苯并[b]芘-6-基甲醇 | 21247-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 苯并[b]芘-6-基甲醇
• 英文名称: 6-(hydroxymethyl)benzopyrene
• 英文别名: 6-hydroxymethylbenzopyrene；6-(hydroxymethyl)benzo[a]pyrene；6-hydroxymethylbenzo[a]pyrene；6-Benzopyrenmethanol-¹³C；6-Hydroxymethylbenzpyren；6-Benzo[a]pyrenmethanol-¹³C；benzo[b]pyren-6-ylmethanol
• CAS: 21247-98-3
• 化学式: C₂₁H₁₄O
• 分子量: 282.342
• InChiKey: FJQLVOHCPDYIFE-UHFFFAOYSA-N

物化性质

• 熔点：
  270.5°C
• 沸点：
  384.95°C (rough estimate)
• 密度：
  1.0771 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

6-羟甲基苯并[a]芘已知的人类代谢物包括6-磺酸氧甲基苯并(a)芘。

6-hydroxymethylbenzo[a]pyrene has known human metabolites that include 6-Sulfooxymethylbenzo(a)pyrene.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2906299090

SDS

制备方法与用途

类别：有毒物品

可燃性危险特性：

• 可燃；
• 燃烧时会产生刺激烟雾。

储运特性：

• 通风、低温和干燥。

灭火剂：

• 干粉、泡沫、沙土、二氧化碳、雾状水。

反应信息

• 作为反应物：
  描述：

  苯并[b]芘-6-基甲醇 在 三溴化磷 作用下， 以 苯 为溶剂， 生成 6-(溴甲基)苯并[b]芘
  参考文献：
  名称：

  与6-羟甲基苯并（a）py有关的化合物的合成和致癌性。

  摘要：

  DOI：

  10.1021/jm00264a034
• 作为产物：
  描述：

  苯并[a]芘 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 苯并[b]芘-6-基甲醇
  参考文献：
  名称：

  与6-羟甲基苯并（a）py有关的化合物的合成和致癌性。

  摘要：

  DOI：

  10.1021/jm00264a034

文献信息

• Radical cations of benzo[α]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA
  作者：D. E. Stack、P. Cremonesi、A. Hanson、E. G. Rogan、E. L. Cavalieri

  DOI：10.3109/00498259509061890

  日期：1995.1

  1. Oxidation of benzo[a]pyrene (BP) by I2 in the presence of AgClO4 in benzene generates the BP.+ClO4-.AgI complex. This same method was used to produce radical cations from 6-FBP, 6-ClBP, 6-BrBP and 6-CH3BP. 2. Reaction of the BP, 6-FBP, 6-ClBP and 6-BrBP radical cation perchlorates with H2O produced BP 1,6-, 3,6- and 6,12- dione, whereas 6-CH3BP.+ClO4-.AgI yielded 6-CH2OHBP. 3. When BP.+ClO4-.AgI

  1.在AgClO4在苯中的存在下，I2氧化苯并[a] py（BP），生成BP。+ ClO4-.AgI复合物。使用相同的方法由6-FBP，6-ClBP，6-BrBP和6-CH3BP产生自由基阳离子。2.BP，6-FBP，6-ClBP和6-BrBP自由基阳离子高氯酸盐与H 2 O反应生成BP 1,6-，3,6-和6,12-二酮，而6-CH3BP。+ ClO4-。 AgI产生6-CH 2 OHBP。3.当BP。+ ClO4-.AgI和6-FBP。+ ClO4-.AgI与NaOAc在H2O / CH3CN（9：1）中反应时，除醌外，还形成了6-OAcBP。在6-ClBP。+ ClO4-.AgI的情况下，除了二酮以外，还形成少量的1-OAc-6-ClBP和3-OAc-6-ClBP，而对于6-BrBP和6-CH3BP反应产物分别为BP二酮和6-CH 2 OHBP。4.这些结果证实了电荷在BP。+中位于
• Synthesis and properties of 6-substituted benzo[a]pyrene derivatives
  作者：F. Dewhurst、D. A. Kitchen

  DOI：10.1039/p19720000710

  日期：——

  An improved route to benzo[a]pyrene-6-carbaldehyde is described, the nature of an impurity in this substance is discussed, the synthesis of a number of 6-substituted benzo[a]pyrene derivatives from the carbaldehyde is described, and the use of N-halogenosuccinimides for preparing 6-halogeno-derivatives of benzo[a]pyrene is examined. The fluorescence spectra and t.l.c. behaviour of the derivatives are

  描述了制备苯并[ a ] py-6-甲醛的改进方法，讨论了该物质中杂质的性质，描述了从甲醛合成许多6-取代的苯并[ a ] py衍生物的方法，研究了N-卤代琥珀酰亚胺在制备苯并[ a ] py的6-卤代衍生物中的用途。描述了衍生物的荧光光谱和tlc行为。
• One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation
  作者：Paolo Cremonesi、Ercole L. Cavalieri、Eleanor G. Rogan

  DOI：10.1021/jo00276a013

  日期：1989.7
• Radical Cations of Benzo[a]pyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles
  作者：Paolo Cremonesi、Douglas E. Stack、Eleanor G. Rogan、Ercole L. Cavalieri

  DOI：10.1021/jo00104a024

  日期：1994.12

  Radical cations of benzo[a]pyrene (BP) and 6-substituted derivatives were synthesized by two methods: reaction of the hydrocarbon with I-2 and AgClO4 in benzene, and reaction of the hydrocarbon with NOBF4 in CH3CN/CH2Cl2. Both the radical cation perchlorates and tetrafluoroborates were stable for prolonged periods of time when stored under argon at subzero temperatures. The radical cations were reacted with nucleophiles of various strengths, namely H2O, AcO- and F-, as a means of best characterizing these intermediates, as well as determining their chemical properties. Reaction of BP, 6-FBP, 6-ClBP, and 6-BrBP radical cation perchlorates with H2O produced BP 1,6- 3,6-, and 6,12-dione, whereas the radical cation derived from 6-CH3BP yielded 6-CH2OHBP. When (BPClO4-)-Cl-.+ and 6-(FBPClO4-)-Cl-.+ were reacted with NaOAc in H2O/CH3CN (9:1), 6-OAcBP was formed, in addition to the quinones. 6-(ClBPClO4-)-Cl-.+ formed a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP, in addition to the diones, whereas for 6-(BrBPClO4-)-Cl-.+ and 6-(CH3BPClO4-)-Cl-.+ the reaction products were BP diones and 6-CH2OHBP, respectively. Reactions conducted under anhydrous conditions, using tetramethylammonium acetate in CH3CN, gave similar results, except that no quinones were formed. These results confirm the reactivity of nucleophiles at the positions of high charge localization in the BP.+, i.e. C-6, followed by C-1 and C-3.
• Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
  作者：Hansruedi Glatt、Karin Pauly、Andrea Piée-Staffa、Albrecht Seidel、Sabine Hornhardt、Andreas Czich

  DOI：10.1016/0378-4274(94)90005-1

  日期：1994.6

  Various environmental chemicals are metabolised to chemically reactive sulfuric acid esters, which may covalently bind to cellular macromolecules and induce mutations and tumours. This activation pathway is usually not taken into account in external xenobiotic-metabolising systems used in short-term tests. We therefore analysed the abilities of cytosols from mammalian cell lines to activate benzylic alcohols (1-hydroxymethylpyrene and 9-hydroxymethyl-anthracene) to mutagens detectable in Salmonella typhimurium TA98. No activation was observed in cell lines which are commonly used in mutagenicity and cell transformation assays, and only low activities were found in epithelial cell lines in culture. We have therefore constructed Chinese hamster V79-derived cell fines which stably express a heterologous sulfotransferase, rat hydroxysteroid sulfotransferase a. Cytosol of these cells effectively activated 1-hydroxymethylpyrene and 9-hydroxymethylanthracene to mutagens detected in S. typhimurium. The hepatocarcinogen 6-hydroxymethylbenzo [a]pyrene induced gene mutations in sulfotransferase-expressing V79-derived cells, whereas it elicited only marginal effects in sulfotransferase-deficient control cells. The new cell lines may allow the detection of novel classes of mutagens, since some externally generated reactive sulfuric acid esters may not readily penetrate target cells due to their short life span and their ionization.