direct black 38 | 22244-14-0

• 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: direct black 38
• 英文别名: 4-amino-3-[4'-(2,4-diamino-phenylazo)-biphenyl-4-ylazo]-5-hydroxy-6-phenylazo-naphthalene-2,7-disulfonic acid；4-Amino-3-[4'-(2,4-diamino-phenylazo)-biphenyl-4-ylazo]-5-hydroxy-6-phenylazo-naphthalin-2,7-disulfonsaeure；Benzol-(1 azo 2)-(8-amino-naphthol-(1)-disulfonsaeure-(3.6))-(7 azo 4)-diphenyl-(4'azo 4)-(phenylendiamin-(1.3))；Direct Black 38 (free acid)；4-amino-3-[[4-[4-[(2,4-diaminophenyl)diazenyl]phenyl]phenyl]diazenyl]-5-hydroxy-6-phenyldiazenylnaphthalene-2,7-disulfonic acid
• CAS: 22244-14-0
• 化学式: C₃₄H₂₇N₉O₇S₂
• 分子量: 737.776
• InChiKey: ATFARZXNCCWOKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  298
• 氢给体数：
  6
• 氢受体数：
  16

ADMET

代谢

单次剂量（100毫克/千克）的纯化直接黑38染料给仓鼠灌胃后，通过尿液分析在排泄的前8小时内揭示了高水平的联苯胺、单乙酰联苯胺、二乙酰联苯胺、4-氨基联苯和联苯胺及4-氨基联苯的碱性可水解结合物。

SINGLE DOSE (100 MG/KG) OF PURIFIED DIRECT BLACK 38 ADMIN TO HAMSTERS REVEALED BY URINE ASSAY HIGH LEVELS OF BENZIDINE, MONOACETYLBENZIDINE, DIACETYLBENZIDINE, 4-AMINOBIPHENYL, & ALKALINE HYDROLYZABLE CONJUGATES OF BENZIDINE & 4-AMINOBIPHENYL DURING 1ST 8 HR OF EXCRETION

来源:Hazardous Substances Data Bank (HSDB)

代谢

直接黑38在动物中被代谢成人类致癌物联苯胺。

DIRECT BLACK 38 WAS SHOWN TO BE METABOLIZED IN ANIMALS TO HUMAN CARCINOGEN BENZIDINE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

警告也由美国国立职业安全与健康研究所（NIOSH）的初步现场研究结果指出，这些结果显示，与这些相同染料（直接黑38、直接棕95和直接蓝6）一起工作的人类也会在尿液中排出高于预期的联苯胺水平。实验室和现场研究都表明，这些由联苯胺衍生的染料可以被代谢为联苯胺，这种物质存在于动物和人类的尿液中。根据短期研究的数据，美国国家癌症研究所的科学家们认为，接触由联苯胺衍生的染料存在致癌潜力，最有可能是通过染料在动物体内被代谢转化为联苯胺的机制。

Caution is also indicated by preliminary results from the NIOSH field studies showing that humans working with these same dyes /Direct Black 38, Direct Brown 95, and Direct Blue 6/ also excrete higher than expected levels of benzidine in their urine. Both laboratory and field studies indicate that these benzidine derived dyes can be metabolized to benzidine, which is present in the urine of animals and humans. Based on the data from the short-term study, National Cancer Institute scientists believe that a cancer causing potential exists on exposure to the benzidine derived dyes, most likely through the mechanism of metabolic conversion of the dyes to benzidine in the animal system.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在为期13周的亚慢性毒性研究中，在大鼠和小鼠的尿液中发现了联苯胺和单乙酰联苯胺，这些动物接触了直接黑38染料。分析24小时尿液样本，在接触染料后4周和12周（大鼠）以及3周和11周（小鼠）显示出食物中染料浓度与排出的联苯胺量之间存在明确的关系。小鼠将更多的染料生物转化为联苯胺，而大鼠则转化较少。

Benzidine and monoacetylbenzidine were found in the urine of rats and mice on the course of 13-week subchronic toxicity studies with Direct Black 38. Analysis of 24-hour urine samples 4 and 12 weeks (rats) and 3 and 11 weeks (mice) later showed a clear-cut relationship between the concentration of dyestuff in the food consumed and the amount of benzidine excreted. Mice biotransformed considerably more dye to benzidine than did rats.

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

国际癌症研究机构(IARC)致癌物 - 1类：国际癌症研究机构将化学品分类为已知的人类致癌物。

IARC Carcinogen - Class 1: International Agency for Research on Cancer classifies chemicals as established human carcinogens.

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

毒理性

• 毒性数据

LCLo（大鼠）= 180,000 毫克/立方米/小时

LCLo (rat) = 180,000 mg/m3/1h

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)

吸收、分配和排泄

在小规模生产直接黑38的单位的18名工人的尿样中，通过高压液相色谱法检测苯肼和单、二乙酰苯肼的存在。所有尿样中都发现了乙酰化代谢物，除两例外，所有尿样中都发现了苯肼。两名工人的尿液中苯肼及其代谢物的含量非常高。这项研究突显了在尚未对基于苯肼的染料制造进行监管的发展中国家此类单位中患膀胱癌的潜在风险。

Urine samples of 18 workers in a small scale unit manufacturing Direct Black 38 were /determined/ by high-pressure liquid chromatography for the presence of benzidine and mono and diacetyl benzidine. Acetylated metabolites were found in all the urine samples, and benzidine was found in all except two. Two workers excreted very high levels of benzidine and its metabolites in their urine. This study highlights the potential risk of bladder cancer in such units of developing countries where manufacture of benzidine based dyes is yet to be regulated.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

对两种偶氮染料的皮肤吸收时间过程在大鼠和家兔中进行了研究。使用了以联苯胺为基的染料CI直接黑38和一种相关的染料CI直接黑19，后者含有对苯二胺结构而不是联苯胺。在左侧背脊处剃毛的无特定病原体雄性新西兰白兔和无特定病原体雄性Fischer 344大鼠上，将放射性标记的染料涂抹在一个2厘米乘2厘米的区域内。... CI直接黑38处理的大鼠体内的放射性物质在尿液和粪便中只有极少量的出现。在144小时内，尿液中放射性物质的累积排泄量为皮肤总剂量的0.05%，粪便中为0.16%。CI直接黑38处理的兔在144小时内的放射性物质累积排泄量更高：尿液中为皮肤总剂量的3.12%，粪便中为5.12%。在144小时时，两种物种的CI直接黑38处理动物体内的放射性物质排泄量仍在增加。...尽管皮肤渗透性和微生物群落的差异可能部分负责，但在实验条件下，CI直接黑38在兔皮上的稳定性低于CI直接黑19。

The time course of dermal absorption of two azo dyes was investigated in rats and rabbits. A benzidine derived dye, CI Direct Black 38 and a related dye CI Direct Black 19 which contained a p-phenylenediamine moiety instead of benzidine, were employed. Specific pathogen free male New Zealand white rabbits and male Fischer 344 rats were shaved on the left dorsum and radiolabeled dye was applied to a 2 centimeter by 2 centimeter area. ... Radioactivity from CI Direct Black 38 treated rats appeared in urine and feces in negligible quantities. Cumulative excretion of radioactivity at 144 hours was 0.05% of the total dermal dose in the urine and 0.16% in the feces. Cumulative excretion of radioactivity from CI Direct Black 38 dosed rabbits was higher at 144 hours: 3.12% of total dermal dose in urine and 5.12 in feces. At 144 hours excretion of radioactivity from CI Direct Black 38 dosed animals of both species was still increasing. ... CI Direct Black 38 is less stable on rabbit skin under experimental conditions than CI Direct Black 19, although differences in skin permeability and microflora may be partially responsible

来源:Hazardous Substances Data Bank (HSDB)