1,2-二氢苯[J]并苊 | 479-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 1,2-二氢苯[J]并苊
• 中文别名: 膽蒽；1,2-二氫苯[J]并苊
• 英文名称: cholanthrene
• 英文别名: Cholanthren；1,2-dihydrobenzo[j]aceanthrylene
• CAS: 479-23-2
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: KVFJBIQWENJTDM-UHFFFAOYSA-N

物化性质

• 熔点：
  173°
• 沸点：
  332.54°C (rough estimate)
• 密度：
  1.1180 (estimate)
• 颜色/状态：
  Faintly yellow plates from benzene + ether
• 溶解度：
  In water, 3.5X10-3 mg/L at 25 °C
• 蒸汽压力：
  5.3X10-8 mm Hg at 25 °C (est)
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 毒性总结

识别和使用：胆烷是一种固体。它是一种用于生物化学研究的 多环芳烃。人类暴露和毒性：没有数据可用。动物研究：胆烷在小鼠皮肤中是一种中等程度的肿瘤引发剂，在200和600纳米剂量的情况下，20周后促进肿瘤的最大产量分别为每只小鼠6.90和8.86个肿瘤。在胆烷的非苯环湾区位置（即碳原子6）引入甲基取代基显著增加了小鼠的肿瘤引发活性。关于苯并(a)蒽的致突变性和代谢的研究报告了在沙门氏菌中。在5种Ames测试菌株的活动谱与苯并(a)芘相似，且TA98菌株的剂量-反应曲线可比较。苯并(a)蒽是一种需要代谢激活的框移突变剂。

IDENTIFICATION AND USE: Cholanthrene is a solid. It is a polycyclic aromatic hydrocarbon used in biochemical research. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: Cholanthrene was a moderate tumor-initiator in mouse skin with maximal tumor yields of 6.90 and 8.86 tumors per mouse at 200 and 600 nmol doses, respectively, after 20 weeks of promotion. The introduction of a methyl substituent at the non-benzo ring bay-region position of cholanthrene (i.e. carbon atom 6) dramatically increased tumor-initiating activity in mice. Studies on the mutagenicity and metabolism of benz(j)aceanthrylene are reported in Salmonella. The activity spectrum over the 5 Ames tester strains is similar to that of benzo(a)pyrene, and the dose-response curves for strain TA98 are comparable. Benz(j)aceanthrylene is a frame-shift mutagen requiring metabolic activation.

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、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。 /芳香烃及其相关化合物/

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Aromatic hydrocarbons and related compounds/

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。密切观察呼吸不足的迹象，如有必要，进行辅助通气。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，并在必要时进行治疗……。监测休克，并在必要时进行治疗……。预防癫痫发作，并在必要时进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。/芳香烃及其相关化合物/

/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 necessary. 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. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。考虑使用药物治疗肺水肿……正压通气技术，使用气囊面罩装置可能有益。考虑使用药物治疗肺水肿……考虑给予β激动剂，如沙丁胺醇，用于严重支气管痉挛……监测心率和必要时治疗心律失常……开始静脉输注5%葡萄糖（D5W）/SRP: "保持开放"，最低流量/。如果出现低血容量迹象，使用0.9%生理盐水（NS）或乳酸钠林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……用地西泮或劳拉西泮治疗癫痫……使用丙美卡因氢氯化物协助眼部冲洗……/芳香烃及其相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：慢性暴露或致癌性/含有五元环的一些碳氢化合物衍生物的致癌活性：胆蒽：中等：在鼠标皮肤上涂画，在大鼠中进行皮下注射；高：在鼠标中进行皮下注射。/来自表格/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Carcinogenic activities of some hydrocarbon derivatives containing five-membered rings: cholanthrene: moderate: painting on mouse skin, subcutaneous injections in rats; high: subcutaneous injections in mice. /From table/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  1,2-二氢苯[J]并苊 在 sodium dichromate 、 溶剂黄146 作用下， 生成 (7,12-dioxo-7,12-dihydro-benz[a]anthracen-8-yl)-acetic acid
  参考文献：
  名称：

  173.八氢菲的合成用途。第一部分

  摘要：

  DOI：

  10.1039/jr9350000767
• 作为产物：
  描述：

  6-乙酰氧基胆蒽 在 氢碘酸 、 次磷酸 、 溶剂黄146 作用下， 反应 0.03h， 以80%的产率得到1,2-二氢苯[J]并苊
  参考文献：
  名称：

  Synthesis of cholanthrene and 6-methylcholanthrene, biologically active analogs of the potent carcinogen 3-methylcholanthrene

  摘要：

  DOI：

  10.1021/jo00378a025

文献信息

• Cabbage seedpod weevil (Coleoptera: Curculionidae): new pest of canola in northeastern North America
  作者：Jacques Brodeur、Luc-André Leclerc、Marc Fournier、Michèle Roy

  DOI：10.4039/ent133709-5

  日期：2001.10

  The cabbage seedpod weevil, Ceutorhynchus obstrictus (Marsham) [= C. assimilis (Paykull)] (Colonnelli 1993), is a univoltine species native to Europe that feeds on canola and other oilseed cruciferous plants. The adult overwinters in debris and soil outside fields and colonizes canola at the blooming stage (Dosdall et al. 2001). Eggs are laid singly into the immature pods and each larva consumes five to seven seeds before cutting a hole in the pod to wriggle out and pupate in the soil (Dmoch 1965). Yield losses are difficult to assess because the plant compensates for bud and pod injuries caused by insects or pathogens (Lamb 1989). Nevertheless, pod feeding by larvae causes much damage, as canola yields can be reduced from 15 to 35% (Homan and McCaffrey 1993). Feeding by adults can also be significant, as it can reduce oil content, seed weight, and seed germination (Buntin et al. 1995).

  卷心菜象鼻虫（Ceutorhynchus obstrictus (Marsham) [= C. assimilis (Paykull)] (Colonnelli 1993)）是一种原产于欧洲的单伏特物种，以油菜籽和其它油籽十字花科植物为食。成虫在田野外的碎石和土壤中越冬，并在油菜开花期定殖（Dosdall 等人，2001 年）。卵单个产在未成熟的豆荚中，每只幼虫吃掉 5 到 7 粒种子，然后在豆荚上凿一个洞，爬出来在土壤中化蛹（Dmoch 1965）。产量损失很难评估，因为植物会对昆虫或病原体造成的花蕾和豆荚损伤进行补偿（Lamb，1989 年）。不过，幼虫取食豆荚会造成很大损失，油菜籽产量会减少 15% 到 35% （霍曼和麦卡弗里，1993 年）。成虫取食也会造成重大损失，因为它会降低含油量、种子重量和种子发芽率（Buntin 等人，1995 年）。
• THE SYNTHESIS OF COMPOUNDS RELATED TO 1,2-BENZANTHRACENE AND CHOLANTHRENE
  作者：W. E. BACHMANN

  DOI：10.1021/jo01222a006

  日期：1938.11
• 147. Synthesis of cholanthrene
  作者：J. W. Cook、G. A. D. Haslewood、A. M. Robinson

  DOI：10.1039/jr9350000667

  日期：——
• Buchta,E.; Meyer,K., Chemische Berichte, 1962, vol. 95, p. 213 - 221
  作者：Buchta,E.、Meyer,K.

  DOI：——

  日期：——
• Cholanthrene and Related Hydrocarbons
  作者：Louis F. Fieser、Arnold M. Seligman

  DOI：10.1021/ja01314a039

  日期：1935.11