1,2,3,4,6-五氯二苯并二恶因 | 36088-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 中文名称: 1,2,3,4,6-五氯二苯并二恶因
• 英文名称: 1,2,3,4,6-pentachlorodibenzo-p-dioxin
• CAS: 36088-22-9
• 化学式: C₁₂H₃Cl₅O₂
• 分子量: 356.42
• InChiKey: LNWDBNKKBLRAMH-UHFFFAOYSA-N

物化性质

• 熔点：
  220.0 °C
• 溶解度：
  In water, 1.20X10-4 mg/l @ 20 °C
• 蒸汽压力：
  5.60X10-10 mm Hg @ 25 °C
• 保留指数：
  2586;2573;2573

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

关于这些化合物在哺乳动物系统中的代谢知之甚少。这些化合物中的一些在人身上的半衰期不是以小时、天、周或月来衡量，而是以年来计算。/多氯二苯并二噁烷/

Little is known about the metabolism of these compounds in mammalian systems. The half-life of some of these compounds in humans can be measured not in hours, days, weeks, or months, but in years. /Polychlorodibenzodioxins/

来源:Hazardous Substances Data Bank (HSDB)

代谢

CDDs通过口服、吸入和皮肤暴露途径被吸收。CDDs通过血清脂质和脂蛋白在血浆中运输，主要分布到肝脏和脂肪组织。CDDs通过微粒体单加氧酶系统非常缓慢地被代谢为极性代谢物，这些代谢物可以与葡萄糖醛酸和谷胱甘肽发生结合反应。它们可能通过诱导I相和II相酶来增加自己的代谢速率。CDDs的主要排泄途径是胆汁和粪便，尽管也有少量通过尿液和哺乳排出。

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

CDDs通过结合芳基烃受体并随后改变某些基因的转录来产生其毒性作用。对Ah受体的亲和力取决于特定CDD的结构。基因表达的改变可能是由于Ah受体及其异二聚体形成伙伴芳基烃受体核移位子与基因调控元件的直接相互作用，或者启动磷酸化/去磷酸化级联反应，随后激活其他转录因子。受影响的基因包括几个癌基因、生长因子、受体、激素和药物代谢酶。这些基因的转录/翻译改变被认为是CDD大多数毒性作用的原因。

CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

整体评估：其他多氯二苯并-对-二噁英对人类致癌性不可分类（第3组）。/多氯二苯并-对-二噁英/

Overall evaluation: Other polychlorinated dibenzo-para-dioxins are not classifiable as to their carcinogenicity to humans (Group 3). /Polychlorinated dibenzo-para-dioxins/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：B2；可能的人类致癌物。分类依据：小鼠和大鼠经灌胃引起的肝脏肿瘤。人类致癌性数据：无。/六氯二苯并-p-二恶英，混合物（HXCDD）/

CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Hepatic tumors in mice and rats by gavage. HUMAN CARCINOGENICITY DATA: None. /Hexachlorodibenzo-p-dioxin, mixture (HXCDD)/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

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

接触大量氯丹类化合物（CDDs）会导致氯痤疮，这是一种严重的皮肤疾病，其特点是在面部和上半身出现类似粉刺的损伤。CDDs还可能引起肝脏损伤，并导致长期的葡萄糖代谢改变和激素水平的微妙变化。此外，研究还表明CDDs可能会干扰内分泌系统，削弱免疫系统，以及造成生殖损害和出生缺陷、中枢和周围神经系统的病理变化、甲状腺疾病、子宫内膜异位症和糖尿病。(L177, L178)

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (L177, L178)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

多氯二苯并-p-二噁英和多氯二苯并呋喃主要储存在脂肪中，但它们也会通过乳汁排出并被胎盘传递。它们还以较低的浓度出现在血液和主要器官中。/多氯二苯并-p-二噁英/

The polychlorinated dibenzo-p-dioxins and the polychlorinated dibenzofurans are predominantly stored in fat, but they are also excreted in milk and pass the placenta. They also appear in the blood and vital organs at lower concentrations. /Polychlorinated dibenzo-p-dioxins/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠中，报告了玉米油中1,2,3,7,8-五氯二苯并对-二噁英的不完全和可变吸收，口服暴露后头两天内有19%至71%的剂量被吸收。

Incomplete and variable absorption of 1,2,3,7,8-pentaCDD in corn oil was reported in rats, with 19 to 71% of the dose absorbed within the first 2 days after oral exposure.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠、豚鼠、仓鼠和小鼠的研究中发现，尿液和胆汁中排出的TCDD衍生的放射性几乎全部对应于TCDD的代谢物。肝脏和脂肪中TCDD代谢物的明显缺失表明，一旦形成，TCDD的代谢物就会迅速排出。因此，尿液和胆汁中TCDD的排出依赖于毒素的代谢。其他化合物的更有限数据也表明，这种关系可能对1,2,3,7,8-五氯二苯并对二恶英、2,3,7,8-四溴二苯并对二恶英、2,3,7,8-四氯二苯并呋喃、1,2,3,7,8-五氯二苯并呋喃、2,3,4,7,8-五氯二苯并呋喃和3,3',4,4'-四氯联苯成立。

Studies in the rat, guinea pig, hamster, and mouse have found that essentially all of the TCDD-derived radioactivity excreted in the urine and bile corresponds to metabolites of TCDD. The apparent absence of TCDD metabolites in liver and fat suggests that once formed, the metabolites of TCDD are excreted readily. Thus, urinary and biliary elimination of TCDD depends on metabolism of the toxin. The more limited data for other compounds also suggest that this relationship may be true for 1,2,3,7,8-pentaCDD, 2,3,7,8-TBDD, 2,3,7,8-TCDF, 1,2,3,7,8-pentaCDF, 2,3,4,7,8-pentaCDF, and 3,3',4,4'-TCB.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

研究了膳食纤维或小球藻在老鼠粪便中PCDDs和PCDFs排泄中的作用。米糠纤维增加了老鼠粪便中PCDDs的排泄量，从0.6增加到2.3倍，PCDFs的排泄量从0.5增加到10.4倍，高于对照组老鼠。小球藻是一种单细胞绿藻，作为健康食品或健康补充剂销售。老鼠饮食中的小球藻也增加了粪便中PCDDs的排泄量，从0.8增加到5.6倍，PCDFs的排泄量从0.9增加到11.1倍，高于对照组老鼠。小球藻中的膳食纤维、叶绿素和/或脂质可能是导致本研究观察到的PCDDs和PCDFs粪便排泄量增加的因素。因此，纤维和/或小球藻可能是能够增加PCDDs和PCDFs粪便排泄量的其他膳食因素。/多氯代二苯并-p-二噁英和二苯并呋喃/

...The role of dietary fiber or Chlorella in the fecal excretion of PCDDs and PCDFs in rats /was investigated/. Rice bran fibers enhanced the fecal excretion of PCDDs form 0.6 to 2.3 and of PCDFs from 0.5- to 10.4 fold above that of rats on a control diet. Chlorella is a unicellular green algae sold as a health food or health supplement. Chlorella in the diet of rats also enhanced the fecal excretion of PCDDs from 0.8 to 5.6 and PCDFs from 0.9- to 11.1-fold above that of rats on a control diet. Dietary fiber, chlorophyll, and /or lipid in the Chlorella may be factors responsible for the enhanced fecal excretion of PCDDs and PCDFs observed in this study. Thus, fiber and/or Chlorella may be other dietary factors capable of increasing the fecal excretion of PCDDs and PCDFs. /Polychlorinated dibenzo-p-dioxins and dibenzofurans/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为产物：
  描述：

  五氯酚 生成 1,2,3,4,6-五氯二苯并二恶因
  参考文献：
  名称：

  DICKSON, L. C.;LENOIR, D.;HUTZINGER, O., CHEMOSPHERE, 19,(1989) N-9, C. 1435-1445

  摘要：

  DOI：

文献信息

• MOLD CAPABLE OF DEGRADING DIOXIN, DEGRADATION OF DIOXIN WITH THE USE OF THE SAME, METHOD FOR PRODUCING COMPOSTS CAPABLE OF DEGRADING DIOXIN AND METHOD FOR GROWING PLANTS
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP1074611A1

  公开（公告）日：2001-02-07

  The invention provides lignin-degradable fungi capable of degrading dioxins that have accumulated in the soil for farm crops, into harmless substances; a method for degrading dioxins by applying the fungi to a dioxin-containing object to such a degree that the cell concentration in the object reaches at least 1 × 102 cfu per gram of the object; compost containing the fungi; a method for producing compost that comprises a step of thermally fermenting a lignin-containing, plant-derived organic material to be compost, at a temperature falling between 65 and 100°C for at least 2 hours, followed by inoculating the thus-fermented material with lignin degrading enzymes-producing fungi and further fermenting it; and a method of using the compost for cultivating plants.

  本发明提供了可降解木质素的真菌，该真菌能够将农作物土壤中积累的二恶英降解为无害物质；一种降解二恶英的方法，该方法是将真菌施用到含二恶英的物体上，使该物体中的细胞浓度达到每克物体至少 1×102 cfu；含有该真菌的堆肥；一种生产堆肥的方法，该方法包括以下步骤：将含有木质素的植物有机材料在 65 至 100°C 的温度下热发酵至少 2 小时，然后将产生木质素降解酶的真菌接种到发酵材料中并进一步发酵；以及将堆肥用于栽培植物的方法。
• Method and apparatus for laser analysis of dioxins
  申请人：Mitsubishi Heavy Industries, Ltd.

  公开号：EP1096546A2

  公开（公告）日：2001-05-02

  A dioxins analyzer of the present invention applies laser light of a broad spectral width to a gas or solution containing dioxins to perform laser multiphoton ionization of the dioxins, and then measures the ionized dioxins. The dioxins contained in a gas such as an exhaust gas or in water such as waste water can be analyzed in real time.

  本发明的二恶英分析仪对含有二恶英的气体或溶液施加宽光谱激光，对二恶英进行激光多光子电离，然后测量电离出的二恶英。可以实时分析废气等气体或废水等水中所含的二恶英。
• WHITE ROT FUNGUS AND METHOD FOR DEGRADING DIOXINS BY USING THE SAME
  申请人：Wakao Construction Co., Ltd.

  公开号：EP1114680A1

  公开（公告）日：2001-07-11

  White rot fungi capable of decomposing dioxin were screened from rotten wood to isolate the MZ-340 strain. This MZ-340 could be cultured in the Kirk liquid medium (HCLN) or PDB medium. New systems that can be used to decompose dioxins in incineration ash were constructed using this MZ-340 strain. The present invention can decompose dioxins in incineration ash effectively and efficiently in both solid phase systems and liquid phase systems. Thus, the present invention enables the prevention of environmental pollution by dioxins generated during incineration and also the clean up of dioxin pollutants.

  从朽木中筛选出能够分解二恶英的白腐真菌，并分离出 MZ-340 菌株。这种 MZ-340 菌株可在 Kirk 液体培养基（HCLN）或 PDB 培养基中培养。利用该 MZ-340 菌株构建了可用于分解焚烧灰中二恶英的新系统。本发明在固相系统和液相系统中都能有效和高效地分解焚烧灰中的二恶英。因此，本发明可以防止焚烧过程中产生的二恶英对环境造成污染，还可以清除二恶英污染物。
• Label-free method for the detection of analytes
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2752664A1

  公开（公告）日：2014-07-09

  The present invention relates to method for the detection and/or characterization of an analyte based on determining and preferably optical determining the alteration of mechanical deformation of hydrogel particles and kits suitable for this method.

  本发明涉及基于测定（最好是光学测定）水凝胶颗粒机械变形的变化来检测和/或表征分析物的方法，以及适用于该方法的试剂盒。
• Synchronised variation of source conditions of an atmospheric pressure chemical ionisation mass spectrometer coupled to a gas chromatograph to improve stability during analysis
  申请人：Micromass UK Limited

  公开号：US10141172B2

  公开（公告）日：2018-11-27

  A mass spectrometer is disclosed comprising a gas chromatography separation device, an atmospheric pressure ionization ion source and a control system arranged and adapted: (i) to operate the atmospheric pressure ionization ion source at one or more first settings for a first period of time while one or more solvents elute from the gas chromatography separation device during a solvent front; and then (ii) to operate the atmospheric pressure ionization ion source at one or more second different settings for a second subsequent period of time while one or more analytes elute from the gas chromatography separation device.

  本发明公开了一种质谱仪，该质谱仪包括气相色谱分离装置、常压电离离子源和控制系统，控制系统的布置和适配：(i) 在溶剂前沿期间，当一种或多种溶剂从气相色谱分离装置洗脱时，在第一时间段内以一种或多种第一设置操作常压电离离子源；然后 (ii) 在随后的第二时间段内，当一种或多种分析物从气相色谱分离装置洗脱时，在一种或多种第二不同设置操作常压电离离子源。