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Triclocarban (3,4,4′-Trichlorocarbanilide) Sale

(Synonyms: 三氯卡班; 3,4,4′-Trichlorocarbanilide) 目录号 : GC32132

Triclocarban is an antibacterial agent common used in personal care products.

Triclocarban (3,4,4′-Trichlorocarbanilide) Chemical Structure

Cas No.:101-20-2

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10mM (in 1mL DMSO)
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500mg
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实验参考方法

Animal experiment:

Rats: Sprague Dawley rats are provided control, 0.2% weight/weight (w/w), or 0.5% w/w triclocarban -supplemented chow through a series of 3 experiments that limited exposure to critical growth periods: gestation, gestation and lactation, or lactation only (cross-fostering) to determine the susceptible windows of exposure for developmental consequences[3].

References:

[1]. Kanbara Y, et al. Nanomolar concentration of triclocarban increases the vulnerability of rat thymocytes to oxidative stress. J Toxicol Sci. 2013 Feb;38(1):49-55.
[2]. Huang H, et al. The in vitro estrogenic activities of triclosan and triclocarban. J Appl Toxicol. 2014 Sep;34(9):1060-7.
[3]. Kennedy RC, et al. Early life triclocarban exposure during lactation affects neonate rat survival. Reprod Sci. 2015 Jan;22(1):75-89.

产品描述

Triclocarban is an antibacterial agent common used in personal care products.

Chemical Properties

Cas No. 101-20-2 SDF
别名 三氯卡班; 3,4,4′-Trichlorocarbanilide
Canonical SMILES ClC1=CC=C(C=C1)NC(NC2=CC=C(C(Cl)=C2)Cl)=O
分子式 C13H9Cl3N2O 分子量 315.58
溶解度 DMSO : ≥ 150 mg/mL (475.32 mM) 储存条件 Store at -20°C
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1 mM 3.1688 mL 15.8438 mL 31.6877 mL
5 mM 0.6338 mL 3.1688 mL 6.3375 mL
10 mM 0.3169 mL 1.5844 mL 3.1688 mL
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Research Update

Evaluation of 3,4,4,9-trichlorocarbanilide to zebrafish developmental toxicity based on transcriptomics analysis

Chemosphere 2021 Sep;278:130349.PMID:33838424DOI:10.1016/j.chemosphere.2021.130349.

Triclocarban (TCC), considered an endocrine-disrupting, persistent, and bioaccumulating organic matter, has attracted a great deal of attention for its pollution and health risks. However, studies on its toxicological mechanism, especially for embryo development are limited. This article explores the cardiac developmental toxicity induced in zebrafish embryos after exposure to different TCC concentrations. First, liquid chromatography-tandem mass spectrometry was used in detecting TCC in embryos in vivo after exposure to various TCC. Results showed that embryonic TCC content reached 9.23 ng after exposure to 300 μg/L TCC, the heart rates of the embryos markedly decreased, heart abnormalities significantly increased. In addition, obvious pericardial effusion was observed in the larvae. Through transcriptome sequencing, 200 differential gene expression (DGE) patterns were detected in the TCC (300 μg/L) experimental and control groups. The results of GO function analysis and KEGG pathway of DGE showed that aryl hydrocarbon receptor (AhR) activation and cyp-related genes (cyp1a, cyp1b1 and cyp1c) were significantly up-regulated. these affected the normal development of zebrafish embryonic heart, tissue edema, and hemorrhage. TCC exhibited strong cardiac teratogenic effects and developmental toxicity, which is partly related to AhR activation. Transcriptome-based results are helpful in precisely determining the risk of TCC exposure. The potential mechanism between TCC and AhR should be further investigated.

Extraction of 3,4,4'-Trichlorocarbanilide from Rat Fecal Samples for Determination by High Pressure Liquid Chromatography-Tandem Mass Spectrometry

Int J Environ Res Public Health 2015 Jul 15;12(7):8125-32.PMID:26184276DOI:10.3390/ijerph120708125.

Triclocarban (3,4,4'-Trichlorocarbanilide; TCC) in the environment has been well documented. Methods have been developed to monitor TCC levels from various matrices including water, sediment, biosolids, plants, blood and urine; however, no method has been developed to document the concentration of TCC in fecal content after oral exposure in animal studies. In the present study, we developed and validated a method that uses liquid extraction coupled with HPLC-MS/MS determination to measure TCC in feces. The limit of detection and limit of quantitation in control rats without TCC exposure was 69.0 ng/g and 92.9 ng/g of feces, respectively. The base levels of TCC in feces were lower than LOD. At 12 days of treatment, the fecal TCC concentration increased to 2220 µg/g among 0.2% w/w exposed animals. The concentration in fecal samples decreased over the washout period in 0.2% w/w treated animals to 0.399 µ/g feces after exposure was removed for 28 days. This method required a small amount of sample (0.1 g) with simple sample preparation. Given its sensitivity and efficiency, this method may be useful for monitoring TCC exposure in toxicological studies of animals.

Bioelectrochemical catabolism of Triclocarban through the cascade acclimation of triclocarban-hydrolyzing and chloroanilines-oxidizing microbial communities

Environ Res 2022 Jul;210:112880.PMID:35123970DOI:10.1016/j.envres.2022.112880.

Chlorinated antimicrobial Triclocarban (3,4,4'-trichlorocarbanilide, TCC) is an emerging refractory contaminant omnipresent in various environments. Preferential microbial hydrolysis of TCC to chloroanilines is essential for its efficient mineralization. However, the microbial mineralization of TCC in domestic wastewater is poorly understood. Here, the bioelectrochemical catabolism of TCC to chloroanilines (3,4-dichloroaniline and 4-chloroaniline) and then to CO2 was realized through the cascade acclimation of TCC-hydrolyzing and chloroanilines-oxidizing microbial communities. The biodegradation of chloroanilines was obviously enhanced in the bioelectrochemical reactors. Pseudomonas, Diaphorobacter, and Sphingomonas were the enriched TCC or chloroanilines degraders in the bioelectrochemical reactors. The addition of TCC enhanced the synergistic effect within functional microbial communities based on the feature of the phylogenetic ecological networks. This study provides a new idea for the targeted domestication and construction of functionally differentiated microbial communities to efficiently remove TCC from domestic wastewater through a green and low-carbon bioelectrochemical method.

Characterization of triclosan-induced hepatotoxicity and triclocarban-triggered enterotoxicity in mice by multiple omics screening

Sci Total Environ 2022 Sep 10;838(Pt 4):156570.PMID:35690209DOI:10.1016/j.scitotenv.2022.156570.

Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether, TCS) and Triclocarban (3,4,4'-trichloro-carbanilide, TCC) are two antimicrobial agents commonly used for personal care products. Previous studies primarily focused on respective harmful effects of TCS and TCC. In terms of their structural similarities and differences, however, the structure-toxicity relationships on health effects of TCS and TCC exposure remain unclear. Herein, global 1H NMR-based metabolomics was employed to screen the changes of metabolic profiling in various biological matrices including liver, serum, urine, feces and intestine of mice exposed to TCS and TCC at chronic and acute dosages. Metagenomics was also applied to analyze the gut microbiota modulation by TCS and TCC exposure. Targeted MS-based metabolites quantification, histopathological examination and biological assays were subsequently conducted to supply confirmatory information on respective toxicity of TCS and TCC. We found that oral administration of TCS mainly induced significant liver injuries accompanied with inflammation and dysfunction, hepatic steatosis fatty acids and bile acids metabolism disorders; while TCC exposure caused marked intestine injuries leading to striking disruption of colonic morphology, inflammatory status and intestinal barrier integrity, intestinal bile acids metabolism and microbial community. These comparative results provide novel insights into structure-dependent mechanisms of TCS-induced hepatotoxicity and TCC-triggered enterotoxicity in mice.

Nationwide reconnaissance of five parabens, triclosan, Triclocarban and its transformation products in sewage sludge from China

J Hazard Mater 2019 Mar 5;365:502-510.PMID:30466048DOI:10.1016/j.jhazmat.2018.11.021.

China's rapid growth of both population size and sanitation infrastructure have created a heightened need for responsible management of sewage sludge. We applied liquid chromatography in conjunction with isotope dilution tandem mass spectrometry to measure multiple endocrine disrupting antimicrobials and their transformation products in 100 sewage sludge samples collected across 21 Chinese provinces/districts. Occurrences (detection frequencies) and concentrations (ng/g dry weight) were as follows: triclosan (99%; <4-4870), Triclocarban (95%; <3-43,300), 2'-hydroxy-triclocarban (94%; <1-2340), 3'-hydroxy-triclocarban (91%; <1-1250), 3,3',4,4'-tetrachlorocarbanilide (100%; 22-580), dichlorocarbanilide (94%; <2-23,890), monocarbanilide (92%; <2-120), carbanilide (90%; <3-1,340), and five parabens: methyl- (98%; <2-630), ethyl- (96%; <2-170), propyl- (99%; <2-27), butyl- (89%; <2-11) and benzyl-paraben (7%; <2-12). The transformation products of Triclocarban were measured for the first time in Chinese wastewater system, and ratios of transformation products to parental Triclocarban indicate ongoing Triclocarban dechlorination during wastewater treatment. Contaminant profiles and concentrations differed by region, treatment capacity, and wastewater type. Extrapolation of collected data yielded an estimate for the total mass of 13 analytes sequestered in Chinese sewage sludge of 68 t/y with an upper bound of 400 t/y. This China-wide survey established baseline levels of selected antimicrobials in sludges whose current disposal is performed with little regulatory oversight and enforcement.