Dibenzo chrysene

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. 

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...

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...

A gas chromatography-flame ionization detector system can be nsed for the separation and detection of nonpolar organic componnds. Semivolatile constitnents are among the analytes that can readily be resolved and detected nsing the system. If a packed column is used, four pairs of compounds may not be resolved adequately and are reported as a quantitative sum anthracene and phenanthrene, chrysene and benzo[a]anthracene, benzo[/ ]fluoranthene and benzo[/ ]fluoranthene, and dibenzo[a,/i]anthracene and indeno[l,2,3-cd]pyrene. This issue can be resolved through the use of a capillary column in place of a packed column. 

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,... 

Aromatic amines Benzo anthracenes Benzo fluoranthracenes Benzo pyrenes Benzoic acids Carbazoles Chrysenes Dibenzo thiophenes Fluorenes Imidazoles Indoles Naphthalenes... 

Extensive studies have been conducted to investigate the formation of chiral columns or helical superstructures in chiral and nonchiral disk- [53], star- [54, 55], and board-shaped [56] molecules. However, spontaneous deracemization has never been unambiguously demonstrated in discotic columnar phases consisting of nonchiral or racemic molecules. We recently observed clear evidence showing chiral resolution in a disk-like molecules with a dibenzo[g,p]chrysene core [57]. 

Fig. 14 Disk-like molecules with a dibenzo[g,/>]chrysene core used for the deracemization experiment...

In practice, we have utilized it for the analysis of molecular systems comprised of 3 to 5 fused benzene rings. Our discussion in this document is limited to the following compounds phenanthrene, anthracene, fluoranthene, pyrene, benz(a)anthracene, chrysene, benzo(e)pyrene, benzo(a)pyrene, and dibenz(a,h)anthracene. The structures for these compounds are presented in Table I. It is important to note that the method has also been adapted to the determination of several other PAH compounds (e.g., benzo(c)phenanthrene, perylene, 3-methylcholanthrene, carbazole, 7H-dibenzo(c,g)carbazole, and indeno(l,2,3-cd)pyrene). 

Figure 22.16. Structures of the dihydrodiol epoxides of several polycyclic aromatic hydrocarbons. (A) Benzo[a]pyrene-fnms-7,8-dihydrodiol-9,10-epoxide (BPDE) (B) benz[a]anthracene-frara-8,9-dihydrodiol-10,11-epoxide (BADE) (C) benzo[fe]fluoranthene-fnms-9,10-dihydrodiol-ll, 12-epoxide (BFDE) (D) chrysene-fnms-l,2-dihydrodiol-3,4-epoxide (CDE) and (E)dibenzo[a,/]pyrene-fra ,s-ll,12-dihydrodiol-13,14-epoxide (DBPDE). Only one enantiomer for each dihydrodiol epoxide is shown.

DIBENZOCARBAZOLE see DCYOOO 7H-DIBENZO(c,g)CARBAZOLE see DCYOOO DIBENZO(b,def)CHRYSENE see DCY200 DIBENZO(def,p)CHRYSENE see DCY400 DIBENZO(def,p)CHRYSENE-l 1,12-DIOL, 11,12-DIHYDRO-, (11S,12S)-REL- see DDC810 DIBENZO-p-DIOXIN, 1,2,3,4,6,7,8-HEPTACHLORO-see HARIOO... 

The siimples were analysed by fluorescence spectroscopy at the conditions for each specific PAH [5] previously determined with the model compounds. The PAH studied are those listed by the US Environmental Protection Agency as priority pollutants [6] Fluorene, Benzo(a)Pyrene, Pyrene, Chrysene, Anthracene, Acenaphthene, Bezo(a)Anthracene, Dibenzo(a,h)Anthracene, Coronene, Perylene and Benzo(k)fluoranthene. In addition, Coronene emissions were also reported due to their important role on PAH stabilization at extreme conditions [7]. These 16 PAH were analysed from all runs in each of the four samples. 

Another transformation of one aromatic compound to another is the Stone-Wales rearrangement of pyracyclene (113), which is a bond-switching reaction. The rearrangement of bifluorenylidene (114) to dibenzo[g,p] chrysene (115) occurs at temperatures as low as 400° C and is accelerated in the presence of decomposing iodomethane, a convenient source of methyl radicals. This result suggested a... 

---