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EC number: 292-607-4
CAS number: 90640-86-1
Distillate from the fractional distillation of coal tar of bituminous coal, with boiling range of 240°C to 400°C (464°F to 752°F). Composed primarily of tri- and polynuclear hydrocarbons and heterocyclic compounds.
PAH are absorbed rapidly through the pulmonary tract, the gastrointestinal tract and to a much lesser extent through skin. Metabolism is complex resulting mostly in hydroxylated species which in part may further be conjugated. Excretion is via urine, bile and faeces. Conjugates excreted into bile can be hydrolysed in the gut and be reabsorbed.Absorption through human skin will be not more than 2 % within and after 8 h of exposure. Permeation through rat skin is much more pronounced (ca. 8 fold) compared to human skin.
Distillates (coal tar), heavy oils
(anthracene oil high (> 50 ppm) BaP, AOH) [CAS no. 90640-86-1] is a UVCB
and consists of a complex combination of polycyclic aromatic
hydrocarbons (PAH).It comprises mainly
3- and 4-ring aromatic compounds and to a much lesser extent PAHs with 5
rings (see Chapter 1.). Main components are phenanthrene, anthracene
(3-ring PAH), fluoranthene, pyrene, benz[a]anthracene, and chrysene
(4-ringPAH) each accounting for ca. 3 to 10 %.The
majority of other components of AOH fall within the molecular size range
of these five substances.Benzo[a]pyrene
(5-ring PAH) is present at a typical concentration distinctly below 1 %
(typical concentration) representing PAH with 5-rings and more.
3- and 4-ring PAH together represent approx.
30 % of total AOH.The accumulated
percentage of all substances that can analytically be identified is
about 50 - 53 % (average ca. 51%), depending on individual AOH samples
and analytical method used. The remainder of AOH is not structurally
known. Identification was not possible applying standard analytical
As AOH basically is composed of PAH,
toxicokinetics of these substance class will determine the toxicokinetic
properties of total AOH.AOH
toxicokinetics can largely be characterised based on information
determined for its PAH constituents. Toxicokinetic characteristics of
PAH are reported based on a Summary from WHO 1998/2003
PAH are absorbed through the pulmonary tract,
the gastrointestinal tract, and the skin.Degree
of absorption may be different for individual substances.The
rate of absorption from the lungs depends on the type of PAH, the size
of the particles on which they are adsorbed, and the composition of the
adsorbent. PAH adsorbed onto particulate matter are cleared from the
lungs more slowly than free hydrocarbons.
Gastrointestinal absorption in rodents has
been reported to be up to 90 % (Grimmer et al. 1991). Effective
absorption by the different routes is also evidenced by observation of
systemic toxicity following exposure by the different routes.Absorption
from the gastrointestinal tract occurs rapidly in rodents, the majority
of metabolites released into the intestine via biliary excretion.
PAH are widely distributed throughout the
organism after administration by any route and are found in almost all
internal organs, but particularly those rich in lipids. Intravenously
injected PAH are cleared rapidly from the bloodstream of rodents but can
cross the placental barrier and have been detected in foetal tissues.
Studies with 32P-postlabelling for the
detection of DNA-adducts after percutaneous absorption of mixtures of
PAH in rodents showed that components of the mixtures reach the lungs,
where they become bound to DNA.
The metabolism of PAH to more water-soluble
derivatives, which is a prerequisite for their excretion, is complex. In
general, parent compounds are converted into intermediate epoxides (a
reaction catalysed by cytochrome P450-dependent mono-oxygenases), which
are further transformed by rearrangement or hydration to yield phenols
or diols.In following steps
conjugation by glutathione, sulphate or glucuronic acid may occur. Alternatively
or in addition, a second oxidation at another position of the aromatic
system is possible to yield tetrols,
which can themselves be conjugated with sulphuric or glucuronic acids or
with glutathione. Most metabolism results in detoxification, but some
PAH are activated to DNA-binding species, principally diol epoxides,
which may initiate tumours.
For phenanthrene only
approx. 3.8 % of the excreted dose were detected as
hydroxy-phenanthrenes (1-, 2-position ca. 60 % of total OH-derivatives,
3-, 4-, and 9-position minor). Dihydro-diols were not detected and may
have escaped determination (Grimmer et al. 1991). In an experiment with
liver microsomes from untreated rats (Jacob et al. 1982), trans
9-,10-dihydro-diol was identified (K-region oxidation) indicating that
hydroxy-derivatives of phenanthrene can be formed other than recovered
in the study of Grimmer et al. 1991
PAH metabolites and their
conjugates are excreted via the urine and faeces, but conjugates
excreted into the bile can be hydrolysed by enzymes of the gut flora and
be reabsorbed. It can be inferred from the available information on the
total human body burden that PAH do not persist in the body and that
turnover is rapid. This inference excludes those PAH moieties that
become covalently bound to tissue constituents, in particular nucleic
acids, and are not removed by repair.
WHO (1998). Selected non-heterocyclic
polycyclic aromatic hydrocarbons. Environmental Health Criteria 202,
Geneva, Switzerland, WHO (World Health Organisation) 1998
WHO (2003). HEALTH RISKS OF PERSISTENT
ORGANIC POLLUTANTS FROM LONG-RANGE TRANSBOUNDARY AIR POLLUTION, JOINT
WHO/CONVENTION TASK FORCE ON THE HEALTH ASPECTS OF AIR POLLUTION. WHO
Regional Office for Europe, World Health Organization 2003
In synopsis of observations from comparative
in-vivo and in-vitro studies (human vs. rodent) on spiked creosote, it
is expected that not more than 2 % of a dermal dose will be absorbed
through human skin within and after 8 hours of exposure (Fasano
2007a,b). The conversion factor human vs. rat skin was found to be 0.12,
which means that the dermal dose absorbable within 8 hours is about
8-fold higher in rat than in human skin.
Studies of Van Rooij et al. 1995 and Sartorelli et al. 1999 show
that lower molecular weight PAH are absorbed faster than higher
molecular weight PAH. For absorption through pig ear (Van Rooij) and
full thickness skin from the abdomen of monkeys (Ceropithecus aetops)
(application in artificial sweat) (Sartorelli), differences in
absorption rates from 103 ng/(h*cm²) (phenanthrene) to 0.8 ng/(h*cm²)
(benzo[a]pyrene) and from 24 ng/(h*cm²) (fluorene) to 0.4 ng/(h*cm²)
(benzo[a]pyrene), respectively, were observed.
Taking into account the PAH composition of AOH (more higher size
PAH compared to creosote) it can be estimated that human dermal
absorption of AOH will at least not be higher than for creosote (Fasano,
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