Dioxins and dioxin-like compounds

251: 710:

after high accidental or occupational exposures like in Yusho and Yucheng poisonings, Seveso accident, and combined occupational cohorts. Therefore, controversies on cancer risk at low population levels of dioxins are understandable. The problem with IARC evaluations is that they only assess hazard, i.e. carcinogenicity at any dose. It is likely that there is a practical safe threshold for the non-genotoxic dioxins, and the present population levels do not possess any risk of cancer. There is thus some agreement on that cancer risk is taken care of as well, if daily intake limits are set to protect from developmental effects. Among fishermen with high dioxin concentrations in their bodies, cancer deaths were decreased rather than increased. All this means that in case of important beneficial food items and breast feeding a thorough benefit/risk analysis is needed before setting limits, in order to avoid increased other risks or lost benefits.

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HSP90 and the blue ovals p23. Dioxin binding to the AHR (1.) leads to its translocation into the nucleus by importin-β, (2.) heterodimerization with ARNT and binding to the DNA at DREs, (3.) modulating expression levels of target genes (green arrows). One of the gene products elevated by this mechanism is AHRR, a repressor protein which forms a feedback loop that inhibits AHR action. The AHR is finally degraded by the ubiquitin–proteasome system (4.). AHR activation can also rapidly increase intracellular Ca concentration (5.) which in turn may ultimately result in augmented Cox2 gene expression. Elevation of Ca activates CaMKs, which appear to have a critical role in the translocation of the AHR. Another example of effects mediated by the AHR via non-canonical pathways is suppression of acute-phase proteins (6.) which does not involve DNA binding.

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significance of dairy products and meat have decreased due to strict emission controls, and brought about the decrease of total intake. E.g. in the United Kingdom the total intake of PCDD/F in 1982 was 239 pg/day and in 2001 only 21 pg/day (WHO-TEQ). Since the half-lives are very long (for e.g. TCDD 7–8 years), the body burden will increase almost over the whole lifetime. Therefore, the concentrations may increase five to tenfold from age 20 to age 60. For the same reason, short term higher intake such as after food contamination incidents, is not crucial unless it is extremely high or lasts for several months or years.

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persistence in the environment and in the organism depends on the presence of so-called "lateral chlorines", in case of dioxins and furans, chlorine substitutes in positions 2,3,7, and 8. Each additional non-lateral chlorine decreases the potency, but qualitatively the effects remain similar. Therefore, a simple sum of different dioxin congeners is not a meaningful measure of toxicity. To compare the toxicities of various congeners and to render it possible to make a toxicologically meaningful sum of a mixture, a toxicity equivalency (TEQ) concept was created.

1102: 1090: 787: 637:(TWI) levels based on the Russian children study. This recommendation can be challenged, because it does not properly consider competing risks following from lost benefits of important and healthy food items such as certain fish. TWI levels are not applied for breast feeding, because benefits of breast milk are judged to be far more important than the remote risks of dioxins. A general conclusion may be that safety margins are not very great concerning developmental effects, but toxic effects are not likely at the present population levels of dioxins. 155: 137: 169: 1151: 629:

after long breast-feeding, when the dioxin concentrations were high in 1970s and 1980s. When the concentrations decreased during 1990s and 2000s, the effects were no longer seen. According to a study in Russia, sperm counts in 18-19 year old young men were lower when dioxin levels were higher at the age of 8 to 9 years. This was in industrial environments causing relatively high exposures to boys as well as their mothers. The contamination panel of the

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those in the 1970s, and the total TEQ concentrations are now of the order of 5-30 pg/g fat (please note the units, pg/g is the same as ng/kg, or the non-standard expression ppt used sometimes in the United States). The decrease is due to strict emission controls and also to the control of concentrations in food. In the U.S. young adult female population (age group 20–39), the concentration was 9.7 pg/g lipid in 2001-2002 (geometric mean).

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most sources where hepta- and octa-congeners may predominate. The WHO panel re-evaluating the TEF values in 2005 expressed their concern that emissions should not be uncritically measured as TEQs, because all congeners are not equally important. They stated that "when a human risk assessment is to be done from abiotic matrices, factors such as fate, transport, and bioavailability from each matrix be specifically considered".

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attach the receptor. Substituents in ortho-positions 2 and 6 prevent rotation and thus hinder the molecule from assuming a planar position. Mono-ortho congeners (one Cl in 2, 2', 6, or 6') have minimal activity. No significant dioxin-like activities have been noticed, if there are two or more o-chlorines. Brominated dioxins and biphenyls have similar properties, but they have been studied much less.

1526:. With the substantial decrease of emissions from municipal waste incinerators, other potentially large sources of dioxin-like compounds, for example from forest and wild fires, have increased relative to industrial sources. They are however not included in the total inventory due to uncertainties in available data. A more recent study on the environmental effects of accidental fires, including 1392:

400 °C (752 °F) to 700 °C (1,292 °F). This means that formation is highest when organic material is burned in less-than-optimal conditions such as open fires, building fires, domestic fireplaces, and poorly operated and/or designed solid waste incinerators. Historically, municipal and medical waste incineration was the most important source of PCDD/Fs.

339:, several natural compounds, and dioxins. Secondly, AH receptors are involved in the activation or silencing of genes that lead to the toxic effects of high doses of dioxins. Because TCDD at high doses can influence the transcription of perhaps hundreds of genes, the genes crucial for the multitude of toxic effects of dioxins are still not known very well. 2796:

the two major data sets that they failed to reference or explain away. The NIOSH statistical treatment obscured the significant reduction in cancer incidence that occurs at low dioxin exposures. Even though cancer incidence may increase at high dioxin exposures, such increase may be preceded at lower exposures by a significant reduction.

508:

and type II effects (lethality, liver damage, anorexia, and tumour promotion). The reason may be different requirements of the transactivation domain structure of the AH receptor for different genes. Some of these low-dose effects can in fact be interpreted as protective rather than toxic (enzyme induction, aversion to novel foods).

1640:, but dioxins are also a possible cause of reproductive effects. Both in America and in Europe, many waterfowl have high concentrations of dioxins, but usually not high enough to disturb their reproductive success. Due to supplementary winter feeding and other measures also, the white-tailed eagle is recovering (see 1728:. The highest concentrations were detected in nonflying enlisted personnel (e.g. filling the tanks of planes), although the variation was huge, 0 to 618 ng/kg TCDD (mean 23.6 ng/kg). Other occupational exposures (working at paper and pulp mills, steel mills and incinerators) have been remarkably lower. 726:(TDI) of dioxin, 1-4 pg/kg body weight per day, i.e. 7x10 to 2.8x10g per 70-kg person per day, to allow for this uncertainty and ensure public safety in all instances. Authorities have then set weekly or monthly intake levels that equal to TDIs around 2 pg/kg. Because dioxins are eliminated very slowly, the 1743:

neither volatile nor water-soluble, and therefore exposure of human beings depends on direct eating of soil or production of dust which carries the chemical. Contamination of ground water or breathing vapour of the chemical are not likely to cause a significant exposure. Currently, in the US, there are 126

747:(TWI) from 14 pg/kg to 2 pg/kg. This is likely to cause another controversy before being accepted by European countries. Dioxin intake and levels in breast milk in 1970s and 1980s were 5 to 10 times higher than presently, and very few effects have been found, possibly mild developmental effects on teeth. 311:, and it acts to modify transcription of a number of genes (see figure). AH receptor activity is necessary for normal development and many physiological functions. Mice lacking the AH receptor (knockouts) are sick with cardiac hypertrophy, liver fibrosis, reproductive problems, and impaired immunology. 1664:

TCDD has been long known to be sensitive to photochemical dechlorination. If exposed to direct sunlight or UV-radiation, it will decompose in a matter of hours. Photocatalysis and other methods have also been tested in attempts to remove dioxins in soils and other environments. Because dioxins adsorb

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has also been reported, leading to uncertainty and debate about the true role of dioxins in cancer rates. The endocrine disrupting activity of dioxins is thought to occur as a down-stream function of AH receptor activation, with thyroid status in particular being a sensitive marker of exposure. TCDD,

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This commentary responds to a recent statistical treatment of cancer incidence data in selected workers exposed to dioxin from an earlier NIOSH chemical plant study. Contrary to the NIOSH authors' new findings, the cancer incidence response to increasing dioxin exposure is J-shaped, just as it is in

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Humans are also at the top of the trophic pyramid, particularly newborns. Exclusively breastfed newborns were estimated to be exposed to a total of 800 pg TEQ/day, leading to an estimated body weight-based dose of 242 pg TEQ/kg/day. Due to a multitude of food sources of adult humans exposure is much

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facilities are proposed. As a result of these concerns, incineration processes have been improved with increased combustion temperatures (over 1,000 °C (1,830 °F)), better furnace control, and sufficient residence time allotted to ensure complete oxidation of organic compounds. Ideally, an

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The same features causing persistence of dioxins in the environment also cause very slow elimination in humans and animals. Because of low water solubility, kidneys cannot excrete them in urine as such. They must first be metabolised to more-water-soluble metabolites, but that metabolism, especially

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TEFs are also approximations with certain amount of scientific judgement rather than scientific facts. Therefore, they may be re-evaluated from time to time. There have been several TEF versions since the 1980s. The most recent re-assessment was by an expert group of the World Health organization in

420:. The symptoms reported to be associated with dioxin toxicity in animal studies are incredibly wide-ranging, both in the scope of the biological systems affected and in the range of dosage needed to bring these about. Acute effects of single high dose dioxin exposure include reduced feed intake and 258:

There are 209 PCB compounds. Analogously to PCDDs at least two lateral chlorines in each ring in positions 3,4, and/or 5 are needed for dioxin-like activity. Because the AH receptor requires a planar (flat) structure, only PCB congeners that can rotate freely along the C—C axis between the rings can

1651:

Because of different physicochemical properties, not all congeners of dioxin-like compounds find their routes to human beings equally well. Measured as TEQs, the dominant congeners in human tissues are 2,3,7,8-TCDD, 1,2,3,7,8-PeCDD, 1,2,3,6,7,8-HxCDD and 2,3,4,7,8-PeCDF. This is very different from

1462:

Improvements and changes have been made to nearly all industrial sources to reduce PCDD/F production. In waste incineration, large amounts of publicity and concern surrounded dioxin-like compounds during the 1980s-1990s continues to pervade the public consciousness, especially when new incineration

775:

The TEQ conversion makes it possible to use all studies on the best studied TCDD to assess the toxicity of a mixture. This is most useful in regulatory work, but it can also be used in scientific studies. This resembles the common measure of all alcoholic drinks: beer, wine and whiskey can be added

730:

accumulated during the whole lifetime is high compared with daily doses, and occasional modest exceedances of limit values do not change it much. Therefore, long-term intake is much more important than daily intake. Specifically, the TDI has been assessed to guarantee the safety of children born to

628:

Effects after low exposures such as from food have been difficult to prove. Levels of dioxins in contemporary population are 5 to 20 pg/g (TEQ in fat) and 50 to 100 pg in older people or at least 1000 times lower than those in poisonings (see above). Tooth deformities have been considered plausible

326:

1A2, CYP1B1, CYP2S1, CYP2A5, ALDH3, GSTA1, UGT1A1, UGT1A6, UGT1A7 and NQO1. This is in essence a protective function preventing toxic or carcinogenic effects of xenobiotics, but in some conditions it may also result in the production of reactive metabolites that are mutagenic and carcinogenic. This

246:

and are toxic via this mechanism. The crucial structures are so called lateral chlorines in positions 2,3,7, and 8. These 4 chlorines also make the congeners persistent, because they prevent microbial degradation. Additional chlorines make the compounds less potent, but basically the effects remain

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in 1999. A tank of recycled fats collected for animal feed production was contaminated by PCB oil containing about 1 g of dioxins and 2 g of DL-PCBs. This caused a major alarm in the European Union, but due to relatively fast response and slow accumulation of dioxins in humans there were no health

1708:

study in the U.S., the average concentration of TCDD in exposed persons was 233 ng/kg (in serum lipid) while it was 7 ng/kg in unexposed workers, even though the exposure had been 15–37 years earlier. This indicates a huge previous exposure. In fact the exact back-calculation is debated,

1617:. Lipid-soluble compounds are first accumulated to microscopic organisms such as phytoplankton (plankton of plant character, e.g. algae). Phytoplankton is consumed by animal plankton, this by invertebrates such as insects, these by small fish, and further by large fish and seals. At every stage or 519:

Toxicity of dioxins at high doses has been well documented after accidents, deliberate poisonings, food contamination episodes, and high industrial exposures. Three women in Vienna, Austria, were poisoned with large doses of TCDD in 1998. The highest concentration of TCDD in fat tissue was 144,000

507:

effects. Surprisingly, enzyme induction, several developmental effects and aversion to novel foods occur at similar dose levels in animals that respond differently to acute high-dose toxicity. Therefore, it has been suggested that dioxin effects be divided to type I effects (enzyme induction etc.)

1742:

Exposure from contaminated soil is possible when dioxins are blown up in dust, or children eat soil. Inhalation was clearly demonstrated in Missouri in the 1970s, when waste oils were used as dust suppressant in horse arenas. Many horses and other animals were killed due to poisoning. Dioxins are

1608:

All groups of dioxin-like compounds are persistent in the environment. Very few soil microbes nor animals can break down the PCDD/Fs with lateral chlorines (positions 2,3,7, and 8). Lipophilicity (tendency to seek for fat-like environments) and very poor water solubility make these compounds move

709:

As with many toxic endpoints of dioxin, a clear dose–response relationship is difficult to establish. After accidental or high occupational exposures there is evidence on human carcinogenicity. Increases in cancer have been modest, in fact reaching statistical significance has been difficult even

648:

and several POP compounds including dioxins. Such observational studies cannot prove causality, i.e. there may be an association which does not prove that one is the cause of the other. The main problem is that similar associations can be found with many quite different POPs, which have only long

371:

lead to a multitude of adverse effects. Therefore, it is important to separate the effects of low doses causing activation of the receptor around the physiological range from the effects of high toxic doses. This is all the more important because of large differences in exposures even among human

283:

A schematic diagram of some AHR signaling pathways. The canonical pathway is depicted with solid black arrows, alternative pathways with dashed arrows, and an intersection of these two with a solid red arrow. The green bars represent the AHR, red bars ARNT, yellow bars ARA9 (AIP, Xap2), blue bars

270:

Many natural compounds have very high affinity to AH receptors. These include indoles, flavones, benzoflavones, imidazoles and pyridines. These compounds are metabolized rapidly, but continuous intake from food may cause similar receptor activation as the background levels of dioxins. They do not

1684:

The most important source of human exposure is fatty food of animal origin (see Human intake, above), and breast milk. There is much variation between different countries as to the most important items. In U.S. and Central Europe, milk, dairy products and meat have been by far the most important

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CBDB1 being an example) of dioxins is very slow, researchers have actively tried to search for mechanisms to increase degradation or to find especially active microbial species for the purposes of bioremediation. By and large, this has not been very successful. In addition, interactions with the

1158:

The highest body burdens were found in Western Europe in the 1970s and early 1980s, and the trends have been similar in the U.S. The most useful measure of time trends is concentration in breast milk measured over decades. In many countries the concentrations have decreased to about one tenth of

705:

has classified TCDD as a human carcinogen (class 1) on the basis of clear animal carcinogenicity and limited human data, and subsequently also 2,3,4,7,8-PCDF and PCB 126 as class 1 carcinogens. The mechanism is thought to be mainly promotion, i.e. dioxins can accelerate the formation of tumours

676:

functions, and even learning and intelligence. While some of these effects might be possible after heavy exposures (like in the Seveso disaster), these claims are only based on potential exposures of population, not supported by actual measurements of dioxin concentrations. E.g. absorption from

1188:

concentrations are found in the liver, but in a few days, adipose tissue will predominate. In rat liver, however, high doses cause induction of CYP1A2 enzyme, and this binds dioxins. Thus, depending on the dose, the ratio of fat and liver tissue concentrations may vary considerably in rodents.

771:

data have been used. After multiplying the actual amount or concentration of a congener by its TEF, the product is the virtual amount or concentration of TCDD having effects of the same magnitude as the compound in question. This multiplication is done for all compounds in a mixture, and these

375:

The most relevant toxic outcomes of dioxins both in humans and animals are cancer and the developmental effects on offspring. Both have been documented at high doses, most accurately in animal experiments. As to developmental effects there is an agreement that the present dioxin levels in many

1685:

sources. In some countries, notably in Finland and to some extent in Sweden, fish is important due to contaminated Baltic fish and very low intake from any other sources. In most countries, a significant decrease of dioxin intake has occurred due to stricter controls during the last 20 years.

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were never synthesized for any purpose, except for small quantities for scientific research. Small amounts of PCDD/Fs are formed whenever organics, oxygen and chlorine are available at suitable temperatures. This is augmented by metal catalysts such as copper. The optimal temperature range is

755:

All dioxin-like compounds share a common mechanism of action via the aryl hydrocarbon receptor (AHR), but their potencies are very different. This means that similar effects are caused by all of them, but much larger doses of some of them are needed than of TCDD. Binding to the AHR as well as

1774:

caused by high dioxin concentrations in their pork exports. The contamination was found to be due to zinc oxide used in pork feed, and caused reputational and financial losses for the country, as well as leading to the introduction of new food safety regulations. These episodes emphasize the

1533:

Open burning of waste (backyard barrel burning) has not decreased effectively, and in the U.S. it is now the most important source of dioxins. Total U.S. annual emissions decreased from 14 kilograms (31 lb) in 1987 to 1.4 kilograms (3.1 lb) in 2000. However, backyard barrel burning

1146:

Most intake of dioxin-like chemicals is from food of animal origin: meat, dairy products, or fish predominate, depending on the country. The daily intake of dioxins and dioxin-like PCBs as TEQ is of the order of 100 pg/day, i.e. 1-2 pg/kg/day. In many countries both the absolute and relative

568:

released its contents to air including many kilograms of TCDD, and contaminated much of the city. The highest TCDD levels were found in children, up to 56,000 pg/g fat. Acute effects were limited to chloracne, although many animals such as rabbits died after eating contaminated grass. Dental

207:

of dioxins, ten furans and twelve PCBs. The reference congener is the most toxic dioxin TCDD which per definition has a TEF of one. In essence, multiplying the amount of a particular congener with its TEF produces the amount toxicologically equivalent to TCDD, and after this conversion all

1137:

and others have argued that the dioxin controversy has been very political and that large companies have tried to play down the seriousness of the problems of dioxin. The companies involved have often said that the campaign against dioxin is based on "fear and emotion" and not on science.

1187:

In mammals, dioxins are found mostly in fat. Concentrations in fat seem to be relatively similar, be it serum fat, adipose tissue fat, or milk fat. This permits measuring dioxin burden by analysing breast milk. Initially, however, at least in laboratory animals, after a single dose, high

2177:

Weber R, Gaus C, Tysklind M, Johnston P, Forter M, Hollert H, Heinisch E, Holoubek I, Lloyd-Smith M, Masunaga S, Moccarelli P, Santillo D, Seike N, Symons R, Torres JP, Verta M, Varbelow G, Vijgen J, Watson A, Costner P, Woelz J, Wycisk P, Zennegg M (2008) Dioxin- and POP-contaminated

1402:). They have entered the environment through accidents such as fires or leaks from transformers or heat exchangers, or from PCB-containing products in landfills or during incineration. Because PCBs are somewhat volatile, they have also been transported long distances by air leading to 372:

beings. Western populations today are exposed to dioxins at doses leading to concentrations of 5 to 100 picograms/g (as TEQ in body fat), and the highest concentrations in accidental or deliberate poisonings have been 10,000 to 144,000 pg/g leading to dramatic but not lethal outcomes.

1175:

Dioxins are absorbed well from the digestive tract if they are dissolved in fats or oils (e.g. in fish or meat). On the other hand, dioxins tend to adsorb tightly to soil particles, and absorption may be quite low: 13.8% of the given dose of TEQs in contaminated soil was absorbed.

392:

along with the other PCDDs, PCDFs and dioxin-like coplanar PCBs are not direct agonists or antagonists of hormones, and are not active in assays which directly screen for these activities such as ER-CALUX and AR-CALUX. These compounds have also not been shown to have any direct

1655:

All POPs are poorly water-soluble, especially dioxins. Therefore, ground water contamination has not been a problem, even in cases of severe contamination due to the main chemicals such as chlorophenols. In surface waters, dioxins are bound to organic and inorganic particles.

1761:

PCBs are also known to flush from industry and land (aka sludge fields) to contaminate fish, as they have up and down the Catawba River in North and South Carolina. State authorities have posted fish consumption advisories due to accumulation of PCBs in fish tissue.

738:

or J-shape, there is little or no risk at the present concentrations. Understanding the mechanisms of toxicity better is hoped to increase the reliability of risk assessment. Recently also developmental effects have been reassessed by the Contamination Panel of the

1546:

added to animal feed. Dioxins have been repeatedly detected in clays from Europe and USA since 1996, with contamination of clay assumed to be the result of ancient forest fires or similar natural events with concentration of the PCDD/F during clay sedimentation.

5779:

Kim M, Kim DG, Choi SW, Guerrero P, Norambuena J, Chung GS (February 2011). "Formation of polychlorinated dibenzo-p-dioxins/dibenzofurans (PCDD/Fs) from a refinery process for zinc oxide used in feed additives: a source of dioxin contamination in Chilean pork".

1613:. Increase in chlorination increases both stability and lipophilicity. The compounds with the very highest chlorine numbers (e.g. octachlorodibenzo-p-dioxin) are, however, so poorly soluble that this hinders their bioaccumulation. Bioaccumulation is followed by 4743:

Commission Implementing Decision (EU) 2019/2010 of 12 November 2019 establishing the best available techniques (BAT) conclusions, under Directive 2010/75/EU of the European Parliament and of the Council, for waste incineration (notified under document C(2019)

4337:

Schecter A, Päpke O, Tung KC, Joseph J, Harris TR, Dahlgren J (March 2005). "Polybrominated diphenyl ether flame retardants in the U.S. population: current levels, temporal trends, and comparison with dioxins, dibenzofurans, and polychlorinated biphenyls".

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and some other environmental groups have called for the chlorine industry to be phased out. However, chlorine industry supporters say that "banning chlorine would mean that millions of people in the third world would die from want of disinfected water".

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1979). The toxic effects have been attributed to dioxin-like PCBs and PCDFs. Their daily intake was up to 100,000 times higher than average intake presently. There were many skin problems, chloracne, swelling of eyelids, and hypersecretion of

1521:

Both in Europe and in U.S.A., the emissions have decreased dramatically since the 1980s, by even 90% (see Figure). This has also led to decreases in human body burdens, which is neatly demonstrated by the decrease of dioxin concentrations in

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or inorganic chlorides prior to the gases passing through the temperature window of 400-700 °C where PCDD/F formation is possible. These substances cannot easily form organic compounds, and HCl is easily and safely neutralized in the

354:

Dioxin toxicity is based on inappropriate activation of a physiologically important receptor, and therefore dose-response must be carefully considered. Inappropriate stimulation of many receptors leads to toxic outcomes, e.g. overdose of

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Mocarelli P, Gerthoux PM, Ferrari E, Patterson DG, Kieszak SM, Brambilla P, Vincoli N, Signorini S, Tramacere P, Carreri V, Sampson EJ, Turner WE, Needham LL (May 2000). "Paternal concentrations of dioxin and sex ratio of offspring".

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populations are not very far from those causing some effects, but there is not yet consensus on the safe level. As to cancer, there is a disagreement on how to extrapolate the risk from high toxic doses to the present low exposures.

3021:

Sorg O, Zennegg M, Schmid P, Fedosyuk R, Valikhnovskyi R, Gaide O, et al. (October 2009). "2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) poisoning in Victor Yushchenko: identification and measurement of TCDD metabolites".

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produces dioxins and it should be done at high enough temperatures and there should be proper filtering of flue gases. For the treatment of gases and pollutants, sugarcane industries often use wet gas scrubbers, such as the

408:

but are not classified as dioxin-like in terms of toxicity. Mutagenic effects have been established for some lower chlorinated chemicals such as 3-chlorodibenzofuran, which is neither persistent nor an AH receptor agonist.

706:

caused by other factors, and adversely affect the normal mechanisms for inhibiting tumour growth. Some researchers have also proposed that dioxin induces cancer progression through a very different mitochondrial pathway.

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for hamsters can be as high as 1 to 5 mg/kg body weight. Even between different mouse or rat strains there may be tenfold to thousandfold differences in acute toxicity. Many pathological findings are seen in the

346:(Chemical Activated LUciferase gene eXpression) bioassay. The results have been comparable to TEQ levels measured by much more expensive gas chromatography-high resolution mass spectrometry in environmental samples. 3702:

FN ISI Export Format VR 1.0 PT J TI Cancer and TCDD: The mitochondrial connection AU Mead, MN SO ENVIRONMENTAL HEALTH PERSPECTIVES VL 116 IS 3 BP A112 EP A112 PY 2008 TC 0 UT WOS:000253670600010 SN 0091-6765 ER

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in some areas are exposed to exceptionally high amounts of dioxins and related substances. This along with high industrial exposures may be the most valuable source of information on the health risks of dioxins.

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Alaluusua S, Lukinmaa PL, Vartiainen T, Partanen M, Torppa J, Tuomisto J (May 1996). "Polychlorinated dibenzo-p-dioxins and dibenzofurans via mother's milk may cause developmental defects in the child's teeth".

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Aylward LL, Brunet RC, Starr TB, Carrier G, Delzell E, Cheng H, Beall C (August 2005). "Exposure reconstruction for the TCDD-exposed NIOSH cohort using a concentration- and age-dependent model of elimination".

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less averaging at 1 pg TEQ/kg-day, and dioxin concentrations in adults are much less at 10-100 pg/g, compared with 9000 to 340,000 pg/g (TEQ in lipid) in eagles or seals feeding almost exclusively on fish.

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Hahn, Mark E.; Karchner, Sibel I. (2011). "Structural and Functional Diversification of AHRs during Metazoan Evolution". The AH Receptor in Biology and Toxicology. John Wiley & Sons, Ltd. pp. 387–403.

602:. Therefore, definitive proof of dioxins as causative factors has been difficult to obtain. By far the best proven effect is chloracne. The suspected effects in adults are liver damage, and alterations in 560:

in the eyes. Babies born to Yusho and Yu-cheng mothers were smaller than normal, they had dark pigmentation and sometimes teeth at birth and tooth deformities. Foetal deaths and miscarriages were common.

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Bock, KW (1 April 2017). "Human and rodent aryl hydrocarbon receptor (AHR): from mediator of dioxin toxicity to physiologic AHR functions and therapeutic options." Biological chemistry 398 (4): 455–464.

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Vartiainen T, Lampi P, Tolonen K, Tuomisto J (1995). "Polychlorodibenzo-p-dioxin and polychlorodibenzofuran concentrations in lake sediments and fish after a ground water pollution with chlorophenols".

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Hoffman E, Alimohammadi M, Lyons J, Davis E, Walker TR, Lake CB (August 2019). "Characterization and spatial distribution of organic-contaminated sediment derived from historical industrial effluents".

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Mocarelli P, Gerthoux PM, Patterson DG, Milani S, Limonta G, Bertona M, Signorini S, Tramacere P, Colombo L, Crespi C, Brambilla P, Sarto C, Carreri V, Sampson EJ, Turner WE, Needham LL (January 2008).

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Lignell S, Aune M, Darnerud PO, Cnattingius S, Glynn A (August 2009). "Persistent organochlorine and organobromine compounds in mother's milk from Sweden 1996-2006: compound-specific temporal trends".

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One important cause for differences in different assessments has been carcinogenicity. If the dose-response of TCDD in causing cancer is linear, it might be a true risk. If the dose-response is of a

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and electric energy for use both in the sugar factory itself and for other consumers), and locally it has been thought to be a remarkable source of dioxins. This basically indicates that burning

1491:

Scrubber and particulate removal systems manage to capture some of the PCDD/F which forms even in sophisticated incineration plants. These PCDD/Fs are generally not destroyed but moved into the

536:, then presidential candidate of Ukraine, in 2004. TCDD concentration in fat was 108,000 pg/g. Also in this case the most prominent symptom was chloracne after initial stomach pain indicating 1542:

Low concentrations of dioxins have been found in some soils without any anthropogenic contamination. A puzzling case of milk contamination was detected in Germany. The source was found to be

779:

The TEQ only applies to dioxin-like effects mediated by the AHR. Some toxic effects (especially of PCBs) may be independent of the AHR, and those are not taken into account by using TEQs.

215:. Therefore, they tend to associate with organic matter such as plankton, plant leaves, and animal fat. In addition, they tend to be adsorbed to inorganic particles, such as ash and soil. 2602:

Tijet N, Boutros PC, Moffat ID, Okey AB, Tuomisto J, Pohjanvirta R (January 2006). "Aryl hydrocarbon receptor regulates distinct dioxin-dependent and dioxin-independent gene batteries".

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Kiviranta H, Tuomisto JT, Tuomisto J, Tukiainen E, Vartiainen T (August 2005). "Polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in the general population in Finland".

5014:

Kim SC, Jeon SH, Jung IR, Kim KH, Kwon MH, Kim JH, et al. (2001). "Removal efficiencies of PCDDs/PCDFs by air pollution control devices in municipal solid waste incinerators".

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decreased only modestly from 0.6 kilograms (1.3 lb) to 0.5 kilograms (1.1 lb), resulting in over one third of all dioxins in the year 2000 from backyard burning alone.

295:(AH receptor) is an ancient receptor, and its many functions have been revealed only recently. It is an over 600-million-year-old protein occurring in all vertebrates, and its 5863: 4381:

Fürst P (October 2006). "Dioxins, polychlorinated biphenyls and other organohalogen compounds in human milk. Levels, correlations, trends and exposure through breastfeeding".

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Mitoma C, Uchi H, Tsukimori K, Yamada H, Akahane M, Imamura T, et al. (September 2015). "Yusho and its latest findings-A review in studies conducted by the Yusho Group".

653:

and tendency to accumulate in lipids in common. This suggests that they may all be related to diet and obesity which are by far the most common causes of type 2 diabetes.

1184:

of several years for all dioxins. That of TCDD is estimated to be 7 to 8 years, and for other PCDD/Fs from 1.4 to 13 years, PCDFs on average slightly shorter than PCDDs.

57:

Some of them are highly toxic, but the toxicity among them varies 30,000-fold. They are grouped together because their mechanism of action is the same. They activate the

314:

The AH receptor is relevant in toxicology for two very different reasons. First, it induces several enzymes important in the metabolism of foreign substances, so called

547:

Two serious food contamination accidents were caused by PCB oils used in heat exchangers. The PCB oil leaked to rice bran oil consumed by thousands of people in Japan (

2075:

Pohjanvirta R, Tuomisto J (December 1994). "Short-term toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in laboratory animals: effects, mechanisms, and animal models".

5433:

Bunge M, Adrian L, Kraus A, Opel M, Lorenz WG, Andreesen JR, et al. (January 2003). "Reductive dehalogenation of chlorinated dioxins by an anaerobic bacterium".

1621:, the concentration is higher, because the persistent chemicals are not "burned off" when the higher organism uses the fat of the prey organism to produce energy. 4259: 208:

dioxin-like congeners can be summed up, and the resulting toxicity equivalent quantity (TEQ) gives an approximation of toxicity of the mixture measured as TCDD.

731:

mothers exposed to such a daily intake of dioxins all their lifetime prior to pregnancy. It is likely that the TDI for other population groups could be higher.

2178:

sites--contemporary and future relevance and challenges: overview on background, aims and scope of the series. Environ Sci Pollut Res Int. Jul;15(5):363–393.

5082:

Koistinen J, Koivusaari J, Nuuja I, Paasivirta J (1995). "PCDEs, PCBs, PCDDs AND PCDFs in black guillemots and white-tailed sea eagles from the Baltic Sea".

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Patterson DG, Turner WE, Caudill SP, Needham LL (August 2008). "Total TEQ reference range (PCDDs, PCDFs, cPCBs, mono-PCBs) for the US population 2001-2002".

250: 3546:

Magliano DJ, Loh VH, Harding JL, Botton J, Shaw JE (February 2014). "Persistent organic pollutants and diabetes: a review of the epidemiological evidence".

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importance of food control, and early detection guarantees that very slowly accumulating dioxins do not increase in humans to levels causing toxic effects.

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are often the only commonly available fuels for cooking and home heating. In addition to dioxins, other harmful products of incomplete combustion - such as

442:

of TCDD varies wildly between species and even strains of the same species, with the most notable disparity being between the seemingly similar species of

379:

While the affinity of dioxins and related industrial toxicants to the Ah receptor may not fully explain all their toxic effects including immunotoxicity,

6024: 2813:

Dragan YP, Schrenk D (April 2000). "Animal studies addressing the carcinogenicity of TCDD (or related compounds) with an emphasis on tumour promotion".

5856: 2280:"Dioxin--contemporary and future challenges of historical legacies. Dedicated to Prof. Dr. Otto Hutzinger, the founder of the DIOXIN Conference Series" 5168: 4508:

Wittsiepe J, Erlenkämper B, Welge P, Hack A, Wilhelm M (April 2007). "Bioavailability of PCDD/F from contaminated soil in young Goettingen minipigs".

2405:

Lindén J, Lensu S, Tuomisto J, Pohjanvirta R (October 2010). "Dioxins, the aryl hydrocarbon receptor and the central regulation of energy balance".

4732:

Consolidated text (11-12-2008): Directive 2000/76/EC of the European Parliament and of the Council of 4 December 2000 on the incineration of waste

1688:

Historically, occupational exposure to dioxins has been a major problem. Dioxins are formed as important toxic side products in the production of

1700:, and other chlorinated organic chemicals. This caused very high exposures to workers in poorly controlled hygienic conditions. Many workers had 772:"equivalents of TCDD" can then simply be added, resulting in TEQ, the amount or concentration of TCDD toxicologically equivalent to the mixture. 4889:

Schmitz M, Scheeder G, Bernau S, Dohrmann R, Germann K, et al. (January 2011). "Dioxins in primary kaolin and secondary kaolinitic clays".

1632:

and some species of seals have approached extinction due to poisoning by persistent organic pollutants. Likewise, in America, the population of

4294:

Norén K, Meironyté D (2000). "Certain organochlorine and organobromine contaminants in Swedish human milk in perspective of past 20-30 years".

2359:"AH receptor agonist activity in human blood measured with a cell-based bioassay: evidence for naturally occurring AH receptor ligands in vivo" 4802:"An Inventory of Sources and Environmental Releases of Dioxin-Like Compounds in the U.S. for the Years 1987, 1995, and 2000 (Final, Nov 2006)" 718:

The uncertainty and variability in the dose–response relationship of dioxins in terms of their toxicity, as well as the ability of dioxins to

5849: 698: 587:

count and motility were affected in different ways in exposed males, depending on whether they were exposed before, during or after puberty.

479:. Very few signs of toxicity are seen in adult animals after low doses, but developmental effects may occur at low dioxin levels, including 5419: 1636:

declined because of POPs causing thinning of eggshells and other reproductive problems. Usually, the failure has been attributed mostly to

544:. These episodes show that a human being is not as sensitive as the most sensitive animals, since the doses must have been up to 25 μg/kg. 4602:"Apparent half-lives of dioxins, furans, and polychlorinated biphenyls as a function of age, body fat, smoking status, and breast-feeding" 4553:"Apparent half-lives of dioxins, furans, and polychlorinated biphenyls as a function of age, body fat, smoking status, and breast-feeding" 3449:"A Longitudinal Study of Peripubertal Serum Organochlorine Concentrations and Semen Parameters in Young Men: The Russian Children's Study" 6029: 5124:

Bull J, Farrand, J Jr (1987). Audubon Society Field Guide to North American Birds: Eastern Region. New York: Alfred A. Knopf. pp. 468–9.

702: 569:

aberrations were found after 25 years in persons exposed as children, and a slightly increased cancer risk was confirmed 35 years later.

4114: 2131:"The 2005 World Health Organization reevaluation of human and Mammalian toxic equivalency factors for dioxins and dioxin-like compounds" 1499:

systems have been designed which destroy vapor-phase PCDD/Fs at relatively low temperatures. This technology is often combined with the

61:(AH receptor), albeit with very different binding affinities, leading to high differences in toxicity and other effects. They include: 2322:

Denison MS, Nagy SR (2003). "Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals".

1596:- are also released when biomass is burned in low oxygen conditions. Using plastic, particularly chlorine-containing plastics such as 1705: 701:

has categorised dioxin, and the mixture of substances associated with sources of dioxin toxicity as a "likely human carcinogen". The

572:

In line with animal studies, developmental effects may be much more important than effects in adults. These include disturbances of

5685:

Kimbrough RD, Carter CD, Liddle JA, Cline RE (1977). "Epidemiology and pathology of a tetrachlorodibenzodioxin poisoning episode".

1755: 473:, and other organs. Some effects such as thymic atrophy are common in many species, but e.g. liver toxicity is typical in rabbits. 3503:"Consultation on assessment of the health risk of dioxins; re-evaluation of the tolerable daily intake (TDI): executive summary". 2563:"An aryl hydrocarbon receptor odyssey to the shores of toxicology: the Deichmann Lecture, International Congress of Toxicology-XI" 1347:

Dioxins have no common uses. They are manufactured on a small scale for chemical and toxicological research, but mostly exist as

129:

dioxin, the basic chemical unit of the more complex dioxins. This simple compound is not persistent and has no PCDD-like toxicity.

342:

Binding of dioxin-like compounds to the AH receptor has made it possible to measure total dioxin-like activity of a sample using

5826: 2956: 247:

the same although at higher doses. There are 135 possible dibenzofurans, and 10 in which the lateral chlorines are dioxin-like.

3864:"Health effects of nutrients and environmental pollutants in Baltic herring and salmon: a quantitative benefit-risk assessment" 4656: 1530:, estimated the emissions from dioxins (PCDD/Fs) to be about equivalent to those from traffic and municipal waste combustion. 5368:

Rathna, R; Varjani, S; Nakkeeran, E (1 October 2018). "Recent developments and prospects of dioxins and furans remediation".

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In occupational settings many symptoms have been seen, but exposures have always been to a multitude of chemicals including

1398:, always containing low concentrations of dioxin-like PCBs and PCDFs, were synthesized for various technical purposes (see 677:

bleached tampons claimed to be associated with endometriosis is insignificant compared with daily dioxin intake from food.

5330:

Kanan, Sofian; Samara, Fatin (January 2018). "Dioxins and furans: A review from chemical and environmental perspectives".

3610:

Schrenk D, Chopra M (20 December 2011). "Dioxin activated AHR and cancer in laboratory animals". In Pohjanvirta R (ed.).

1739:). This is equivalent to a dose of 20 to 30 μg/kg TCDD, a dose that would be lethal to guinea pigs and some rat strains. 1518:

The European Union limit for concentration of dioxin-like compounds in the discharged flue gas is 0.1 ng/Nm³ TEQ.

4935:

Choong Kwet Yive NS, Tiroumalechetty M (June 2008). "Dioxin levels in fly ash coming from the combustion of bagasse".

4270: 424:, and typically a delayed death of the animal in 1 to 6 weeks. By far most toxicity studies have been performed using 5720: 5129: 5064: 4028: 3619: 2647:"Mathematical model developed for environmental samples: prediction of GC/MS dioxin TEQ from XDS-CALUX bioassay data" 2486: 2465: 1816:

The 2019 version of this article was updated by an external expert under a dual publication model. The corresponding

1735:

were 56,000 ng/kg, and the highest exposure ever recorded was found in Austria in 1998, 144,000 ng/kg (see

84:, differing in the number and location of chlorine atoms, and 7 of them are specifically toxic, the most toxic being 4731: 1584:, is responsible for much of the negative health effects of indoor air pollution and is a particular problem in the 5937: 1736: 833: 425: 136: 85: 5961: 4983:"Removal of polychlorinated dibenzo–p–dioxins and dibenzofurans in flue gases by Venturi scrubber and bag filter" 4844: 3581: 2645:

Brown DJ, Orelien J, Gordon JD, Chu AC, Chu MD, Nakamura M, Handa H, Kayama F, Denison MS, Clark GC (June 2007).

1101: 1089: 896: 112:, of which 12 are "dioxin-like". Under certain conditions PCBs may form dibenzofurans through partial oxidation. 4755:

Quass U, Fermann M, Bröker G (March 2004). "The European dioxin air emission inventory project--final results".

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contained trace amounts of dioxin impurities and caused severe health issues as a result. The wood preservative

3913:

Tuomisto J (September 2005). "Does mechanistic understanding help in risk assessment--the example of dioxins".

1758:

enacted emergency sludge regulations after PCBs were found to have been discharged to a waste treatment plant.

388: 154: 142: 65: 3262:"Dioxin exposure, from infancy through puberty, produces endocrine disruption and affects human semen quality" 1974:"Dioxins and dioxin-like compounds: toxicity in humans and animals, sources, and behaviour in the environment" 1831:"Dioxins and dioxin-like compounds: toxicity in humans and animals, sources, and behaviour in the environment" 6098: 5933: 3761:"Cancer incidence in the population exposed to dioxin after the "Seveso accident": twenty years of follow-up" 3689:

2,3,7,8-tetrachlorodibenzopara-dioxin, 2,3,4,7,8-pentachlorodibenzofuran, and 3,3',4,4',5-pentachlorobiphenyl

1504: 776:

together as absolute alcohol, and this sum gives the toxicologically meaningful measure of the total impact.

199:

atoms. Because dioxins refer to such a broad class of compounds that vary widely in toxicity, the concept of

160: 91: 35: 1791:

Dioxins and dioxin-like compounds: toxicity in humans and animals, sources, and behaviour in the environment

6051: 5206: 2709:"Risk for animal and human health related to the presence of dioxins and dioxin-like PCBs in feed and food" 387:, toxic responses appear to be typically dose-dependent within certain concentration ranges. A multiphasic 4669: 319: 168: 4011:

Tuomisto, Jouko (2011). "The Toxic Equivalency Principle and its Application in Dioxin Risk Assessment".

1417:("backyard barrel burning"), accidental fires, wildfires. These are presently the most important sources. 875: 740: 630: 4742: 3156:

Alaluusua S, Calderara P, Gerthoux PM, Lukinmaa PL, Kovero O, Needham L, et al. (September 2004).

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Claes Bernes: Persistent organic pollutants. Swedish Environmental Protection Agency, Stockholm 1998.

763:(TEF). This indicates its relative toxicity as compared with TCDD. Most TEFs have been extracted from 5883: 5872: 1399: 292: 243: 203:(TEF) has been developed to facilitate risk assessment and regulatory control. TEFs exist for seven 58: 5486:"Photodegradation of polychlorinated dibenzo-p-dioxins and dibenzofurans in soil with vegetable oil" 4600:

Milbrath, MO; Wenger, Y; Chang, CW; Emond, C; Garabrant, D; Gillespie, BW; Jolliet, O (March 2009).

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Mínguez-Alarcón L, Sergeyev O, Burns JS, Williams PL, Lee MM, Korrick SA, et al. (March 2017).

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Liem AK, Fürst P, Rappe C (April 2000). "Exposure of populations to dioxins and related compounds".

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Van den Berg M, Birnbaum LS, Denison M, De Vito M, Farland W, Feeley M, et al. (October 2006).

1580:. These methods may be insufficient Improperly burned biomass, which undergoes only low temperature 6093: 3685: 1771: 1510: 760: 496: 200: 174: 105: 47: 3821:

Turunen AW, Verkasalo PK, Kiviranta H, Pukkala E, Jula A, Männistö S, et al. (October 2008).

1731:

Accidental exposures have been huge in some cases. The highest concentrations in people after the

5956: 4044: 2974:"Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: clinical and laboratory effects" 2856:

Matsumoto M, Ando M (1991). "Mutagenicity of 3-chlorodibenzofuran and its metabolic activation".

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toxicity data on animals, but if these are missing (e.g. in case of some PCBs), less reliable

6088: 4551:

Milbrath MO, Wenger Y, Chang CW, Emond C, Garabrant D, Gillespie BW, Jolliet O (March 2009).

4111: 3113:

Sweeney MH, Mocarelli P (April 2000). "Human health effects after exposure to 2,3,7,8-TCDD".

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Decrease of dioxins in ambient air in different regions (redrawn from Dopico and Gomez, 2015)

1423:

Chlorine bleaching of pulp and paper - historically important source of PCDD/Fs to waterways.

1414: 1163: 641: 400:

activity. Their main action in causing cancer is cancer promotion. A mixture of PCBs such as

308: 5141: 524:, a serious skin disease. The victim survived, and other symptoms were modest after initial 5965: 5929: 5789: 5643: 5560: 5497: 5442: 5377: 5339: 5277: 5230: 5091: 5023: 4944: 4898: 4764: 4696: 4517: 4425: 4303: 4216: 4170: 3969: 3922: 3772: 3413: 3074: 2865: 2770: 2658: 2515:

Poellinger L (April 2000). "Mechanistic aspects – the dioxin (aryl hydrocarbon) receptor".

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Tuomisto JT, Pekkanen J, Kiviranta H, Tukiainen E, Vartiainen T, Tuomisto J (March 2004).

2357:

Connor KT, Harris MA, Edwards MR, Budinsky RA, Clark GC, Chu AC, et al. (July 2008).

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and the concentrations may have been even several times higher than originally estimated.

8: 6034: 6005: 4461:"Polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in fishermen in Finland" 1403: 786: 5981: 5793: 5647: 5501: 5446: 5381: 5343: 5281: 5234: 5095: 5027: 4948: 4902: 4768: 4700: 4521: 4429: 4307: 4220: 4174: 3973: 3926: 3776: 3673:

IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Volume 69, Lyon, 1997

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impacts. There was a similar incidence in Ireland in 2008. In 2008, Chile experienced a

1609:

from water environment to living organisms having lipid cell structures. This is called

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There have been several food contamination episodes, one of the best known occurred in

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have been discovered in invertebrates and insects. It is classified as a member of the

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Dioxins And Dioxin-Like Compounds In The Food Supply: Strategies To De-crease Exposure

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of 7 to 9 years in humans. Incidents of contamination with PCBs are often reported as

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Birnbaum LS, Tuomisto J (April 2000). "Non-carcinogenic effects of TCDD in animals".

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Perhaps the best known dioxin accident occurred in Seveso, Italy, in 1976. A tank of

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Knowledge articles with corresponding articles published in WikiJournal of Medicine

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An example of the variation in responses is clearly seen in a study following the

548: 211:

Dioxins are virtually insoluble in water but have a relatively high solubility in

4437: 4118: 3636:"Methods for Estimating the Carcinogenic Health Risks from Dioxin-Like Compounds" 3559: 3086: 2972:

Geusau A, Abraham K, Geissler K, Sator MO, Stingl G, Tschachler E (August 2001).

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tightly to soil particles, and microbial degradation (mostly via dehalogenation,

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is vented to the atmosphere. Inorganic chlorides are incorporated into the ash.

1406:

including the Arctic. Only a minor portion of PCBs in mixtures are dioxin-like.

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in animal studies, although the precise mechanism is not clear. Dioxins are not

327:

enzyme induction can be initiated by many natural or synthetic compounds, e.g.,

182: 5973: 5969: 5351: 4020: 3934: 1673: 1559:

after extraction of sugar is used in large amounts for energy production (both

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Pesatori AC, Consonni D, Rubagotti M, Grillo P, Bertazzi PA (September 2009).

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Creative Commons Attribution-Share Alike 3.0 (Unported) (CC-BY-SA 3.0) license

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which is used on farm fields in certain countries. In 2011 in South Carolina,

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may also cause quite high exposures, as clearly demonstrated by the users of

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Over the years there have been speculations on various effects of dioxins on

227: 73: 5836: 5265: 4870: 3729: 3686:

IARC Working Group on the Evaluation of Carcinogenic Risk to Humans (2012).

3329: 3126: 2923: 2826: 2706: 2579: 2528: 2296: 2279: 2146: 2050: 1990: 1973: 1850: 487:, and possibly pubescent stages. Well established developmental effects are 195:

Dioxins have different toxicity depending on the number and position of the

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Further, PCBs are known to pass through treatment plants and accumulate in

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Due to bioaccumulation and biomagnification, the species at the top of the

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for guinea pigs is as low as 0.5 to 2 μg/kg body weight, whereas the oral

46:

of burning or various industrial processes or, in the case of dioxin-like

5992: 5706: 5305: 5266:"Environmental degradation of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)" 4476: 3839: 3822: 2989: 2761:

Kayajanian GM (January 2002). "The J-shaped dioxin dose response curve".

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Xu J, Ye Y, Huang F, Chen H, Wu H, Huang J, et al. (November 2016).

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Dioxins are extremely stable and consequently tend to accumulate in the

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Decrease of dioxin concentrations in breast milk in Sweden and Finland

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pg/g, the highest ever reported in human beings. The main feature was

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Tuomisto JT, Asikainen A, Meriläinen P, Haapasaari P (January 2020).

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reach concentrations causing typical dioxin-like toxicity, however.

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Smidt, H; de Vos, WM (2004). "Anaerobic microbial dehalogenation".

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sites with a completed exposure pathway contaminated with dioxins.

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Lee WS, Chang-Chien GP, Chen SJ, Wang LC, Lee WJ, Wang YH (2004).

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Isosaari, Pirjo; Tuhkanen, Tuula; Vartiainen, Terttu (May 2004).

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Agency for Toxic Substances and Disease Registry (ATSDR) (1998).

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Dioxins & Furans: The Most Toxic Chemicals Known to Science

4934: 3758: 1751: 1600:, as a fuel or firestarter further increases dioxin emissions. 1543: 1426:

Synthesis side products of several chemicals, especially PCBs,

470: 5721:"PCB contamination found on Upstate waste company's equipment" 5219: 4415: 2404: 222:. They are eliminated very slowly in animals, e.g. TCDD has a 4888: 4507: 4206: 3958: 1628:

are most vulnerable to dioxin-like compounds. In Europe, the

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often contained dioxins and dibenzofurans as impurities. The

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Journal of the Air & Waste Management Association (1995)

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Journal of Exposure Science & Environmental Epidemiology

2198:

Public health statement chlorinated dibenzo-p-dioxins (CDDs)

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Environmental Science and Pollution Research International

1829:

Jouko Tuomisto (2019). Keith Brain; Thomas Shafee (eds.).

266:

Structures of biphenyl and 3,3’,4,4’,5-pentachlorobiphenyl

238:

There are 75 possible congeners of polychlorinated dibenzo

5632: 5169:"Infant exposure to dioxin-like compounds in breast milk" 3716:

Kogevinas M (April 2000). "Studies of cancer in humans".

3064: 3020: 2952: 1637: 1572:

type. In addition, other treatment systems also used are

1180:

in humans, is extremely slow. This results in biological

532:. Another acute incident was the deliberate poisoning of 5871: 4845:"Inventory of Dioxin Sources and Environmental Releases" 4599: 4550: 3545: 1644:). Also, ringed seals in the Baltic Sea are recovering. 1082:(T = tetra, Pe = penta, Hx = hexa, Hp = hepta, O = octa) 102:. There are 135 isomers; 10 have dioxin-like properties. 5582:

Atashgahi, S; Shetty, SA; Smidt, H; de Vos, WM (2018).

4336: 230:

since these are of most public and regulatory concern.

5367: 4980: 4136:

Global spin: The corporate assault on environmentalism

4099:

Global Spin: The Corporate Assault on Environmentalism

4086:

Global Spin: The Corporate Assault on Environmentalism

3364:"Soft-tissue sarcoma and dioxin: A case-control study" 2601: 1351:

of industrial processes such as chlorine bleaching of

118:

analogs of the above classes may have similar effects.

4151:

Food and Nutrition Board (FNB), Institute of Medicine

2707:

EFSA Panel on Contaminants in the Food Chain (2018).

2644: 72:(PCDDs), or simply dioxins. PCDDs are derivatives of 5432: 4459:

Kiviranta H, Vartiainen T, Tuomisto J (April 2002).

4066:'The dioxin controversy: spilling over into schools' 5213: 2074: 5778: 4754: 4340:Journal of Occupational and Environmental Medicine 4112:Book Review: Dying From Dioxin by Lois Marie Gibbs 3823:"Mortality in a cohort with high fish consumption" 1375:banned the production and use of dioxins in 2001. 1192:Elimination half-lives in humans of some PCDD/Fs. 363:resulting in e.g. malformations, and overdoses of 242:dioxins, but only 7 of them have affinity for the 5884: 2277: 1507:system at the tail end of an incineration plant. 6065: 4869:Martin, D., Tomida, M. & Meacham, B. (2016) 4659:– ToxFAQs: Chemical Agent Briefing Sheets (CABS) 4015:. John Wiley & Sons, Ltd. pp. 317–330. 3440: 3112: 2909: 1793:at the Wikiversity, which is licensed under the 1789:Some content in this article was extracted from 1170: 810:WHO Toxic Equivalence Factors (WHO-TEF) for the 722:, have led WHO experts to recommending very low 3954: 3952: 1967: 1965: 1963: 1961: 1959: 1957: 1955: 1953: 1951: 1949: 1947: 1945: 1943: 1941: 1939: 1937: 1935: 1933: 1931: 1929: 1927: 1925: 1923: 1921: 1919: 1917: 1915: 1913: 1911: 1909: 1907: 1905: 1903: 322:enzymes and conjugative phase II enzymes, e.g. 5166: 5013: 4293: 3816: 3814: 3357: 3355: 3315: 2702: 2700: 2698: 1901: 1899: 1897: 1895: 1893: 1891: 1889: 1887: 1885: 1883: 1359:manufacture, and combustion processes such as 5857: 5772: 4796: 4794: 3609: 2855: 2812: 2756: 2754: 2441: 2220: 1604:Environmental persistence and bioaccumulation 699:United States Environmental Protection Agency 5626: 5490:Environmental Science and Pollution Research 5332:Trends in Environmental Analytical Chemistry 5077: 5075: 5073: 4748: 4501: 4452: 4409: 4330: 4202: 4200: 3949: 3752: 3711: 3709: 3582:"ERC Responds to Recent Endometriosis Study" 3252: 3198: 2638: 2324:Annual Review of Pharmacology and Toxicology 2317: 2315: 1679: 1468:incineration process oxidizes all carbon to 286:(simplified and modified from Lindén et al.) 5575: 5546: 5363: 5361: 5329: 4682: 3811: 3396: 3352: 2695: 2447: 2321: 1880: 703:International Agency for Research on Cancer 5864: 5850: 5678: 5263: 5162: 5160: 5158: 4976: 4974: 4791: 4004: 3855: 3539: 3498: 3496: 3494: 3492: 3108: 3106: 3104: 2760: 2751: 2514: 2278:Weber R, Tysklind M, Gaus C (March 2008). 2046: 2044: 2042: 2040: 2038: 2036: 2034: 2032: 2030: 1141: 404:may contain PCB compounds which are known 5609: 5599: 5192: 5142:"EU Dioxin exposure and health data 1999" 5070: 4998: 4820:"Forest Fires: A Major Source of Dioxins" 4708: 4625: 4576: 4484: 4197: 4122:Journal of Land Use and Environmental Law 4088:, Scribe Publications, chapters 9 and 13. 4013:The AH Receptor in Biology and Toxicology 3889: 3879: 3838: 3794: 3784: 3715: 3706: 3681: 3679: 3612:The AH receptor in biology and toxicology 3603: 3472: 3406:Environmental Toxicology and Pharmacology 3379: 3285: 3227: 3181: 2997: 2967: 2965: 2957:Dioxins and their effects on human health 2808: 2806: 2804: 2734: 2724: 2678: 2578: 2450:The AH Receptor in Biology and Toxicology 2400: 2398: 2396: 2394: 2374: 2336:10.1146/annurev.pharmtox.43.100901.135828 2312: 2295: 2254: 2154: 2011: 2009: 1989: 1849: 5420:"Scientists find dioxin-eating bacteria" 5358: 5325: 5323: 4676: 4045:"Dioxin Controversy - What are Dioxins?" 4010: 3912: 3058: 2905: 2903: 1971: 1555:In sugarcane cultivation, the remaining 1509: 1457: 1383: 1149: 798:numbering scheme of the parent compound 785: 576:development, and of sexual development. 278: 261: 249: 5155: 5007: 4971: 4930: 4928: 4383:Molecular Nutrition & Food Research 3962:Environmental Monitoring and Assessment 3669: 3667: 3665: 3663: 3661: 3659: 3489: 3311: 3309: 3307: 3305: 3101: 2858:Environmental and Molecular Mutagenesis 2556: 2554: 2124: 2122: 2120: 2118: 2070: 2068: 2066: 2064: 2062: 2060: 2058: 2027: 1659: 750: 244:aryl hydrocarbon receptor (AH receptor) 6066: 5561:10.1146/annurev.micro.58.030603.123600 5055: 5053: 4891:Environmental Science & Technology 4683:Dopico, M; Gómez, A (September 2015). 4254: 4252: 4250: 4248: 4246: 3676: 2962: 2801: 2763:Ecotoxicology and Environmental Safety 2651:Environmental Science & Technology 2391: 2271: 2116: 2114: 2112: 2110: 2108: 2106: 2104: 2102: 2100: 2098: 2006: 1550: 1413:Uncontrolled combustion, particularly 412: 274: 5845: 5320: 4380: 4133: 4080: 4078: 4060: 4058: 3827:International Journal of Epidemiology 2900: 2595: 359:leads to inappropriate activation of 4925: 4070:Australian Science Teachers' Journal 3656: 3302: 3014: 2560: 2551: 2474: 2055: 1802: 743:(EFSA). They propose decreasing the 5370:Journal of Environmental Management 5264:Crosby, D.; Wong, A. (1977-03-25). 5050: 4243: 3915:Toxicology and Applied Pharmacology 2214: 2189: 2095: 13: 5167:Lorber M, Phillips L (June 2002). 4879:, 5 . Retrieved 14 September 2020. 4352:10.1097/01.jom.0000158704.27536.d2 4138:. Devon: Green Books. p. 154. 4075: 4055: 4037: 713: 680: 14: 6110: 5957:Modified low-density lipoproteins 5889:Tooltip Aryl hydrocarbon receptor 5820: 5802:10.1016/j.chemosphere.2010.12.040 5173:Environmental Health Perspectives 4606:Environmental Health Perspectives 4557:Environmental Health Perspectives 4530:10.1016/j.chemosphere.2006.05.129 4465:Environmental Health Perspectives 4229:10.1016/j.chemosphere.2007.08.074 4183:10.1016/j.chemosphere.2005.01.064 3453:Environmental Health Perspectives 3266:Environmental Health Perspectives 3162:Environmental Health Perspectives 2978:Environmental Health Perspectives 1409:Other sources of PCDD/F include: 511: 5962:Polycyclic aromatic hydrocarbons 5754: 5731: 5713: 5687:Archives of Environmental Health 5656:10.1111/j.1539-6924.2005.00645.x 4987:Aerosol and Air Quality Research 2448:Pohjanvirta, Raimo, ed. (2011). 1807: 1784: 1537: 1445:, which contained the additives 1112: 1100: 1088: 644:have shown associations between 331:polycyclic hydrocarbons such as 181: 167: 153: 135: 86:2,3,7,8-tetrachlorodibenzodioxin 5540: 5477: 5426: 5412: 5257: 5134: 5118: 4882: 4871:"Environmental impact of fire." 4863: 4837: 4812: 4736: 4725: 4662: 4650: 4593: 4544: 4374: 4287: 4154: 4142: 4127: 4104: 4091: 3906: 3718:Food Additives and Contaminants 3696: 3628: 3574: 3505:Food Additives and Contaminants 3368:International Journal of Cancer 3318:Food Additives and Contaminants 3149: 3115:Food Additives and Contaminants 2946: 2912:Food Additives and Contaminants 2849: 2815:Food Additives and Contaminants 2517:Food Additives and Contaminants 2508: 2491: 2407:Frontiers in Neuroendocrinology 2350: 759:Each congener has been given a 318:. These include both oxidative 254:Critical structures of PCDD/Fs. 5934:polychlorinated dibenzodioxins 5739:"POTENTIAL FOR HUMAN EXPOSURE" 5699:10.1080/00039896.1977.10667259 4937:Journal of Hazardous Materials 4672:. National Toxicology Program. 4101:, Scribe Publications, p. 153. 3643:Minnesota Department of Health 2171: 1124: 893:Polychlorinated dibenzofurans 633:(EFSA) recommended decreasing 228:dioxin contamination incidents 1: 6052:Receptor/signaling modulators 5549:Annual Review of Microbiology 5390:10.1016/j.jenvman.2018.06.095 5036:10.1016/S0045-6535(00)00432-X 4957:10.1016/j.jhazmat.2007.11.045 4777:10.1016/S0045-6535(03)00251-0 4710:10.1080/10962247.2015.1058869 4316:10.1016/s0045-6535(99)00360-4 3586:Endometriosis Research Center 3220:10.1016/S0140-6736(00)02290-X 3036:10.1016/s0140-6736(09)60912-0 1778: 1714:chlorophenoxy acid herbicides 1698:chlorophenoxy acid herbicides 1475:and converts all chlorine to 1432:chlorophenoxy acid herbicides 1171:Fate of dioxins in human body 1107:The 2,3,7,8-substituted PCDFs 1095:The 2,3,7,8-substituted PCDDs 685:Dioxins are well established 596:chlorophenoxy acid herbicides 161:Polychlorinated dibenzofurans 92:Polychlorinated dibenzofurans 36:persistent organic pollutants 5837:Synopsis on dioxins and PCBs 5243:10.1016/0045-6535(95)00037-9 5104:10.1016/0045-6535(95)00053-B 4670:"15th Report on Carcinogens" 4438:10.1016/j.envres.2009.04.011 3560:10.1016/j.diabet.2013.09.006 3426:10.1016/1382-6689(96)00007-5 3087:10.1016/j.envint.2015.05.004 2051:Synopsis on dioxins and PCBs 1162:Certain professions such as 1072:2,3,3’,4,4’,5,5’-HpCB (189) 1013:Mono-ortho-substituted PCBs 233: 7: 4072:, November 1998, pp. 28-34. 2419:10.1016/j.yfrne.2010.07.002 1588:where biomass like wood or 1574:electrostatic precipitators 1441:(Historical) Engines using 1420:Metal smelting and refining 978:Non-ortho-substituted PCBs 761:toxicity equivalence factor 741:European Food Safety Agency 631:European Food Safety Agency 426:2,3,7,8-tetrachlorodibenzo- 349: 121:"Dioxin" can also refer to 98:. PCDFs are derivatives of 16:Class of chemical compounds 10: 6115: 5352:10.1016/j.teac.2017.12.001 4021:10.1002/9781118140574.ch23 3935:10.1016/j.taap.2005.01.053 1378: 1064:2,3’,4,4’,5,5’-HxCB (167) 1056:2,3,3’,4,4’,5’-HxCB (157) 1005:3,3’,4,4’,5,5’-HxCB (169) 892: 389:dose–response relationship 6043: 5882: 5873:Aryl hydrocarbon receptor 5827:WHO fact sheet on dioxins 5000:10.4209/aaqr.2004.07.0003 3982:10.1007/s10661-019-7763-y 3881:10.1186/s12889-019-8094-1 3548:Diabetes & Metabolism 3511:(4): 223–40. April 2000. 3067:Environment International 2184:10.1007/s11356-008-0024-1 1820:article was published in 1712:Handling and spraying of 1680:Sources of human exposure 1400:Polychlorinated biphenyls 1048:2,3,3’,4,4’,5-HxCB (156) 1012: 977: 829: 825:Toxic Equivalence Factor 293:aryl hydrocarbon receptor 175:Polychlorinated biphenyls 106:Polychlorinated biphenyls 59:aryl hydrocarbon receptor 5601:10.3389/fphys.2018.00888 4260:"WHO Fact sheet on POPs" 2726:10.2903/j.efsa.2018.5333 1972:Tuomisto, Jouko (2019). 1823:WikiJournal of Medicine 830:Polychlorinated dioxins 201:toxic equivalency factor 5588:Frontiers in Physiology 3730:10.1080/026520300283388 3330:10.1080/026520300283324 3127:10.1080/026520300283379 2924:10.1080/026520300283351 2827:10.1080/026520300283360 2529:10.1080/026520300283333 2297:10.1065/espr2008.01.473 2077:Pharmacological Reviews 1978:WikiJournal of Medicine 1838:WikiJournal of Medicine 1342: 1142:Human intake and levels 1040:2’,3,4,4’,5-PeCB (123) 1032:2,3’,4,4’,5-PeCB (118) 1016:2,3,3’,4,4’-PeCB (105) 997:3,3’,4,4’,5-PeCB (126) 745:tolerable weekly intake 642:cross-sectional studies 635:tolerable weekly intake 143:Polychlorinated dibenzo 66:Polychlorinated dibenzo 5988:Tapinarof (benvitimod) 5766:catawbariverkeeper.org 5290:10.1126/science.841331 4418:Environmental Research 4395:10.1002/mnfr.200600008 4134:Beder S (March 2002). 3786:10.1186/1476-069X-8-39 2783:10.1006/eesa.2001.2115 2616:10.1124/mol.105.018705 2604:Molecular Pharmacology 2567:Toxicological Sciences 2376:10.1038/sj.jes.7500607 2135:Toxicological Sciences 1818:academic peer reviewed 1515: 1155: 1024:2,3,4,4’,5-PeCB (114) 806: 724:tolerable daily intake 660:, sexual development, 614:functions, as well as 301:basic helix-loop-helix 288: 267: 255: 5930:aromatic hydrocarbons 5185:10.1289/ehp.021100325 4084:Sharon Beder (2000). 2878:10.1002/em.2850170207 2580:10.1093/toxsci/kfm096 2561:Okey AB (July 2007). 2504:10.1515/hsz-2016-0303 2458:10.1002/9781118140574 2147:10.1093/toxsci/kfl055 1991:10.15347/wjm/2019.008 1851:10.15347/WJM/2019.008 1582:incomplete combustion 1513: 1458:In waste incineration 1415:open burning of waste 1384:Environmental sources 1164:subsistence fishermen 1153: 814:congeners of concern 789: 620:immunological effects 309:transcription factors 307:(bHLH/PAS) family of 282: 265: 253: 108:(PCBs), derived from 24:dioxin-like compounds 6099:Endocrine disruptors 5966:3-methylcholanthrene 4477:10.1289/ehp.02110355 4215:(1 Suppl): S261-77. 4097:Sharon Beder (2000) 3765:Environmental Health 2990:10.1289/ehp.01109865 1826:and can be cited as: 1660:Remediation research 1373:Stockholm Convention 1325:1,2,3,4,7,8,9-HpCDF 1317:1,2,3,4,6,7,8-HpCDF 1245:1,2,3,4,6,7,8-HpCDD 962:1,2,3,4,7,8,9-HpCDF 954:1,2,3,4,6,7,8-HpCDF 751:Toxicity equivalents 80:. There are 75 PCDD 6035:Cyproterone acetate 5917:Dietary carotenoids 5794:2011Chmsp..82.1225K 5648:2005RiskA..25..945A 5502:2004ESPR...11..181I 5455:10.1038/nature01237 5447:2003Natur.421..357B 5382:2018JEnvM.223..797R 5344:2018TEAC...17....1K 5282:1977Sci...195.1337C 5276:(4284): 1337–1338. 5235:1995Chmsp..30.1439V 5096:1995Chmsp..30.1671K 5028:2001Chmsp..43..773S 4949:2008JHzM..155..179C 4903:2011EnST...45..461S 4769:2004Chmsp..54.1319Q 4701:2015JAWMA..65.1033D 4522:2007Chmsp..67S.355W 4430:2009ER....109..760L 4308:2000Chmsp..40.1111N 4221:2008Chmsp..73S.261P 4175:2005Chmsp..60..854K 4110:Ronald Christaldi. 3974:2019EMnAs.191..590H 3927:2005ToxAP.207....2T 3777:2009EnvHe...8...39P 3418:1996EnvTP...1..193A 3079:2015EnInt..82...41M 2870:1991EnvMM..17..104M 2775:2002EcoES..51....1K 2663:2007EnST...41.4354B 2239:2016NatSR...638012X 1551:Dioxins and biomass 1404:global distribution 1193: 981:3,3’,4,4’-TCB (77) 876:1,2,3,4,6,7,8-HpCDD 815: 413:Toxicity in animals 275:Mechanism of action 5510:10.1007/bf02979673 4851:. 24 November 2014 4117:2013-10-29 at the 3840:10.1093/ije/dyn117 2227:Scientific Reports 2186:. Epub 2008 Jul 3. 1676:are poorly known. 1642:White-tailed eagle 1630:white-tailed eagle 1598:polyvinyl chloride 1516: 1447:1,2-Dichloroethane 1309:2,3,4,6,7,8-HxCDF 1301:1,2,3,7,8,9-HxCDF 1293:1,2,3,6,7,8-HxCDF 1285:1,2,3,4,7,8-HxCDF 1237:1,2,3,7,8,9-HxCDD 1229:1,2,3,6,7,8-HxCDD 1221:1,2,3,4,7,8-HxCDD 1191: 1156: 989:3,4,4’,5-TCB (81) 946:2,3,4,6,7,8-HxCDF 938:1,2,3,7,8,9-HxCDF 930:1,2,3,6,7,8-HxCDF 922:1,2,3,4,7,8-HxCDF 867:1,2,3,7,8,9-HxCDD 859:1,2,3,6,7,8-HxCDD 851:1,2,3,4,7,8-HxCDD 809: 807: 606:metabolism, serum 551:1968) and Taiwan ( 501:sexual development 495:, disturbances in 361:retinoid receptors 289: 268: 256: 42:. They are mostly 32:chemical compounds 6061: 6060: 6025:7-Ketocholesterol 4911:10.1021/es103000v 4618:10.1289/ehp.11781 4569:10.1289/ehp.11781 4302:(9–11): 1111–23. 3921:(2 Suppl): 2–10. 3868:BMC Public Health 3517:10.1080/713810655 3381:10.1002/ijc.11635 3278:10.1289/ehp.10399 3214:(9218): 1858–63. 3030:(9696): 1179–85. 2671:10.1021/es062602+ 2657:(12): 4354–4360. 2247:10.1038/srep38012 1876: 1875: 1722:Malayan Emergency 1451:1,2-Dibromoethane 1369:pentachlorophenol 1363:. The defoliant 1340: 1339: 1200:Half-life, years 1079: 1078: 534:Victor Yushchenko 497:tooth development 406:estrogen agonists 30:) are a group of 6106: 5982:β-naphthoflavone 5911:prostaglandin G2 5900:Arachidonic acid 5890: 5886: 5866: 5859: 5852: 5843: 5842: 5814: 5813: 5776: 5770: 5769: 5758: 5752: 5751: 5749: 5748: 5743: 5735: 5729: 5728: 5717: 5711: 5710: 5682: 5676: 5675: 5630: 5624: 5623: 5613: 5603: 5579: 5573: 5572: 5544: 5538: 5537: 5481: 5475: 5474: 5441:(6921): 357–60. 5430: 5424: 5423: 5416: 5410: 5409: 5365: 5356: 5355: 5327: 5318: 5317: 5261: 5255: 5254: 5229:(8): 1439–1451. 5217: 5211: 5210: 5205:. Archived from 5196: 5164: 5153: 5152: 5146: 5138: 5132: 5122: 5116: 5115: 5090:(9): 1671–1684. 5079: 5068: 5057: 5048: 5047: 5011: 5005: 5004: 5002: 4978: 4969: 4968: 4932: 4923: 4922: 4886: 4880: 4867: 4861: 4860: 4858: 4856: 4841: 4835: 4834: 4832: 4830: 4816: 4810: 4809: 4798: 4789: 4788: 4752: 4746: 4740: 4734: 4729: 4723: 4722: 4712: 4680: 4674: 4673: 4666: 4660: 4654: 4648: 4647: 4629: 4597: 4591: 4590: 4580: 4548: 4542: 4541: 4505: 4499: 4498: 4488: 4456: 4450: 4449: 4413: 4407: 4406: 4378: 4372: 4371: 4334: 4328: 4327: 4291: 4285: 4284: 4282: 4281: 4275: 4269:. Archived from 4264: 4256: 4241: 4240: 4204: 4195: 4194: 4158: 4152: 4146: 4140: 4139: 4131: 4125: 4108: 4102: 4095: 4089: 4082: 4073: 4062: 4053: 4052: 4041: 4035: 4034: 4008: 4002: 4001: 3956: 3947: 3946: 3910: 3904: 3903: 3893: 3883: 3859: 3853: 3852: 3842: 3818: 3809: 3808: 3798: 3788: 3756: 3750: 3749: 3713: 3704: 3700: 3694: 3693: 3683: 3674: 3671: 3654: 3653: 3651: 3650: 3640: 3632: 3626: 3625: 3607: 3601: 3600: 3598: 3597: 3588:. Archived from 3578: 3572: 3571: 3543: 3537: 3536: 3500: 3487: 3486: 3476: 3444: 3438: 3437: 3400: 3394: 3393: 3383: 3359: 3350: 3349: 3313: 3300: 3299: 3289: 3256: 3250: 3249: 3231: 3202: 3196: 3195: 3185: 3174:10.1289/ehp.6920 3153: 3147: 3146: 3110: 3099: 3098: 3062: 3056: 3055: 3018: 3012: 3011: 3001: 2969: 2960: 2950: 2944: 2943: 2907: 2898: 2897: 2853: 2847: 2846: 2810: 2799: 2798: 2758: 2749: 2748: 2738: 2728: 2704: 2693: 2692: 2682: 2642: 2636: 2635: 2599: 2593: 2592: 2582: 2558: 2549: 2548: 2512: 2506: 2495: 2489: 2478: 2472: 2471: 2445: 2439: 2438: 2402: 2389: 2388: 2378: 2354: 2348: 2347: 2319: 2310: 2309: 2299: 2275: 2269: 2268: 2258: 2218: 2212: 2211: 2209: 2208: 2202: 2193: 2187: 2175: 2169: 2168: 2158: 2126: 2093: 2092: 2072: 2053: 2048: 2025: 2024: 2013: 2004: 2003: 1993: 1969: 1871: 1853: 1835: 1811: 1803: 1788: 1615:biomagnification 1389:PCDD/F-compounds 1277:2,3,4,7,8-PeCDF 1269:1,2,3,7,8-PeCDF 1213:1,2,3,7,8-PeCDD 1194: 1190: 1119:Dioxin-like PCBs 1116: 1104: 1092: 914:2,3,4,7,8-PeCDF 906:1,2,3,7,8-PeCDF 843:1,2,3,7,8-PeCDD 816: 808: 792:skeletal formula 670:white blood cell 583:indicating that 558:Meibomian glands 553:Yu-cheng disease 526:gastrointestinal 422:wasting syndrome 185: 171: 157: 139: 6114: 6113: 6109: 6108: 6107: 6105: 6104: 6103: 6094:Organochlorides 6064: 6063: 6062: 6057: 6039: 5974:benzanthracenes 5888: 5878: 5870: 5823: 5818: 5817: 5777: 5773: 5760: 5759: 5755: 5746: 5744: 5741: 5737: 5736: 5732: 5719: 5718: 5714: 5683: 5679: 5631: 5627: 5580: 5576: 5545: 5541: 5482: 5478: 5431: 5427: 5418: 5417: 5413: 5366: 5359: 5328: 5321: 5262: 5258: 5218: 5214: 5209:on 27 May 2010. 5165: 5156: 5144: 5140: 5139: 5135: 5123: 5119: 5080: 5071: 5058: 5051: 5012: 5008: 4979: 4972: 4943:(1–2): 179–82. 4933: 4926: 4887: 4883: 4868: 4864: 4854: 4852: 4843: 4842: 4838: 4828: 4826: 4824:DioxinFacts.org 4818: 4817: 4813: 4800: 4799: 4792: 4753: 4749: 4741: 4737: 4730: 4726: 4681: 4677: 4668: 4667: 4663: 4655: 4651: 4598: 4594: 4549: 4545: 4506: 4502: 4457: 4453: 4414: 4410: 4379: 4375: 4335: 4331: 4292: 4288: 4279: 4277: 4273: 4262: 4258: 4257: 4244: 4205: 4198: 4159: 4155: 4147: 4143: 4132: 4128: 4119:Wayback Machine 4109: 4105: 4096: 4092: 4083: 4076: 4063: 4056: 4043: 4042: 4038: 4031: 4009: 4005: 3957: 3950: 3911: 3907: 3860: 3856: 3819: 3812: 3757: 3753: 3714: 3707: 3701: 3697: 3684: 3677: 3672: 3657: 3648: 3646: 3638: 3634: 3633: 3629: 3622: 3608: 3604: 3595: 3593: 3580: 3579: 3575: 3544: 3540: 3502: 3501: 3490: 3445: 3441: 3401: 3397: 3360: 3353: 3314: 3303: 3257: 3253: 3203: 3199: 3154: 3150: 3111: 3102: 3063: 3059: 3019: 3015: 2970: 2963: 2951: 2947: 2908: 2901: 2854: 2850: 2811: 2802: 2759: 2752: 2705: 2696: 2643: 2639: 2600: 2596: 2559: 2552: 2513: 2509: 2496: 2492: 2479: 2475: 2468: 2446: 2442: 2403: 2392: 2355: 2351: 2320: 2313: 2276: 2272: 2219: 2215: 2206: 2204: 2200: 2194: 2190: 2176: 2172: 2127: 2096: 2073: 2056: 2049: 2028: 2015: 2014: 2007: 1970: 1881: 1872: 1833: 1828: 1827: 1812: 1781: 1733:Seveso accident 1682: 1674:gut microbiomes 1668:Dehalococcoides 1662: 1626:trophic pyramid 1611:bioaccumulation 1606: 1594:carbon monoxide 1553: 1540: 1487: 1473: 1465:waste-to-energy 1460: 1436:hexachlorophene 1386: 1381: 1345: 1173: 1144: 1127: 1120: 1117: 1108: 1105: 1096: 1093: 753: 716: 714:Risk assessment 683: 681:Carcinogenicity 666:thyroid hormone 646:type 2 diabetes 581:Seveso disaster 514: 462: 455: 440: 415: 385:tumor promotion 365:corticosteroids 352: 277: 236: 191: 186: 177: 172: 163: 158: 149: 140: 17: 12: 11: 5: 6112: 6102: 6101: 6096: 6091: 6086: 6081: 6076: 6059: 6058: 6056: 6055: 6048: 6044: 6041: 6040: 6038: 6037: 6032: 6027: 6018: 6017: 6000: 5990: 5985: 5959: 5954: 5949: 5924: 5919: 5914: 5893: 5891: 5880: 5879: 5869: 5868: 5861: 5854: 5846: 5840: 5839: 5834: 5829: 5822: 5821:External links 5819: 5816: 5815: 5771: 5753: 5730: 5712: 5677: 5625: 5574: 5539: 5496:(3): 181–185. 5476: 5425: 5411: 5357: 5319: 5256: 5212: 5179:(6): A325-32. 5154: 5133: 5117: 5069: 5049: 5022:(4–7): 773–6. 5006: 4970: 4924: 4881: 4862: 4836: 4811: 4790: 4763:(9): 1319–27. 4747: 4735: 4724: 4695:(9): 1033–49. 4675: 4661: 4649: 4592: 4543: 4516:(9): S355-64. 4500: 4451: 4408: 4389:(10): 922–33. 4373: 4346:(3): 199–211. 4329: 4286: 4242: 4196: 4153: 4141: 4126: 4103: 4090: 4074: 4064:Sharon Beder. 4054: 4036: 4029: 4003: 3948: 3905: 3854: 3833:(5): 1008–17. 3810: 3751: 3705: 3695: 3675: 3655: 3627: 3620: 3602: 3573: 3538: 3488: 3459:(3): 460–466. 3439: 3395: 3374:(6): 893–900. 3351: 3301: 3251: 3197: 3168:(13): 1313–8. 3148: 3100: 3057: 3013: 2961: 2945: 2899: 2864:(2): 104–111. 2848: 2821:(4): 289–302. 2800: 2750: 2694: 2637: 2610:(1): 140–153. 2594: 2550: 2523:(4): 261–266. 2507: 2490: 2473: 2466: 2440: 2413:(4): 452–478. 2390: 2369:(4): 369–380. 2349: 2311: 2270: 2213: 2188: 2170: 2141:(2): 223–241. 2094: 2083:(4): 483–549. 2054: 2026: 2005: 1878: 1877: 1874: 1873: 1815: 1813: 1806: 1799: 1798: 1780: 1777: 1681: 1678: 1661: 1658: 1605: 1602: 1552: 1549: 1539: 1536: 1485: 1471: 1459: 1456: 1455: 1454: 1439: 1424: 1421: 1418: 1385: 1382: 1380: 1377: 1344: 1341: 1338: 1337: 1334: 1330: 1329: 1326: 1322: 1321: 1318: 1314: 1313: 1310: 1306: 1305: 1302: 1298: 1297: 1294: 1290: 1289: 1286: 1282: 1281: 1278: 1274: 1273: 1270: 1266: 1265: 1262: 1258: 1257: 1254: 1250: 1249: 1246: 1242: 1241: 1238: 1234: 1233: 1230: 1226: 1225: 1222: 1218: 1217: 1214: 1210: 1209: 1206: 1202: 1201: 1198: 1172: 1169: 1143: 1140: 1126: 1123: 1122: 1121: 1118: 1111: 1109: 1106: 1099: 1097: 1094: 1087: 1084: 1083: 1077: 1076: 1073: 1069: 1068: 1065: 1061: 1060: 1057: 1053: 1052: 1049: 1045: 1044: 1041: 1037: 1036: 1033: 1029: 1028: 1025: 1021: 1020: 1017: 1014: 1010: 1009: 1006: 1002: 1001: 998: 994: 993: 990: 986: 985: 982: 979: 975: 974: 971: 967: 966: 963: 959: 958: 955: 951: 950: 947: 943: 942: 939: 935: 934: 931: 927: 926: 923: 919: 918: 915: 911: 910: 907: 903: 902: 899: 894: 890: 889: 886: 882: 881: 878: 872: 871: 868: 864: 863: 860: 856: 855: 852: 848: 847: 844: 840: 839: 836: 831: 827: 826: 823: 820: 752: 749: 736:threshold-type 715: 712: 682: 679: 662:liver function 626:Low exposures. 513: 512:Human toxicity 510: 493:hydronephrosis 460: 453: 438: 414: 411: 351: 348: 276: 273: 235: 232: 193: 192: 187: 180: 178: 173: 166: 164: 159: 152: 150: 141: 134: 131: 130: 119: 116:Polybrominated 113: 103: 89: 38:(POPs) in the 15: 9: 6: 4: 3: 2: 6111: 6100: 6097: 6095: 6092: 6090: 6087: 6085: 6082: 6080: 6077: 6075: 6072: 6071: 6069: 6054: 6053: 6049: 6046: 6045: 6042: 6036: 6033: 6031: 6028: 6026: 6023: 6020: 6019: 6015: 6011: 6007: 6004: 6001: 5998: 5994: 5991: 5989: 5986: 5983: 5979: 5978:benzoflavones 5975: 5971: 5967: 5963: 5960: 5958: 5955: 5953: 5950: 5947: 5943: 5942:dibenzofurans 5939: 5935: 5931: 5928: 5925: 5923: 5920: 5918: 5915: 5912: 5908: 5904: 5901: 5898: 5895: 5894: 5892: 5887: 5881: 5877: 5874: 5867: 5862: 5860: 5855: 5853: 5848: 5847: 5844: 5838: 5835: 5833: 5830: 5828: 5825: 5824: 5811: 5807: 5803: 5799: 5795: 5791: 5788:(9): 1225–9. 5787: 5783: 5775: 5767: 5763: 5757: 5740: 5734: 5726: 5722: 5716: 5708: 5704: 5700: 5696: 5692: 5688: 5681: 5673: 5669: 5665: 5661: 5657: 5653: 5649: 5645: 5642:(4): 945–56. 5641: 5637: 5636:Risk Analysis 5629: 5621: 5617: 5612: 5607: 5602: 5597: 5593: 5589: 5585: 5578: 5570: 5566: 5562: 5558: 5554: 5550: 5543: 5535: 5531: 5527: 5523: 5519: 5515: 5511: 5507: 5503: 5499: 5495: 5491: 5487: 5480: 5472: 5468: 5464: 5460: 5456: 5452: 5448: 5444: 5440: 5436: 5429: 5421: 5415: 5407: 5403: 5399: 5395: 5391: 5387: 5383: 5379: 5375: 5371: 5364: 5362: 5353: 5349: 5345: 5341: 5337: 5333: 5326: 5324: 5315: 5311: 5307: 5303: 5299: 5295: 5291: 5287: 5283: 5279: 5275: 5271: 5267: 5260: 5252: 5248: 5244: 5240: 5236: 5232: 5228: 5224: 5216: 5208: 5204: 5200: 5195: 5190: 5186: 5182: 5178: 5174: 5170: 5163: 5161: 5159: 5150: 5143: 5137: 5131: 5130:0-394-41405-5 5127: 5121: 5113: 5109: 5105: 5101: 5097: 5093: 5089: 5085: 5078: 5076: 5074: 5066: 5065:91-620-1189-8 5062: 5056: 5054: 5045: 5041: 5037: 5033: 5029: 5025: 5021: 5017: 5010: 5001: 4996: 4992: 4988: 4984: 4977: 4975: 4966: 4962: 4958: 4954: 4950: 4946: 4942: 4938: 4931: 4929: 4920: 4916: 4912: 4908: 4904: 4900: 4896: 4892: 4885: 4878: 4875: 4872: 4866: 4850: 4846: 4840: 4825: 4821: 4815: 4807: 4803: 4797: 4795: 4786: 4782: 4778: 4774: 4770: 4766: 4762: 4758: 4751: 4745: 4739: 4733: 4728: 4720: 4716: 4711: 4706: 4702: 4698: 4694: 4690: 4686: 4679: 4671: 4665: 4658: 4653: 4645: 4641: 4637: 4633: 4628: 4623: 4619: 4615: 4612:(3): 417–25. 4611: 4607: 4603: 4596: 4588: 4584: 4579: 4574: 4570: 4566: 4563:(3): 417–25. 4562: 4558: 4554: 4547: 4539: 4535: 4531: 4527: 4523: 4519: 4515: 4511: 4504: 4496: 4492: 4487: 4482: 4478: 4474: 4471:(4): 355–61. 4470: 4466: 4462: 4455: 4447: 4443: 4439: 4435: 4431: 4427: 4423: 4419: 4412: 4404: 4400: 4396: 4392: 4388: 4384: 4377: 4369: 4365: 4361: 4357: 4353: 4349: 4345: 4341: 4333: 4325: 4321: 4317: 4313: 4309: 4305: 4301: 4297: 4290: 4276:on 2011-02-08 4272: 4268: 4261: 4255: 4253: 4251: 4249: 4247: 4238: 4234: 4230: 4226: 4222: 4218: 4214: 4210: 4203: 4201: 4192: 4188: 4184: 4180: 4176: 4172: 4169:(7): 854–69. 4168: 4164: 4157: 4150: 4145: 4137: 4130: 4123: 4120: 4116: 4113: 4107: 4100: 4094: 4087: 4081: 4079: 4071: 4067: 4061: 4059: 4050: 4046: 4040: 4032: 4030:9781118140574 4026: 4022: 4018: 4014: 4007: 3999: 3995: 3991: 3987: 3983: 3979: 3975: 3971: 3967: 3963: 3955: 3953: 3944: 3940: 3936: 3932: 3928: 3924: 3920: 3916: 3909: 3901: 3897: 3892: 3887: 3882: 3877: 3873: 3869: 3865: 3858: 3850: 3846: 3841: 3836: 3832: 3828: 3824: 3817: 3815: 3806: 3802: 3797: 3792: 3787: 3782: 3778: 3774: 3770: 3766: 3762: 3755: 3747: 3743: 3739: 3735: 3731: 3727: 3724:(4): 317–24. 3723: 3719: 3712: 3710: 3699: 3691: 3690: 3682: 3680: 3670: 3668: 3666: 3664: 3662: 3660: 3644: 3637: 3631: 3623: 3621:9780470601822 3617: 3613: 3606: 3592:on 2016-02-02 3591: 3587: 3583: 3577: 3569: 3565: 3561: 3557: 3553: 3549: 3542: 3534: 3530: 3526: 3522: 3518: 3514: 3510: 3506: 3499: 3497: 3495: 3493: 3484: 3480: 3475: 3470: 3466: 3465:10.1289/EHP25 3462: 3458: 3454: 3450: 3443: 3435: 3431: 3427: 3423: 3419: 3415: 3411: 3407: 3399: 3391: 3387: 3382: 3377: 3373: 3369: 3365: 3358: 3356: 3347: 3343: 3339: 3335: 3331: 3327: 3324:(4): 241–59. 3323: 3319: 3312: 3310: 3308: 3306: 3297: 3293: 3288: 3283: 3279: 3275: 3271: 3267: 3263: 3255: 3247: 3243: 3239: 3235: 3230: 3225: 3221: 3217: 3213: 3209: 3201: 3193: 3189: 3184: 3179: 3175: 3171: 3167: 3163: 3159: 3152: 3144: 3140: 3136: 3132: 3128: 3124: 3121:(4): 303–16. 3120: 3116: 3109: 3107: 3105: 3096: 3092: 3088: 3084: 3080: 3076: 3072: 3068: 3061: 3053: 3049: 3045: 3041: 3037: 3033: 3029: 3025: 3017: 3009: 3005: 3000: 2995: 2991: 2987: 2983: 2979: 2975: 2968: 2966: 2958: 2954: 2949: 2941: 2937: 2933: 2929: 2925: 2921: 2918:(4): 275–88. 2917: 2913: 2906: 2904: 2895: 2891: 2887: 2883: 2879: 2875: 2871: 2867: 2863: 2859: 2852: 2844: 2840: 2836: 2832: 2828: 2824: 2820: 2816: 2809: 2807: 2805: 2797: 2792: 2788: 2784: 2780: 2776: 2772: 2768: 2764: 2757: 2755: 2746: 2742: 2737: 2732: 2727: 2722: 2718: 2714: 2710: 2703: 2701: 2699: 2690: 2686: 2681: 2676: 2672: 2668: 2664: 2660: 2656: 2652: 2648: 2641: 2633: 2629: 2625: 2621: 2617: 2613: 2609: 2605: 2598: 2590: 2586: 2581: 2576: 2572: 2568: 2564: 2557: 2555: 2546: 2542: 2538: 2534: 2530: 2526: 2522: 2518: 2511: 2505: 2501: 2494: 2488: 2487:9781118140574 2484: 2477: 2469: 2467:9781118140574 2463: 2459: 2455: 2451: 2444: 2436: 2432: 2428: 2424: 2420: 2416: 2412: 2408: 2401: 2399: 2397: 2395: 2386: 2382: 2377: 2372: 2368: 2364: 2360: 2353: 2345: 2341: 2337: 2333: 2329: 2325: 2318: 2316: 2307: 2303: 2298: 2293: 2290:(2): 96–100. 2289: 2285: 2281: 2274: 2266: 2262: 2257: 2252: 2248: 2244: 2240: 2236: 2232: 2228: 2224: 2217: 2199: 2192: 2185: 2181: 2174: 2166: 2162: 2157: 2152: 2148: 2144: 2140: 2136: 2132: 2125: 2123: 2121: 2119: 2117: 2115: 2113: 2111: 2109: 2107: 2105: 2103: 2101: 2099: 2090: 2086: 2082: 2078: 2071: 2069: 2067: 2065: 2063: 2061: 2059: 2052: 2047: 2045: 2043: 2041: 2039: 2037: 2035: 2033: 2031: 2022: 2018: 2012: 2010: 2001: 1997: 1992: 1987: 1983: 1979: 1975: 1968: 1966: 1964: 1962: 1960: 1958: 1956: 1954: 1952: 1950: 1948: 1946: 1944: 1942: 1940: 1938: 1936: 1934: 1932: 1930: 1928: 1926: 1924: 1922: 1920: 1918: 1916: 1914: 1912: 1910: 1908: 1906: 1904: 1902: 1900: 1898: 1896: 1894: 1892: 1890: 1888: 1886: 1884: 1879: 1869: 1865: 1861: 1857: 1852: 1847: 1843: 1839: 1832: 1825: 1824: 1819: 1814: 1810: 1805: 1804: 1801: 1796: 1792: 1787: 1783: 1782: 1776: 1773: 1768: 1763: 1759: 1757: 1753: 1748: 1746: 1740: 1738: 1734: 1729: 1727: 1723: 1719: 1715: 1710: 1707: 1703: 1699: 1695: 1694:chlorophenols 1691: 1686: 1677: 1675: 1670: 1669: 1657: 1653: 1649: 1645: 1643: 1639: 1635: 1631: 1627: 1622: 1620: 1619:trophic level 1616: 1612: 1601: 1599: 1595: 1591: 1587: 1583: 1579: 1575: 1571: 1566: 1562: 1558: 1548: 1545: 1538:Other sources 1535: 1531: 1529: 1525: 1519: 1512: 1508: 1506: 1502: 1498: 1494: 1489: 1483: 1478: 1474: 1466: 1452: 1448: 1444: 1440: 1437: 1433: 1429: 1428:chlorophenols 1425: 1422: 1419: 1416: 1412: 1411: 1410: 1407: 1405: 1401: 1397: 1396:PCB-compounds 1393: 1390: 1376: 1374: 1370: 1366: 1362: 1358: 1354: 1350: 1335: 1332: 1331: 1327: 1324: 1323: 1319: 1316: 1315: 1311: 1308: 1307: 1303: 1300: 1299: 1295: 1292: 1291: 1287: 1284: 1283: 1279: 1276: 1275: 1271: 1268: 1267: 1263: 1261:2,3,7,8-TCDF 1260: 1259: 1255: 1252: 1251: 1247: 1244: 1243: 1239: 1236: 1235: 1231: 1228: 1227: 1223: 1220: 1219: 1215: 1212: 1211: 1207: 1205:2,3,7,8-TCDD 1204: 1203: 1199: 1196: 1195: 1189: 1185: 1183: 1177: 1168: 1165: 1160: 1152: 1148: 1139: 1136: 1131: 1115: 1110: 1103: 1098: 1091: 1086: 1085: 1081: 1080: 1074: 1071: 1070: 1066: 1063: 1062: 1058: 1055: 1054: 1050: 1047: 1046: 1042: 1039: 1038: 1034: 1031: 1030: 1026: 1023: 1022: 1018: 1015: 1011: 1007: 1004: 1003: 999: 996: 995: 991: 988: 987: 983: 980: 976: 972: 969: 968: 964: 961: 960: 956: 953: 952: 948: 945: 944: 940: 937: 936: 932: 929: 928: 924: 921: 920: 916: 913: 912: 908: 905: 904: 900: 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Retrieved 5733: 5724: 5715: 5693:(2): 77–86. 5690: 5686: 5680: 5639: 5635: 5628: 5591: 5587: 5577: 5552: 5548: 5542: 5493: 5489: 5479: 5438: 5434: 5428: 5414: 5373: 5369: 5335: 5331: 5273: 5269: 5259: 5226: 5222: 5215: 5207:the original 5176: 5172: 5148: 5136: 5120: 5087: 5083: 5019: 5015: 5009: 4990: 4986: 4940: 4936: 4897:(2): 461–7. 4894: 4890: 4884: 4876: 4874:Fire Sci Rev 4873: 4865: 4853:. Retrieved 4848: 4839: 4827:. Retrieved 4823: 4814: 4805: 4760: 4756: 4750: 4738: 4727: 4692: 4688: 4678: 4664: 4652: 4609: 4605: 4595: 4560: 4556: 4546: 4513: 4509: 4503: 4468: 4464: 4454: 4424:(6): 760–7. 4421: 4417: 4411: 4386: 4382: 4376: 4343: 4339: 4332: 4299: 4295: 4289: 4278:. Retrieved 4271:the original 4266: 4212: 4208: 4166: 4162: 4156: 4144: 4135: 4129: 4121: 4106: 4098: 4093: 4085: 4069: 4048: 4039: 4012: 4006: 3965: 3961: 3918: 3914: 3908: 3871: 3867: 3857: 3830: 3826: 3768: 3764: 3754: 3721: 3717: 3698: 3688: 3647:. Retrieved 3642: 3630: 3611: 3605: 3594:. Retrieved 3590:the original 3585: 3576: 3551: 3547: 3541: 3508: 3504: 3456: 3452: 3442: 3412:(3): 193–7. 3409: 3405: 3398: 3371: 3367: 3321: 3317: 3269: 3265: 3254: 3211: 3207: 3200: 3165: 3161: 3151: 3118: 3114: 3070: 3066: 3060: 3027: 3023: 3016: 2984:(8): 865–9. 2981: 2977: 2955:fact sheet: 2948: 2915: 2911: 2861: 2857: 2851: 2818: 2814: 2794: 2766: 2762: 2719:(11): 5333. 2716: 2713:EFSA Journal 2712: 2654: 2650: 2640: 2607: 2603: 2597: 2570: 2566: 2520: 2516: 2510: 2493: 2476: 2449: 2443: 2410: 2406: 2366: 2362: 2352: 2327: 2323: 2287: 2283: 2273: 2230: 2226: 2216: 2205:. Retrieved 2191: 2173: 2138: 2134: 2080: 2076: 2020: 1981: 1977: 1841: 1837: 1822: 1821: 1800: 1764: 1760: 1749: 1741: 1730: 1718:Agent Orange 1711: 1687: 1683: 1666: 1663: 1654: 1650: 1646: 1623: 1607: 1586:Global South 1561:process heat 1554: 1541: 1532: 1528:forest fires 1520: 1517: 1490: 1461: 1408: 1395: 1394: 1388: 1387: 1365:Agent Orange 1361:incineration 1346: 1186: 1178: 1174: 1161: 1157: 1145: 1135:Sharon Beder 1128: 897:2,3,7,8-TCDF 834:2,3,7,8-TCDD 811: 801: 781: 778: 774: 768: 764: 758: 754: 733: 717: 708: 684: 655: 640:A number of 639: 625: 624: 589: 578: 571: 563: 546: 542:pancreatitis 516: 515: 489:cleft palate 476: 475: 450:. The oral 434: 427: 417: 416: 383:effects and 378: 374: 369:sex hormones 353: 341: 334: 329:carcinogenic 313: 305:Per-Arnt-Sim 290: 285: 269: 257: 239: 237: 217: 210: 194: 144: 126: 100:dibenzofuran 94:(PCDFs), or 75: 67: 56: 27: 23: 19: 18: 6006:derivatives 5970:benzopyrene 5927:Halogenated 5903:metabolites 5782:Chemosphere 5376:: 797–806. 5223:Chemosphere 5084:Chemosphere 5016:Chemosphere 4855:3 September 4829:3 September 4757:Chemosphere 4510:Chemosphere 4296:Chemosphere 4209:Chemosphere 4163:Chemosphere 4049:herinst.org 3645:. 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