Polycyclic Aromatic Hydrocarbons Evaluation of Sources and Effects (1983) / Chapter Skim
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APPENDIX A: LISTS OF POLYCYCLIC AROMATIC HYDROCARBONS
APPENDIX A: LISTS OF POLYCYCLIC AROMATIC HYDROCARBONS
Pages 395-414
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From page 395... ...
pyrene ~,'Z ~ 3 5 sW6 Benz[e] pyrene ~Perylene 9 ~ 7 8 ~ S 1^ ~ .- I ~ 3 Molecular Weight 228.0939 0/+ 252.0939 ++ 252.0939 0/+ 252.0939 0 Benzo[j~fluoranthene 252.0939 ++ A-11 Carcinogenic Activity ~...
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From page 396... ...
Table A-2 (continued) Structural Formula Name 2 1'~s 9 8 7 2 44 18 1l ~ 13 Molecular Carcinogenic Weight Activity Benz~e]
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From page 397... ...
Table A-2 (continued) Structural Formula 3 ~2 ~ 7 12 2 3 4 12 2 34 8 7 6 2 12 ~ 4 IO ~ 8 9 12 1 1l ~ 2 Molecular Carcinogenic ___ Weight Activity Benzo[~]
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From page 398... ...
_ 1l 12 9~3 _.. 9~3 1~3 12 0~8 2 I `~3 'I 12 ION ,7 9 8 3 2~4 1~6 7 2 19 11 R0 Molecular We ight u~uenzo [clef ,mno I-276.0939 chrysene ~ Anthanthrene ~ Indeno ~ 1, 2, 3-cd ~ pyrene276.0939 + Dibenz [a ,h ~ anthracene ~ 278.1096 + Benzotcichrysene278.1096 + Benzo ~ g ~ chrysene A-14 Carc inogenic Activity lo 278.1096 +
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From page 399... ...
Table A-2 (continued) Molecular Carcinogenic Structural Formula Name Weight Activity 2 3 8 10[ ~ 3 8 7 6 2 21 ~ 4 - 2 I,> ~ 14 12 2 ~o~l.
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From page 400... ...
Care inogenic Ac t ivity 0/+ ++ Dibenzo[def,p] chrysene 302.1096 ++ ( Dibenzo [ a, 1 ]
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From page 401... ...
TABLE A-3 Nitroarenes Detected in Diesel-Exhaust Particulate Extracts: Molecular Formulas and Molecular Weights Struc ture Molecular Molecular No. Name Formula Weight Mononitroarenes: 1 Nitroindene C9H7NO2 161.16 2 Nitroacenaphthylene C12H7NO2 197.19 3 N~troacenaphthene C12HgNO2 199.21 4 N~trobiphenyl C12H9NO2 199.21 5 Nitrofluorene C13H9NO2 211.22 6 Nitromethylacenaphthylene C13H9NO2 21L.22 7 Nitromethylacenap~thene C13HllNO2 213.24 8 Nitromethylbiphenyl C13HllNO2 213.24 9 Nitroanthracene C14HgNO2 223.23 10 Nitrophenanthrene C14H9NO2 223.23 11 Nitromethylflourene C14HllNO2 225.25 12 Nitromethylanthracene ClsHLlNO2 237.26 13 Nitromethylphenanthrene C15HLlNO2 237.26 14 Nitrotrimethylnap~thylene C13H13NO2 215.25 15 N~trofluoranthene C16HgNO2 247.25 16 N~tropyrene C16HgNO2 247.25 17 Nitro(C2-alkyl~anthracene C16H13NO2 251.29 18 N,tro(C2-alkyl~phenanthrene C16H13N~2 251.29 19 N~trobenzofluorene C17HllNO2 261.28 20 Nitromethylfluoranthrene C17HllNO2 261.28 21 Nitromethylpyrene C17H12NO2 262.29 22 Nitro(C3-alkyl~anthracene C17H15NO2 265.31 23 Nitro(C3-alkyl~phenanthrene C17H15NO2 265.31 24 Nitrochrysene C18HllNO2 273.29 25 Nitrobenzanthracene C18HllNO2 273.29 26 Nitronaphthacene C18HllNO2 273.29 27 Nitrotriphenylene C18HllNO2 273.29 28 Nitromethylchrysene Cl9H13NO2 287.32 29 Nitromethylbenzanthracene Cl9H13NO2 287.32 30 Nitromethyltriphenylene ClgH13NO2 287.32 31 Nitrobenzopyrene C20HllNO2 297.31 32 N~troperylene C20HllNO2 297.31 33 N~trobenzofluoranthene C20HllNO2 297.31 Polynitroarenes: 34 Dinitromethylnaphthylene CllHgN2O4 233.20 35 Dinitrofluorene C13H8N2O4 256.22 36 Dinitromethylbiphenyl C13HloN2o4 258.23 37 Din~trophenantl~rene C14H8N2O4 268.23 38 D~-nitropyrene C16H8N2O4 292.25 39 Tr~nitropyrene C16H7N3O6 337.25 40 Trinitro(C5-alkyl)
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From page 402... ...
Nitro-oxyarenes: 43 NitronapUthaquinone CloH5NO4 203.L5 44 Nitrodihydroxynap~thalene CloH8NO4 206.18 45 Nitronaphthalic acid CloH8NO4 206.18 46 Nitrofluorenone C13H7NO3 225.20 47 Nitroanthrone C14H9NO3 239.23 48 Nitrophenanthrone C14H9NO3 239.23 49 Nitroanthraquinone C14H7NO4 253.21 50 Nitrohydroxymethyliluorene C14HllNO3 241.25 51 Nitrofluoranthone C16H~NO3 262.24 52 Nitrofluoranthenequinone C16H7NO4 277.24 53 Nitropyrenequinone C16H8NO4 278.24 54 Nitropyrone C16HgNO3 263.25 55 Nitrodimethylanthracene C17H12NO3 278.29 carboxaldehyde 56 Nitrodimethylphenanthrene C17Hl2No3 278.29 carboxaldehyde Other nitrogen compounds: 57 - Benzocinnoline C12HgN2 180.21 58 Methylbenzocinnoline C13HloN2 194.24 59 Phenyloaphthylamine C 16H13N 219. 29 6 0 ( C2-Alkyl )
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From page 403... ...
TABLE A-4 Struc Lures of Nitroarenesa H H N02 ¢ 1 N 0 2~3 AS N02~1 9J12~1 7/ 22 o 11 No2~3 H H ~7 o ., No2~3 11 o ~9 N02~ 27,30 No7~1 I 2,6 ~ H No2~3 5.L1 N O 2 10,1~.1l,~ it, N02 16, 2 N 0 2 2`,2 N O2-~`J 31 C~5 H ~3 59,60 Hi; A-19 .
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From page 404... ...
3 14 Nit 3 N O -~3 N O 2-~ ~ o H ) 2 lo 57,58 o ~C`oH NO2 ~5 NOW 0 48 ,, N O2-Id 54 o 11 NO 2H ~7 o ll N 0 2 ~6 O ,0 N 0 2- ~N 0 2- o " O C-H " NO2- ~NO2 55 , ~53 ~6 "Numbers under structures refer to compounds listed in Table A-3.
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From page 405... ...
Dibenzopyrenes (4 isomers) Indeno(1,2,3-cd~pyrene Chrysene Perylene BenzotghilperyLene Coronene Picene Benzotc~phenanthrene Benzotb~chrysene Benzotc~tetraphene Hexahydrochrysene Dihydrobenzo~ciphenanthrene Dihydrobenz~aJanthracene Dihydrochrysene Benzacenaphthylene Binaphthyl (3 isomers)
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From page 406... ...
02-0 .6 6 Me thylquino 1 ine 0.03 6 2 , 6-D imethylquinol ine 0 .03 6 Dimethylquinolines 0. 04-0.09 6 Ethylquinol ines 0.
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From page 407... ...
carbazole Phenoxazine C; Alkylquinolines Me thylphenanthr id ine s Methylbenzoquinolines Me thylbenzoisoquino 1 ines Azabenzofluorenes Methylazapyrenes Me-thylazafluoranthenes Azabenz~aJanthracene Azachrysenes Azabenzopyrenes Azabenzofluoranthenes Dibenzoquinolines Dibenzoisoq~inolines Quinones: 9,lO-Anthraquinone Benzotaipyrene 6,12-quinone Benzota~pyrene 1,6-quinone Benzo~aipyrene 3,6-quinone Dibenzo~b,def~chrysene 7,L4-quinone Phenaten-l-one Benzanthrone Perinaphthanone Carboxylic acids: Nap~thalene carboxylic acid Phenanthrene carboxylic acid Anthracene carboxylic acid Pyrene carboxylic acid Ambient concentration, ng/m3 0.01-0.2 0.01-0.3 0.1 0.02 0.14-0.18 0.17-0.31 0.06 0.07-0.16 0.03 0.03-0.11 0.005 0.02-13 trace-3 1.0 .0 a a a a a a a a a a a a a a a b b b b b 0.3-17 0.6-48 a a B-3 References 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 1 l 1 l ll 5,6 6 1 ..
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From page 408... ...
Methylnaphthobenzathiophenes (3 isomers) Nitro derivatives: 1-Nitropyrene 3-Nitrofluoranthene 5-Nitroacenaphthene 6-Nitrobenzota~pyrene Ambient conce~ tration, ng/m References a 0.014-0.02 b b b b b b b b b l 2 4 4 4 4 4 4 7 3 aConcentration reported in micrograms per gram of part iculate matter or micrograms per gram of benzene-soluble fraction, but not in nanograms pe cubic meter.
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From page 409... ...
Bartle. Gas chromatography/mass spectrometic and nuclear magnetic resonance determination of poly nuclear aromatic hydrocarbons in airborne particulates.
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From page 411... ...
The major known human cancer associated with exposure to chemical mixtures containing PAHs is undoubtedly lung cancer. Although cigarette-smoking is of overwhelming importance as a cause of lung cancers ~ 40 and cigarette smoke does contain PAHs, this appendix is concerned with cigarette-smoking only insofar as the information derived from epidemiologic study of the smoking population is essential in measuring the health effects that might be expected when Germans are exposed to other PAH-containing mixtures.
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From page 412... ...
This measure has been found particularly useful in comparing human data and experimental-animal data and forms the basis of current methods of extrapolating animal data to man.3 The lifetime risk is virtually identical with the cumulative incidence rate (to age 70) used by the International Agency for Research on Cancer.3'39 CIGARETTE-SMOKING AS A SOURCE OF PAR EXPOSURE Much of what has been learned about the quantitative relationship between cigarette-smoking and lung cancer over the last 30 yr may be summarized by the statement, "The excess lung-cancer incidence of a smoker, compared with a nonsmoker, is proportional to the number of cigarettes smoked per day and to the duration of smoking raised to the C-2
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From page 413... ...
smokers.8 For U.S. smokers the constant a must be decreased by 25-50%.12,13,19 33 The reasons for this include the use of different tobaccos in the two countries and the mode of cigarette-smoking -- in particular, British smokers tend to smoke their cigarettes down to a considerably shorter butt.7343 Similar reasons probably explain the exis fence of a range.
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From page 414... ...
BaP concentrations have since decreased by 1969, the median BaP concentration in urban air was less than 2 ng/m .2 However3 some cities were still experiencing average annual BaP concentrations of nearly 10 ng/m3. BaP is not a perfect indicator of either PAR in the air or its carcinogenicity,35 and it accounts for a much Smaller fraction of the carcinogenicity of cigarettes than of air.il,4 It should be emphasized C-4
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