Hydrocarbons fluoranthene

Saxena et al. [512] used polyurethane foams to concentrate trace quantities of six representatives of polynuclear aromatic hydrocarbons (fluoranthene, benzo(k)fluoranthene, benzo(j)fluoranthene, benzo(a) pyrene, benzo(ghi) perylene, and indeno(l,2,3-cd)pyrene) prior to regular screening of these compounds in US raw and potable waters. Final purification and resolution of samples was by gas chromatography and two-dimensional thin layer chromatography, followed by fluorometric analysis and quantification. 

Willett KL, Wassenberg D, Lienesch L, Reichert W, Di Guilio RT. 2001. In vivo and in vitro inhibition of CYPlA-dependent activity in Fundulus heteroclitus by the polynuclear aromatic hydrocarbon fluoranthene. Toxicol Appl Pharmacol 177 264—271. 

L.Ren,X.-D.Huang,B.J.McConkey,D.G.Dixon,B.M.Greenberg(1994).Photoinduced toxicity of three polycyclic aromatic hydrocarbons (fluoranthene, pyrene, naphthalene) to the duckweed, Lemna gibba L. G-3, Ecotoxicol. Environ. Saf, 28,... 

Fig. 6-2 The carbon-atom connectivity of the non-alternant hydrocarbon, fluoranthene.

Being interested here in the volatile components of coffee aroma, we shall arbitrarily limit the list of the aromatic hydrocarbons to tricyclic structures. The higher fused polycyclic hydrocarbons (fluoranthene [206-44-0], pyrene [129-00-0], chrysene [218-01-9], benz[ ]anthracene (1,2-benzanthracene) [56-55-3], benz[< ]acephenanthrylene (3,4-benzofluoranthene) [205-99-2], benzo[ ]pyrene (3,4-benzopyrene, 3,4-BP) [50-32-8], benzo[e]pyrene (1,2-benzopyrene) [192-97-2], perylene [198-55-0], benzo[g,/i,/]perylene (1,12-benzopyrene) [191-24-2], and dibenz[ ,//]anthracene (1,2,5,6-dibenzanthracene) [53-70-3]) cannot be considered as a part of the aroma. However, as some of these, specially benzo[o pyrene, are known for carcinogenic properties, they have been particularly analyzed in food subject to roasting or smoke-curing. 

A means to deposit energy in multiply charged cation complexes is by the exothermic addition of an electron. The technique of electron transfer dissociation (ETD) employs as an electron donor the polycyclic aromatic hydrocarbon fluoranthene anion, CieHio , the electron binding energy for which is only 0.6 eV. An important characteristic of ETD when applied to metal ion complexes is that the process results in both charge reduction and chemi-... 

The limits of lifetime detection and resolution in on-the-flight fluorescence lifetime detection in hplc were evaluated for simple, binary systems of polycycHc hydrocarbons (70). Peak homogeneity owing to coelution was clearly indicated for two compounds having fluorescence lifetime ratios as small as 1.2 and the individual peaks could be recovered using predeterrnined lifetimes of the compounds. Limits of lifetime detection were deterrnined to be 6 and 0.3 pmol for benzo[b]fluoranthene and benzo[k]fluoranthene, respectively. 

Fig. 42 Chromatogram of polycyclic aromatic hydrocarbons on caffeine-impregnated precoated silica gel 60 HPTLC plates with concentrating zone (Merck). The following can be recognized in increasing Rf value. — 1. benzo(ghi)perylene, 2. indeno(l,2,3-cd)pyrene, 3 benzo(a)pyrene, 4. benzo(b)fluoranthene, 5. benzo(k)fluoranthene, 6. fluoranthene.

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. 

Fig. 34.3. UV-visible spectra of two polyaromatic hydrocarbons (PAHs), fluoranthene and chrysene.

Polycyclic (also called polynuclear) aromatic hydrocarbons (PAHs) are composed of multiple rings connected by shared carbon atoms (i.e., separate rings are combined by sharing two carbon atoms). All these compounds are pure hydrocarbons except for the two benzo-fluoranthenes, polychlorinated biphenyls (PCBs), and 2-chloronaphthalene. Moore and Ramamoorthy110 review the behavior of PAHs in natural waters. 

Fig. 7.15 is constructed from reactivity diagrams of aromatic hydrocarbons already published. The reactivity of fluoranthene has often been investigated in detail from both, the experimental and theoretical aspects 116>. The values of /rE> calculated by the Pariser-Parr method (SCF) 117> as well as by the Hiickel MO (HMO) modified by considering... 

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. 

At least experiments with fluoranthene and other aromatic hydrocarbons having lower triplet energies than fluoranthene resulted only in fluoranthene singlet emission- this excited singlet appears to be generated directly and not by triplet-triplet annihilation. 

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...

Beckles, D.M., C.H. Ward, and J.B. Hughes. 1998. Effect of mixtures of polycyclic aromatic hydrocarbons and sediments on fluoranthene biodegradation patterns. Environ. Toxicol. Chem. 17 1246-1251. 

Boeda et al. (1996) identified bitumen on a flint scraper and a Levallois flake, discovered in Mousterian levels (about 40 000 BP) at the site of Umm el Tlel in Syria. The occurrence of polyaromatic hydrocarbons such as fluoranthene, pyrene, phenanthrenes and chrysenes suggested that the raw bitumen had been subjected to high temperature. The distribution of the sterane and terpane biomarkers in the bitumen did not correspond to the well-known bitumen occurrences in these areas. In other studies of bitumen associated with a wide variety of artefacts of later date, especially from the 6th Millennium BC onwards, molecular and isotopic methods have proved successful in recognizing different sources of bitumen enabling trade routes to be determined through time (Connan et al., 1992 Connan and Deschesne, 1996 Connan, 1999 Harrell and Lewan, 2002). 

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... 

Fig. 5 Typical deformations detected in 96 hpf zebrafish embryos exposed at the indicated concentrations of the carcinogenic polycyclic aromatic hydrocarbons Benzo[a]Pyrene (b) and Benazo [k]Fluoranthene (c), or to the reportedly nontoxic AhR-ligand (3-naphthofiavone (d). A nonexposed, normal specimen is shown in (a). Arrows indicate (a) pericardial edema, (b) malformation of the lower jaw, (c) malformation of the tail, (tf) color of the yolk, and (e) coagulation...

Uses. Fluoranthene is a component of polynuclear aromatic hydrocarbons, also known as polycyclic aromatic hydrocarbons, and is usually bound to small particulate matter present in urban air, industrial and natural combustion emissions, and cigarette smoke. 

Fullerenes can also be obtained by pyrolysis of hydrocarbons, preferably aromatics. The first example was the pyrolysis of naphthalene at 1000 °C in an argon stream [58, 59], The naphthalene skeleton is a monomer of the Cjq structure. FuUerenes are formed by dehydrogenative coupUng reactions. Primary reaction products are polynaphthyls with up to seven naphthalene moieties joined together. FuU dehydrogenation leads to both Cjq as well as C7Q in yields less than 0.5%. As side products, hydrofuUerenes, for example CjqHjj, have also been observed by mass spectrometry. Next to naphthalene, the bowl-shaped corannulene and benzo[k]fluoranthene were... 

Polycyclic Aromatic Hydrocarbons with Two or Three Fused Rings Polycyclic Aromatic Hydrocarbons PAH PNA POM Polycyclic Hydrocarbons, Nonalternant Compounds with Four Fused Rings Fluoranthene... 

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