Benzo phenanthrene 12-Methyl

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. 

Fig. 5a-c. A typical distribution of polycyclic aromatic hydrocarbons in a atmospheric fallout sample, Alexandria City - Egypt b bottom incineration ash leachate of municipal solid waste - USA c hydrothermal petroleum, Escanaba Trough, NE Pacific Ocean. PAH Compound identifications N = naphthalene, MN = methylnaphthalene, DMN = dimethylnaphthalenes, P = phenanthrene, MP = methylphenanthrene, Fl = fluoranthene, Py = pyrene, BaAN = benzol anthracene, DH-Py = dihydropyrene, 2,3-BF = 2,3-benzofluorene, BFL = benzo[fc,/c]fluoranthene, BeP = benzo[e]pyrene, BaP = benzo[a]pyrene, Per = perylene, Cx-228 = methyl-228 series, Indeno = indeno[ l,2,3-c,d]pyrene, DBAN = dibenz[a,/z]anthracene, BPer = benzo[g,/z,z] perylene, AAN = anthanthrene, DBTH = dibenzothiophene, Cor = coronene, DBP = dibenzo [a,e]pyrene, DBPer = dibenzo [g,h,i] perylene... 

GC-MS examination of the PAH fraction of sample S2 (S2-C2) gave very similar results the total ion chromatogram is shown in Figure 5. Major constituents were phenanthrene, fluoranthene, pyrene, and methyl, dimethyl/ethylphenanthrene/anthracene. Relative abundance of some C2-alkylphenanthrenes/anthracenes were higher in this sample than in S1-C2. Smaller quantities of benzo[ghi]fluoranthene, chrysene, benzo[ajanthracene, tripheny-lene, benzo[b,j, k]fluoranthenes, and benzo[e aJpyrenes and were characterized by MS. In addition, most compounds listed in Table 1 were also detected in this sample. 

Figure 3. Total ion chromatogram of extractable organics in a typical lot of Ambersorb XE-340 resin (SP-2100,10-m capillary column, temperature program 50(2)-250 at 5 °C/min, 1.0-pL splitless injection). 1, naphthalene 2,1- or 2-methylnaphthalene 3, biphenyl 4, 1,V-biphenyl, 2- or 3-methyl 5, fluorene 6, anthracene-phenanthrene 7tl- or 2-phenylnaphthalene 8, pyrene 9, fluoranthene 10, terphenyl isomer 11, benzo[b]naphthothiophene isomer 12, binaphthalene isomer 13, benzofluoranthene isomer. (Reproduced from...

BENZOPHENANTHRENE see BBC250 BENZO(def)PHENANTHRENE see PON250 BENZOPHENONE see BCS250 BENZOPHENONE-3 see MESOOO p-BENZOPHENONE, METHYL- see MHF750 BENZOPHOSPHATE see BDJ250... 

Figure 2 Structures of polycyclic aromatic hydrocarbons. Symbols used in this figure and text Na (naphthalene). Ay (acetonaphthylene), Ae (acenaphthene), FI (fluorene). Pa (phenanthrene), A (anthracene), MPa (methyl phenanthrene), F (fluoranthene), Py (pyrene), BaA (benz(a)anthracene), Chy (chrysene), BlcF (benzo(k)fluoranthene), BbF (benzo(b)fluoranthene), BaP (benzo(a)pyrene), IP (indenopyrene), B(ghi)Pe (benzo(ghi)perylene), and Db(ah)A...

Thermolysis of the isolated aminonitrile (89), mp. 169° (85%) obtained by condensing (88) with (7b) in pyridine, gives rise to the formation of a mixture (83%) of two different isomeric nitriles in nearly equal amounts, the expected 2-methyl-benzo(c)phenanthrene-4-carbonitrile (90) and the 9-methylbenzo(a)anthracene-l 1-carbonitrile (91). 

The reaction of benzo[f]quinoline with methylsulphinyl carbanion prepared from dimetl lsulphoxide and sodium hydride leads to the 5-methyl and the 6-methyl derivatives in a 1 4 ratio. Although benzo[flquinoline-4-oxide gives a high yield of phenanthrene under these conditions, the carbanion generated using potassium t-butoxide as the base leads to alkylation at C-3 and to simultaneous deoxygenation (Y. Hamada and I. Takeuchi. J. org. Chem.. 1977. fa, 4209). 

In detail, several alkylated and nonalkylated polycyclic aromatic compounds (PAHs) were detected and dominated by acenaphthene with a maximum concentration of 24 pg/L in sample B. Total concentrations of methyl- and dimethylnaphthalenes reached 5.1 pg/L and 24 pg/L, respectively. Tricyclic aromatic compounds and oxygenated PAH species were detected comprising e.g. phenanthrene, 9H-fluorenone and acenaphthenone. Methylated and dimethylated benzo(b)thiophenes as well as dibenzothiophene were also present. 

Abbreviations PAH, polycyclic aromatic hydrocarbon DE, diol epoxide PAHDE, polycyclic aromatic hydrocarbon diol epoxide PAHTC, polycyclic aromatic hydrocarbon triol carbocation TC, triol carbocation BaP, benzo[a]pyrene BeP, benzo[e]pyrene BA, benz[a]anthracene DBA, dibenz[a,h]anthracene BcPh, benzo[c)phenanthrene Ch, chrysene MCh, methylchrysene MBA, 7-methyl benz[a]anthracene DMBA, 7,12-dimethyl benz[a]anthracene EBA, 7-ethyl benz[a]anthracene DB(a,l)P, dibenzo[a,l]pyrene MSCR, mechanism-based structure-carcinogenicity relationship PMO, Perturbational molecular orbital method dA, deoxyadenosine dC, deoxycytosine dG, deoxyguanosine MOS, monoxygenase enzyme system EH, epoxide hydrolase enzyme system N2(G), exocyclic nitrogen of guanine C, electrophilic centre of PAHTC K, intercalation constant CD, circular dichroism LD, linear dichroism. 

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