Tetrasodium;4-amino-6-[[4-[4-[(8-amino-1-oxido-3-sulfo-6-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Tetrasodium;4-amino-6-[[4-[4-[(8-amino-1-oxido-3-sulfo-6-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate
• 英文别名: tetrasodium;4-amino-6-[[4-[4-[(8-amino-1-oxido-3-sulfo-6-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate
• 化学式: C32H20N6Na4O14S4
• 分子量: 932.8
• InChiKey: MPCYPRXRVWZKGF-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  60
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  404
• 氢给体数：
  4
• 氢受体数：
  20

ADMET

代谢

偶氮染料

Benzidine derived azo dyes may be degraded metabolically in the gut or liver in man to free benzidine or monoacetylbenzidine. /Benzidine derived azo dyes/

来源:Hazardous Substances Data Bank (HSDB)

代谢

环境样本和尿液样本在六家工厂收集，这些工厂的工人可能暴露于基于联苯胺的染料（两家基于联苯胺的染料制造商，两家纺织品染色厂，一家皮革染色厂和一家纸张染色的工厂）。在其中一家染料制造厂，8名工人中有2名的尿液中检出了单乙酰联苯胺，水平为3和7 ppb。在第二家工厂，4名工人暴露于平均浓度为7.9、5.2、11.7和17.4 mg总颗粒物/立方米的环境中，对应的尿液中联苯胺浓度为52、11、10和112 ppb；在含有112、52和11 ppb联苯胺的尿样中检出了590、248和22 ppb单乙酰联苯胺。还检出了微量的二乙酰联苯胺、邻联甲苯胺和对联苯胺。在一家使用直接黑38和直接蓝2的纺织品染色厂中，工人的尿液中也检出了联苯胺（0-39 ppb）和/或单乙酰联苯胺。总悬浮颗粒物水平（以重量法测量）为1-4 mg/立方米。其他设施的工人的尿液中没有检出联苯胺。染料中的微小杂质水平无法解释尿样中检出的联苯胺及其衍生物的量。

Environmental and urine samples were collected at six factories where workers were potentially exposed to benzidine based dyes (two benzidine based dye manufacturers, two textile dyeing plants, a leather dyeing plant and a mill where paper was dyed). Monoacetylbenzidine was detected in the urine of 2/8 workers at one of the dye manufacturing plants at levels of 3 and 7 ppb. At the second factory, 4 workers exposed to average levels of 7.9, 5.2, 11.7 and 17.4 mg total particulate/cu m had corresponding urinary concentrations of 52, 11, 10 and 112 ppb benzidine; 590, 248 and 22 ppb monoacetylbenzidine were detected in urine samples containing 112, 52 and 11 ppb benzidine. Traces of diacetylbenzidine, ortho-tolidine and ortho-dianisidine were also detected. Benzidine (0-39 ppb) and/or monoacetylbenzidine was detected in the urine of workers in one textile dyeing factory where Direct Black 38 and Direct Blue 2 were being used. The total level of airborne particulates (measured gravimetrically) was 1-4 mg/cu m. Benzidine was not detected in the urine of workers from the other facilities. Minute levels of impurities in the dyestuffs could not account for the quantity of benzidine and its derivatives that were found in the urine samples.

来源:Hazardous Substances Data Bank (HSDB)

代谢

从苯胺、邻甲苯胺或邻联甲苯胺衍生出的六种偶氮染料分别通过口服灌胃给予大鼠。收集了24小时内的尿液。六种染料，直接黑38、直接棕95、直接蓝6、刚果红、锥虫蓝和芝加哥天蓝都被发现被还原、N-乙酰化和N-结合。然而，没有检测到N,N'-二乙酰化代谢物。在通过肝门静脉注射相同染料后，通过胆管插管收集了3小时内的胆汁。三小时结束时，通过注射器从膀胱中抽取尿液。分析了两种体液中的还原产物，只在直接黑38、直接棕95和直接蓝6的情况下发现了还原产物。在检测的六种染料中，只有三种直接染料在不存在黄素单核苷酸的情况下对S. typhimurium菌株TA98和TA1538具有致突变性。同样的三种染料也是大鼠肝微粒体偶氮还原酶酶的底物，而刚果红、锥虫蓝和芝加哥天蓝被证明是无效的。

Six azodyes derived from benzidine, o-tolidine or o-dianisidine were separately administered orally by gavage to rats. Urine was collected over a 24 hr period. All six dyes, direct black 38, direct brown 95, direct blue 6, Congo red, trypan blue and Chicago sky blue were found to be reduced, N-acetylated and N-conjugated. However, no N,N'-diacetylated metabolites were detected. After administration of the same dyes via injection into the hepatic portal vein, bile was collected over a 3 hr period by cannulation of the bile duct. Urine was withdrawn from the bladder by syringe at the end of the three hours. Both body fluids were analyzed for reduction products which were found only in the case of direct black 38, direct brown 95 and direct blue 6. Of the six dyes examined only the three direct dyes were mutagenic to S. typhimurium strains TA98 and TA1538 in the absence of flavin mononucleotide. The same three dyes were also substrates for rat liver microsomal azoreductase enzymes whereas Congo red, trypan blue and Chicago sky blue were shown to be inactive.

来源:Hazardous Substances Data Bank (HSDB)

代谢

研究了三种偶氮染料的偶氮还原、乙酰化和体内的致突变激活。在大鼠肝脏9000克上清液的存在下，直接黑38和直接棕95释放了联苯胺，而在直接蓝6的培养过程中几乎没有产生联苯胺。将联苯胺与分离的大鼠肝细胞一起培养，导致出现二乙酰联苯胺。除非将乙酰化反应的辅因子乙酰辅酶A添加到培养介质中，否则在大鼠肝脏9000克上清液中培养联苯胺时不会形成二乙酰联苯胺。分离的大鼠肝细胞能够在不补充乙酰辅酶A的情况下，从直接黑38、直接蓝6或直接棕95产生二乙酰联苯胺。大鼠肝脏具有相当大的还原偶氮化合物的能力。

The azo reduction and acetylation in vitro and the mutagenic activation in vivo of three azo dyes were studied. In the presence of rat-liver 9000 g supernatant benzidine was released from direct black 38 and direct brown 95, whereas hardly any benzidine was produced during incubation of direct blue 6. Incubation of benzidine with isolated rat hepatocytes resulted in the appearance of diacetylbenzidine. No diacetylbenzidine was formed during incubation of benzidine with rat-liver 9000 g supernatant, unless the cofactor for the acetylation reaction, acetyl coenzyme A, was added to the incubation medium. Isolated rat hepatocytes were capable to produce diacetylbenzidine from direct black 38, direct blue 6 or direct brown 95 without supplementation with acetyl coenzyme A. Rat liver has a considerable capacity to reduce azo compounds.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

致癌性分类：1）人类证据：不足；2）动物证据无数据。对人类致癌风险的总体评估为2A组：该物质很可能对人类致癌。/来自表格；联苯胺基染料/

Classification of carcinogenicity: 1) evidence in humans: inadequate; 2) No data for evidence in animals. Overall summary evaluation of carcinogenic risk to humans is Group 2A: The agent is probably carcinogenic to humans. /From table; Benzidine-based dyes/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

染料代谢为联苯胺：已知是人类致癌物。/染料代谢为联苯胺（联苯胺染料类）/

Dyes Metabolized to Benzidine: known to be human carcinogens. /Dyes Metabolized to Benzidine (Benzidine Dye Class)/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

职业性肝毒素 - 第二类肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。 IARC致癌物 - 1类：国际癌症研究机构将化学物质分类为已知的人类致癌物。 NTP致癌物 - 已知是人类致癌物。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. IARC Carcinogen - Class 1: International Agency for Research on Cancer classifies chemicals as established human carcinogens. NTP Carcinogen - Known to be a human carcinogen.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 医疗监测

尿液细胞学监测在评估染料厂工人肿瘤方面已被证明是有用的。该系统包括两阶段测试：定期尿液细胞学检查，然后在可疑情况下进行泌尿科检查。/联苯胺/

Urine cytology surveillance has proved useful in evaluating tumors in dyestuff plant workers. The system consists of two-stage tests: periodic urine cytology, followed by, in suspicious cases, urological examinations. /Benzidine/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 医疗监测

对于"致癌物"的预防措施：每当需要进行医疗监测时，尤其是在暴露于致癌物的情况下，应就.../细胞遗传学和其他/可能变得有用或必须进行的测试做出特别决定。/化学致癌物/

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

恒河猴在通过灌胃接受两种不同剂量的直接蓝6号染料后，尿液中平均排出了1.25%的联苯胺加上单一乙酰联苯胺的联苯胺部分，而纯联苯胺的灌胃则导致了1.45%的排出量。

Rhesus monkeys excreted an average of 1.25% benzidine plus monoacetylbenzidine of the benzidine moiety in Direct Blue 6 in the urine after receiving two different doses by gavage, whereas gavage with pure benzidine yielded 1.45%.

来源:Hazardous Substances Data Bank (HSDB)