4-(3,5-二甲基-3-庚基)苯酚 | 186825-36-5

• 物质功能分类: 分析化学 - 标准品 - 有机污染物标样
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3,5-二甲基-3-庚基)苯酚
• 中文别名: 4-(1-乙基-1,3-二甲基戊基)苯酚
• 英文名称: 4-(1-ethyl-1,3-dimethylpentyl)phenol
• 英文别名: 4(3',5'-dimethyl-3'-heptyl)-phenol；4-(3,5-dimethylheptan-3-yl)phenol
• CAS: 186825-36-5
• 化学式: C₁₅H₂₄O
• mdl: MFCD11870117
• 分子量: 220.355
• InChiKey: RYIHVIPUIXFRNI-UHFFFAOYSA-N

物化性质

• 沸点：
  316.0±11.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)
• 保留指数：
  1734;1734;1710;1716

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  C,N
• 安全说明：
  S26,S36/37/39,S45,S46,S60,S61
• 危险类别码：
  R63,R22,R34,R50/53,R62
• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲基-3-庚醇 、 苯酚 在 三氟化硼乙醚 作用下， 以 Petroleum ether 为溶剂， 反应 0.25h， 生成 4-(3,5-二甲基-3-庚基)苯酚
  参考文献：
  名称：

  Synthesis of tertiary¹⁴C-labelled nonylphenol isomers

  摘要：

  三种带有14C标记的对壬基酚(NP)异构体被合成，用于代谢和吸附研究： - 4(3',5'-二甲基-3'-庚基)-酚(p353NP) - 4(3',6'-二甲基-3'-庚基)-酚(p363NP) - 4(2',6'-二甲基-2'-庚基)-酚(p262NP) 合成方法是使用BF3作为催化剂，对14C标记的酚和相应的叔壬醇进行傅-克烷基化反应。 通过制备薄层色谱纯化后: - p262NP放射化学产率为62.8%,比活度332 MBq/mmol,放射化学纯度97.6% - p363NP放射化学产率为64.6%,比活度88.2 MBq/mmol,放射化学纯度99.0% 另外还开发了这两种异构体使用非标记酚的大规模合成方法,无需进一步纯化即可得到纯度分别为96%和99%的产品。 p353NP作为非对映异构体混合物生成,粗产品的放射化学纯度为96.9%(放射化学产率76.0%,比活度298 MBq/mmol),因此无需纯化。 所有产物均通过气相色谱-质谱、1H-NMR、13C-NMR和IR进行表征。

  DOI：

  10.1002/jlcr.641

文献信息

• Synthesis of tertiary¹⁴C-labelled nonylphenol isomers
  作者：Ralph Vinken、Burkhard Schmidt、Andreas Schäffer

  DOI：10.1002/jlcr.641

  日期：2002.12

  The ring-14C-labelled p-nonylphenol (NP) isomers 4(3′,5′-dimethyl-3′-heptyl)-phenol (p353NP), 4(3′,6′-dimethyl-3′-heptyl)-phenol (p363NP) and 4(2′,6′-dimethyl-2′-heptyl)-phenol (p262NP) were synthesized for application in metabolism and sorption studies. Friedel–Crafts alkylation of 14C-labelled phenol and the corresponding tertiary nonylalcohol with BF3 as catalyst was used. After clean-up of p262NP and p363NP by preparative thin-layer chromatography radiochemical yields amounted to 62.8 and 64.6%, specific radioactivities were 332 and 88.2 MBq/mmol, and radiochemical purities 97.6 and 99.0%. For both isomers, a large-scale synthesis with non-labelled phenol was additionally developed, which led to pure products (96 and 99%, respectively) without further purification steps. In the case of p353NP, which was formed as a diastereomeric mixture, the crude synthetic product had a radiochemical purity of 96.9% (radiochemical yield: 76.0%; specific activity: 298 MBq/mmol); thus, purification was not necessary. All products were characterized by means of gas chromatography-mass spectroscopy, 1H- and 13C-NMR, as well as IR. Copyright © 2002 John Wiley & Sons, Ltd.

  三种带有14C标记的对壬基酚(NP)异构体被合成，用于代谢和吸附研究： - 4(3',5'-二甲基-3'-庚基)-酚(p353NP) - 4(3',6'-二甲基-3'-庚基)-酚(p363NP) - 4(2',6'-二甲基-2'-庚基)-酚(p262NP) 合成方法是使用BF3作为催化剂，对14C标记的酚和相应的叔壬醇进行傅-克烷基化反应。 通过制备薄层色谱纯化后: - p262NP放射化学产率为62.8%,比活度332 MBq/mmol,放射化学纯度97.6% - p363NP放射化学产率为64.6%,比活度88.2 MBq/mmol,放射化学纯度99.0% 另外还开发了这两种异构体使用非标记酚的大规模合成方法,无需进一步纯化即可得到纯度分别为96%和99%的产品。 p353NP作为非对映异构体混合物生成,粗产品的放射化学纯度为96.9%(放射化学产率76.0%,比活度298 MBq/mmol),因此无需纯化。 所有产物均通过气相色谱-质谱、1H-NMR、13C-NMR和IR进行表征。
• Role of dissolved humic acids in the biodegradation of a single isomer of nonylphenol by Sphingomonas sp.
  作者：Chengliang Li、Rong Ji、Ralph Vinken、Gregor Hommes、Marko Bertmer、Andreas Schäffer、Philippe F.X. Corvini

  DOI：10.1016/j.chemosphere.2007.01.080

  日期：2007.8

  This study shows the important role of humic acids in the degradation of (14) C and C-13 labeled isomer of NP by Sphingomonas sp. strain TTNP3 and the detoxification of the resulting metabolites. Due to the association of NP with humic acids, its solubility in the medium was enhanced and the extent of mineralization of nonylphenol increased from 20% to above 35%. This was accompanied by the formation of significant amounts of NP residues bound to the humic acids, which also occurred via abiotic reactions of the major NP metabolite hydroquinone with the humic acids. Gel permeation chromatography showed a non-homogenous distribution of NP residues with humic acids molecules, with preference towards molecules with high-molecular-weight. Solid state C-13 nuclear magnetic resonance spectroscopy indicated that the nonextractable residues resulted exclusively from the metabolites. The chemical shifts of the labeled carbon indicated the possible covalent binding of hydroquinone to the humic acids via ester and possibly ether bonds, and the incorporation of degradation products of hydroquinone into the humic acids. This study provided evidences for the mediatory role of humic acids in the fate of NP as a sink for bacterial degradation intermediates of this compound. (c) 2007 Elsevier Ltd. All rights reserved.
• Degradation of the Radioactive and Non-labelled Branched 4(3',5'-dimethyl 3'-heptyl)-phenol Nonylphenol Isomer by Sphingomonas TTNP3
  作者：P.F.X. Corvini、R. Vinken、G. Hommes、B. Schmidt、M. Dohmann

  DOI：10.1023/b:biod.0000009937.20251.d2

  日期：2004.2

  The degradation of the 4( 3', 5'- dimethyl- 3'- heptyl)- phenol ( p353NP) nonylphenol isomer in cultures of Sphingomonas TTNP3 supplemented with the technical mixture of nonylphenol was first assessed. Then the radioactive and non- labelled form of these diastereomers were both synthesised. The radioactive isomers were synthesised using [ ring- U-C-14]- labelled phenol and 3,5- dimethyl- 3- heptanol by Friedel and Crafts alkylation. The time- course of degradation was performed with and without C-14- p353NP; balancing of radioactivity was calculated from different soluble fractions ( organic, aqueous), bacterial biomass, and (CO2)-C-14 evolved as mineralization product. The noticeable portion of C-14 bound to biomass showed that at least the aromatic ring of C-14- p353NP was degraded and served as energy source and probably as carbon source for bacterial growth. In addition, the appearance of 3,5dimethyl- 3- heptanol, the nonanol corresponding with the side- chain of p353NP, was demonstrated in the bacterial media, and its concentration determined during the course of fermentation. Besides the parent C-14- p353NP, no other radioactive compounds, i. e. metabolites of C-14- p353NP were detected in the media.
• Estrogen equivalent concentration of 13 branched para-nonylphenols in three technical mixtures by isomer-specific determination using their synthetic standards in SIM mode with GC–MS and two new diasteromeric isomers
  作者：Takao Katase、Keiji Okuda、Yun-Seok Kim、Heesoo Eun、Hideshige Takada、Taketo Uchiyama、Hiroaki Saito、Mitsuko Makino、Yasuo Fujimoto

  DOI：10.1016/j.chemosphere.2007.09.049

  日期：2008.2

  9+/-0.3% to 3.0+/-0.2%. Additionally, structures of four new isomers of more than 1% portion present in a technical mixture were elucidated as two pairs of diastereomeric isomers: two types of 4-(3,4-dimethylheptan-4-yl)phenol (344NP) and those of 4-(3,4-dimethylheptan-3-yl)phenol (343NP). By estrogenic assay of 13 isomers with yeast estrogen screen system, the activity of 3E22NP was the highest, while

  通过SIM的结构特异性离子m / z 135、149或163的合成标准品，使用GC-MS，通过合成标准物，在三种技术混合物中选择了13种支链对壬基酚（对-NP）异构体。在13种异构体中，有4种异构体，分别是4-（2,4-二甲基庚基-4-基）苯酚，4-（4-甲基辛基-4-基）苯酚，4-（3-乙基-2-甲基己-2-基）首先将用于测定的）苯酚（3E22NP）和4-（2,3-二甲基庚基-2-基）苯酚用作标准物质。工业混合物中的13种异构体的质量百分比含量分别超过2％。东京化学工业公司（TCI），Aldrich和Fluka的混合物中的总质量百分比分别为89 +/- 2％，75 +/- 4％和77 +/- 2％。三种混合物中4-（3,6-二甲基庚基-3-基）苯酚的丰度最大，为11.1 +/- 2％至9。9 +/- 0.3％，而4-（2-甲基辛烷-2-基）苯酚最小，为2.9 +/- 0.3％至3.0 +/-