1,2,3,4,8,9-六氯二苯并呋喃 | 92341-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 1,2,3,4,8,9-六氯二苯并呋喃
• 英文名称: 1,2,3,4,8,9-hexachlorodibenzofuran
• CAS: 92341-07-6
• 化学式: C₁₂H₂Cl₆O
• 分子量: 374.865
• InChiKey: VSDUQUBUJRNREH-UHFFFAOYSA-N

物化性质

• 沸点：
  475.5±40.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)
• 保留指数：
  2779;2780

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在现有文献中没有找到关于二苯并呋喃在哺乳动物体内的代谢信息。细菌Sphingomonas、Brevibacterium、Terrabacter和Staphylococcus auricularis通过二苯并呋喃4,4a-双加氧酶将二苯并呋喃降解为2,2',3-三羟基联苯。

No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

卤素代二苯并呋喃（PCDFs和PBDFs）与芳基烃受体（AhR）结合，增加了其在XRE（外源化合物响应元件）启动子区域激活转录的能力。具体来说，AhR与PCDF结合，将其转运到细胞核，并与芳烃核转运蛋白（ARNT）和异生物质响应元件（XRE）一起，增加了CYP1A1和芳基烃羟化酶（CYP1B1）的表达。AhR信号还通过环氧合酶-2增加花生四烯酸转化为前列腺素，改变Wnt/β-连环蛋白信号通路，下调Sox9，并改变炎症细胞因子受体的信号传导。AhR信号还改变类固醇激素受体的蛋白酶体降解，改变细胞的UVB应激反应，并改变某些T细胞亚群的分化。由此产生的AhR介导的激活和改变导致体重减轻、癌症和胸腺萎缩（免疫和内分泌紊乱的特征），这些都是PCDFs和相关有毒卤素代芳烃的常见毒性反应。

Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 无法归类其对人类致癌性的类别。(L135)

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

CDFs会导致呕吐和腹泻、贫血、更频繁的肺部感染、麻木以及对神经系统等其他影响，以及肝脏的轻微变化。然而，在摄入CDFs的人群中没有发现永久性的肝脏变化或明确的肝脏损伤。

CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L952）；皮肤（L952）；口服（L952）

Inhalation (L952) ; dermal (L952) ; oral (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

皮肤和眼部刺激，尤其是严重的痤疮、肤色变黑以及带有分泌物的肿胀眼睑是CDF中毒最明显的健康影响。

Skin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为产物：
  描述：

  晕苯 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 1,2,3,4,8,9-六氯二苯并呋喃
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k

文献信息

• Isomer Distributions of Polychlorinated Dibenzo-<i>p</i>-dioxins/Dibenzofurans Formed during De Novo Synthesis on Incinerator Fly Ash
  作者：Ruud Addink、Harrie A. J. Govers、Kees Olie

  DOI：10.1021/es971077z

  日期：1998.7.1

  Polychlorinated dibenzo-p-dioxins (PCDD) and dibenzofurans (PCDF) emitted from municipal waste incinerators appear to have a chlorination pattern that is quite constant across various samples and conditions. This suggested that these patterns may he controlled by thermodynamic properties of the individual PCDD/F congeners, such as the free Gibbs energy of formation (Delta G degrees(f,T)) This would make prediction of the isomer composition of a particular sample (and hence its TEQ value) possible, based on values of Delta G degrees(f.T). A laboratory scale study was carried out with activated carbon on fly ash as the source of PCDD/F formation. Although it was found that the isomer distributions within homologues were independent of the reaction time (proof of thermodynamic control), other observations (lack of equilibrium/isomerization between isomers and lack of similarity between isomer distributions measured and predicted by Delta G degrees(f,T)) contradicted the possibility of thermodynamic control. Hence, this study could not confirm that de novo formation of PCDD/F could explain thermodynamically controlled isomer distributions in incinerators. Some recommendations for further work-time-based studies with precursors, isomerization studies with single congeners, and more data on Delta G degrees(f,T) values of PCDD/F-were made.
• Prediction of polychlorinated dibenzofuran congener distribution from gas-phase phenol condensation pathways
  作者：Jae-Yong Ryu、James A. Mulholland、Jeong-Eun Oh、Duane T. Nakahata、Do-Hyong Kim

  DOI：10.1016/j.chemosphere.2004.01.002

  日期：2004.6

  A model for predicting the distribution of dibenzofuran and polychlorinated dibenzofuran (PCDF) congeners from a distribution of phenols was developed. The model is based on a simplified chemical mechanism. Relative rate constants and reaction order with respect to phenol precursors were derived from experimental results using single phenols and equal molar mixtures of up to four phenols. For validation, experiments were performed at three temperatures using a distribution of phenol and 19 chlorinated phenols as measured in municipal waste incinerator exhaust gas. Comparison of experimental measurements and model predictions for PCDF isomer distributions and homologue pattern shows agreement within measurement uncertainty. The R-squared correlation coefficient exceeds 0.9 for all PCDF isomer distributions and the distribution of PCDF homologues. These results demonstrate that the distribution of dibenzofuran and the 135 PCDF congeners from gas-phase condensation of phenol and chlorinated phenols can be predicted from measurement of the distribution of phenol and the 19 chlorinated phenol congeners. (c) 2004 Elsevier Ltd. All rights reserved.
• A comparative study of the photolytic degradation of octachlorodibenzofuran (OCDF) and octachlorodibenzo-p-dioxin (OCDD)
  作者：W.J. Wagenaar、E.J. Boelhouwers、H.A.M. de Kok、C.P. Groen、H.A.J. Govers、K. Olie、J. de Gerlache、C.G. de Rooij

  DOI：10.1016/0045-6535(95)00158-5

  日期：1995.8

  Photolysis at 290 nm and higher wavelengths of octachlorodibenzofuran (OCDF) and octachlorodibenzo-p-dioxin (OCDD) was studied in three organic solvents hexane, 1,4-dioxane and methanol. It appeared that the degradation kinetics strongly depended on the type of solvent. OCDD degraded fastest in hexane, whereas OCDF degraded fastest in methanol. Less than 5% of the total loss of OCDD degraded by reductive dechlorination, with preferential loss of chlorine atoms at the 1 or 9 positions. 35 to 50% of the total loss of OCDF degraded via reductive dechlorination, with preferential loss of lateral chlorine. OCDF degraded faster than OCDD in all studied solvents.Photolysis at 290 nn and higher wavelengths of OCDD and OCDF adsorbed onto alumina impregnated with copper (alumina/Cu) in the presence of natural and distilled water was also investigated. Under these more relevant environmental aquatic conditions, photolysis of OCDD and OCDF was much slower than photolysis in the studied organic solvents. Significant loss was only found for OCDF. A part of the loss of OCDF could be explained by reductive dechlorination; the results suggested that other mechanisms of degradation occurred in addition to reductive dechlorination.All photolysis experiments showed that OCDF was photochemically less stable than OCDD.
• ZODEH, A. M.;SIKORA, D. S., REC. CONF. PAP., NEW YORK (N. Y.),(1988) C. 29-33
  作者：ZODEH, A. M.、SIKORA, D. S.

  DOI：——

  日期：——
• Methods and compositions for increasing the efficacy of biologically-active ingredients
  申请人：Windsor Brian J.

  公开号：US20060276339A1

  公开（公告）日：2006-12-07

  The invention provides methods and compositions for modulating the sensitivity of cells to cytotoxic compounds and other active agents. In accordance with the invention, compositions are provided comprising combinations of ectophosphatase inhibitors and active agents. Active agents include antibiotics, fungicides, herbicides, insecticides, chemotherapeutic agents, and plant growth regulators. By increasing the efficacy of active agents, the invention allows use of compositions with lowered concentrations of active ingredients.