卵苯 | 190-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 卵苯
• 英文名称: ovalene
• 英文别名: Ovalen；Qualen
• CAS: 190-26-1
• 化学式: C₃₂H₁₄
• 分子量: 398.463
• InChiKey: LSQODMMMSXHVCN-UHFFFAOYSA-N

物化性质

• 熔点：
  475-476 °C
• 沸点：
  456.64°C (rough estimate)
• 密度：
  0.8530 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  10.0
• 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

多环芳烃（PAHs）的代谢发生在所有组织中，通常通过细胞色素P-450及其相关酶进行。多环芳烃被代谢成反应性中间体，包括环氧中间体、二氢二醇、酚、醌及其各种组合。酚、醌和二氢二醇都可以与葡萄糖苷酸和硫酸酯结合；醌还可以形成谷胱甘肽结合物。

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

多环芳烃（PAHs）能够与血液中的蛋白质，如白蛋白结合，从而在体内进行传输。许多多环芳烃通过结合芳烃受体或甘氨酸N-甲基转移酶蛋白，诱导细胞色素P450酶的表达，尤其是CYP1A1、CYP1A2和CYP1B1。这些酶将多环芳烃代谢成其有毒的中间产物。多环芳烃的活性代谢物（环氧化物中间体、二氢二醇、酚、醌及其各种组合）与DNA和其他细胞大分子共价结合，启动突变和致癌过程。

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列入国际癌症研究机构(IARC)名单。IARC已评估了其他多环芳烃(L2154)。

Not listed by IARC. IARC has evaluated other PAHs (L2154).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

多环芳烃（PAHs）是致癌物，与皮肤癌、呼吸道癌、膀胱癌、胃癌和肾癌的风险增加有关。它们还可能引起生殖效应并抑制免疫系统。

PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L10）；吸入（L10）

Oral (L10) ; inhalation (L10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

急性暴露于多环芳烃会导致皮肤和肺组织的刺激和炎症。

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2901299090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  卵苯 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 2,4,7,8-四氯二苯并呋喃
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 calcium hydroxide 、 sodium hydroxide 作用下， 400.0 ℃ 、133.32 Pa 条件下， 生成 卵苯
  参考文献：
  名称：

  卵黄烯的合成

  摘要：

  IF 苝与马来酸酐和硝基苯一起煮沸，形成 1 : 12-苯并苝-1' : 2'-二羧酸酐1。在相同条件下，中间-蒽-二蒽2 (I) 定量地产生酸酐 (II)，暗红色针状物在 430° 分解（未校正）（发现：C, 86·48 ; H, 3·01. C34 H12 O3要求：C, 87·17; H, 2·58%)，并且中-石脑油-二蒽2 (III) 反应两次形成二酐(IV)，为深棕色晶体，在高温下碳化。

  DOI：

  10.1038/161238b0

文献信息

• High-temperature stabilities of hydrocarbons
  作者：Stephen E. Stein、A. Fahr

  DOI：10.1021/j100263a027

  日期：1985.8
• Lang,K.F.; Buffleb,H., Chemische Berichte, 1961, vol. 94, p. 1075 - 1082
  作者：Lang,K.F.、Buffleb,H.

  DOI：——

  日期：——
• Synthesis of Ovalene
  作者：E. CLAR

  DOI：10.1038/161238b0

  日期：1948.2

  IF perylene is boiled with maleic anhydride and nitrobenzene, 1 : 12-benzperylene-l′ : 2′-dicarboxylic acid anhydride is formed1. Under the same conditions meso-anthra-dianthrene2 (I) yields quantitatively the anhydride (II), as dark red needles decomposing at 430° (uncorr.) (found : C, 86·48 ; H, 3·01. C34 H12 O3 requires: C, 87·17; H, 2·58 per cent), and meso-naphtha-dianthrene2 (III) reacts twice

  IF 苝与马来酸酐和硝基苯一起煮沸，形成 1 : 12-苯并苝-1' : 2'-二羧酸酐1。在相同条件下，中间-蒽-二蒽2 (I) 定量地产生酸酐 (II)，暗红色针状物在 430° 分解（未校正）（发现：C, 86·48 ; H, 3·01. C34 H12 O3要求：C, 87·17; H, 2·58%)，并且中-石脑油-二蒽2 (III) 反应两次形成二酐(IV)，为深棕色晶体，在高温下碳化。
• De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes
  作者：F. Iino、T. Imagawa、M. Takeuchi、M. Sadakata

  DOI：10.1021/es980857k

  日期：1999.4.1

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

表征谱图