3,4:8,9-二苯并芘 | 189-64-0

• 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: 3,4:8,9-二苯并芘
• 中文别名: 二苯并[b,def]芘；二苯并(A,H)芘；二苯并(a,h)芘；二苯并[a,h]嵌二萘；二苯并[b,def]屈；二苯并[a,h]芘
• 英文名称: dibenz[a,h]pyrene
• 英文别名: dibenzopyrene；dibenzo[b,def]chrysene；dibenzo[a,h]pyrene；Dibenzo[ah]pyrene；dibenzo[b,def]chrysene；Dibenzo[b,def]chrysen；hexacyclo[10.10.2.02,7.09,23.013,18.020,24]tetracosa-1(23),2,4,6,8,10,12(24),13,15,17,19,21-dodecaene
• CAS: 189-64-0；58615-36-4
• 化学式: C₂₄H₁₄
• 分子量: 302.375
• InChiKey: RXUSYFJGDZFVND-UHFFFAOYSA-N

物化性质

• 熔点：
  308 °C
• 沸点：
  596 °C
• 密度：
  1.1762 (estimate)
• 闪点：
  -11 °C
• 溶解度：
  可溶于氯仿（非常轻微，加热），DMSO（非常轻微，加热）
• 物理描述：
  Dibenzo(a,h)pyrene appears as yellow odorless crystals or flakes. Water insoluble.
• 颜色/状态：
  Golden-yellow plates, recrystallized from xylene or trichlorobenzene
• 气味：
  Odorless
• 蒸汽压力：
  6.4X10-12 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Stable under recommended storage conditions.[Sigma-Aldrich; Safety Data Sheet for Dibenzo
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 碰撞截面：
  164.6 Ų [M+H]+
• 保留指数：
  3541;3537;3537;3537

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

1,2-和3,4-二氢二醇被识别为二苯并(a,h)芘在经过大鼠肝脏制剂孵化后的代谢物。... 1,2-二氢二醇在存在外源代谢系统时对细菌具有诱变性...并且在小鼠皮肤上是一个肿瘤启动剂，在新生小鼠中具有致瘤性...。

The 1,2- and 3,4-dihydrodiols have been identified as metabolites of dibenzo(a,h)pyrene following incubation of this cmpd with rat-liver preparations. ... The 1,2-dihydrodiol is mutagenic to bacteria in the presence of an exogenous metabolic system ... and is a tumor initiator on mouse skin and tumorigenic in newborn mice ... .

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：二苯并(a,h)芘（DB(a,h)P）形成金色的黄色片状物。它被用作实验性致癌物。人类暴露和毒性：DB(a,h)P 被合理预期为人类致癌物。DB(a,h)P 在人类B淋巴细胞中具有突变性。动物研究：一组24只雌性小鼠单次皮肤涂抹240微克DB(a,h)P；对照组23只小鼠仅用溶剂处理。一周后，所有小鼠每周两次皮肤涂抹4.26纳米摩尔12-O-十四烷基佛波醇-13-醋酸盐，持续25周，每只100微升丙酮。DB(a,h)P处理的24只小鼠中有18只出现乳头状瘤（每只小鼠5.3个肿瘤），而溶剂处理的23只对照组小鼠中只有2只出现乳头状瘤（每只小鼠0.1个肿瘤）。一项研究发现，在4只大鼠中，有2只在静脉注射0.5-1.0毫克DB(a,h)P后7到8个月死亡时出现肿瘤。实验持续至少8个月。在另一项研究中，6只雌性大鼠单次注射0.5毫克DB(a,h)P，5.5个月和8个月时出现2个肉瘤。无论有无代谢激活，DB(a,h)P 在沙门氏菌伤寒杆菌TM67中均无突变性。DB(a,h)P 在沙门氏菌伤寒杆菌TA98和TA100中具有突变性。

IDENTIFICATION AND USE: Dibenzo(a,h)pyrene (DB(a,h)P) forms golden yellow plates. It is used as an experimental carcinogen. HUMAN EXPOSURE AND TOXICITY: DB(a,h)P is reasonably anticipated to be a human carcinogen. DB(a,h)P was mutagenic in human B-lymphoblastoid cells. ANIMAL STUDIES: A group of 24 female mice received a single dermal application of 240 ug DB(a,h)P; a control group of 23 mice was treated with the solvent alone. One week later, all mice received twice weekly dermal applications of 4.26 nmol 12-O-tetradecanoylphorbol-13-acetate in 100 uL acetone for 25 weeks. Papillomas occurred in 18/24 mice treated with DB(a,h)P (5.3 tumors/mouse) compared with 2/23 solvent-treated control mice (0.1 tumors/mouse). One study found 2 tumors in 4 rats dying after 7 to 8 months following im administration of 0.5-1.0 mg of DB(a,h)P. The duration of the experiment was at least 8 months. In another study, 6 female rats were injected with single dose of 0.5 mg DB(a,h)P, and 2 sarcomas appeared at 5.5 and 8 months. DB(a,h)P was not mutagenic in Salmonella typhimurium TM67 with or without metabolic activation. DB(a,h)P was mutagenic in Salmonella typhimurium TA98 and TA100.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

2B组：该物质对人类可能是致癌的。

Group 2B: The agent is possibly carcinogenic to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

二苯并(a,h)芘：合理预期为人类致癌物。/多环芳烃/

Dibenzo(a,h)pyrene: reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/

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：二苯并[a,h]芘

IARC Carcinogenic Agent:Dibenzo[a,h]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：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  F,T
• 安全说明：
  S26,S36/37,S53,S62
• 危险类别码：
  R45
• WGK Germany：
  3
• RTECS号：
  HO5775000
• 海关编码：
  2902909090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  2811

反应信息

• 作为反应物：
  描述：

  3,4:8,9-二苯并芘 生成 (23S,24R)-hexacyclo[10.10.2.02,7.09,23.013,18.020,24]tetracosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
  参考文献：
  名称：

  MITCHELL, R. H.;WILLIAMS, R. V.;DINGLE, T. W., J. AMER. CHEM. SOC., 1982, 104, N 9, 2560-2571

  摘要：

  DOI：
• 作为产物：
  描述：

  7,14-dihydro-dibenzo[b,def]chrysene 在 铜 作用下， 生成 3,4:8,9-二苯并芘
  参考文献：
  名称：

  Buu-Hoi; Lavit, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 249, p. 1364

  摘要：

  DOI：

文献信息

• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• New Synthetic Approaches to Polycyclic Aromatic Hydrocarbons and Their Carcinogenic Oxidized Metabolites:  Derivatives of Benzo[<i>s</i>]picene, Benzo[<i>r</i><i>st</i>]pentaphene, and Dibenzo[<i>b</i>,<i>d</i><i>ef</i>]chrysene
  作者：Fang-Jie Zhang、Cecilia Cortez、Ronald G. Harvey

  DOI：10.1021/jo9918044

  日期：2000.6.1

  synthetic method provides convenient access to as many as three different polycyclic aromatic ring systems from a single Suzuki coupled intermediate. It was utilized to synthesize substituted derivatives of benzo[s]picene, benzo[rst]pentaphene, dibenzo[b,def]chrysene, and 13,14-dihydro-benz[g]indeno[2,1-a]fluorene, as well as the putative carcinogenic bisdihydrodiol metabolites of benzo[s]picene, benzo[rst]pentaphene

  描述了一种新的合成多环芳族化合物的方法，该方法需要在关键步骤中将PAH双硼酸衍生物与邻溴代芳基醛进行双Suzuki偶联，以提供芳基二醛，然后通过（a）转化为二烯烃将其转化为更大的多环芳环系统通过维蒂希反应，然后进行光环化，或（b）用三氟甲磺酸和1,3-丙二醇进行还原环化。这种合成方法可方便地从单个Suzuki偶联中间体访问多达三个不同的多环芳族环系统。它被用来合成苯并[s]吡啶，苯并[r]戊苯，二苯并[b，def]丙烯和13,14-二氢-苯并[g]茚并[2,1-a]芴的取代衍生物，以及苯并[s]]烯，苯并[rst]五苯芬的可能致癌的双二氢二醇代谢物，
• Spiral, Herringbone, and Triple-Decker Silver(I) Complexes of Benzopyrene Derivatives Assembled through <i>η</i>²-Coordination
  作者：Jian Chu Zhong、Megumu Munakata、Takayoshi Kuroda-Sowa、Masahiko Maekawa、Yusaku Suenaga、Hisashi Konaka

  DOI：10.1021/ic001352+

  日期：2001.6.1

  benzo[e]pyrene (L(3)) coordinated to silver(I) ions generating a closed triple-decker tetranuclear complex [Ag(4)(L(3))(4)(p-xylene)(ClO(4))(4)] (3) which can be regarded as a stacking polymer owing to existing intermolecular pi-pi stack interactions. The structural diversity of the silver(I) coordination polymers with polycyclic aromatic hydrocarbons is not only related to the stacking patterns of free polycyclic

  本文合成并表征了三种新型的具有苯并re衍生物的银（I）配合物。用7-甲基苯并[a] py（L（1））处理AgClO（4）* H（2）O得到[Ag（2）（L（1））（甲苯）（0.5）（ClO（4）） （2）]（n）（）（1）表现出具有双链螺旋图案的二维片状结构。AgCF（3）SO（3）与二苯并[b，def]丙烯（L（2））的反应产生了前所未有的共结晶结构，（[Ag（2）（L（2））（CF（3）SO （3））（2）] [Ag（2）（甲苯）（2）（CF（3）SO（3））（2）]）（n）（）（2），由二维中性形成层状聚合物和一维中性棒状聚合物。配体苯并[e] py（L（3））与银（I）离子配位，生成闭合的三层四核复合物[Ag（4）（L（3））（4）（对二甲苯）（ClO（ 4））（4）]（3）由于存在分子间的pi-pi堆栈相互作用而被视为堆栈聚合物。银（I）配位聚合物与多环芳烃的结构多样性不仅与处于
• A new general synthesis of polycyclic aromatic compounds based on enamine chemistry
  作者：Ronald G. Harvey、John Pataki、Cecilia Cortez、Pasquale Di Raddo、Cheng Xi Yang

  DOI：10.1021/jo00003a050

  日期：1991.2

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.
• Benzannelated annulenes. 8. Toward the understanding of benzannelated annulenes: synthesis and properties of [a,h]- and [a,i]-ring dibenzannelated dihydropyrenes
  作者：Reginald H. Mitchell、Richard Vaughan Williams、Thomas W. Dingle

  DOI：10.1021/ja00373a038

  日期：1982.5

表征谱图