3,4-Benzopyrene

ACS Symposium Series American Chemical Society Washington, DC, 1980. 

Additionally, in vitro tests should not elimate animal testing but may help in tests with animals. The proper use of several in vitro test systems will greatly aid our understanding of which metal compounds are hazardous. These screening tests may also allow us to identify carcinogens in air samples from the industrial environment. 

Metals Induce Cancer When Administered to Experimental Animals. Again, the reader is referred to many recent comprehensive reviews which discuss the evidence that certain metals cause cancer in experimental animals (9,10,J1). The most credible data implicates cadmium, chromium, co 6 a TT, and nickel as carcinogens in experimental animals. It should be noted that while arsenic has been shown to be responsible for the induction of human cancer, attempts to induce cancer in experimental animals with arsenic and its compounds have not been successful. In contrast, while cobalt induced cancer in experimental animals, numerous epidemiological studies have failed to show a correlation between excessive human exposure to cobalt and the induction of human neoplasia. One of the most studied metal carcinogens are the nickel compounds, of which crystalline Ni3 2 appears to be the most potent (1,2,12). Ni3 2 has been shown to induce cancer at 

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Finally it is likely that attention will be focused on emissions of polynuclear aromatics (PNA) in diesel fuels. Currently the analytical techniques for these materials in exhaust systems are not very accurate and will need appreciable improvement. In conventional diesel fuels, emissions of PNA thought to be carcinogenic do not exceed however, a few micrograms per km, that is a car will have to be driven for several years and cover at least 100,000 km to emit one gram of benzopyrene for example These already very low levels can be divided by four if deeply hydrotreated diesel fuels are used. 

It is interesting to note that recent evidence shows that even extra-terrestrially formed hydrocarbons can reach the Earth. The Earth continues to receive some 40,000 tons of interplanetary dust every year. Mass-spectrometric analysis has revealed the presence of hydrocarbons attached to these dust particles, including polycyclic aromatics such as phenanthrene, chrysene, pyrene, benzopyrene, and pentacene of extraterrestrial origin indicated by anomalous isotopic ratios. 

In Group 14 (IV), carbon serves as a Lewis base in a few of its compounds. In general, saturated ahphatic and aromatic hydrocarbons are stable in the presence of BF, whereas unsaturated ahphatic hydrocarbons, such as propjdene or acetylene, are polymerized. However, some hydrocarbons and their derivatives have been reported to form adducts with BF. Typical examples of adducts with unsaturated hydrocarbons are 1 1 adducts with tetracene and 3,4-benzopyrene (39), and 1 2 BF adducts with a-carotene and lycopene (40). 

Polycychc aromatic hydrocarbons (PAHs) are carcinogens produced by the thermal breakdown of organic materials. These are widely distributed in both food and the environment, and are some of the principal carcinogens in cigarette tar and air pollution. Of over 20 PAHs isolated, benzopyrene and quinoline compounds are the most commonly encountered in foods, particularly those which are broiled or fried (111). Shellfish living in petroleum contaminated waters may also contain PAHs (112). 

S I M O N I S Benzopyrone synthesis Benzopyrene synthesis Irem phenols and p ketoesters... 

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

Benzopyrene Midgut gland. Carcinus crab Induced Fossi et al. 

Fossi C, Lari L, Mattei N, SaveUi C, Sanchez-Hemandez JC, Castellani S, Depledge M, Bamber S, Walker C, Savaa D, et al. 1996. Biochemical and genotoxic biomarkers in the Mediterranean crab Carcinus aestuarii) experimentally exposed to polychlo-robiphenyls, benzopyrene and methyl-mercury. Mar Environ Res 42 29-32. 

Many aromatic compounds, such as benzopyrene, are carcinogenic because —... 

Common Name Benzo[a]pyrene Synonym BaP, B(a)P, 3,4-benzopyrene Chemical Name benzo[a]pyrene CAS Registry No 50-32-8 Molecular Formula C20H12 Molecular Weight 252.309 Melting Point (°C) ... 

Payne [30] carried out a field investigation of benzopyrene hydrolysate induction as monitor for marine petroleum pollution. Isaaq et al. [31] isolated stable mutagenic ultraviolet photodecomposition products of benzo(a)pyrene by thin-layer chromatography. 

One of the first applications of the new mesh and node intramolecular circuit rules discussed above is the well-known problem in electrical circuit theory of the balancing of a Wheatstone bridge. In Fig. 21, a molecular Wheatstone bridge is presented, made of loop-like 4 tolane molecular wires bonded via benzopyrene end-groups for nano-pads 1 and 3, and via pyrene end-groups for nano-pads 2 and 4. This four-electrode and four-branch molecule is connected to a battery and an ammeter. 

Dean, J.H., et al., Selective immunosuppression resulting from exposure to the carcinogenic congener of benzopyrene in B6C3F1 mice, Clin. Exp. Immunol., 52, 199, 1983. 

Following an aviation kerosin spill, hydrocarbons were detected in trout stream sediments and fish up to 14 months after the spill [13]. After a fire at a weed treatment plant in 1970 a large area of mixed forested ecosystem became contaminated with polycyclic aromatic hydrocarbons and creosote [66], High polyaromatic concentrations in stream sediments adversely affected micro- and meiobenthic communities at all trophic levels. Stein et al. [67] have studied the uptake by bethnic fish (English sole, Parophrys vetulus) of benzopyrene and polychlorinated biphenyls from sediments. Accumulation of contaminants from sediments was a significant route of uptake by English sole. 

Columns. ODS-silica, YMC ODS, 15 cm x 6.0 mm i.d., phenyl-bonded silica gel, YMC phenyl, 10 cm x 6.0 mm i.d. eluent, aqueous acetonitrile. Compounds, x, polycyclic aromatic hydrocarbons O, alkylbenzenes O,polychlorobenzenes +, alkanols A, alkanes 1, benzene 2, benzopyrene 3, toluene 4, heptylbenzene 5, hexachlorobenzene 6, hexanol 7, tetra-decanol 8, pentane and 9, octane. 

Figure 3.13 n-Electron selectivity of different octadecyl-bonded silica gels towards the retention of polycyclic aromatic hydrocarbons. Columns. , LOC-ODS-E, O, LOC-ODS-NE O, HIC-ODS-E, A, HIC-ODS-NE, eluent, 80% aqueous acetonitrile at 30°C. Compounds polycyclic aromatic hydrocarbons 1, benzene, 2, naphthalene 3, pyrene 4, 3,4-benzopyrene. 

As described elsewhere in this chapter, alterations in the activity of a number of lung enzymes have been described after acute and chronic ozone exposure. With the possible exceptions of the sulfhydryl-containing enzyme succinic dehydrogenase and the cytochrome P-4 en me benzopyrene hydroxylase, it is difficult to determine whether these findings are due to a direct oxidative effect of ozone or are secondary to changes in protein synthesis, concentrations of intermediates, or destruction of cells or organelles. 

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