trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4H-pyrazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4H-pyrazole-3-carboxylate
• 化学式: C16H9N4Na3O9S2
• 分子量: 534.4
• InChiKey: UJMBCXLDXJUMFB-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  -9.89
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  229
• 氢给体数：
  0
• 氢受体数：
  12

ADMET

代谢

口服给药后，酒石黄在胃肠道微生物的作用下被广泛代谢为磺胺酸和对氨基吡唑啉酮（后者随后可能进一步裂解为磺胺酸和α-氨基-β-酮丁酸片段，后者通过中间代谢进一步分解，释放二氧化碳）。

After oral administration there is extensive metabolism of Tartrazine by the gastrointestinal microflora to sulphanilic acid and aminopyrazalone (which may then be subsequently cleaved to sulphanilic acid and alpha-amino-beta-ketobutyric acid fragments with the latter breaking down further via intermediary metabolism with release of carbon dioxide).

来源:Hazardous Substances Data Bank (HSDB)

代谢

吸收和代谢放射性碳标记的酒石黄（FD & C 黄色 No. 5）和高分子量聚合物衍生物在大鼠中的比较。在第一次24小时内，尿液和胆汁中排泄出0.1%至1.5%的未改变的单体染料。在给予聚合物衍生物后，没有未改变的染料被吸收。...在用酒石黄及其聚合物衍生物给药的动物中，裂解产物氨基吡唑啉酮及其代谢物的吸收率分别为4.0%和4.6%。偶氮键的裂解在聚合物衍生物中似乎并没有减少。然而，两种染料的磺胺酸部分仍然附着在聚合物的主链上，导致聚合物酒石黄中磺胺酸吸收量减少了95%。

Absorption and metabolism of (14)C-labelled tartrazine (FD & C Yellow No. 5) and high molecular weight polymeric derivatives were compared in rats. A trace to 1.5% of unchanged monomeric dyes was excreted in urine and bile during the first 24 hr after dosing. No unchanged dye was absorbed after administration of the polymeric derivatives. ...In animals dosed with tartrazine and its polymer derivative, absorption of the cleavage product aminopyrazolone and its metabolites was 4.0 and 4.6%, respectively. Azo bond cleavage did not appear to be decreased in the polymer derivatives. However, the sulphanilic acid moiety of both dyes remained attached to the polymer backbone, resulting in a 95% decrease in sulphanilic acid absorption with polymeric tartrazine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

4-硫酸苯肼代谢物也用硫-35标记，并通过口服和腹腔注射给药。这种代谢物的排泄途径与给药途径有关（口服后48小时内尿液中为35%，粪便中为49%；腹腔注射后48小时内尿液中为90%，粪便中为5%）。口服给药后，48小时内尿液排泄的放射性中有69%是磺基苯甲酸，21%是4-硫酸苯肼；而腹腔注射给药后，48小时内尿液排泄的放射性中有9%是磺基苯甲酸，73%是4-硫酸苯肼。这些数据表明，4-硫酸苯肼在大肠腔内显著转化为磺基苯甲酸。/4-硫酸苯肼/

The 4-sulphophenylhydrazine metabolite was also labeled with sulphur-35 and administered orally and intraperitoneally. Excretion of this metabolite differed with the route of administration (35 and 49 % in urine and feces, respectively, 48 hours following oral, and 90 and 5 % in urine and feces, respectively, 48 hours following intraperitoneal administration). Following oral administration, 69 % of urinary radioactivity excreted in 48 hours was sulphanilic acid and 21 % was 4-sulphophenylhydrazine, whereas following intraperitoneal administration, 9 % of urinary radioactivity excreted in 48 hours was sulphanilic acid and 73% was 4-sulphophenylhydrazine. These data suggest there is a marked conversion of 4- sulphophenylhydrazine to sulphanilic acid presumably in the gut lumen. /4-sulphophenylhydrazine/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

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

毒理性

• 相互作用

在2006年，韩国食品和药品管理局报告称，在食品制造中广泛使用了诸如所有ura红AC（R40）、酒石黄（Y4）、日落黄FCF（Y5）、苋菜红（R2）和亮蓝FCF（B1）等食用色素组合。尽管基于可接受日摄入量（ADI）对单个食用色素进行了控制，但目前尚无明确信息说明这些添加剂组合如何影响食品安全。在当前研究中，检测了单一使用和组合使用/allura红AC、酒石黄、日落黄FCF、苋菜红和亮蓝FCF/对神经祖细胞（NPC）毒性的效力，NPC是发育阶段的生物标志物，以及对神经发生的影响，这是成人中枢神经系统（CNS）功能的指标。/allura红AC/和/苋菜红/在发育中的CNS模型中减少了小鼠多能NPC的增殖和存活率。在经过测试的几种小鼠模型组合中，/酒石黄/和/亮蓝FCF/的组合，其剂量是韩国平均日摄入量的1000倍，显著减少了成年小鼠海马区新生细胞数量，表明对海马神经发生有强烈的负面影响。然而，包括/allura红AC/和/苋菜红/在内的其他组合并没有影响齿状回的成年海马神经发生。证据表明，大多数食用色素的单一使用和组合使用在发育NPC和成年海马神经发生方面可能是安全的。然而，对过高的剂量组合/tartrazine/和/brilliant blue FCF/的反应表明，可能有协同效应来抑制成人海马NPC的增殖。数据表明，食用色素的组合可能对发育中的和成年的海马神经发生产生不利影响...

In 2006, the Korea Food and Drug Administration reported that combinations of dietary colors such as allura red AC (R40), tartrazine (Y4), sunset yellow FCF (Y5), amaranth (R2), and brilliant blue FCF (B1) are widely used in food manufacturing. Although individual tar food colors are controlled based on acceptable daily intake (ADI), there is no apparent information available for how combinations of these additives affect food safety. In the current study, the potencies of single and combination use of / allura red AC, tartrazine, sunset yellow FCF, amaranth, and brilliant blue FCF / were examined on neural progenitor cell (NPC) toxicity, a biomarker for developmental stage, and neurogenesis, indicative of adult central nervous system (CNS) functions. /allura red AC/and /amaranth/ reduced NPC proliferation and viability in mouse multipotent NPC, in the developing CNS model. Among several combinations tested in mouse model, combination of /tartrazine/ and /brilliant blue FCF/ at 1000-fold higher than average daily intake in Korea significantly decreased numbers of newly generated cells in adult mouse hippocampus, indicating potent adverse actions on hippocampal neurogenesis. However, other combinations including /allura red AC/ and /amaranth/ did not affect adult hippocampal neurogenesis in the dentate gyrus. Evidence indicates that single and combination use of most tar food colors may be safe with respect to risk using developmental NPC and adult hippocampal neurogenesis. However, the response to excessively high dose combination of /tartrazine/and /brilliant blue FCF/ is suggestive of synergistic effects to suppress proliferation of NPC in adult hippocampus. Data indicated that combinations of tar colors may adversely affect both developmental and adult hippocampal neurogenesis...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

从纯化的大鼠腹膜肥大细胞释放组胺的过程，可以通过特异性抗原（卵白蛋白）、复合物48/80和钙离子载体A23187来诱导，这一过程会受到塔塔兹的修饰。由48/80和抗原诱导的组胺释放可以通过存在1x10-5至1x10-2 M浓度的塔塔兹来抑制。当塔塔兹与卵白蛋白同时添加时，对卵白蛋白诱导的组胺释放的抑制效果最大，并且随着细胞与塔塔兹预孵育时间的增加而减弱。在高浓度下，塔塔兹对离子载体诱导的释放有轻微的抑制作用，但在1x10-3和1x10-4 M的塔塔兹浓度下，会增强组胺的释放。在细胞与塔塔兹预孵育0-5分钟时，对离子载体诱导释放的增强效果最大。

The release of histamine from purified rat peritoneal mast cells induced by specific antigen (egg albumin), compound 48/80 and calcium ionophore A23187 was modified by tartrazine. Histamine release induced by 48/80 and antigen was inhibited by the presence of 1x10-5 to 1x10-2 M tartrazine. The inhibitory effect on egg albumin induced histamine release was maximal when the tartrazine was added simultaneously with egg albumin, and was reduced by increased preincubation of the cells with tartrazine. Tartrazine had a small inhibitory effect on ionophore induced release at high concentrations, but augmented histamine release at tartrazine concentrations of 1x10-3 and 1x10-4 M. Augmentation of ionophore induced release was maximal at between 0-5 min preincubation of the cells with tartrazine.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽，有强烈的干呕反射，并且不流口水，则冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒物A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 对日落黄中的吡唑片段的命运进行了研究，使用了带有硫-35标记的日落黄和1-(4-磺苯基)-3-甲基-4-(4-磺苯基偶氮)-5-吡唑啉酮（SPMP，日落黄的类似物）以及碳-14标记的SPMP。口服给药后，带有硫-35标记的日落黄和SPMP主要随粪便排出（72小时后分别为剂量的90%和89%），少量随尿液排出（72小时后分别为剂量的8%和7.2%）。在48小时内，使用磺胺酸和4-磺苯基肼排出的尿液中放射性活性分别为23%和23%（日落黄给药后），以及54%和22%（SPMP给药后）；其余的放射性活性未被鉴定。

... The fate of the pyrazole fragment of Tartrazine /was examined/ using sulphur-35 labelled Tartrazine and 1-(4-sulphophenyl)-3-methyl-4-(4-sulphophenylazo)-5-pyrazolone (SPMP an analogue of Tartrazine) and carbon-14 labeled SPMP. Following oral administration, both Tartrazine and SPMP labeled with sulphur-35 were predominantly excreted in feces (90 and 89 % of the dose respectively after 72 hours) with small amounts in urine (8 and 7.2 % of the dose, respectively, after 72 hours). The urinary radioactivity excreted in 48 hours with sulphanilic acid and 4-sulphophenylhydrazine was 23 and 23 % after Tartrazine administration, and 54 and 22 % after SPMP administration; the remaining radioactivity was not characterized.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

碳-14标记在偶氮苯基团中的酒石黄的代谢在大鼠、兔和人体中进行了研究。在这两种动物中，酒石黄通过口服和腹腔注射给药，而人类则通过口服酒石黄。在向6只大鼠腹腔注射2.4毫克/千克体重的酒石黄后，24小时内尿液中未改变的部分占剂量的64%至96%；没有报告其他代谢产物。在兔中，以2.4毫克/千克体重的剂量腹腔注射酒石黄，24小时内尿液中回收了94%的未改变剂量，另外1.4%以结合磺胺脒酸的形式回收。然而，在兔中腹腔注射1000毫克剂量后...24小时内尿液中仅回收了57.3%的未改变剂量，另外25.7%和6%分别以游离和结合磺胺脒酸的形式回收。在向3只大鼠口服5毫克/只的剂量后...没有测量到游离酒石黄，但分别以游离和结合磺胺脒酸的形式在尿液中回收了平均28%和34.6%。在兔中给药1000毫克...24小时内尿液中未改变的部分回收了8.2%，在72小时内进一步以游离和结合磺胺脒酸的形式分别回收了27%和26.8%。在4名服用含89-100毫克酒石黄的单个胶囊的人类中...任何受试者的尿液中都没有测量到游离酒石黄；在一项受试者中，106%以游离磺胺脒酸的形式回收，而对于其他3名受试者，游离和结合磺胺脒酸的平均回收率分别为40.6%和49.7%。

... The metabolism of carbon-14 Tartrazine randomly labeled in the phenyl azo group /was studied/ in rat, rabbit and human. In both animal species Tartrazine was administered orally and intraperitoneally whilst humans received oral Tartrazine. ... After intraperitoneal administration to 6 rats of 2.4 mg/kg bw of Tartrazine, between 64 and 96 % of the dose was recovered unchanged in urine within 24 hours; no other products were reported. In rabbit, at a dose of 2.4 mg/kg bw of Tartrazine administered intraperitoneally, 94 % of the dose was recovered unchanged in urine within 24 hours, with a further 1.4 % recovered as conjugated sulphanilic acid. However, after an intraperitoneal dose of 1000 mg in the rabbit ... only 57.3% was recovered unchanged in urine within 24 hours, with a further 25.7 and 6 % recovered as free and conjugated sulphanilic acid, respectively. After oral administration to 3 rats at 5 mg/rat ..., no free Tartrazine was measured but means of 28 and 34.6 % were recovered in urine as free and conjugated sulphanilic acid, respectively. In the rabbit dosed 1000 mg ... 8.2 % was recovered unchanged in urine within 24 hours with a further 27 and 26.8 % as free and conjugated sulphanilic acid respectively within 72 hours. In 4 humans receiving a single capsule containing 89-100 mg of Tartrazine ..., no free Tartrazine was measured in urine for any subject; in one subject 106 % was recovered as free sulphanilic acid whilst for the other 3 subjects mean recoveries of free and conjugated sulphanilic acid were 40.6 and 49.7 % respectively. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

黄色的排泄量较低（1%）在静脉注射了未指明的剂量后得到证实。...低胆汁排泄是由于羧基团。在2毫克的剂量后...可以在胆汁中检测到未改变的黄色，但没有环分裂产物的证据。在腹膜内注射后，一种未确定和未量化的黄色结合物迅速在胆汁中排出，但再次没有先前报道的还原环分裂产物。

Low biliary excretion of Tartrazine (1 %) /was demonstrated/ following intravenous administration of an unspecified dose. ... low biliary excretion was due to the carboxyl group. After a dose of 2 mg ... unchanged Tartrazine could be detected in bile, but there was no evidence of ring fission products. Following intraperitoneal injection, an unidentified and unquantified Tartrazine conjugate was rapidly excreted in bile, but again none of the previously reported reductive ring fission products.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  8-(5-Nitro-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid 、 trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4H-pyrazole-3-carboxylate 在 钯 水 、 乙醇 、 乙醚 、 trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4H-pyrazole-3-carboxylate 作用下，