Polycyclic aromatic hydrocarbons. A review

Figures & data

Table 1. Abbreviations and atomic mass units of common PAHs (Wenzl, Simon et al., 2006)

			US-EPA	SCF	JECFA
Acenaphthene	ACP	154 AMU	x
Acenaphthylene	ACY	152 AMU	x
Anthracene	ANT	178 AMU	x
Fluoranthene	FLT	202 AMU	x
Fluorene	FLR	166 AMU	x
Naphthalene	NAP	128 AMU	x
Phenanthrene	PHE	178 AMU	x
Pyrene	PYR	202 AMU	x
Benz[a]anthracene	BaA	228 AMU	x	x	x
Benzo[b]fluoranthene	BbF	252 AMU	x	x	x
Benzo[j]fluoranthene	BjF	252 AMU	x	x
Benzo[k]fluoranthene	BkF	252 AMU	x	x	x
Benzo[ghi]perylene	BgP	276 AMU	x	x
Benzo[a]pyrene	BaP	252 AMU	x	x	x
Chrysene	CHR	228 AMU	x	x	x
Cyclopenta[cd]pyrene	CPP	226 AMU	x
Dibenz[a,h]anthracene	DhA	278 AMU	x	x	x
Dibenzo[a,e]pyrene	DeP	302 AMU	x	x
Dibenzo[a,h]pyrene	DhP	302 AMU	x	x
Dibenzo[a,i]pyrene	DiP	302 AMU	x	x
Dibenzo[a,l]pyrene	DlP	302 AMU	x	x
Indeno[1,2,3-cd]pyrene	IcP	276 AMU	x	x	x
5-Methylchrysene	5MC	242 AMU	x	x

Table 2. Some PAH ratios (Veyrand, Brosseaud et al. 2007, Tobiszewski and Namieśnik, 2012)

PAH ratio	Value Range	Source	References
Phe/An	<10	Pyrolytic
Phe/An	>15	Petrogenic
Chr/BaA	<1	Pyrolytic
Chr/BaA	>1	Petrogenic
Flu/Pyr	>1	Pyrolytic
Flu/Pyr	<1	Petrogenic
Flu/Flu+Pyr	>0.5	Pyrolytic
Flu/Flu+Pyr	<0.5	Petrogenic
LMW/HMW	low	Pyrolytic	(Zhang, Zhang et al. 2008)
LMW/HMW	high	Petrogenic
BaP/BghiP	<6	on-traffic emission	(Katsoyiannis, Terzi et al., 2007)
	>6	Traffic emission
BbF/B	2.5-2.9	Aluminium smelter emission
FL/(FL+PYR)	<5	Petrol emission	(Ravindra K, Sokhi R et al., 2008)
	>5	Diesel emission
ANT/(ANT+PHE)	<1	Petrogenic	(Pies, Hoffmann et al. 2008)
	>1	Petrogenic
FLA/(FLA+PYR)	<0.4	Petrogenic	(De La Torre-Roche, Lee et al. 2009)

Figure 1. Chemical structures of some commonly studied PAH(Haritash and Kaushik 2009).

Figure 2. Flow chart showing short and long term health effects of exposure to PAHs(Kim, Jahan et al. 2013).

Table 3. Common analytical methods used in analysis of PAHs

S/N	Analytical methods	Target PAHs	Reference
1	Synchronious fluorecence spectrophtometry	Water	(Baudot, Viriot et al. 1992, Vo-Dinh, Fetzer et al. 1998)
2	fluorimetry	Food and environmental sample	(Zhang, Yuan et al. 1998, Wenzl, Simon et al., 2006)
3	IR	Forensic samples	(Douglas, Emsbo-Mattingly et al. 2015, Tommasini, Lucotti et al. 2016)
4	HPLC-fluorescence	Indoor samples	(Liaud, Millet et al. 2015)
5	Gas chromatography-mass spectrometry	Roasted coffee	(Guatemala-Morales, Beltrán-Medina et al. 2016)
6	GC–MS/MS	Petrochemical soil	(Shang, Kim et al. 2014, Zhao, Zhang et al. 2015, Shimada, Takenaka et al. 2016)
7	HPLC and MS	Slurge	(Viguri, Verde et al. 2002)
8	fluorescence spectroscopy	Waste slurge	(Aemig, Chéron et al., 2016)
9	HPLC-fluorescence	Fire events	(Denis, Toney et al. 2012)
10	LDM (localization-delocalization matrix	Water	(Sumar, Cook et al. 2015)
11	FT-IR	soil	(Swaathy, Kavttha et al. 2014)
12	gaschromatography-triple quadrupole mass spectrometry	Fruit and vegetable	(Banerjee et al., 2012)
13	near-infrared (NIR)	Air	(Doney, Candian et al. 2016)
14	GC/MS	sediment	(Retnam, Zakaria et al. 2013, Sanil Kumar, Nair et al. 2016)
15	HPLC-fluorescence	indoor air	(Liaud, Millet et al. 2015)
16	miniaturized membrane inlet mass spectrometer (mini-MIMS)	Sand and Soil	(Frandsen, Janfelt et al. 2008)
17	two-dimensional fluorescence correlation spectroscopy	water	(Zhou, Zhao et al. 2016)
18	polythiophene sensors	air	(Tiu, Krupadam et al. 2016)
19	LC-MS/MS	Waste	(Pitarch, Cervera et al. 2016)
20	HPLC with fluorescence and chemiluminescence detections,	air	(Hayakawa 2016)
21	UHPLC-MS/MS	Biological sample	(Han, Sapozhnikova et al. 2016)
22	Graphene nanosensor	Aqeuos solution	(Church, Wang et al. 2016)

Figure 3. Schematic of the fate of PAHs in the atmosphere (Kim, Jahan et al. 2013).

Table 4. Maximum levels of benzo[a]pyrene in food, specified in Commission Regulation (EC) 208/2005 (Numbering of food groups is identical with numbering in Regulation)(Wenzl, Simon et al., 2006)

Product		Maximum level(lg/kg wet weight)
7.1.1.	Oils and fats intended for direct human consumption or use as an ingredient in foods	2.0
7.1.2.	Foods for infants and young children	1.0
7.1.2.1.	Baby food and processed cereal-based foods for infants and young children
7.1.2.2.	Infant formulae and follow-on formulae, including infant milk and follow-on milk
7.1.2.3.	Dietary foods for special medical purposes intended specifically for infants
7.1.3.	Smoked meats and smoked meat products	5.0
7.1.4.	Muscle meat of smoked fish and smoked fishery products excluding bivalve mollusks	5.0

Table 5. Carcinogenic classifications of selected PAHs by specific agencies(Kim, Jahan et al. 2013)

Order	Agency	PAH compound(s)	Carcinogenic classification	Reference
1	Agency for Toxic Substances and Disease Registry (ATSDR)	• Benz(a)anthracene	Known animal carcinogens	(ATSDR (Agency for Toxic Substances 1995)
	• Benzo(b)fluoranthene
	• Benzo(a)pyrene,
	• Dibenz(a,h)anthracene,
	• Benz(a)anthracene and Benzo(a)pyrene		Probably carcinogenic to humans
2	International Agency for Research on Cancer (IARC)	Benzo(a)fluoranthene	Possibly carcinogenic to humans	(2010;92:765–71 2010)
	• Benzo(k)fluoranthene,
	• Ideno(1,2,3-c,d)pyrene
	• Anthracene,		Not classifiable as to their carcinogenicity to humans
	• Benzo(g,h,i)perylene,
	• Benzo(e)pyrene,
	• Fluoranthene,
	• Fluorene
	• Phenanthrene,
	• Pyrene
3	U.S. Environmental Protection Agency(EPA)	Benz(a)anthracene,	Probable human carcinogens	(Agency). 2008)
	• Benzo(a)pyrene,
	• Benzo(b)fluoranthene
	• Benzo(k)fluoranthene,
	• Chrysene
	• Dibenz(a,h)anthracene
	• Indeno(1,2,3-c,d)pyrene
	• Acenaphthylene		Not classifiable as to human carcinogenicity
	• Anthracene,
	• Benzo(g,h,i)perylene
	• Fluoranthene

Figure 4. Fungal degradation pathway of Phenanthrene using Irpex lacteus(Cajthaml, Mode et al., 2002).

Figure 5. Proposed anaerobic biotransformation pathway of phenanthrene by sulfate-reducing bacteria.

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