O,P’-滴滴涕 | 789-02-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: O,P’-滴滴涕
• 中文别名: 滴滴涕(O,P)/2,2-双(4-氯苯基)-1,1,1-三氯乙烷；2,4'-滴滴涕标样；2-邻氯苯基-2-对氯苯基-1,1,1-三氯乙烷；2,4-滴滴涕/1,1-双(4-氯苯基)2,2,2-三氯乙烷；O,P'-DDT/O,P'滴滴涕；邻,对’-滴滴涕；2,4´-滴滴涕；O,P'-滴滴涕；2,4-滴滴涕
• 英文名称: o,p'-DDT
• 英文别名: 1-chloro-2-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
• CAS: 789-02-6
• 化学式: C₁₄H₉Cl₅
• mdl: MFCD00036120
• 分子量: 354.49
• InChiKey: CVUGPAFCQJIYDT-UHFFFAOYSA-N

物化性质

• 熔点：
  76℃
• 沸点：
  440.74°C (rough estimate)
• 密度：
  1.3938 (rough estimate)
• 闪点：
  11 °C
• 溶解度：
  氯仿：微溶
• 蒸汽压力：
  1.35e-06 mmHg
• 保留指数：
  2263.6;2229.1;2248;2234.2;2199;2247.7;2225.8;2220;2237.9;2220.1

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

DDT在胃和肠道被吸收后，进入淋巴系统，随后在全身传播并融入脂肪组织。DDT的代谢主要通过肝脏和肾脏中的细胞色素P-450酶进行，在那里它经历还原脱氯作用，转化为DDD（二氯二苯基二氯乙烷）和DDE（二氯二苯基二氯乙烯）。这些化合物进一步分解成更多的代谢物，主要是DDA（双（对氯苯基）醋酸），它们通过尿液排出体外。

DDT is absorbed in the stomach and intestine, after which it enters the lymphatic system and is carried throughout the body and incorporated into fatty tissues. Metabolism of DDT occurs mainly via cytochrome P-450 enzymes in the liver and kidney, where it undergoes reductive dechlorination to DDD (dichlorodiphenyldichloroethane) and DDE (dichlorodiphenyldichloroethylene). These compounds are further degraded into additional metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), which are excreted in the urine. (L85)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

DDT的毒性至少通过四种机制发生，这些机制可能同时发挥作用。DDT减少了跨膜的钾离子传输。DDT抑制了通过钠离子通道的孔道失活。这些通道正常激活（打开），但失活（关闭）缓慢，从而干扰了神经轴突在复极化过程中钠离子的主动运输，导致一种超兴奋状态。DDT还抑制了神经元的腺苷三磷酸酶（ATP酶），尤其是Na+K+-ATP酶和Ca2+-ATP酶，这些酶在神经元复极化中起着至关重要的作用。DDT还抑制了钙调蛋白（神经中的钙介质）运输钙离子的能力，这对于神经递质的释放至关重要。所有这些被抑制的功能都降低了去极化的速率，并增加了神经元对那些在完全去极化的神经元中不会引起反应的小刺激的敏感性。DDT还被认为是通过模仿内源性激素并绑定到雌激素和雄激素受体，对生殖系统产生不利影响。

DDT toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDT reduces potassium transport across the membrane. DDT inhibits inactivation of the porous channels through which sodium ions pass. The channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization, causing a state of hyperexcitability. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. DDT is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (T10, L85)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

DDT可能对人类有致癌性（2B组）。

DDT is possibly carcinogenic to humans (Group 2B). (L2151)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

DDT暴露会导致体重下降和厌食。DDT中毒会影响人类的神经系统功能，但在肝脏和生殖器官中可以观察到病理变化。暴露于高浓度DDT后，肝细胞和亚细胞器如线粒体的肥大、平滑内质网的增殖、中央小叶坏死以及肝脏肿瘤发生率增加的情况已被注意到。

Exposure to DDT causes loss of weight and anorexia. DDT poisoning affects CNS function in humans, but pathologic changes are observed in the liver and reproductive organs. Hypertrophy of hepatocytes and subcellular organelles such as mitochondria, proliferation of smooth endoplasmic reticulum, centrolobular necrosis after exposure to high concentrations, and an increase in the incidence of hepatic tumors have been noted. (T10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L85）

Oral (L85)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

滴滴涕急性中毒的迹象包括口服摄入后的感觉异常。研究表明，被滴滴涕类物质中毒的哺乳动物会表现出周期性的持续震颤和/或痉挛性发作，这表明神经元有重复放电。这些重复的震颤和发作可以通过触觉和听觉刺激引发。 (T10)

Acute signs of DDT poisoning include paresthesia after oral ingestion. Studies have shown that a mammal poisoned with DDT-type agents displays periodic persistent tremoring and/or convulsive seizures that are suggestive of repetitive discharges in neurons. These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. (T10)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险品标志：
  F,T,N
• 危险类别码：
  R40,R50/53,R11,R23/24/25,R39/23/24/25,R25,R48/25
• 危险品运输编号：
  UN1230 3/PG 2
• 储存条件：
  请将低温和避光保存的信息存放在以下格式中：低温保存，并避免光照。

制备方法与用途

类别：有毒物品

• 毒性分级：中毒
• 急性毒性：
  • 口服（大鼠）LD₅₀ >1000毫克/公斤
  • 口服（小鼠）LD₅₀ 1000毫克/公斤

可燃性危险特性：可燃；燃烧时会产生有毒的氯化物烟雾。

储运特性：库房需通风、低温且干燥。

灭火剂：干粉、泡沫、沙土、二氧化碳或雾状水。

反应信息

• 作为反应物：
  描述：

  O,P’-滴滴涕 在 chromium(VI) oxide 、 sodium hydroxide 、 溶剂黄146 作用下， 生成 2,4'-二氯二苯甲酮
  参考文献：
  名称：

  The Chemical Composition of Technical DDT¹

  摘要：

  DOI：

  10.1021/ja01225a058
• 作为产物：
  描述：

  (2-Chlorophenyl)magnesium bromide 在 乙醚 、 硫酸 作用下， 生成 O,P’-滴滴涕
  参考文献：
  名称：

  The Chemical Composition of Technical DDT¹

  摘要：

  DOI：

  10.1021/ja01225a058

文献信息

• Facile and catalytic degradation method of DDT using Pd/C–Et3N system under ambient pressure and temperature
  作者：Yasunari Monguchi、Akira Kume、Hironao Sajiki

  DOI：10.1016/j.tet.2006.06.041

  日期：2006.8

  degradation method of p,p′-DDT [1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane] and its regioisomer o,p′-DDT [1,1,1-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane] using the Pd/C–Et3N system under ambient hydrogen pressure and temperature was established. The presence of Et3N was necessary for the quick and complete breakdown of DDT. The independent degradation study of two intermediates, p,p′-DDD

  的催化降解方法p，p滴滴涕[1,1,1-三氯-2,2-双（p -氯苯基）乙烷]和其部位异构体ö，p滴滴涕[1,1,1-三氯在环境氢气压力和温度下，使用Pd / C-Et 3 N系统建立了2-（邻氯苯基）-2-（对氯苯基）乙烷] 。Et 3 N的存在对于DDT的快速彻底分解是必需的。对两种中间体p，p' -DDD [2,2-双（p-氯苯基）-1,1-二氯乙烷]和p，p的独立降解研究使用GC-MS的'-DDE [2,2-双（对氯苯基）-1,1-二氯乙烯]让我们推测了p，p' -DDT的降解途径。在反应的初始阶段，p，p′ -DDT的降解分为两种方式：脱氯化氢途径和加氢脱氯途径。在每种途径中，反应均从脂肪族部分开始，随后逐步从苯部分进行加氢脱氯。前者途径导致1,1-二苯乙烷的形成，后者途径导致1,1-二氯-2,2-二苯乙烷的形成。这些二苯乙烷类似物，与p，p相比，毒性较小'-DDT是我们系统中的
• Synthesis of β-3H-mitotane for use in a rapid assay for mitotane metabolism
  作者：Mayra L. Piñeiro-Sánchez、Alfin D. N. Vaz、Raymond E. Counsell、Mohamed Ruyan、David E. Schteingart、Joseph E. Sinsheimerl

  DOI：10.1002/jlcr.2580360204

  日期：1995.2

  A 3H+-release method has been developed for the assay of β-hydroxylation of the adrenolytic drug mitotane. β-3H-mitotane was synthesized by the reduction of 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2,2-trichloroethane by an aluminium-Hg2Cl2 couple in the presence of 3H2O. For β-hydroxylation of mitotane, the 3H+-release assay is more efficient and sensitive than a method utilizing 14C-mitotane and chromatographic separation of metabolites by HPLC. The 3H+-release assay has been used to evaluate the ability of adrenal tumors to metabolize mitotane via the β- hydroxylation route.

  β-3H-米托坦是由 1-(2-氯苯基)-1-(4-氯苯基)-2,2,2-三氯乙烷在 3H2O 存在下通过铝-Hg2Cl2 对偶还原合成的。与利用 14C-itotane 和 HPLC 色谱分离代谢物的方法相比，3H+ 释放测定法在米托坦的β-羟基化方面更有效、更灵敏。3H+ 释放测定法已被用于评估肾上腺肿瘤通过 β- 羟基化途径代谢米托坦的能力。
• Absolute configuration determination through the unique intramolecular excitonic coupling in the circular dichroisms of o,p′-DDT and o,p′-DDD. A combined experimental and theoretical study
  作者：Hiroki Tanaka、Yoshihisa Inoue、Takeshi Nakano、Tadashi Mori

  DOI：10.1039/c6pp00438e

  日期：2017.4

  Circular dichroisms (CDs) of the o,p′-isomers of 1,1,1-trichloro- and 1,1-dichloro-2,2-bis(chlorophenyl)ethanes (DDT and DDD) were investigated experimentally and theoretically. A series of strong Cotton effect peaks in a characteristic negative–negative–positive–negative, or its mirror-imaged, pattern were observed in the CD spectra of these persistent organic pollutants. The theoretical CD spectra

  所述的圆形dichroisms（CDS）ø，p '的1,1,1-三氯和1,1-二氯-2,2-双（氯苯基） -异构体乙烷（DDT和DDD）进行了实验和理论研究。在这些持久性有机污染物的CD光谱中，观察到了一系列强烈的棉花效应峰，这些峰以特征性的负-负-正-负模式或镜像模式出现。SAC-CI / B95（d）和RI-CC2 / def2-TZVPP水平的理论CD光谱很好地再现了实验光谱，使我们能够明确地将（+）- DDT和（-）- DDD的绝对构型指定为小号。
• ISOFLAVONE METABOLITES
  申请人：Joannou George Eustace

  公开号：US20080125481A1

  公开（公告）日：2008-05-29

  There are disclosed compounds of formulae (I) or (II) in which A is selected from the group consisting of (1), (2), (3) and (4); OH, and one of R 1 and R 2 is selected from H, OH and OCH 3 , and the other of R 1 and R 2 is selected from OH and OCH 3 ; one of R3 and R4 is selected from H, OH and OCH3, and the other of R3 and R4 is selected from OH and OCH3; provided that at least one of the pairs R 1 , R 2 and R 3 , R 4 are both OH; R 5 is selected from OH and OCH 3 ; and denotes a single or double bond; and pharmaceutically acceptable salts and prodrugs thereof. The compounds of the invention are useful for the treatment of hormone-dependent conditions and cancers.

  公开了式（I）或（II）的化合物，其中A从（1），（2），（3）和（4）组成的群体中选择；OH，R1和R2中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；R3和R4中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；前提是R1，R2和R3，R4中至少有一对是OH；R5选择自OH和OCH3；并表示单键或双键；以及其药学上可接受的盐和前药。本发明的化合物用于治疗激素依赖性疾病和癌症。
• Compounds That Act To Modulate Insect Growth And Methods And Systems For Identifying Such Compounds
  申请人：Henrich Vincent C.

  公开号：US20110207707A1

  公开（公告）日：2011-08-25

  Disclosed are methods and systems for screening for compounds that act to modulate insect growth. Bioassays including cell culture and/or transgenic insects engineered with various components of the ecdysoid receptor (EcR) and/or the farsenoid-X receptor (RXR) systems to identify compounds that act as insecticides and/or hormone receptor activators are described. Also described are compounds, and compositions, identified as being putative insecticides based upon their ability to activate EcR and/or FXR mediated transcription.

  本发明涉及筛选调节昆虫生长的化合物的方法和系统。本发明描述了生物测定方法，包括细胞培养和/或转基因昆虫，这些昆虫经过工程设计，具有各种成分的ecdysoid受体（EcR）和/或farsenoid-X受体（RXR）系统，以识别作为杀虫剂和/或激素受体激活剂的化合物。本发明还描述了通过其激活EcR和/或FXR介导的转录而被认为是杀虫剂的化合物和组合物。

表征谱图