(Z)-2-氯-3-(二氯甲基)丁-2-烯二酸 | 126572-80-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (Z)-2-氯-3-(二氯甲基)丁-2-烯二酸
• 中文别名: 5-[3(R)-[[(1,1-二羰基四氢噻嗯基-3(S)-氧代)羰基]氨基]-4-(苯基硫代)-2(R)-羟基丁基]-N-(1,1-二甲基乙基)八氢噻吩并[3,2-c]吡啶-6(R)-甲酰胺
• 英文名称: (E)-2-Chloro-3-(dichloromethyl)-2-butenedioic acid
• 英文别名: (E)-2-chloro-3-(dichloromethyl)but-2-enedioic acid
• CAS: 126572-80-3
• 化学式: C₅H₃Cl₃O₄
• 分子量: 233.43
• InChiKey: CNMCESFYDAVNPQ-UPHRSURJSA-N

物化性质

• 溶解度：
  In water, 3,586 mg/L at 25 °C (est)
• 蒸汽压力：
  6.93X10-6 mm Hg at 25 °C (est)
• 解离常数：
  pKa = 2.28 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 非人类毒性摘录

遗传毒性... 强致突变剂3-氯-4-(二氯甲基)-5-羟基-2(5H)-呋喃酮(MX)及其几何异构体E-2-氯-3-(二氯甲基)-4-氧代丁烯酸(E-MX)已被发现在氯化饮水中存在。MX大约占总突变性的30%，而E-MX只占几个百分点。MX和E-MX在水中的稳定性较差，会发生pH依赖的异构化（MX与E-MX处于平衡）和水解降解。MX类似物3-氯-4-(二氯甲基)-2(5H)-呋喃酮(红-MX)和2-氯-3-(二氯甲基)-2-丁烯二酸(氧-MX)也已在氯化水中被识别。然而，这些化合物的相对较低的致突变性表明，它们对氯化水总体致突变性的贡献仅为中等程度。

/GENOTOXICITY/ ... The strong Ames mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2 (5H)-furanone (MX) and its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (E-MX) have been shown to be present in chlorinated drinking waters. MX accounts for approximately 30% and E-MX for a few percent of the overall mutagenicity. MX and E-MX are unstable in water and undergo both pH dependent isomerization (MX in equilibrium E-MX) and hydrolytic degradation. ... The MX analogues 3-chloro-4-(dichloromethyl)-2 (5H)-furanone (red-MX) and 2-chloro-3-(dichloromethyl)-2-butenedioic acid (ox-MX) have also been identified in chlorinated water. However, the relatively low mutagenicity of these compounds suggests that their contribution to the overall mutagenicity of chlorinated water is of only moderate significance.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

/遗传毒性/ 最近在氯化饮用水中识别出的氯化丁烯酸的诱变活性通过沙门氏菌微体试验和SOS色测试验进行了确定。使用了没有S9混合物和有S9混合物的沙门氏菌鼠伤寒测试菌株TA97、TA98和TA100。在SOS色测试验中，使用了大肠杆菌PQ37作为指示生物，有无代谢激活。此外，通过小鼠腹腔注射处理的微核试验，研究了极其强效的Ames试验诱变剂(Z)-2-氯-3-(二氯甲基)-4-氧代丁烯酸（MX，开放形式）。沙门氏菌试验和SOS色测试验的结果显示，MX是所测试化合物中最强的诱变剂。MX的还原形式(Z)-2-氯-3-(二氯甲基)-4-羟基丁-2-烯酸（red-MX）和MX的几何异构体(E)-2-氯-3-(二氯甲基)-4-氧代丁烯酸（EMX）也能诱导突变。然而，由于EMX的溶液中大约含有5%的MX，它的活性大部分可能归因于MX。EMX的氧化形式(E)-2-氯-3-(二氯甲基)-丁二酸（ox-EMX）仅在SOS色测试验中略有活性。所有这些化合物都是直接作用的诱变剂，在有代谢激活（S9混合物）的情况下，它们不会产生诱变性。MX的氧化形式(Z)-2-氯-3-(二氯甲基)-丁二酸（ox-MX）在测试的剂量水平下没有诱变性。MX没有在小鼠骨髓中诱导微核。

/GENOTOXICITY/ The mutagenic activities of the chlorinated butenoic acids recently identified in chlorinated drinking waters were determined by the Salmonella microsome assay and by the SOS chromotest. The Salmonella typhimurium tester strains TA97, TA98 and TA100 were used without and with S9 mix. In the SOS chromotest Escherichia coli PQ37 was used as an indicator organism with and without metabolic activation. In addition, the extremely potent Ames test mutagen (Z)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (MX, in the open form), was studied by the micronucleus test with mice using intraperitoneal treatment. The results of the Salmonella assay and the SOS chromotest showed that MX was by far the most potent mutagen of the compounds tested. Mutations were also induced by the reduced form of MX, (Z)-2-chloro-3-(dichloromethyl)-4-hydroxybut-2-enoic acid (red-MX), and by the geometric isomer of MX, (E)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (EMX). However, since the solution of EMX contained approximately 5% MX, most of its activity might be attributable to MX. The oxidised form of EMX, (E)-2-chloro-3-(dichloromethyl)-butenedioic acid (ox-EMX), was marginally active in the SOS chromotest only. All these compounds were directly acting mutagens and in the presence of metabolic activation (S9 mix) they did not generate mutagenicity. The oxidized form of MX, (Z)-2-chloro-3-(dichloromethyl)-butenedioic acid (ox-MX), was not mutagenic at the dose levels tested. MX did not induce micronuclei in the bone marrow of mice.

来源:Hazardous Substances Data Bank (HSDB)