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Dioxins
Dioxins and dioxin-like compounds (DLCs) are a group of chemical compounds that are persistent organic pollutants (POPs) in the environment. They are mostly by-products of burning or various industrial processes or, in the case of dioxin-like PCBs and PBBs, unwanted minor components of intentionally produced mixtures. 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 aryl hydrocarbon receptor (AH receptor), albeit with very different binding affinities, leading to high differences in toxicity and other effects. They include: * Polychlorinated dibenzo''-p-''dioxins (PCDDs), or simply dioxins. PCDDs are derivatives of dibenzo''-p-''dioxin. There are 75 PCDD congeners, differing in the number and location of chlorine atoms, and 7 of them are specifically toxic, the most toxic being 2,3,7,8-tetrachlorodibenzodioxin (TCDD). * Polychlorinated dibenzofurans (PCDFs) ...
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Polychlorinated Dibenzodioxins
Polychlorinated dibenzodioxins (PCDDs), or simply dioxins, are a group of long-lived polyhalogenated organic compounds that are primarily anthropogenic, and contribute toxic, persistent organic pollution in the environment. They are commonly but inaccurately referred to as dioxins for simplicity, because every PCDD molecule contains a dibenzo-1,4-dioxin skeletal structure, with 1,4-dioxin as the central ring. Members of the PCDD family bioaccumulate in humans and wildlife because of their lipophilic properties, and may cause developmental disturbances and cancer. Because dioxins can persist in the environment for more than 100 years, the majority of PCDD pollution today is not the result of recent emissions, but the cumulative result of synthetic processes undertaken since the beginning of the 20th century, including organochloride-related manufacturing, incineration of chlorine-containing substances such as polyvinyl chloride (PVC), and chlorine bleaching of paper. For ...
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2,3,7,8-Tetrachlorodibenzodioxin
2,3,7,8-Tetrachlorodibenzo-''p-''dioxin (TCDD) is a polychlorinated dibenzo''-p-''dioxin (sometimes shortened, though inaccurately, to simply ''dioxin'') with the chemical formula CHClO. Pure TCDD is a colorless solid with no distinguishable odor at room temperature. It is usually formed as an unwanted product in burning processes of organic materials or as a side product in organic synthesis. TCDD is the most potent compound ( congener) of its series (polychlorinated dibenzodioxins, known as PCDDs or simply dioxins) and became known as a contaminant in Agent Orange, an herbicide used in the Vietnam War. TCDD was released into the environment in the Seveso disaster. It is a persistent organic pollutant. Biological activity in humans and animals TCDD and dioxin-like compounds act via a specific receptor present in all cells: the aryl hydrocarbon (AH) receptor. This receptor is a transcription factor which is involved in the expression of genes; it has been shown that hi ...
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Persistent Organic Pollutants
Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released. The effect of POPs on human and environmental health was discussed, with intention to eliminate or severely restrict their production, by the international community at the Stockholm Convention on Persistent Organic Pollutants in 2001. Most POPs are pesticides or insecticides, and some are also solvents, pharmaceuticals, and industrial chemicals. Although some POPs arise naturally (e.g. from volcanoes), most are man-made. The "dirty dozen" POPs identified by the Stockholm Convention include aldrin, chlordane, dieldrin, endrin, heptachlor, HCB, mirex, toxaphene, PCBs ...
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Polychlorinated Dibenzofurans
Polychlorinated dibenzofurans (PCDFs) are a family of organic compounds with one or several of the hydrogens in the dibenzofuran structure replaced by chlorines. For example, 2,3,7,8-tetrachlorodibenzofuran (TCDF) has chlorine atoms substituted for each of the hydrogens on the number 2, 3, 7, and 8 carbons (see structure in the upper left corner of the second image). Polychlorinated dibenzofurans with chlorines at least in positions 2,3,7 and 8 are much more toxic than the parent compound dibenzofuran, with properties and chemical structures similar to polychlorinated dibenzodioxins. These groups together are often inaccurately called dioxins. They are known developmental toxicants, and suspected human carcinogens. PCDFs tend to co-occur with polychlorinated dibenzodioxins (PCDDs). PCDFs can be formed by pyrolysis or incineration at temperatures below 1200 °C of chlorine containing products, such as PVC, PCBs, and other organochlorides, or of non-chlorine containing pr ...
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Toxic Equivalency Factor
Toxic equivalency factor (TEF) expresses the toxicity of dioxins, furans and PCBs in terms of the most toxic form of dioxin, 2,3,7,8-TCDD.Van den Berg M, Birnbaum LS, Denison M, De Vito M, Farland W, Feeley F, Fiedler H, Hakansson H, Hanberg A, Haws L, Rose M, Safe S, Schrenk D, Tohyama C, Tritscher A, Tuomisto J, Tysklind M, Walker N, Peterson RE. 2006. The 2005 World Health Organization reevaluation of human and mammalian toxic equivalency factors for dioxins and dioxin-like compounds, Toxicol. Sci. 93:223–241, doi:10.1093/toxsci/kfl055. The toxicity of the individual congeners may vary by orders of magnitude. With the TEFs, the toxicity of a mixture of dioxins and dioxin-like compounds can be expressed in a single number – the toxic equivalency (TEQ). It is a single figure resulting from the product of the concentration and individual TEF values of each congener. The TEF/TEQ concept has been developed to facilitate risk assessment and regulatory control. While the init ...
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Aryl Hydrocarbon Receptor
The aryl hydrocarbon receptor (also known as AhR, AHR, ahr, ahR, AH receptor, or as the dioxin receptor) is a protein that in humans is encoded by the AHR gene. The aryl hydrocarbon receptor is a transcription factor that regulates gene expression. It was originally thought to function primarily as a sensor of xenobiotic chemicals and also as the regulator of enzymes such as cytochrome P450s that metabolize these chemicals. The most notable of these xenobiotic chemicals are aromatic (aryl) hydrocarbons from which the receptor derives its name. More recently, it has been discovered that AhR is activated (or deactivated) by a number of endogenous indole derivatives such as kynurenine. In addition to regulating metabolism enzymes, the AhR has roles in regulating immune cells, stem cell maintenance, and cellular differentiation. The aryl hydrocarbon receptor is a member of the family of basic helix-loop-helix transcription factors. AhR binds several exogenous ligands such as ...
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Dibenzodioxin
Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-''p''-dioxin (dibenzo-''para''-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxygen atoms occupy opposite ( ''para''-) positions in the six-membered dioxin ring. Dibenzodioxin is the carbon skeleton of the poisonous polychlorinated dibenzodioxins (PCDDs), often called dioxins. The most harmful PCDD is 2,3,7,8-tetrachlorodibenzodioxin (TCDD). Dioxins and dioxin-like compounds is a category of pollutants that includes PCDDs and other compounds that have similar structure, toxicity, and persistence. Dibenzodioxin is also the skeleton of the polybrominated dibenzodioxins. Isomer The general name dibenzodioxin usually refers to dibenzo-''p''-dioxin. The isomeric compound dibenzo-''o''-dioxin (dibenzo-''ortho''-dioxin) or dibenzo-1,2-dioxin, like the unstable 1,2-dioxin, has two adjacent oxygen atoms ( ''ortho''-). No ...
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Polychlorinated Biphenyl
Polychlorinated biphenyls (PCBs) are organochlorine compounds with the formula Carbon, C12Hydrogen, H10−''x''Chloride, Cl''x''; they were once widely used in the manufacture of carbonless copy paper, as heat transfer fluids, and as dielectric and coolant fluids for electrical equipment. They are highly toxic and carcinogenic chemical compounds, formerly used in industrial and consumer electronic products, whose production was banned internationally by the Stockholm Convention on Persistent Organic Pollutants in 2001. Because of their longevity, PCBs are still widely in use, even though their manufacture has declined drastically since the 1960s, when a multitude of problems was identified. With the discovery of PCBs' environmental toxicity, and classification as persistent organic pollutants, their production was banned for most uses by United States federal law on January 1, 1978. The International Agency for Research on Cancer (IARC) rendered PCBs as definite carcinogens i ...
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PAS Domain
A Per-Arnt-Sim (PAS) domain is a protein domain found in all kingdoms of life. Generally, the PAS domain acts as a molecular sensor, whereby small molecules and other proteins associate via binding of the PAS domain. Due to this sensing capability, the PAS domain has been shown as the key structural motif involved in protein-protein interactions of the circadian clock, and it is also a common motif found in signaling proteins, where it functions as a signaling sensor. Discovery PAS domains are found in a large number of organisms from bacteria to mammals. The PAS domain was named after the three proteins in which it was first discovered: * Per – period circadian protein * Arnt – aryl hydrocarbon receptor nuclear translocator protein * Sim – single-minded protein Since the initial discovery of the PAS domain, a large quantity of PAS domain binding sites have been discovered in bacteria and eukaryotes. A subset called PAS LOV proteins are responsive to oxygen, light ...
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Polychlorinated Biphenyl
Polychlorinated biphenyls (PCBs) are organochlorine compounds with the formula Carbon, C12Hydrogen, H10−''x''Chloride, Cl''x''; they were once widely used in the manufacture of carbonless copy paper, as heat transfer fluids, and as dielectric and coolant fluids for electrical equipment. They are highly toxic and carcinogenic chemical compounds, formerly used in industrial and consumer electronic products, whose production was banned internationally by the Stockholm Convention on Persistent Organic Pollutants in 2001. Because of their longevity, PCBs are still widely in use, even though their manufacture has declined drastically since the 1960s, when a multitude of problems was identified. With the discovery of PCBs' environmental toxicity, and classification as persistent organic pollutants, their production was banned for most uses by United States federal law on January 1, 1978. The International Agency for Research on Cancer (IARC) rendered PCBs as definite carcinogens i ...
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Chlorine
Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidizing agent, oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Electronegativity#Pauling electronegativity, Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval Alchemy, alchemists, which commonly involved the heating of chloride Salt (chemistry), salts like ammonium chloride (sal ammoniac) and sodium chloride (common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and . However, the nature of fre ...
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1,4-Dioxin
1,4-Dioxin (also referred as dioxin or ''p''-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula CHO. There is an isomeric form of 1,4-dioxin, 1,2-dioxin (or ''o''-dioxin). 1,2-Dioxin is very unstable due to its peroxide-like characteristics. The term "dioxin" is most commonly used for a family of derivatives of 1,4-dioxin, known as polychlorinated dibenzodioxins (PCDDs). Preparation 1,4-Dioxin can be prepared by cycloaddition, namely by the Diels–Alder reaction of furan and maleic anhydride. The adduct formed has a carbon-carbon double bond, which is converted to an epoxide. The epoxide then undergoes a retro-Diels–Alder reaction, forming 1,4-dioxin and regenerating maleic anhydride. Derivatives The word " dioxin" can refer in a general way to compounds which have a dioxin core skeletal structure with substituent molecular groups attached to it. For example, dibenzo-1,4-dioxin is a compound whose structure consists of two benz ...
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