对壬基酚 | 104-40-5

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 对壬基酚
• 中文别名: 对壬基苯酚；4-壬基苯酚；4-正壬基酚；4-正壬氧基苯酚
• 英文名称: 4-Nonylphenol
• 英文别名: p-n-nonylphenol；4-n-nonylphenol；p-nonylphenol
• CAS: 104-40-5
• 化学式: C₁₅H₂₄O
• mdl: MFCD00002396
• 分子量: 220.355
• InChiKey: IGFHQQFPSIBGKE-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44°C
• 沸点：
  293-297 °C
• 密度：
  0.937 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  25°C 时微溶 (0.020 g/L)。
• 介电常数：
  5.2000000000000002
• LogP：
  5.76
• 物理描述：
  Pale yellow viscous liquid; [HSDB] White crystalline solid; [MSDSonline]
• 颜色/状态：
  Viscous, yellow liquid
• 蒸汽压力：
  0.109 Pa at 25 °C /8.18X10-4 mm Hg/
• 亨利常数：
  Henry's Law constant = 3.40X10-5 atm-cu m/mol at 25 °C (est)
• 分解：
  When heated to decomposition it emits acrid smoke and irritating vapors.
• 折光率：
  Index of refraction: 1.513 at 20 °C
• 碰撞截面：
  161.07 Ų [M-H]-
• 保留指数：
  1871.8 ;1876.7 ;1883.4 ;1889 ;1877
• 稳定性/保质期：
  避免与氧化物接触。它具有腐蚀性和刺激性，可能会引起烧伤。在使用时，请穿戴防护服装。

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

烷基酚是一类弱雌激素性的环境污染物，已被证明会干扰野生动物的内分泌功能。本研究调查了生物转化、组织分布和消除对生物活性的影响，研究对象是单次静脉给药后的小型虹鳟鱼，给药物质为[(3)H]4-壬基酚。通过取样燃烧和液闪计数法（LSC）测定了在给药后1、2、4、24、48、72和144小时取样的组织中的[(3)H]4-壬基酚残留物的分布和消除情况。给药144小时后，虹鳟鱼体内总3H标记残留物浓度依次为：胆汁 >> 粪便 >> 肝脏 > 幽门盲囊 > 肾脏 > 大脑、鳃、性腺、心脏、血浆、骨骼肌和皮肤。组织和血浆中[(3)H]残留物的耗竭动力学呈双相性，肌肉和肝脏的β相半衰期延长至99小时。对胆汁、肝脏、幽门盲囊和粪便样本中的代谢物进行放射性高效液相色谱（Radio-HPLC）分析，显示出相似的代谢物轮廓，与肌肉中仅发现母化合物形成对比。胆汁中的主要代谢物是4-壬基酚的葡萄糖苷酸结合物。其他代谢物包括环或侧链羟基化的4-壬基酚的葡萄糖苷酸结合物。肝脏中含有低水平的（1.7%）共价结合残留物。使用隔离的虹鳟鱼肝细胞进行的代谢研究产生了类似的代谢物范围，以及羟基化4-壬基酚的硫酸盐结合物。尽管代谢和排泄迅速，但肌肉中仍留有大量的母化合物，这将对于维持4-壬基酚残留物及相关生物活性产生影响。

Alkylphenols are weak estrogenic environmental contaminants and have been implicated in the disruption of endocrine function in wildlife. The influence of biotransformation, tissue distribution, and elimination on biological activity was investigated in juvenile rainbow trout following a single iv dose of [(3)H]4-nonylphenol. Distribution and elimination of [(3)H]4-nonylphenol residues in tissues sampled 1, 2, 4, 24, 48, 72, and 144 hr after dosing was determined by sample combustion and liquid scintillation counting (LSC). Total 3H-labeled residue concentrations in trout 144 hr after dosing were in order: bile >> feces >> liver > pyloric caeca > kidney > brain, gill, gonad, heart, plasma, skeletal muscle, and skin. The depletion kinetics of [(3)H]residues from tissues and plasma was biphasic with prolonged beta-phase half-lives in muscle and liver of 99 hr. Radio-HPLC analysis of metabolites in bile, liver, pyloric caeca, and feces samples demonstrated similar profiles and contrasted with muscle where only parent compound was found. The predominant metabolite in bile was a glucuronide conjugate of 4-nonylphenol. Other metabolites included glucuronide conjugates of ring or side chain hydroxylated 4-nonylphenol. Liver contained a low level (1.7%) of covalently bound residues. Metabolism studies using isolated trout hepatocytes produced a similar range of metabolites and a sulfate conjugate of hydroxylated 4-nonylphenol. Despite rapid metabolism and excretion, a substantial depot of parent compound remained in muscle which will have implications for the maintenance of 4-nonylphenol residues and associated biological activity.

来源:Hazardous Substances Data Bank (HSDB)

代谢

4-壬基酚（4-NP）是一种众所周知的有毒环境污染物。本研究的主要目标是识别4-NP的活性代谢物。在将4-NP与含有NADPH和GSH的人肝脏微粒体一起孵化后，通过使用质量缺陷过滤方法的超高效液相色谱/四极飞行时间质谱（UPLC/Q-TOF MS）检测到了6种GSH结合物以及19种氧化代谢物。为了结构鉴定，化学合成了几种真实的关键代谢物标准品。发现三种GSH结合物来自醌甲烷中间体，另外三种来自邻苯醌中间体。醌甲烷与GSH的结合产生了通过1,6加成定向的苄基GSH结合物，而邻苯醌中间体的反应提供了芳香定向的GSH结合物。4-NP转化为醌甲烷和邻羟基醌需要细胞色素P450，特别是CYPs1A2、2C19、2D6、2E1和3A4，而邻苯醌的氧化成相应的苯醌显然与微粒体酶无关。来自4-NP的邻苯醌异构化为相应的羟基醌甲烷，前者占后者的比例大约为20:1。对醌甲烷和苯醌代谢物的发现加剧了对4-NP暴露对人体健康影响的担忧。

4-Nonylphenol (4-NP) is a well-known toxic environmental contaminant. The major objective of the present study was to identify reactive metabolites of 4-NP. Following incubations of 4-NP with NADPH- and GSH-supplemented human liver microsomes, 6 GSH conjugates, along with 19 oxidized metabolites, were detected by UPLC/Q-TOF mass spectrometry utilizing the mass defect filter method. Several authentic key metabolite standards were chemically synthesized for structural identification. Three GSH conjugates were found to derive from quinone methide intermediates, and the other three resulted from ortho-benzoquinone intermediates. Conjugation of the quinone methides with GSH produced benzylic-orientated GSH conjugates by 1,6-addition, while the reaction of the ortho-benzoquinone intermediates offered aromatic-orientated GSH conjugates. The conversion of 4-NP to the quinone methides and ortho-hydroquinones required cytochromes P450, specifically CYPs1A2, 2C19, 2D6, 2E1, and 3A4, while the oxidation of ortho-benzohydroquinones to the corresponding benzoquinones was apparently independent of microsomal enzymes. The ortho-benzoquinone derived from 4-NP was isomerized to the corresponding hydroxyquinone methide, and the former dominated the latter at a rate of approximately 20:1. The findings of the quinone methide and benzoquinone metabolites intensified the concern on the impact of 4-NP exposure on human health.

来源:Hazardous Substances Data Bank (HSDB)

代谢

4-壬基苯酚已知的人类代谢物包括(4-壬基苯基)硫酸氢盐。

4-nonylphenol has known human metabolites that include (4-Nonylphenyl) hydrogen sulfate.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

识别与用途：4-壬基酚（4-NP）是一种淡黄色的粘稠液体。它通常与混合金属稳定剂一起用作塑料生产过程中的热稳定共稳定剂。它还用作生产酚醛树脂的起始材料。人体研究：4-NP是一种普遍存在的环境毒素，在常规家用物品的制造和/或污水处理过程中形成副产品。由于4-NP具有疏水性，它可以轻易在生物体中积累，包括人类，在其中表现出广泛的毒性效应。4-NP似乎通过促进或延长胃肠道中炎症的负面进展，增加了发展炎症性肠病的风险。通过饮食长期暴露于4-NP可能导致肠粘膜局部损伤，对肠道稳态和功能产生潜在的负面影响。暴露于4-NP可能有助于增加自身免疫敏感性或加剧现有的自身免疫状况，通过影响细胞因子的正常表达。动物研究：壬基酚在外部对兔眼进行测试时引起了严重损伤。在小鼠中，4-NP在体内干扰了脂肪生成和脂生成途径的关键调节因子。围产期暴露于4-NP增加了后代体重、脂肪质量以及血清总胆固醇和葡萄糖水平。4-NP可能会增加肥胖症的发病率，并可作为肥胖和肥胖相关疾病的潜在化学应激源。在围产期暴露于4-NP的大鼠中，F1代雄性和雌性后代的脂肪生成受到 影响，这种影响可以通过母系传给F2代。使用酿酒酵母的D7株对4-NP的遗传毒性进行了评估。结果显示，4-NP在50 mg/L的浓度下对S. cerevisiae细胞产生了显著的细胞毒性效应，以及在最低测试浓度（12和25 mg/L）下产生了致突变效应。生态毒性研究：基于体外和体内动物研究，4-NP被认为是一种内分泌干扰化学物质（EDC）。例如，暴露于4-NP的贻贝体内积累4-NP，同时17-β-雌二醇和睾酮水平总体下降。在鲽鱼（Solea solea）中，测试动物在暴露于环境相关浓度（10^(-6) M）的4-NP后，血浆卵黄蛋白原水平和雌激素受体β（ERβ）mRNA表达均增加。在斑马鱼中，4-NP能够干扰胚胎发育期间的中轴索形态发生、肌肉功能和神经内分泌系统。血浆性类固醇水平分析显示，暴露于4-NP的虹鳟鱼幼雄性和雌性血浆中17β-雌二醇和睾酮水平显著增加。此外，观察到血浆皮质醇水平显著增加。另一方面，4-NP在处理7天和14天后降低了血浆三碘甲状腺原氨酸和甲状腺素。在持续喂食4-NP，浓度范围为0.05至0.4 g/kg的家蚕幼虫中，性腺发育受到抑制，成熟度在雄性和雌性蛹中均降低，而性比不受4-NP暴露的影响。

IDENTIFICATION AND USE: 4-Nonylphenol (4-NP) is a pale yellow viscous liquid. It is routinely used as a co-stabilizer with mixed-metal stabilizers for heat stabilization during plastic production. It is also used as starting material for the production of phenolic resins. HUMAN STUDIES: 4-NP is a ubiquitous environmental toxin that is formed as a byproduct in the manufacturing and/or sewage treatment of regular household items. Due to its hydrophobic nature, 4-NP can easily accumulate in living organisms, including humans, where it displays a wide range of toxic effects. 4-NP appears to increases the risk of developing inflammatory bowel disease by promoting or prolonging adverse progression of inflammation in the gastrointestinal tract. Prolonged exposure to 4-NP through the diet may lead to local damage at the level of intestinal mucosa, with potentially negative consequences for intestinal homeostasis and functionality. Exposure to 4-NP may contribute to autoimmune susceptibility and/or exacerbate existing autoimmune conditions by affecting normal expression of cytokines. ANIMAL STUDIES: Nonylphenol produced severe injury when tested externally on the eyes of rabbits. In mice 4-NP perturbed key regulators of adipogenesis and lipogenic pathway in vivo. Perinatal exposure to 4-NP increased body weight, fat mass, and serum total cholesterol and glucose levels in offspring. 4-NP may be expected to increase the incidence of obesity and can act as a potential chemical stressor for obesity and obesity-related disorders. In rats perinatal exposure to 4-NP affects the adipogenesis in both male and female F1 offspring, and this effect can be progressed to the F2 offspring through the maternal line. The genotoxicity of 4-NP was evaluated by using the D7 strain of Saccharomyces cerevisiae. The results showed that 4-NP induced significant cytotoxic effect on S. cerevisiae cells at 50 mg/L, as well as mutagenic effects at the lowest tested concentrations (12 and 25 mg/L). ECOTOXICITY STUDIES: On the basis of in vitro and in vivo animal studies 4-NP is considered an endocrine disrupting chemical (EDC). For example, build-up of 4-NP in exposed mussels and an overall decrease of 17-beta-estradiol and testosterone levels were demonstrated. In sole (Solea solea) both plasma vitellogenin level and estrogen receptor beta (ERbeta) mRNA expression were increased in tested animals following a short exposure to environmental relevant concentrations (10(-6) M) of 4-NP. In zebrafish, 4-NP is able to disrupt the notochord morphogenesis, muscle function and the neuroendocrine system during embryonic development. The analysis of plasma sex steroid levels revealed a significant increase in 17beta-estradiol and testosterone in plasma of 4-NP exposed juvenile males and females of rainbow trout, respectively. Furthermore, a significant increase was observed in plasma cortisol levels. On the other hand, 4-NP decreased both plasma triiodothyronine and thyroxine after 7 and 14 days of treatment. In Bombyx mori larvae constantly fed 4-NP at concentrations ranging from 0.05 to 0.4 g/kg gonad development was retarded and maturity was decreased in both male and female pupae, while the sex ratio was unaffected by 4-NP exposure.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 副作用

生殖毒素 - 对生殖系统有毒的化学物质，包括对后代缺陷和男性或女性生殖功能的损害。生殖毒性包括发育效应。参见生殖毒性风险评估指南。 皮肤毒素 - 皮肤烧伤。 中毒性肺炎 - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. Dermatotoxin - Skin burns. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

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

毒理性

• 相互作用

溶血磷脂酸（LPA）通过G蛋白偶联的跨膜LPA受体（LPA1至LPA6）信号传递，介导了多种细胞功能，包括细胞增殖、迁移、形态发生和分化。最近，我们证明了雌激素通过不同的方式诱导LPA受体，调节大鼠肝上皮细胞WB-F344的细胞运动活性。在当前研究中，为了评估内分泌干扰物（EDs）是否通过LPA信号参与细胞功能，我们在用双酚A（BPA）和4-壬基酚（4-NP）处理的WB-F344细胞中测量了细胞运动活性和LPA受体表达。使用定量实时RT-PCR分析，BPA处理细胞的Lpar1表达升高，而Lpar3表达降低。相比之下，4-NP增加了Lpar3的表达，但Lpar1和Lpar2没有增加。使用细胞培养插入物进行细胞运动实验，BPA处理细胞的运动活性显著低于未处理细胞。相反，4-NP显著增强了细胞运动活性。BPA和4-NP对细胞运动的影响被Lpar1或Lpar3的敲低所抑制。这些结果表明，BPA和4-NP可能通过在WB-F344细胞中不同地诱导LPA受体来调节细胞运动活性。

Lysophosphatidic acid (LPA) signaling via G protein-coupled transmembrane LPA receptors (LPA1 to LPA6) mediates a variety of cellular functions, including cell proliferation, migration, morphogenesis, and differentiation. Recently, we demonstrated that the different induction of LPA receptors by estrogens regulates cell motile activity of rat liver epithelial WB-F344 cells. In the present study, to assess whether endocrine disruptors (EDs) are involved in cellular functions through LPA signaling, we measured cell motile activity and LPA receptor expressions in WB-F344 cells treated with bisphenol A (BPA) and 4-nonylphenol (4-NP). Using quantitative real time RT-PCR analysis, the Lpar1 expression was elevated in BPA-treated cells, whereas the Lpar3 expression was decreased. In contrast, 4-NP increased the Lpar3 expression, but not the Lpar1 and Lpar2. For cell motility assay with a Cell Culture Insert, cell motile activity of BPA-treated cells was significantly lower than that of untreated cells. In contrast, 4-NP markedly enhanced cell motile activity. The effects of BPA and 4-NP on cell motility were inhibited by the Lpar1 or Lpar3 knockdown. These results suggest that BPA and 4-NP may regulate cell motile activity through the different induction of LPA receptors in WB-F344 cells.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

水系统中的污染物暴露通常涉及复杂的化学混合物。鉴于环境中存在大量化合物，快速识别有害的化学相互作用至关重要。目前的研究利用了一种新型高通量检测原型，通过量化行为随时间的变化来识别影响毒性的化学相互作用。研究了两种化学物质——地亚农（一种杀虫剂）和4-壬基酚（一种洗涤剂代谢物）——对淡水甲壳类动物水蚤（Daphnia pulex）游泳行为的独立和联合影响。通过光学跟踪重复测量90分钟内的累积距离和方向变化。暴露于低浓度的地亚农（0.125-2微摩尔）或4-壬基酚（0.25-4微摩尔）会显著影响游泳行为，并呈现出浓度和时间依赖性。单独暴露于0.5微摩尔4-壬基酚并未显著改变平均累积距离，但确实引起了一个小的、显著的平均角度增加，这是方向变化的衡量指标。当0.5微摩尔4-壬基酚与地亚农（0.125-0.5微摩尔）联合使用时，它增强了地亚农对水蚤游泳行为的不利影响。此外，在地亚农挑战前24小时暴露于处理过的废水排放物的动物中，观察到了对地亚农的敏感性增强。目前的实验表明，暴露于4-壬基酚和复杂化学混合物（例如，处理过的废水）可以增强杀虫剂地亚农的毒性。

Contaminant exposure in aqueous systems typically involves complex chemical mixtures. Given the large number of compounds present in the environment, it is critical to identify hazardous chemical interactions rapidly. The present study utilized a prototype for a novel high-throughput assay to quantify behavioral changes over time to identify chemical interactions that affect toxicity. The independent and combined effects of 2 chemicals, diazinon (an insecticide) and 4-nonylphenol (a detergent metabolite), on the swimming behavior of the freshwater crustacean Daphnia pulex were examined. Cumulative distance and change in direction were measured repeatedly via optical tracking over 90 min. Exposure to low concentrations of diazinon (0.125-2 uM) or 4-nonylphenol (0.25-4 uM) elicited significant concentration- and time-dependent effects on swimming behavior. Exposure to 0.5 uM 4-nonylphenol alone did not significantly alter mean cumulative distance but did elicit a small, significant increase in mean angle, the measure of change in direction. When 0.5 uM 4-nonylphenol was used in combination with diazinon (0.125-0.5 uM), it augmented the adverse impact of diazinon on the swimming behavior of Daphnia. Additionally, enhanced sensitivity to diazinon was observed in animals exposed to treated wastewater effluent for 24 hr prior to a diazinon challenge. The present experiments demonstrate that exposure to 4-nonylphenol and complex chemical mixtures (e.g., treated wastewater) can enhance the toxicity of exposure to the insecticide diazinon.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

4-壬基酚（4-NP）是一种具有雌激素活性的内分泌干扰化学物质，存在于洗涤剂中，并且已知会污染食品和饮用水。目前研究的目的是评估4-NP是否能够穿越人类胎盘，如果可以，到什么程度。从健康足月单胎妊娠中获得的人类胎盘被用于双外植体胎盘灌注模型。在母体灌注液中加入4-NP（30 ng/mL）后，对六个胎盘进行180分钟的灌注。使用安替比林和FITC葡聚糖分别作为阳性和阴性对照来验证电路的完整性。通过高效液相色谱与荧光检测（HPLC-FD）测量4-NP。经过180分钟的灌注后，安替比林和4-NP的转移百分比分别为25.6 +/- 1.4%（平均值 +/- 标准误，n = 6）和22.75 +/- 3.76%，4-NP的转移指数为0.8。我们得出结论，尽管速度较慢，但在环境相关浓度下，完整的4-NP形式可以穿越人类胎盘。

4-nonylphenol (4-NP) is an estrogenic endocrine active chemical that is present in detergents and is known to contaminate food and drinking water. The aim of the present study was to evaluate whether 4-NP crosses the human placenta and if so, to what extent. Human placentae obtained from healthy term singleton pregnancies were utilized in a dual ex-vivo re-circulating model of placental perfusion. Six placentae were perfused for 180 min following addition of 4-NP (30 ng/mL) to the maternal perfusate. Antipyrine and FITC dextran were used as positive and negative controls respectively to validate the integrity of the circuits. 4-NP was measured by High Performance Liquid Chromatography coupled with Fluorescence Detection (HPLC-FD). After 180 min of perfusion the transfer percentages for antipyrine and 4-NP were 25.6 +/- 1.4% (mean +/- s.e.m, n = 6) and 22.75 +/- 3.76% respectively and the transfer index for 4-NP was 0.8. We conclude that the intact form of 4-NP at environmentally relevant concentrations can transfer across the human placenta albeit at a slow rate.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45,S60,S61
• 危险类别码：
  R22,R34,R52/53
• WGK Germany：
  3
• RTECS号：
  SM5650000
• 海关编码：
  2907131000
• 包装等级：
  III
• 危险类别：
  8
• 危险品运输编号：
  UN 3145 8/PG 2
• 储存条件：
  储存于阴凉、通风良好的库房中，远离火源、热源及水源，并确保容器密封。与氧化剂分开存放，切忌混储。配备相应种类和数量的消防器材。储区应备有合适的材料以处理泄漏物。

SDS

Name:	4-Nonylphenol 99% (GC) Mixture of Isomers Material Safety Data Sheet
Synonym:	p-Nonylphenol
CAS:	104-40-5

Section 1 - Chemical Product MSDS Name:4-Nonylphenol 99% (GC) Mixture of Isomers Material Safety Data Sheet
Synonym:p-Nonylphenol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
104-40-5	4-Nonylphenol	99	203-199-4

Hazard Symbols: XI
Risk Phrases: 43 53

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
May cause sensitization by skin contact. May cause long-term adverse effects in the aquatic environment.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
Ingestion:
May cause digestive tract disturbances. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water fog, dry chemical, carbon dioxide or alcohol type foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 104-40-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear pale yellow
Odor: phenol-like
pH: Not available.
Vapor Pressure: 0.109 Pa @ 25C
Viscosity: Not available.
Boiling Point: 293 - 297 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 141 deg C ( 285.80 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: Slightly soluble.
Specific Gravity/Density: .9450g/cm3
Molecular Formula: C15H24O
Molecular Weight: 220.35

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 104-40-5: SM5630000 LD50/LC50:
CAS# 104-40-5: Oral, rat: LD50 = 1620 mg/kg.
Carcinogenicity:
4-Nonylphenol - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S
.*
Hazard Class: 9
UN Number: 3082
Packing Group: III
IMO
Shipping Name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S
.
Hazard Class: 9
UN Number: 3082
Packing Group: III
RID/ADR
Shipping Name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S
.
Hazard Class: 9
UN Number: 3082
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 43 May cause sensitization by skin contact.
R 53 May cause long-term adverse effects in the
aquatic environment.
Safety Phrases:
S 24 Avoid contact with skin.
S 37 Wear suitable gloves.
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 104-40-5: 3
Canada
CAS# 104-40-5 is listed on Canada's DSL List.
CAS# 104-40-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 104-40-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

该物质主要是一部分阴离子表面活性剂和绝大部分的非离子表面活性剂（如壬基酚聚氧乙烯醚）。它具有良好的耐酸碱性、抗氧化性和润湿、乳化、清洗等性能，应用范围广泛。

反应信息

• 作为反应物：
  描述：

  对壬基酚 在 溴 作用下， 生成 2,6-二溴-4-壬基苯酚
  参考文献：
  名称：

  Brominated materials

  摘要：

  描述了由（烷基，溴基）苯氧基烷基（甲基）丙烯酸酯单体制备的聚合物。

  公开号：

  US06359170B1
• 作为产物：
  描述：

  4-壬基苯基乙酸酯 在 aluminum (III) chloride 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 反应 11.0h， 生成 对壬基酚
  参考文献：
  名称：

  [EN] PROCESS FOR THE PURIFICATION OF HYDROXYARYL-ALDHYDES AND KETONES AND THEIR USE IN THE PRODUCTION OF HYDROXYARYL OXIME DERIVATIVES
  [FR] PROCESSUS DE PURIFICATION D'HYDROXYARYL ALDEHYDES ET CETONES ET LEUR UTILISATION DANS LA PRODUCTION DE DERIVES D'HYDROXYARYL OXIME

  摘要：

  一种用于纯化羟基芳基醛和酮的过程，包括以下步骤：1）向包含羟基芳基醛或羟基芳基酮的第一组分中加入矿酸；2）用水洗涤步骤1中得到的混合物；3）从步骤2中分离出包含羟基芳基醛或羟基芳基酮的第二个组分。

  公开号：

  WO2004054954A1
• 作为试剂：
  描述：

  异胡薄荷醇 在 三(乙酰丙酮酸)钌(III) 、 对壬基酚 作用下， 180.0 ℃ 、107.0 kPa 条件下， 反应 4.0h， 生成 (-)-薄荷酮 、 (+)-异薄荷酮
  参考文献：
  名称：

  Ruthenium-phenol catalysts and method of preparing menthone from isopulegol

  摘要：

  本发明涉及一种催化剂，其可通过在原位接触钌前体和酚衍生物而获得。此外，本发明涉及将所述催化剂用于转移氢化反应。具体地，本发明涉及一种从异薄荷醇制备薄荷酮的方法。

  公开号：

  US09790157B2

文献信息

• [EN] NOVEL ANTIVIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIVIRAUX
  申请人：UNIV LEUVEN KATH

  公开号：WO2014170368A1

  公开（公告）日：2014-10-23

  The present invention relates to a series of novel compounds and derivatives thereof, methods to prevent or treat viral infections by using the novel compounds, processes for their preparation, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, preferably infections with viruses belonging to the family of the Togaviridae and more preferably infections with chikungunya virus (CHIKV).

  本发明涉及一系列新化合物及其衍生物，利用这些新化合物预防或治疗病毒感染的方法，以及它们的制备过程，用于治疗或预防病毒感染以及用于制造治疗或预防病毒感染的药物，最好是用于治疗属于Togaviridae家族的病毒，更好地是用于治疗寨卡病毒感染。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [EN] QUINOLINE AND QUINAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS QUINOLÉINE ET QUINAZOLINE
  申请人：ACERTA PHARMA BV

  公开号：WO2016055982A1

  公开（公告）日：2016-04-14

  In some embodiments, the invention relates to quinazoline and quinoline compounds of Formula I: (I) or a pharmaceutically acceptable salt thereof, or to pharmaceutical compositions comprising these compounds and to their use in therapy. In particular, in some embodiments, the present invention relates to quinazoline and quinoline compounds, pharmaceutical compositions thereof, and the use of the compounds and pharmaceutical compositions in the treatment of Bruton's tyrosine kinase (BTK) mediated disorders.

  在某些实施例中，该发明涉及式I的喹唑啉和喹啉化合物：(I)或其药用可接受盐，或者涉及包含这些化合物的药物组合物以及它们在治疗中的应用。具体而言，在某些实施例中，本发明涉及喹唑啉和喹啉化合物、其药物组合物以及这些化合物和药物组合物在治疗布鲁顿氨基酸激酶（BTK）介导的疾病中的应用。
• Immunosuppressive effects of pteridine derivatives
  申请人：——

  公开号：US20030236255A1

  公开（公告）日：2003-12-25

  Novel poly-substituted pteridinediones (lumazines), and mono- or polysubstituted 2-thiolumazines, 4-thiolumazines or 2,4-dithiolumazines, having disclosed substituents in positions 1, 3, 6 and 7 of the pteridine ring, and pharmaceutically acceptable salts thereof, are useful as biologically active ingredients in preparing pharmaceutical compositions especially for the treatment or prevention of a CNS disorder, a cell proliferative disorder, a viral infection, an immune or auto-immune disorder or a transplant rejection. Combinations of the pteridine derivatives of the invention with an immunosuppressant or immunomodulator drug, an antineoplastic drug or an antiviral agent, providing potential synergistic effects, are also disclosed.

  新型多取代的喹啉二酮（卢马嗪），以及单取代或多取代的2-硫代卢马嗪，4-硫代卢马嗪或2,4-二硫代卢马嗪，在喹啉环的1、3、6和7位上具有已披露的取代基，并且其药学上可接受的盐，在制备药物组合物中作为生物活性成分特别用于治疗或预防中枢神经系统疾病、细胞增殖障碍、病毒感染、免疫或自身免疫障碍或移植排斥。本发明的喹啉衍生物与免疫抑制剂或免疫调节剂药物、抗肿瘤药物或抗病毒药物的组合，提供潜在的协同效应。
• [EN] HETEROAROMATIC AND HETEROBICYCLIC AROMATIC DERIVATIVES FOR THE TREATMENT OF FERROPTOSIS-RELATED DISORDERS<br/>[FR] DÉRIVÉS AROMATIQUES HÉTÉROBICYCLIQUES ET HÉTÉROAROMATIQUES POUR LE TRAITEMENT DE TROUBLES LIÉS À LA FERROPTOSE
  申请人：COLLABORATIVE MEDICINAL DEV LLC

  公开号：WO2020185738A1

  公开（公告）日：2020-09-17

  The present application discloses heteroaromatic and heterobicyclic aromatic derivative compounds and compositions, and methods for treating ferroptosis-related disorders and diseases in patients using the compounds and compositions as disclosed herein.

  本申请公开了杂芳和杂双环芳香衍生物化合物和组合物，以及利用所公开的化合物和组合物治疗患者的铁死亡相关疾病和疾病的方法。

表征谱图