6-硝基苯[a]嵌二萘 | 63041-90-7

• 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 - 芘
• 中文名称: 6-硝基苯[a]嵌二萘
• 中文别名: 6-硝基苯并[a]芘；6-硝基苯并(A)芘
• 英文名称: 6-nitrobenzo(a)pyrene
• 英文别名: 6-nitrobenzopyrene；6-Nitrobenzo[a]pyrene
• CAS: 63041-90-7
• 化学式: C₂₀H₁₁NO₂
• 分子量: 297.313
• InChiKey: NMMAFYSZGOFZCM-UHFFFAOYSA-N

物化性质

• 熔点：
  255.5°C
• 沸点：
  438.82°C (rough estimate)
• 密度：
  1.2310 (rough estimate)
• 颜色/状态：
  Orange-yellow needles, recrystallzed from benzene; yellow crystalline solid; orange crystals
• 溶解度：
  Limited solubility in toluene and benzene
• 蒸汽压力：
  1.0X10-10 mm Hg at 25 °C (est)
• 分解：
  When heated to decomposition it emits toxic fumes of NOx.
• 保留指数：
  490.9

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

1-, 3-和6-硝基苯并[a]芘（硝基-BaP）是环境污染物，已被证明是有效的细菌诱变剂。通过将大鼠肠道微生物与每种同分异构体一起培养48小时，研究了这些异构体硝基-BaP的厌氧代谢。在几个时间间隔内取出样品，提取、通过高压液相色谱（HPLC）进行分离，并确定放射性。通过将代谢物的色谱、紫外-可见吸收和质谱性质与真实标准进行比较来识别代谢物。这些同分异构体的硝基还原程度顺序是3-硝基-BaP大于6-硝基-BaP大于1-硝基-BaP。在暴露48小时后，添加的3-硝基-BaP中有84%以3-氨基-BaP形式存在，51%的6-硝基-BaP被代谢为6-氨基-BaP，1-硝基-BaP被还原为1-氨基-BaP（13%）和1-亚硝基-BaP（4%）。这些硝基-BaP同分异构体的微生物硝基还原程度顺序与基于电子和立体阻碍效应的预测不同。这些结果表明，肠道微生物硝基还原酶对硝基-BaP表现出明显的高底物特异性，这影响了硝基还原的程度。

The compounds 1-, 3-, and 6-nitrobenzo[a]pyrene (nitro-BaP) are environmental pollutants and have been shown to be potent bacterial mutagens. The anaerobic metabolism of these isomeric nitro-BaPs was investigated by the incubation of rat intestinal microflora with each isomer for 48 hr. Aliquots were removed at several time intervals, extracted, fractionated by high-pressure liquid chromatography (HPLC), and the radioactivity determined. Metabolites were identified by comparison of their chromatographic, ultraviolet-visible absorption, and mass spectral properties with those of authentic standards. The order of the extent of nitroreduction for these isomers was 3-nitro-BaP greater than 6-nitro-BaP greater than 1-nitro-BaP. After 48 hr of exposure, 84% of the added 3-nitro-BaP was present as 3-amino-BaP, 51% of the 6-nitro-BaP was metabolized to 6-amino-BaP, and 1-nitro-BaP was reduced to 1-amino-BaP (13%) and 1-nitroso-BaP (4%). The order of the extent of microbial nitroreduction for these nitro-BaP isomers is different from the predictions based on electronic and steric hindrance effects. These results suggest that intestinal microflora nitroreductases exhibit a markedly high degree of substrate specificity toward nitro-BaPs that affects the extent of nitroreduction.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：6-硝基苯并(a)芘在实验动物中的致癌性证据有限。没有来自人类研究中关于6-硝基苯并(a)芘致癌性的数据。总体评估：6-硝基苯并(a)芘的致癌性对人类不予分类（第3组）。

Evaluation: There is limited evidence for the carcinogenicity in experimental animals of 6-nitrobenzo(a)pyrene. No data were available from studies in humans on the carcinogenicity of 6-nitrobenzo(a)pyrene. Overall evaluation: 6-Nitrobenzo(a)pyrene is not classifiable as to its carcinogenicity to humans (Group 3).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：6-硝基苯并[a]芘

IARC Carcinogenic Agent:6-Nitrobenzo[a]pyrene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第7卷补充：致癌性的总体评估：更新国际癌症研究机构专著第1至42卷，1987年；440页；ISBN 92-832-1411-0（已绝版）

IARC Monographs:Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

来源:International Agency for Research on Cancer (IARC)

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、袋阀面罩装置或口袋面罩，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。如果发生呕吐，让患者前倾或置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止窒息。保持患者安静，维持正常体温。寻求医疗救助。 /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)

安全信息

• 海关编码：
  2904209090
• 储存条件：
  | 2-8°C |

SDS

反应信息

• 作为反应物：
  描述：

  6-硝基苯[a]嵌二萘 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 6-氨基苯并(a)芘
  参考文献：
  名称：

  Isocyanates of 3,4-Benzpyrene and 10-Methyl-1,2-benzanthracene

  摘要：

  DOI：

  10.1021/ja01847a062
• 作为产物：
  描述：

  6-nitro-7,8,9,10-tetrahydrobenzopyrene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 15.0h， 以85%的产率得到6-硝基苯[a]嵌二萘
  参考文献：
  名称：

  1-，3-和6-硝基苯并[a] py的合成，光谱分析和诱变性。

  摘要：

  合成了诱变性环境污染物1-，3-和6-硝基苯并[a] re。在环境温度下用硝酸钠在三氟乙酸和乙酸酐中硝化7,8,9,10-四氢苯并[a] re，得到1-，3-和6-硝基-7,8,9,10-的混合物四氢苯并[a] py，通过色谱分离。用2，3-二氯-4，5-二氰基-1，6-苯醌对分离的硝基四氢苯并[a] py进行脱氢，可高产率地产生1-，3-和6-硝基苯并[a] py。将这些化合物的光谱数据与直接硝化苯并[a] py的光谱数据进行比较，证实1-和3-硝基苯并[a]]确实是后者反应的次要产物。该证实还证实1-和3-硝基苯并[a] py是在模型大气中形成的次要硝化的苯并[a] py的硝化产物。在鼠微粒体（S9）活化系统存在下，鼠伤寒沙门氏菌测试株TA98和TA100中的1-，3-和6-硝基苯并[a] re具有致突变性。在这些菌株中，1-硝基苯并[3-] py和6-硝基苯并[a] py均不是直接作

  DOI：

  10.1021/jm00375a012

文献信息

• Chemical Oxidation of Nitrated Polycyclic Aromatic Hydrocarbons: Hydroxylation with Superoxide Anion Radical
  作者：Kiyoshi Fukuhara、Naoki Miyata

  DOI：10.1021/tx00043a003

  日期：1995.1

  Nitrated polycyclic aromatic hydrocarbon (nitroPAH) is a potent mutagen which is reductively and/or oxidatively metabolized. Biological oxidation of nitroPAH, such as hydroxylation and epoxidation, is known, but chemical oxidation has been reported in only a few papers. NitroPAH is barely oxidized by various chemical oxidants because of the electron deficient property of the aromatic ring with the nitro

  硝化的多环芳烃（nitroPAH）是一种强力的诱变剂，可以通过还原和/或氧化方式代谢。硝基PAH的生物氧化（例如羟基化和环氧化）是已知的，但是仅在几篇论文中报道了化学氧化。由于具有硝基取代基的芳环的电子不足特性，NitroPAH几乎不会被各种化学氧化剂氧化。超氧阴离子自由基的亲核反应性是已知的，因此本研究中进行了硝基PAH与化学生成的超氧阴离子自由基的氧化。当1-硝基py与KO2 / 18-crown-6在二甲基甲酰胺中反应时，可以制备产率得到5-，6-，8-和9-羟基-1-硝基py和1-羟基py。三个异构体二硝基nitro，3-硝基荧蒽，6-硝基苯并[a] py，和6-硝基铬被氧化为羟基衍生物，其中一些对应于硝基PAH的氧化代谢产物。用三氟过氧乙酸将二硝基吡啶氧化，得到K区氧化产物。
• Synthesis, chemical properties and mutagenicity of 1,6- and 3,6-dinitrobenzo(a)pyrenes.
  作者：Kiyoshi FUKUHARA、Naoki MIYATA、Michiko MATSUI、Keiko MATSUI、Motoi Jr. ISHIDATE、Shozo Kamiya

  DOI：10.1248/cpb.38.3158

  日期：——

  Nitration of benzo[a]pyrene (BaP) with HNO3 (d = 1.38) produced a mixture of dinitroBaPs (1,6- and 3,6-isomers) and mononitroBaPs (1-, 3- and 6-isomers). Pure 1,6-dinitroBaP and 3,6-dinitroBaP were obtained by the reduction of the dinitroBaPs mixture with NaSH to yield the separable products 1-amino-6-nitroBaP and 3-amino-6-nitroBaP, followed by conversion to dinitroBaPs via the the diazonium salts

  苯并[a] py（BaP）与HNO3（d = 1.38）硝化产生了dinitroBaPs（1,6-和3,6-异构体）和mononitroBaPs（1-，3-和6-异构体）的混合物。通过用NaSH还原dinitroBaPs混合物，得到纯的1,6-dinitroBaP和3,6-dinitroBaP，得到可分离的产物1-amino-6-nitroBaP和3-amino-6-nitroBaP，然后通过转化为dinitroBaPs重氮盐。测量了与二硝基BaPs的单电子还原相对应的半波电势（E1 / 2），并讨论了这些值与诱变性之间的关系。
• Atmospheric Heterogeneous Reactions of Benzo(a)pyrene
  作者：M. Cazaunau、K. Le Ménach、H. Budzinski、E. Villenave

  DOI：10.1524/zpch.2010.6145

  日期：2010.8.1

  This experimental study deals with heterogeneous reactions of benzo(a)pyrene (BaP) with ozone, nitrogen dioxide and hydroxyl radicals. BaP was adsorbed on silica particles chosen here as a model of mineral atmospheric particles. Compound extractions were assisted by focused microwave and analyses were performed by gas chromatography coupled with mass spectroscopy in single ion monitoring mode. Pseudo-first order rate constants were obtained from the fit of experimental decays of particulate-BaP concentration versus reaction time. Second order rate constants were determined considering the different oxidant gaseous concentrations except for the case of hydroxyl radicals where only a pseudo-first order rate constant was proposed. Values obtained at room temperature are (2.1±0.5)×10⁻¹⁵ cm³ molecule⁻¹ s⁻¹ for (BaP + ozone), (5.8±1.4)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹ for (BaP + nitrogen dioxide) and (3.4±0.8)×10⁻² s⁻¹ for (BaP + OH) reactions. Products have only been investigated for the NO₂ and the OH (in the presence of NO_x) reactions. 1-, 3- and 6-nitrobenzo(a)pyrenes were detected as degradation products and quantified. Reaction rate constants for product formation are (3.7±0.9)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹ for 6-NBaP, (2.2±0.6)×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹ for 1-NBaP and (5.3±1.3)×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹ for 3-NBaP. 1-, 3- and 6-nitroBaP account respectively for approximately 5%, 12% and 83% of total nitrated species. If in the presence of only nitrogen dioxide, BaP was totally degraded within few minutes, only 20 to 25 % of the initial BaP led to nitrated compounds when reacting with OH (in the presence of NO_x).

  摘要：本实验研究了苯并(a)芘（BaP）与臭氧、二氧化氮和羟基自由基的异质反应。BaP被吸附在二氧化硅颗粒上，作为大气矿物颗粒的模型。化合物的提取采用了聚焦微波辅助，分析采用气相色谱-质谱联用技术，在单离子监测模式下进行。通过实验浓度衰减曲线与反应时间的拟合，得到了伪一级速率常数。考虑不同氧化剂气态浓度，确定了二级速率常数，但对于羟基自由基的情况，只提出了伪一级速率常数。在室温下，得到的值为(BaP+臭氧)为(2.1±0.5)×10⁻¹⁵ cm³ molecule⁻¹ s⁻¹，(BaP+二氧化氮)为(5.8±1.4)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹，(BaP+OH)反应为(3.4±0.8)×10⁻² s⁻¹。仅对NO₂和OH（在NO_x存在下）反应的产物进行了研究。检测到并量化了1-、3-和6-硝基苯并(a)芘作为降解产物。产物形成的反应速率常数为6-NBaP为(3.7±0.9)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹，1-NBaP为(2.2±0.6)×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹，3-NBaP为(5.3±1.3)×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹。1-、3-和6-硝基苯并(a)芘分别占总硝化物的约5％、12％和83％。如果只有二氧化氮存在，BaP会在几分钟内完全降解，但在OH（在NO_x存在下）反应时，只有20％至25％的初始BaP会生成硝化化合物。
• Mutagenic nitrated benzo[a]pyrene derivatives in the reaction product of benzo[a]pyrene in NO2–air in the presence of O3 or under photoirradiation
  作者：Satoko Ishii、Yoshiharu Hisamatsu、Koji Inazu、Takaaki Kobayashi、Ken-ichi Aika

  DOI：10.1016/s0045-6535(00)00029-1

  日期：2000.12

  should be considered. Benzo[a]pyrene lactones were identified in a highly mutagenic fraction of the products of the dark reaction in the presence of O3 and photoreaction and a nitrobenzo[a]pyrene lactone was also identified in a highly mutagenic fraction of the dark reaction products in the presence of O3. Nitrated oxygenated benzo[a]pyrene derivatives such as nitrobenzo[a]pyrene lactone were considered

  为了阐明硝化产物在各种条件下在NO2-空气中苯并[a] py的反应产物的直接诱变活性的贡献，沉积在过滤器中的BaP的异相反应在含有10 ppm NO2的空气中具有在黑暗中或在光照射下进行。通过气相色谱分析了反应产物，并且在不存在S9混合物的情况下，通过制备型HPLC对产物的诱变性进行了鼠伤寒沙门氏菌TA98和YG1024菌株的诱变分析。3,6-二硝基苯并[a] py和1,3-二硝基苯并[a] py是很强的直接作用诱变剂，在很大程度上决定了深色反应产物在NO 2-空气中的总直接作用诱变性。另一方面，在O3存在下的暗反应和在NO2-空气中的光反应都导致形成的硝基苯并[a] py比在不存在O3的暗反应中观察到的要少得多。这些结果表明，在这些反应中，应考虑其他直接作用的诱变剂对产物的总直接作用诱变性的贡献。在存在O3和光反应的情况下，在黑暗反应产物的高度诱变部分中鉴定出苯并[a] py内酯，并且在
• Packaging Inserts with Myoglobiin Blooming Agents, Packages and Methods of Packaging
  申请人：Curwood, Inc.

  公开号：EP1905584A2

  公开（公告）日：2008-04-02

  Food packaging inserts comprising a myoglobin blooming agent that promote or preserve the desirable appearance of food products, food packages, and methods of food packing comprising the same, are provided.

  本发明提供了由肌红蛋白绽放剂组成的食品包装插件，可促进或保持食品、食品包装的理想外观，以及由其组成的食品包装方法。

表征谱图