(1RS)-cis-permethrin | 54774-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1RS)-cis-permethrin
• 英文别名: (3-phenoxyphenyl)methyl (1RS)-cis-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate；3-phenoxybenzyl (¹⁴C)(1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate；3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate；cis-permethrin；permethrin；(3-phenoxyphenyl)-methyl(+)cis-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate；(-)-cis-Permethrin；(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 54774-46-8
• 化学式: C₂₁H₂₀Cl₂O₃
• 分子量: 391.294
• InChiKey: RLLPVAHGXHCWKJ-IEBWSBKVSA-N

物化性质

• 沸点：
  505.74°C (rough estimate)
• 密度：
  1.1531 (rough estimate)
• 保留指数：
  2632;2634;2674.1;2657;2657

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用总结：由于局部应用后吸收少于2%，并且迅速代谢为无活性代谢物，以及可以直接安全地应用于婴儿皮肤，局部使用 permethrin 产品在哺乳期母亲中是可以接受的。广泛的暴露，例如来自农业使用或疟疾控制，可能会因残留在母乳中而引起长期健康问题。只有水溶性乳膏、凝胶或液体产品应应用于乳房，因为软膏可能会使婴儿通过舔舐接触到高水平的矿物石蜡。 ◉ 对哺乳婴儿的影响：在一项电话随访研究中，5位在哺乳期间使用 permethrin 的母亲报告她们的哺乳婴儿没有不良反应。 ◉ 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:Because less than 2% is absorbed after topical application, rapid metabolism to inactive metabolites and safe application directly on infants' skin, topical permethrin products are acceptable in nursing mothers. Extensive exposure, such as from agricultural use or malaria control might have long-term health concerns because residues can be found in breastmilk. Only water-miscible cream, gel or liquid products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking. ◉ Effects in Breastfed Infants:In a telephone follow-up study, 5 mothers who used permethrin during breastfeeding reported no adverse reactions in their breastfed infants. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  (1RS)-cis-permethrin 在 KO₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3-phenoxyphenyl)methyl (1R,3S)-3-(2-chloroethynyl)-2,2-dimethylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Superoxide-mediated dehydrohalogenation reactions of the pyrethroid permethrin and other chlorinated pesticides

  摘要：

  DOI：

  10.1016/s0040-4039(00)85557-4
• 作为产物：
  描述：

  (+/-)-cis-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarbonitrile 在 sodium hydroxide 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 17.0h， 生成 (1RS)-cis-permethrin
  参考文献：
  名称：

  Badanyan; Stepanyan; Mikaelyan, Russian Journal of Organic Chemistry, 1997, vol. 33, # 1, p. 34 - 41

  摘要：

  DOI：

文献信息

• Molecular Cloning, Purification, and Biochemical Characterization of a Novel Pyrethroid-Hydrolyzing Esterase from <i>Klebsiella</i> sp. Strain ZD112
  作者：Pei C. Wu、Yu H. Liu、Zhuo Y. Wang、Xiao Y. Zhang、He Li、Wei Q. Liang、Na Luo、Ji M. Hu、Jia Q. Lu、Tian G. Luan、Li X. Cao

  DOI：10.1021/jf052691u

  日期：2006.2.1

  and the organophosphorus insecticide malathion, but also hydrolyzed rho-nitrophenyl esters of various fatty acids, indicating that EstP is an esterase with broad substrates. The K(m) for trans- and cis-permethrin and k(cat)/K(m) values indicate that EstP hydrolyzes both these substrates with higher efficiency than the carboxylesterases from resistant insects and mammals. The catalytic activity of EstP

  来自克雷伯菌的编码拟除虫菊酯水解酯酶（EstP）的基因。菌株ZD112被克隆到大肠杆菌中并测序。对负责estP基因的DNA进行的序列分析揭示了一个1914 bp的开放阅读框，编码一个637个氨基酸残基的蛋白质。使用酯酶和脂肪酶的核苷酸序列和推导的氨基酸序列，通过数据库同源性搜索未发现相似性。EstP在大肠杆菌中异源表达并纯化。通过凝胶过滤测定，天然酶的分子量约为73kDa。十二烷基硫酸钠-聚丙烯酰胺凝胶电泳的结果和推断的EstP氨基酸序列分别表明分子量为73和73.5 kDa，表明EstP是单体。纯化的EstP不仅降解了许多拟除虫菊酯农药和有机磷杀虫剂马拉硫磷，而且还水解了各种脂肪酸的Rho-硝基苯基酯，这表明EstP是具有广泛底物的酯酶。反式和顺氯菊酯的K（m）值和k（cat）/ K（m）值表明，EstP水解这两种底物的效率均高于抗性昆虫和哺乳动物的羧酸酯酶。Hg2 +，Ag +和rho
• Assignment of absolute configurations of permethrin and its synthon 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid by electronic circular dichroism, optical rotation, and X-ray crystallography
  作者：Wolfgang Bicker、Karol Kacprzak、Marcin Kwit、Michael Lämmerhofer、Jacek Gawronski、Wolfgang Lindner

  DOI：10.1016/j.tetasy.2009.03.035

  日期：2009.5

  3-phenoxybenzyl alcohol yielded PM. Electronic circular dichroism (ECD) spectra of DCCA and PM stereoisomers were measured in non-polar (cyclohexane containing 5% v/v 1,2-dichloroethane) and non-protic polar (acetonitrile) solvents. Cotton effects suitable to distinguish the four stereoisomers of each DCCA and PM were obtained. Absolute configurations of DCCA were determined by confrontation of calculated

  生物/毒理学相关手性化合物（如拟除虫菊酯型杀虫剂氯菊酯（PM））的单一立体异构体的可用性以及其绝对构型的可靠测定对于详细研究和正确选择立体选择效应至关重要。在这种情况下，从所有四种立体异构体的对映异构体混合物中分离出3-（2,2-二氯乙烯基）-2,2-二甲基环丙烷羧酸（DCCA），PM的前体，代谢产物和环境降解产物的单一立体异构体通过第一步色谱中的非对映选择性反相分离与第二步中的直接对映异构体分离相结合的两步色谱法，获得了> 99％的过量残留物。用3-苯氧基苄醇酯化DCCA立体异构体得到PM。在非极性（含有5％v / v 1,2-二氯乙烷的环己烷）和非质子极性（乙腈）溶剂中测量DCCA和PM立体异构体的电子圆二色性（ECD）光谱。获得了适合区分每种DCCA和PM的四种立体异构体的棉花效应。DCCA的绝对构型由计算值（使用B3LYP混合函数的时变密度泛函理论）和实验ECD和旋光（OR）数据的
• Method for the synthesis of permethrin
  申请人：BIOPHORE INDIA PHARMACEUTICALS PVT. LTD.

  公开号：US10647655B2

  公开（公告）日：2020-05-12

  An improved method for the synthesis of substantially pure Permethrin having purity greater than 99.5% by Gas Chromatography provided. The embodiments also relates to a purification process of Permethrin by recrystallization from methanol-water mixture.

  本发明提供了一种通过气相色谱法合成纯度大于 99.5%的高纯度氯菊酯的改进方法。本发明还涉及一种通过从甲醇-水混合物中重结晶来提纯氯菊酯的工艺。
• Purification and Characterization of a Novel Pyrethroid Hydrolase from<i> Aspergillus niger</i> ZD11
  作者：Wei Q. Liang、Zhuo Y. Wang、He Li、Pei C. Wu、Ji M. Hu、Na Luo、Li X. Cao、Yu H. Liu

  DOI：10.1021/jf051460k

  日期：2005.9.1

  The pyrethroid pesticides residues on foods and environmental contamination are a public safety concern. Pretreatment with pyrethroid hydrolase has the potential to alleviate the conditions. For this purpose, a fungus capable of using pyrethroid pesticides as a sole carbon source was isolated from the soil and characterized as Aspergillus nigerZD11. A novel pyrethroid hydrolase from cell extract was purified 41.5-fold to apparent homogeneity with 12.6% overall recovery. It is a monomeric structure with a molecular mass of 56 kDa, a pl of 5.4, and the enzyme activity was optimal at 45 degrees C and pH 6.5. The activities were strongly inhibited by Hg2+, Ag+, and p-chloromercuribenzoate, whereas less pronounced effects (5-10% inhibition) were observed in the presence of the remaining divalent cations, the chelating agent EDTA and phenanthroline. The purified enzyme hydrolyzed various insecticides with similar carboxylester. trans-Permethrin is the preferred substrate.
• Insecticidal perhaloalkylvinylcyclopropanecarboxylates
  申请人：FMC Corporation

  公开号：EP0003336B1

  公开（公告）日：1984-02-22