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TDCPP (Tris(1,3-dichloroisopropyl)phosphate) Sale

(Synonyms: 磷酸三(1,3-二氯异丙基)酯,Tris(1,3-dichloroisopropyl)phosphate) 目录号 : GC34128

TDCPP(三(1,3-二氯异丙基)磷酸酯)是磷酸三(2,3-二溴丙基)酯(Tris)的氯化类似物,它是环境中检测到最多的有机磷阻燃剂(OPFR)之一。

TDCPP (Tris(1,3-dichloroisopropyl)phosphate) Chemical Structure

Cas No.:13674-87-8

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10mM (in 1mL DMSO)
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100mg
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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Kinase experiment:

The cellular ATP contents are determined in HCECs grown in DMEM containing 0, 2, 20, or 200 μg/mL TDCPP using a luciferase-based ATP assay kit according to the manufacturer's guideline. Briefly, after 24 h exposure, HCECs are lysed with lysis buffer. Lysates are then centrifuged at 12,000 g at 4°C for 5 min. Then, 100 μL of supernatant is mixed with 100 μL ATP detection working dilution. Luminance is examined by an fluorescence microplate reader[1].

Cell experiment:

To examine the effects of TDCPP on cell viability, HCECs are planted into 96-well plate (100 μL/well) at density of 1×105 cells/mL overnight. Then, the medium is changed into fresh medium containing 0.034, 0.34, 3.4, 34, 68, 136, 272, or 340 μg/mL of TDCPP and solvent vehicle (0.1%, v/v) and incubated for 24 h. Cell viability is detected using CCK-8 cell viability assay kit according to the manufacturer's instructions. After exposure, cellular morphology is observed and recorded by an inverted microscopy[1].

References:

[1]. Xiang P, et al. Effects of organophosphorus flame retardant TDCPP on normal human corneal epithelial cells: Implications for human health. Environ Pollut. 2017 Nov;230:22-30.
[2]. Killilea DW, et al. Flame retardant tris(1,3-dichloro-2-propyl)phosphate (TDCPP) toxicity is attenuated by N-acetylcysteine in human kidney cells. Toxicol Rep. 2017 May 17;4:260-264.

产品描述

TDCPP is a chlorinated analog of tris(2,3-dibromopropyl)phosphate (Tris) which is one of the most detected organophosphorus flame retardants (OPFRs) in the environment.

Exposure to TDCPP does not significantly affect cell viability until at concentration >68 μg/mL. HCECs show a 16% cell viability loss after exposing to 136 μg/mL TDCPP. Moreover, TDCPP induces a sharp decrease in viable cells (87%) after exposing to ≥272 μg/mL TDCPP. Based on cell viability, the LC50 value for TDCPP is 202 μg/mL using a nonlinear regression. Compare to controls, TDCPP-exposed cells exhibit a concentration-dependent increase in apoptosis. Anti-apoptotic Bcl-2 protein expression is increased to 1.4 fold after exposing to 2 μg/mL TDCPP, 1.2-folds at 20 μg/mL but dynamically decreased to 0.4 fold at 200 μg/mL compare to control. The caspase-3 activity is increased to 2.1 folds of the control at 200 μg/mL TDCPP[1]. TDCPP inhibits cell growth at lower concentrations (IC50 of 27 μM), while cell viability and toxicity are affected at higher concentrations (IC50 of 171 μM and 168 μM, respectively)[2].

[1]. Xiang P, et al. Effects of organophosphorus flame retardant TDCPP on normal human corneal epithelial cells: Implications for human health. Environ Pollut. 2017 Nov;230:22-30. [2]. Killilea DW, et al. Flame retardant tris(1,3-dichloro-2-propyl)phosphate (TDCPP) toxicity is attenuated by N-acetylcysteine in human kidney cells. Toxicol Rep. 2017 May 17;4:260-264.

Chemical Properties

Cas No. 13674-87-8 SDF
别名 磷酸三(1,3-二氯异丙基)酯,Tris(1,3-dichloroisopropyl)phosphate
Canonical SMILES O=P(OC(CCl)CCl)(OC(CCl)CCl)OC(CCl)CCl
分子式 C9H15Cl6O4P 分子量 430.9
溶解度 DMSO : ≥ 62.5 mg/mL (145.05 mM);Water : < 0.1 mg/mL (insoluble) 储存条件 Store at -20°C
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1 mM 2.3207 mL 11.6036 mL 23.2072 mL
5 mM 0.4641 mL 2.3207 mL 4.6414 mL
10 mM 0.2321 mL 1.1604 mL 2.3207 mL
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Research Update

Neurotoxicity of Tris (1,3-dichloroisopropyl) phosphate in Caenorhabditis elegans

As a new type of flame retardant, Organic Phosphate Flame Retardant has been widely used worldwide. The purpose of our research is to determine the neurotoxicity of Tris (1,3-dichloroisopropyl) phosphate (TDCPP) to Caenorhabditis elegans and its mechanism. L1 larvae wild-type C. elegans were exposed to different concentrations of TDCPP, and the effects on motor behavior (head thrashes, body bends, pumping times, chemotaxis index), ROS levels, and p38MAPK signaling pathway-related gene expression levels were measured. Three transgenic nematode strains, BZ555, DA1240, and EG1285, were also used to study the effects of TDCPP on nematode dopamine neurons, glutamate neurons, and GABA neurons. The results showed that TDCPP can inhibit the head thrashes and body bends of the nematode, reduce dopamine production, increase the level of ROS in the body, and affect the expression of genes related to the p38MAPK signaling pathway. We next employed ROS production and motor behavior as toxicity assessment endpoints to determine the involvement of p38 MAPK signaling in the regulation of response to TDCPP. The results showed that the nematodes with low expression of pmk-1 were less sensitive to the TDCPP. It was suggested that TDCPP had neurotoxicity and regulated neurotoxicity to C. elegans by activating the p38-MAPK signaling pathway. The research in this article provides important information for revealing the environmental health risks of organophosphorus flame retardants and their toxic mechanism of action.

Particle size-specific distributions and preliminary exposure assessments of organophosphate flame retardants in office air particulate matter

In this study, the concentrations, size-specific distributions, and preliminary exposure assessments of 10 organophosphate flame retardants (OPFRs) were investigated in suspended particulate matter collected from offices. OPFRs were detected in a range of 5.00-147.77 ng/m(3). Tri(chloropropyl) phosphate (TCPP) was the most abundant analog followed by tri(2-chloroethyl) phosphate (TCEP) and triphenyl phosphate (TPhP). Chlorinated OPFRs (TCPP, TCEP, and tris(1,3-dichloroisopropyl) phosphate (TDCPP)) contributed to about 77% of the total OPFRs. Size-specific distributions revealed that TCEP, tri-n-propyl phosphate (TnPP), TCPP, and tri-n-butyl phosphate (TnBP) shared a similar distribution pattern with a peak in the fraction 4.7-5.8 μm. A peak was also found in the distributions of tricresyl phosphate (TCrP), 2-ethylhexyl diphenyl phosphate (EHDPP), and tri(2-ethylhexyl) phosphate (TEHP) but in different fractions. A bimodal distribution was observed for TDCPP, TPhP, and tributoxyethyl phosphate (TBEP). The results of mass median aerodynamic diameter (MMAD) indicated that TDCPP, TCrP, and TEHP were mainly located on ultrafine particles (≤1 μm), while TnPP, TBEP, and EHDPP mainly on fine particles (≤2.5 μm). Furthermore, MMADs of OPFRs were found to be positively correlated with their vapor pressures (Vp) (p < 0.01), indicating that OPFR analogs with low Vp were inclined to adsorb on small size particles. Preliminary exposure assessments suggested a low risk of exposure to OPFRs for people working in such offices, and inhaled OPFRs would mainly deposit in the head region of the respiratory tract.

Flame Retardant Applications in Camping Tents and Potential Exposure

Concern has mounted over health effects caused by exposure to flame retardant additives used in consumer products. Significant research efforts have focused particularly on exposure to polybrominated diphenyl ethers (PBDEs) used in furniture and electronic applications. However, little attention has focused on applications in textiles, particularly textiles meeting a flammability standard known as CPAI-84. In this study, we investigated flame retardant applications in camping tents that met CPAI-84 standards by analyzing 11 samples of tent fabrics for chemical flame retardant additives. Furthermore, we investigated potential exposure by collecting paired samples of tent wipes and hand wipes from 27 individuals after tent setup. Of the 11 fabric samples analyzed, 10 contained flame retardant additives, which included tris(1,3-dichloroisopropyl) phosphate (TDCPP), decabromodiphenyl ether (BDE-209), triphenyl phosphate, and tetrabromobisphenol-A. Flame retardant concentrations were discovered to be as high as 37.5 mg/g (3.8% by weight) in the tent fabric samples, and TDCPP and BDE-209 were the most frequently detected in these samples. We also observed a significant association between TDCPP levels in tent wipes and those in paired hand wipes, suggesting that human contact with the tent fabric material leads to the transfer of the flame retardant to the skin surface and human exposure. These results suggest that direct contact with flame retardant-treated textiles may be a source of exposure. Future studies will be needed to better characterize exposure, including via inhalation and dermal sorption from air.

Comparison of rates of direct and indirect migration of phosphorus flame retardants from flame-retardant-treated polyester curtains to indoor dust

In this study, the pathways for migration of phosphorus flame retardants (PFRs), tris(1,3-dichloroisopropyl) phosphate (TDCPP) and tricresyl phosphate (TCsP) which were detected from curtains often, from flame-retardant-treated polyester curtains to indoor dust were investigated. Two possible migration pathways were compared quantitatively: (1) an indirect pathway in which the PFRs in the curtains first evaporate from the curtains and are then adsorbed onto indoor dust and (2) a direct pathway in which the PFRs are directly transferred to dust placed on the curtains. The contribution of the indirect pathway was evaluated by means of emission cell tests, which showed that the area-specific emission rates from curtains treated with PFRs were 0.044 (TDCPP, Curtain 5), 0.17 (TDCPP, Curtain 8), and 0.060 (TCsP, Curtain 12) μg m-2 h-1 at 20 °C (averaged during 24 h). The contribution of the direct pathway was evaluated by measurement of the time dependence of PFR concentrations on the indoor dust placed on the curtains. These measurements indicated that PFR concentrations on the dust increased with time and that the direct migration rates of PFRs from curtains treated with PFRs were 4.4 (TDCPP, Curtain 5), 12 (TDCPP, Curtain 8), and 7.0 (TCsP, Curtain 12) μg m-2 h-1 at 20 °C (averaged during 24 h), or 71-120 times the indirect migration rate. This result suggests that the direct pathway can be expected to predominate.

Aerobic and Anaerobic Biodegradability of Organophosphates in Activated Sludge Derived From Kitchen Garbage Biomass and Agricultural Residues

Organophosphates (also known as organophosphate esters, OPEs) have in recent years been found to be significant pollutants in both aerobic and anaerobic activated sludge. Food waste, such as kitchen garbage and agricultural residues, can be used as co-substrates to treat the active sludge in sewage treatment plants (STPs). We investigated the biodegradability of nine OPEs derived from kitchen garbage biomass and agricultural residues under different conditions. Under anaerobic conditions, the rate of removal of triphenyl ester OPEs was significantly higher than that of chloride and alkyl OPEs. The addition of FeCl3 and Fe powder increased the rate of degradation of triphenyl ester OPEs, with a DT50 for triphenyl ester OPEs of 1.7-3.8 d for FeCl3 and 1.3-4.7 d for Fe powder, compared to a DT50 of 4.3-6.9 d for the blank control. Addition of an electron donor and a rhamnolipid increased the rate of removal of chlorinated OPEs, with DT50 values for tris(2-carboxyethyl)phosphine) (TCEP) and tris(1,3-dichloroisopropyl)phosphate (TDCPP) of 18.4 and 10.0 d, respectively, following addition of the electron donor, and 13.7 and 3.0 d, respectively, following addition of the rhamnolipid. However, addition of an electron donor, electron acceptor, surfactant, and Fe powder did not always increase the degradation of different kinds of OPEs, which was closely related to the structure of the OPEs. No treatment increased the removal of alkyl OPEs due to their low anaerobic degradability. Tween 80, a non-ionic surfactant, inhibited anaerobic degradation to some degree for all OPEs. Under aerobic conditions, alkyl OPEs were more easily degraded, chlorinated OPEs needed a long adaptation period to degrade and finally attain a 90% removal rate, while the rates of degradation of triphenyl ester OPEs were significantly affected by the concentration of sludge. Higher sludge concentrations help microorganisms to adapt and remove OPEs. This study provides new insights into methods for eliminating emerging pollutants using activated sludge cultured with kitchen garbage biomass and agricultural residues.