3,3',4,4',5,5'-六氯联苯 | 32774-16-6

• 物质功能分类: 分析化学 - 食品安全 - 二噁英，多氯联苯，呋喃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3',4,4',5,5'-六氯联苯
• 中文别名: 3,3,4,4,5,5-六氯联苯
• 英文名称: 33'44'55'-hexachlorinated biphenyl
• 英文别名: 3,3',4,4',5,5'-Hexachlorobiphenyl；1,2,3-trichloro-5-(3,4,5-trichlorophenyl)benzene
• CAS: 32774-16-6
• 化学式: C₁₂H₄Cl₆
• 分子量: 360.882
• InChiKey: ZHLICBPIXDOFFG-UHFFFAOYSA-N

物化性质

• 熔点：
  202°C
• 沸点：
  446.99°C (rough estimate)
• 密度：
  1.5940 (rough estimate)
• 物理描述：
  White solid; [MSDSonline]
• 溶解度：
  1.41e-09 M
• 蒸汽压力：
  0.00000058 [mmHg]
• 稳定性/保质期：
  ... PCB's are chemically very inert and are stable to conditions of hydrolysis and oxidation in industrial use. Photochemical degradation may be one route of their breakdown in the environment. ...
• 分解：
  When heated to decomposition it emits toxic fumes of Chloride.
• 碰撞截面：
  169.4 Ų [M-Cl+O]-
• 保留指数：
  2479

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

多氯联苯（PCBs）通过吸入、口服和皮肤接触途径被吸收。它们通过血液传输，通常与白蛋白结合。由于其亲脂性，它们倾向于在富含脂质的组织中积累，如肝脏、脂肪组织和皮肤。多氯联苯的代谢非常缓慢，并且根据氯化的程度和位置而有所不同。多氯联苯通过微粒体单加氧酶系统进行代谢，该系统由细胞色素P-450酶催化，转化为极性代谢物，这些代谢物可以与谷胱甘肽和葡萄糖醛酸结合。主要代谢物是羟基化产物，通过胆汁和粪便排出。多氯联苯的缓慢代谢意味着它们倾向于在身体组织中积累。

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are trasported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

PCB的作用机制因具体类型而异。类似于二噁烷的PCB会与芳基烃受体结合，通过改变基因的转录来扰乱细胞功能，主要是通过诱导肝脏第一阶段和第二阶段酶的表达，特别是细胞色素P450家族。人们认为PCB的大多数毒性效应是Ah受体结合的结果。其他PCB被认为会干扰钙通道和/或改变大脑中的多巴胺水平。PCB还通过改变甲状腺激素的生成和与雌激素受体结合来引起内分泌紊乱，这可能会刺激某些癌细胞的生长并产生其他类雌激素效应，如生殖功能障碍。它们还会通过结合如uteroglobin等受体蛋白而生物累积。(A3, A4, A30, A66)

The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

1, 对人类致癌。

1, carcinogenic to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

PCBs最常见的健康影响是皮肤状况，如氯痤疮和皮疹。长期暴露于PCBs还可能导致肝脏、胃和肾脏损害、黄疸、水肿、贫血、免疫系统变化、行为改变以及生殖能力受损。

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L4级）；吸入（L4级）；皮肤给药（L4级）

Oral (L4) ; inhalation (L4) ; dermal (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

慢性 PCB 暴露会导致如下症状：腹痛、恶心、呕吐、腹泻、头痛、眩晕、抑郁、神经紧张、皮肤和眼睛损伤、疲劳、月经周期不规律以及免疫力下降。

Chronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

在给泌乳期奶牛口服给药后，3,3',4,4',5,5'-六氯联苯在牛奶中的浓度在第二天和第三天之间达到峰值，之后迅速下降。

FOLLOWING ORAL ADMIN TO LACTATING COW, LEVELS OF 3,3',4,4',5,5'-HEXACHLOROBIPHENYL REACHED PEAK CONCENTRATIONS IN MILK BETWEEN THE 2ND & 3RD DAY, & RAPIDLY DECLINED THEREAFTER.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

37种PCB同类物在脂肪组织-血浆中的分配情况及28种PCB同类物的职业暴露人群中的分布进行了研究。研究表明，脂肪组织和血浆中PCB的浓度与暴露的持续时间和强度有关。脂肪组织中PCB的浓度与血浆中的浓度成比例，回归分析表明总PCB的分配比例大约为190:1。在血浆和脂肪组织中，两个苯环的4位上都有氯取代的PCB同类物是主要成分。而3,4位上未取代或只有一个苯环的3,4位未取代的PCB同类物浓度较低。相比之下，两个苯环的2,4位和3,4位上都有取代基的化合物在血液或脂肪组织中的比例远高于所使用的PCB混合物。这些组分在脂肪组织-血浆分配方面也高于那些3,4位未取代的化合物，无论氯化的程度如何。

DISPOSITION OF 37 PCB CONGENERS & ADIPOSE TISSUE-PLASMA PARTITION OF 28 PCB CONGENERS WERE STUDIED IN 26 PERSONS OCCUPATIONALLY EXPOSED TO VARIOUS PCBS (20-54% CL). CONCN OF PCBS IN ADIPOSE TISSUE & PLASMA WERE RELATED TO DURATION & INTENSITY OF EXPOSURE. PCB CONCN IN ADIPOSE TISSUE WAS PROPORTIONAL TO THAT IN PLASMA, WITH A PARTITION FOR TOTAL PCBS OF APPROX 190:1 INDICATED FROM REGRESSION ANALYSIS. PCB CONGENERS WITH CL IN BOTH 4-POSITIONS OF BIPHENYL RING WERE MAJOR COMPONENTS IN PLASMA & ADIPOSE TISSUE. CONGENERS WITH UNSUBSTITUTED 3,4-POSITIONS ON 1 OR BOTH OF BIPHENYL RINGS WERE OBSERVED AT LOWER CONCENTRATIONS. IN CONTRAST, THOSE COMPOUNDS WITH SUBSTITUENTS AT 2,4- & 3,4-POSITIONS ON BOTH RINGS WERE PRESENT IN MUCH HIGHER PROPORTIONS IN BLOOD OR ADIPOSE TISSUE THAN IN PCB MIXTURES USED. THESE COMPONENTS ALSO HAD HIGHER ADIPOSE TISSUE-PLASMA PARTITION THAN THOSE WITH UNSUBSTITUTED 3,4-POSITIONS, REGARDLESS OF DEGREE OF CHLORINATION.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2903999090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3,3',4,4',5,5'-六氯联苯 在 硝酸 作用下， 生成 3,4,5,3',4',5'-hexachloro-2,2'-dinitro-biphenyl
  参考文献：
  名称：

  van Roosmalen, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 359,362

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-二乙酰联苯胺 在 硫酸 、 氯 、 溶剂黄146 作用下， 生成 3,3',4,4',5,5'-六氯联苯
  参考文献：
  名称：

  van Roosmalen, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 359,362

  摘要：

  DOI：

文献信息

• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• [EN] PFKFB3 INHIBITORS AND THEIR USES<br/>[FR] INHIBITEURS DE PFKFB3 ET LEURS UTILISATIONS
  申请人：GERO DISCOVERY LLC

  公开号：WO2020080979A1

  公开（公告）日：2020-04-23

  This disclosure relates to new phthalimide and isoindolinone derivatives and other PFKFB3 inhibitors for use in the treatment of diseases. The invention further relates to pharmaceutical compositions containing such PFKFB3 inhibitors, methods of preparation thereof, methods for their use as therapeutic agents, and methods of preparation of a medicament for use in therapy, as well as kits and other inventiions comprising such PFKFB3 inhibitors. These PFKFB3 inhibitors are useful for the treatment and prophylaxis of cancer, neurodegenerative diseases, autoimmune diseases, inflammatory disorders, multiple sclerosis, metabolic diseases, inhibition of angiogenesis and other diseases and conditions, where the modulation of PFKFB3 and/or PFKFB4 has beneficial effect as well as neuroprotection.

  这项披露涉及新的邻苯二甲酰亚胺和异吲哚酮衍生物以及其他PFKFB3抑制剂，用于治疗疾病。该发明还涉及含有此类PFKFB3抑制剂的药物组合物，其制备方法，作为治疗剂的使用方法，以及用于治疗的药物的制备方法，以及包含此类PFKFB3抑制剂的工具包和其他发明。这些PFKFB3抑制剂对于治疗和预防癌症、神经退行性疾病、自身免疫疾病、炎症性疾病、多发性硬化症、代谢性疾病、抑制血管生成以及其他疾病和情况具有用途，在这些情况下，PFKFB3和/或PFKFB4的调节具有益处，以及神经保护作用。
• Instruments for detecting low-molecular weight substance
  申请人：Mizukami Haruki

  公开号：US20050148097A1

  公开（公告）日：2005-07-07

  To provide the following instruments 1 and 2 as a low-molecular-weight substance detection instrument employing immunochromatography capable of detecting conveniently and sensitively detecting a low-molecular weight substance such as an environmental pollutant (e.g., a dioxin), as a target substance contained in a test sample: 1. an instrument, which comprises 1) a test sample application section with which a test sample is brought into contact; 2) a label product reaction section containing a label product containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, the label product being not bound to the reaction section; 3) an unbound label product capturing section containing an element capable of capturing the label product which is not bound to the target substance, the element being bound to the capturing section; and 4) a detection section containing a detection element which, when coming into contact with the target substance bound to the label product, causes a visually observable change, and 2. an instrument wherein a test sample is reacted with a labeled antibody containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, and the resultant reaction product is employed for detecting the target substance contained in the test sample.

  提供以下仪器1和2作为低分子量物质检测仪器，采用免疫层析技术，能够方便敏感地检测低分子量物质，例如环境污染物（例如二恶英），作为测试样品中包含的目标物质：1. 仪器，包括1）测试样品应用部分，用于将测试样品接触；2）标签产物反应部分，包含一种标签产物，其中包含一种能够结合到测试样品中的目标物质的抗体，标签产物未结合到反应部分；3）未结合标签产物捕获部分，包含一种能够捕获未结合到目标物质的标签产物的元素，该元素与捕获部分结合；以及4）检测部分，包含一种检测元素，当与结合到标签产物的目标物质接触时，会引起可视的变化；2. 仪器，其中测试样品与标记抗体反应，其中一部分包含能够结合到测试样品中的目标物质的抗体，产生的反应产物用于检测测试样品中包含的目标物质。
• METHODS FOR TREATING TRANSTHYRETIN AMYLOID DISEASES
  申请人：Kelly Jeffery W.

  公开号：US20100120919A1

  公开（公告）日：2010-05-13

  Kinetic stabilization of the native state of transthyretin is an effective mechanism for preventing protein misfolding. Because transthyretin misfolding plays an important role in transthyretin amyloid diseases, inhibiting such misfolding can be used as an effective treatment or prophylaxis for such diseases. Treatment methods are disclosed.

  转甲状腺素原生态状态的动力学稳定是预防蛋白质错折的有效机制。因为转甲状腺素错折在转甲状腺素淀粉样病中起着重要作用，抑制这种错折可以用作有效的治疗或预防此类疾病的方法。本文公开了治疗方法。
• Base-catalyzed H/D exchange of polychlorinated biphenyls
  作者：Zhihao Xiang、Shiqing Huang、Liang-Liang Zhao、Zengyu Zhang、Ke Chen、Wanqiang Cao、Keyu Zheng、Xiaoyu Yan

  DOI：10.1016/j.tetlet.2022.154200

  日期：2022.11

  pollutants at present. With the rapid development of mass spectrometry-based analysis method, it is necessary to develop synthetic methods for isotopologues of polychlorinated biphenyls. Herein, a novel base-catalyzed H/D exchange reaction of polychlorinated biphenyls with DMSO‑d6/D2O has been disclosed. This protocol provides excellent deuterium incorporation with good ortho-selectivity.

  多氯联苯是目前最普遍、最有害的环境污染物之一。随着基于质谱的分析方法的快速发展，有必要开发多氯联苯同位素体的合成方法。在此，已公开了一种新型的碱催化多氯联苯与 DMSO- d 6 /D 2 O 的 H/D 交换反应。该协议提供了出色的氘掺入和良好的邻位选择性。