Benzo chrysene

BghiP = benzo(g,h,i)perylene CHy = chrysene Per = perylene BbF = benzo-(b)fluoranthene BkF = benzo-(k)fluoranthene BaP = benzo-(a)pyrene IP = indeno-(l,2,3-cd)pyrene Att = anthanthrene. 

Benzo[c]phenanthridine alkaloids are widespread in Papaveraceae, Fumariaceae, and Rutaceae. Fagaridine (118), the structure of which had to be revised, is a derivative of the unknown 5-methyl-benzo[c]phenan-thridine-8-olate (119) which is isoconjugate with the 2-methyl-chrysene anion (Scheme 43). Thus, Fagaridine is a member of class 1 of conjugated heterocyclic mesomeric betaines, which are isoconjugate with odd alternant hydrocarbon anions. 

Figure 1.4 Two-dimensional plot of HPLC (log /J and GC (log Iq) retention indexes (1) naphthalene (2) 2-methylnaphthalene (3) 2,3-dimethylnaphthalene (4) 2,3,6-trimethyl-naphthalene (5) biphenyl (6) fluorene (7) dibenzothiophen (8) phenanthrene (9) 2-methylphenanthrene (10) 3,6-dimethylphenanthrene (11) benzo[a]fluorene (12) chrysene (data replotted from reference (31)).

Figure 3 depicts profiles of Total PAH fluxes vs. time (36). The following polycyclic hydrocarbons have been determined by high performance liquid chromatography, variable wavelength absorption detection Naphthalene, acenaphthylene, 7,12-dimethylbenzanthracene, 2-methylnaphtalene, fluorene, acenaphtene, phenanthrene, 2,3-dimethylnaphtalene, anthracene, fluoranthene, 1-methylphenanthrene, pyrene, 2,3-benzofluorene, triphenylene, benz(a)anthracene, chrysene, benzo(b)fluoranthene, benzo(k)fluoranthene, perylene, benzo(e)pyrene, 1,2,3,4-dibenzanthracene, benzo(a)pyrene, and 1,2,5,6-dibenzanthracene. 

Turning to the acute toxicity of PAH, terrestrial organisms will be dealt with before considering aquatic organisms, to which somewhat different considerations apply. The acute toxicity of PAHs to mammals is relatively low. Naphthalene, for example, has a mean oral LD50 of 2700 mg/kg to the rat. Similar values have been found with other PAHs. LC50 values of 150 mg/kg and 170-210 mg/kg have been reported, for phenanthrene and fluorene, respectively, in the earthworm. The NOEL level for survival and reproduction in the earthworm was estimated to be 180 mg/ kg dry soil for benzo[a]pyrene, chrysene, and benzoMfluoranthene (Enviromnental Health Criteria 202). 

Note Bi, biphenyl Nap, naphthalene Phe, phenanthrene Anth, anthracene Hu, fluoranthene Pyr, pyrene Chr, chrysene BaAnth, benz[a]anthracene BaPyr, benzo[a]pyrene BbFlu, benzo[h]fluoranthene DBaAnth, dibenz[a,/i]anthracene 3-Me-Chol, 3-methylcholanthrene. 

The biodegradation of pyrene, chrysene, fluoranthene, benz[a]anthracene, dibenz[a,/t] anthracene, benzo[a]pyrene, and coronene by Stenotrophomonas maltophilia has been studied in the presence of a range of synthetic surfactants (Boonchan et al. 1998). Nonneutral surfactants were toxic, biodegradation was also inhibited by the neutral Igepal CA-630, and the positive enhancement of removal of substrates was generally low—in the range of 10%. 

In contrast to the three-ring compounds, residues of benz[a]anthracene, chrysene, and benzo[fl]pyrene were found after 15 weeks incubation in compost-amended soil. 

Coman et al. [82] used a new modeling of the chromatographic separation process of some polar (hydroxy benzo[a]pyrene derivatives) and nonpolar (benzo[a]pyrene, dibenz[a,/ ]anthracene, and chrysene) polycyclic aromatic compounds in the form of third-degree functions. For the selection of the optimum composition of the benzene-acetone-water mobile phase used in the separation of eight polycyclic aromatic compounds on RP-TLC layers, some computer programs in the GW-BASIC language were written. 

The most significant differences (i.e. independence) in the analytical methods are provided in the final chromatographic separation and detection step using GC/ MS and LC-FL. GC and reversed-phase LG provide significantly different separation mechanisms for PAHs and thus provide the independence required in the separation. The use of mass spectrometry (MS) for the GC detection and fluorescence spectroscopy for the LG detection provide further independence in the methods, e.g. MS can not differentiate among PAH isomers whereas fluorescence spectroscopy often can. For the GC/MS analyses the 5% phenyl methylpolysiloxane phase has been a commonly used phase for the separation of PAHs however, several important PAH isomers are not completely resolved on this phase, i.e. chrysene and triphenylene, benzo[b]fluoranthene and benzofjjfluoranthene, and diben-z[o,h]anthracene and dibenz[a,c]anthracene. To achieve separation of these isomers, GC/MS analyses were also performed using two other phases with different selectivity, a 50% phenyl methylpolysiloxane phase and a smectic liquid crystalline phase. 

LutherW, WinT, Vaessen HAMG, van de KampCG, Jekel AA, Jacob J, and Boenke A (1997). The certification of the mass fractions of pyrene, chrysene, benzo[fe]fluoranthene, benzo[o]pyrene, ben-zo[gW]perylene and indeno[i,2,3-cd]pyrene in two coconut oil reference materials (CRM 458 and CRM 459), BCR Information, Reference Materials. Report EUR 17545 EN, 61 pp. 

PAHs Benzo[a]pyrene, chrysene, fluoranthene Oil industry (P,D) Gasoline stations (P) Manufactured gas plants (P,D) Wood preservation sites (P) Municipal waste incineration (P,D) Automobile exhaust (D) 13.3 [43, 45]... 

Hemoglobin is another heme-containing protein, which has been shown to be active towards PAH, oxidation in presence of peroxide [420], This protein was also modified via PEG and methyl esterification to obtain a more hydrophobic protein with altered activity and substrate specificity. The modified protein had four times the catalytic efficiency than that of the unmodified protein for pyrene oxidation. Several PAHs were also oxidized including acenaphthene, anthracene, azulene, benzo(a)pyrene, fluoranthene, fluorene, and phenanthrene however, no reaction was observed with chrysene and biphenyl. Modification of hemoglobin with p-nitrophenol and p-aminophenol has also been reported [425], The modification was reported to enhance the substrate affinity up to 30 times. Additionally, the solvent concentration at which the enzyme showed maximum activity was also higher. Both the effects were attributed to the increase in hydrophobicity of the active site. 

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. 

The carcinogenicity of PAH with relativelyTigh IP, such as benzo[c]phenanthrene, benz[a]anthracene, chrysene, 5-methyl chrysene and dibenz[a,h]anthracene (Table I), can be related to the formation of bay-region diol epoxides catalyzed by monooxygenase enzymes (j>). However, the most potent carcinogenic PAH have IP < ca. 7.35 eV. 

These findings indicate that PGH synthase in the presence of arachidonate can catalyze the terminal activation step in BP carcinogenesis and that the reaction may be general for dihydrodiol metabolites of polycyclic hydrocarbons. Guthrie et. al. have shown that PGH synthase catalyzes the activation of chrysene and benzanthracene dihydrodiols to potent mutagens (33). As in the case with BP, only the dihydrodiol that is a precursor to bay region diol epoxides is activated. We have recently shown that 3,4-dihydroxy-3,4-dihydro-benzo(a)anthracene is oxidized by PGH synthase to tetrahydrotetraols derived from the anti-diol epoxide (Equation 4) (34). 

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...

Single ip injection of 99.5 pmol/kg BW of BaP, chrysene, fluoranthene, pyrene, or benzo[g/7/]perylene... 

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