pyrene and dibenzo[a,h]pyrene. These PAH can be activated both by one-electron oxidation and/or monooxygenation. There are a few PAH with low IP which are inactive (Table I), such as perylene, or weakly active, such as anthanthrene. This indicates that low IP is a necessary, but not sufficient factor for determining carcinogenic activity by one-electron oxidation. These inactive or weakly active PAH have the highest density of positive charge delocalized over several aromatic carbon atoms in their radical cations, whereas the active PAH with low IP have charge mainly localized on one or a few carbon atoms in their radical cations. 

Figure 5.12 Polyaromatic hydrocarbon species (1) phenanthrene, (2) anthracene, (3) pyrene, (4) benz[o]anthracene, (5) chrysene, (6) naphthacene, (7) benzo[c]phenanthrene, (8) benzo[ghi] fluoranthene, (9) dibenzo[c,g]phenanthrene, (10) benzo[g/ ]perylene, (11) triphenylene, (12) o-terphenyl, (13) m-terphenyl, (14) p-terphenyl, (15) benzo[o]pyrene, (16) tetrabenzonaphthalene, (17) phenanthro[3,4-c]phenanthrene, (18) coronene...

To evaluate the potential risk of Ebro river sediments, the concentrations detected were compared to actual legislation. The WFD does not specifically address sediment management [95]. In contrast to this, the Canadian sediment quality guidelines for the protection of aquatic life [96] provide data for different types of sediments and include 33 compounds, PAHs and DDTs among them. All the PAHs included in the Canadian guidelines are present above the limit, ranging from 3% of the samples for naphthalene to 90% for dibenzo(a,h)anthracene. Special attention has to be paid to benzo(a)pyrene and dibenzo(a,h)anthracene, considered... 

Finally, three additional individual data matrices were obtained for soil (so1 so2, and so3), in this case with the same number of samples (rows) for each of them. A new soil data matrix (SO) was obtained after individual matrix concatenation containing 36 samples in total (12 samples analyzed in 3 sampling campaigns) (see Fig. 7). Fifteen variables (all of them detected in SE as well) were measured in every sample PAHs (acenaphtylene, phenanthrene, anthracene, fluoranthene, pyrene, benzo(a)anthracene, chrysene, benzo(b)fluoranthene, benzo(a)pyrene, indeno (l,2,3-cd)pyrene, dibenzo(a,h)anthracene, and benzo(g,h,i)perylene), an organophosphate compound (tributylphosphate), and an OC (4,4 -DDE). 

Fig. 10 Composition and spatial distribution of the main patterns of contamination identified in sediment of the Ebro River basin from year 2004 to 2006. Different temporal distribution of the PAHs pattern of contamination over the territory and constant distribution in time of the APs and heavier PAHs as well as the OCs pattern. Big circles representing higher levels of pattern contribution than small circles. Variables identification 1, naphthalene 2, acenaphtylene 3, acenapthene 4, fluorene 5, phenanthrene 6, anthracene 7, fluoranthene 8, pyrene 9, benzo(a) anthracene 10, chrysene 11, benzo(b)fluoranthene 12, benzo(k)fluoranthene 13, benzo(a)pyr-ene 14, indeno(l,2,3-cd)pyrene 15, dibenzo(a,h)anthracene 16, benzo(g,h,i)perylene 17, octyl-phenol 18, nonylphenol 19, tributylphosphate 20, a-HCH 21, HCB 22,2,4-DDE 23,4,4-DDE 24, 2,4-DDD 25, 4,4-DDD 26, 2,4-DDT 27, 4,4-DDT...

Fig. 11 Composition of the identified patterns of contamination (loadings) in sediment and soil of the Ebro River basin and patterns contribution to the analyzed samples (scores) in fall from year 2004 to 2006. Samples ordered for both compartments from first to third sampling campaigns and, for each campaign, from NW to SE. Variables identification 1, acenaphtylene 2, phenanthrene 3, anthracene 4, fluoranthene 5, pyrene 6, benzo(a)anthracene 7, chrysene 8, benzo(b)fluor-anthene 9, benzo(k)fluoranthene 10, benzo(a)pyrene 11, indeno(l,2,3-cd)pyrene 12, dibenzo (a.h)anthracene 13, benzo(g,h,i)perylene 14, tributylphosphate 15, 4,4-DDE...

XVII. Dibenz[a,h]anthracene XVIII. Coronene XIX. Dibenzo[a,e]pyrene... 

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