p,p'-Dicofol
(Synonyms: 三氯杀螨醇) 目录号 : GC47852
An organochlorine pesticide
Cas No.:115-32-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >85.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
p,p'-Dicofol is an organochlorine pesticide that is active against mites.1 It is an agonist of the estrogen receptor (EC50 = 1.6 µM for human recombinant receptors).
1.Hoekstra, P.F., Burnison, B.K., Garrison, A.W., et al.Estrogenic activity of dicofol with the human estrogen receptor: Isomer- and enantiomer-specific implicationsChemosphere64(1)174-177(2006)
| Cas No. | 115-32-2 | SDF | |
| 别名 | 三氯杀螨醇 | ||
| Canonical SMILES | ClC1=CC=C(C(C(Cl)(Cl)Cl)(O)C2=CC=C(Cl)C=C2)C=C1 | ||
| 分子式 | C14H9Cl5O | 分子量 | 370.5 |
| 溶解度 | DMSO: Slightly soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.6991 mL | 13.4953 mL | 26.9906 mL |
| 5 mM | 0.5398 mL | 2.6991 mL | 5.3981 mL |
| 10 mM | 0.2699 mL | 1.3495 mL | 2.6991 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Mechanism and kinetics studies of the atmospheric oxidation of p,p'-Dicofol by OH and NO3 radicals
Chemosphere 2019 Mar;219:645-654.PMID:30557720DOI:10.1016/j.chemosphere.2018.12.048.
As an effective organochlorine pesticide, Dicofol has been extensively applied in more than 30 countries for protecting over 60 different crops. Considering its large consumption and potential adverse effect on human health (endocrine disrupting and carcinogenicity), the fate of Dicofol sprayed into the air is of public concern. In this study, we conducted a comprehensive study on the reaction mechanisms of p,p'-Dicofol with OH and NO3 radicals using DFT method. Comparing the abstrations by OH and NO3 radical, OH and NO3 radical addition reactions are predominant due to the lower potential barriers and stronger heat release. The phenolic substances (P1P5), epoxides (P11 and P15), dialdehyde (P13) and other species (P8, P9, P10 and P14) are generated by OH additions and their subsequent reactions while OH abstraction reactions produce DCBP, P7 and chlorphenyl radical. Particularly, NO3 additions and their subsequent reactions yield dialdehydes (P16 and P17) and 2,8-DCDD, which is the first report of the generation of dioxin from atmospheric oxidation of p,p'-Dicofol. Additionally, based on the structure optimization and energy calculation, rate constants and Arrhenius formulas of the elementary reactions of p,p'-Dicofol with OH and NO3 radicals were obtained over the temperature range of 280-380 K and at 1 atm. The rate constants for the reactions of p,p'-Dicofol with OH and NO3 radicals are 1.51 × 10-12 and 8.88 × 10-14 cm3 molecule-1 s-1, respectively. The lifetime (τTotal) of p,p'-Dicofol determined by the reactions of OH and NO3 radical is 5.86 h, indicating a potential long-range transport in the atmosphere.
Estrogenic activity of dicofol with the human estrogen receptor: Isomer- and enantiomer-specific implications
Chemosphere 2006 Jun;64(1):174-7.PMID:16337670DOI:10.1016/j.chemosphere.2005.10.043.
Dicofol is a non-systemic acaricide/miticide currently registered in the US and Canada for use on a wide variety of crops. This agrochemical has been identified as a potential candidate substance for the United Nations Economic Commission for Europe (UN-ECE) Persistent Organic Pollutant (POP) Protocol and implicated as a potential "endocrine disrupting compound". The technical product is usually synthesized from technical DDT and consists of approximately 80% and 20% of p,p'- and o,p'-dicofol isomers. The o,p'-substituted isomer of dicofol is chiral and may have enantiomer-specific activity; however, the stereospecific activity of o,p'-dicofol has not been reported. In this study, we examined the isomer- and enantiomer-specific endocrine disruption potential of dicofol using yeast-based steroid hormone receptor gene transcription assay designed with the human estrogen receptor (hER). Estrogenic activity of (+)-17-beta estradiol (positive control), p,p'-Dicofol, racemic o,p'-dicofol [(+/-)-o,p'-dicofol] and the individual o,p'-dicofol enantiomers was measured via quantification of beta-galactosidase. The (+/-)-o,p'- and p,p'-Dicofol were weak estrogen mimics (EC(50): 4.2 x 10(-6) and 1.6 x 10(-6)M, respectively) relative to estradiol (3.7 x 10(-10)M). For o,p'-dicofol, the beta-galactosidase induction by (-)-o,p'-dicofol (EC(50): 5.1 x 10(-7)M) was greater than the racemic mixture. However, the (+)-o,p'-dicofol enantiomer was found to have negligible estrogenic activity. These data indicate that dicofol is a weak hER agonist due to activity of the achiral p,p'-isomer and (-)-o,p'-substituted enantiomer and emphasizes the influence of chemical structure and configuration on biological responses to exposure from chiral compounds.
Evaluation of the impact of in-ovo exposure to dicofol on avian reproduction
Environ Toxicol Chem 2010 Oct;29(10):2316-22.PMID:20872696DOI:10.1002/etc.274.
To assess the possible impact of the currently used organochlorine insecticide, dicofol, on the development and reproduction of avian species, in ovo exposure experiments to its p,p' and o,p' isomers were performed using Japanese quail (Coturnix japonica) eggs. o,p'-Dicofol (0.3-100 µg/g of egg) and p,p'-Dicofol (3-100 µg/g) were injected into the yolk prior to incubation and hatched chicks were raised to adulthood. In ovo treatment with o,p'-dicofol impaired the eggshell-forming ability of female quails after sexual maturity; eggshell strength, mass, and thickness were significantly reduced at minimum dosages of 3, 1, and 0.3 µg/g, respectively. o,p'-Dicofol also caused abnormal development of the right oviduct independently of the dose; even a female exposed at the lowest dose tested (0.3 µg/g) possessed a large right oviduct. Minor but significant mass reductions of both the left oviduct and the testis were observed only at 10 µg/g. In addition, the transcript of a gene encoding cytochrome P450 cholesterol side-chain cleavage in the gonads of male hatchlings was markedly reduced by o,p'-dicofol treatment. p,p'-Dicofol did not have any marked effects on the reproductive systems, although some significant changes in eggshell formation and oviduct morphology were observed. The results indicate that transovarian exposure, especially to o,p'-dicofol, could damage avian reproduction mainly through eggshell thinning.
Chromatographic determination of dicofol and metabolites in egg yolks
Arch Environ Contam Toxicol 1990 Jan-Feb;19(1):154-6.PMID:2331150DOI:10.1007/BF01059825.
Egg yolk was spiked with p,p'-Dicofol (p,p'-DCF) (0.1-2.0 micrograms/gm), p,p'-dichlorobenzophenone (p,p'-DCBP) (0.1-2.0 micrograms/gm), and 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (p,p'-DDE) (0.05-1.0 micrograms/gm). The fortified egg yolk (2-5 g) was mixed with acetonitrile to extract non-fat organic materials. After removal of acetonitrile, the spiked chemicals were separated with a column chromatograph packed with acid alumina. Recovery efficiencies for p,p'-DCBP and p,p'-DDE were determined by gas chromatography, and for p,p'-Dicofol by high performance liquid chromatography. The recovery efficiencies for p,p'-Dicofol, p,p'-DCBP and p,p'-DDE were 77.2-93.8%, 84.1-101.1%, and 88.5-96.0%, respectively.
Sources and transformation pathways for dichlorodiphenyltrichloroethane (DDT) and metabolites in soils from Northwest Fujian, China
Environ Pollut 2018 Apr;235:560-570.PMID:29329097DOI:10.1016/j.envpol.2017.12.071.
Dicofol (2,2,2-trichloro-1,1-bis-(p-chlorophenyl)ethanol) found in the environment is not only a miticide originated from commercial use, but also a metabolite of dichlorodiphenyltrichloroethane (DDT), which is often overlooked. To verify the sources and transformation pathways of DDT and related metabolites in soils, we measured p,p'-(dicofol + DBP) (sum of p,p'-Dicofol and 4,4'-dichlorobenzophenone), DDT and six metabolites in soils from Northwest Fujian, China. The ratios of 1,1,1-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane (o,p'-DDT)/1,1,1-trichloro-2,2-bis-(p-chlorophenyl)ethane (p,p'-DDT) and the mass balance demonstrated that p,p'-(dicofol + DBP) predominantly originated from p,p'-DDT transformation rather than from actual dicofol application. p,p'-(dicofol + DBP) accounted for 45.0% as the primary metabolites of DDT in this study, more than 1,1-dichloro-2,2-bis-(p-chlorophenyl)ethylene (p,p'-DDE) and 1,1-dichloro-2,2-bis-(p-chlorophenyl)ethane (p,p'-DDD), which might lead to large overestimations of the fresh DDT input by using the traditional ratio of (∑2DDD + ∑2DDE)/∑2DDT (with all o,p'- and p,p'- isomers included). In paddy fields where the conditions alternate between aerobic (dry period) and anaerobic (wet period), both p,p'-DDD and p,p'-DDE were likely to degrade to 1-chloro-2,2-bis-(p-chlorophenyl)ethylene (p,p'-DDMU), which further transformed to 2,2-bis(p-chlorophenyl)ethylene (p,p'-DDNU). Degradation of p,p'-DDMU to p,p'-DDNU mainly occurred in waterlogged paddy soils. However, p,p'-DDNU might not transform to other higher-order metabolites in aerobic surface soils. Overall, our study confirmed p,p'-(dicofol + DBP) as metabolites of p,p'-DDT, suggested DDE and DDD were parallel precursors of DDMU, and further verified the transformation pathways of DDT in surface soils.