Tris(2-butoxyethyl) phosphate
(Synonyms: TBEP) 目录号 : GC26011Oral exposure to low-dose Tris (2-butoxyethyl) phosphate (TBEP) levels equivalent to tolerable daily intake may exacerbate allergic pulmonary inflammation by promoting a skewed T-helper 2 cell response, upregulation of ERα and dysregulation of both MLN and BM microenvironments.
Cas No.:78-51-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
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- Datasheet
Oral exposure to low-dose Tris (2-butoxyethyl) phosphate (TBEP) levels equivalent to tolerable daily intake may exacerbate allergic pulmonary inflammation by promoting a skewed T-helper 2 cell response, upregulation of ERα and dysregulation of both MLN and BM microenvironments.
[1] Yanagisawa R, et al. J Appl Toxicol. 2020 Nov;40(11):1498-1510.
| Cas No. | 78-51-3 | SDF | Download SDF |
| 别名 | TBEP | ||
| 分子式 | C18H39O7P | 分子量 | 398.47 |
| 溶解度 | 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 | 2.5096 mL | 12.548 mL | 25.096 mL |
| 5 mM | 0.5019 mL | 2.5096 mL | 5.0192 mL |
| 10 mM | 0.251 mL | 1.2548 mL | 2.5096 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 |
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| % 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。
Tris(2-butoxyethyl) phosphate (TBEP): A flame retardant in solid waste display hepatotoxic and carcinogenic risks for humans
Chemosphere 2022 Jun;296:133977.PMID:35216979DOI:10.1016/j.chemosphere.2022.133977.
Recent reports have confirmed that Tris(2-butoxyethyl) phosphate (TBEP), an organophosphorous flame retardants (OPFRs), profoundly detected in the dust from solid waste (SW), e-waste dumping sites, landfills, and wastewater treatment facilities. Herein, we evaluated the hepatotoxic and carcinogenic potential of TBEP in human liver cells (HepG2). HepG2 cells exhibited cytotoxicity after 3 days of exposure, especially at greater concentrations (100-400 μM). TBEP induced severe DNA damage and cell cycle disturbances that trigger apoptosis in HepG2. TBEP treated cells showed an elevated level of esterase, nitric oxide (NO), reactive oxygen species (ROS), and influx of Ca2+ in exposed cells. Thereby, causing oxidative stress and proliferation inhibition. TBEP exposed HepG2 cells exhibited dysfunction in mitochondrial membrane potential (ΔΨm). Immunofluorescence analysis demonstrated cytoplasmic and nucleolar localization of DNA damage (P53) and apoptotic (caspase 3 and 9) proteins in HepG2 grown in the presence of TBEP for 3 days. Within the cohort of 84 genes of cancer pathway, 10 genes were upregulated and 3 genes were downregulated. The transcriptomic and toxicological data categorically emphasize that TBEP is hepatotoxic, and act as a putative carcinogenic agent. Thereby, direct or indirect ingestion of TBEP containing dusts by workers involved in handling and disposal of SW, as well as residents living nearby the disposal areas are prone to its adverse health risks.
Exposure to Tris(2-butoxyethyl) phosphate induces abnormal sperm morphology and testicular histopathology in male rats
Ecotoxicol Environ Saf 2022 Aug;241:113718.PMID:35660377DOI:10.1016/j.ecoenv.2022.113718.
Tris(2-butoxyethyl) phosphate (TBEP) is one of the most abundant organophosphate flame retardants in the environment. This study aimed to evaluate the effect of TBEP exposure during adolescence on male reproductive function in adult rats. Male Sprague-Dawley rats were treated with 20 and 200 mg/kg body weight of TBEP or corn oil from postnatal day (PND) 42 to PND 105. A significant increase in the proportion of sperm with abnormal morphology (flattened head and bent tail) and superoxide anion (O2-.) production in the sperm of the 200 mg/kg treated group was observed (p < 0.05). Excessive production of sperm hydrogen peroxide (H2O2) was found in both the 20 and 200 mg/kg treatment groups (p < 0.05). Disruption of testicular structure was observed in the 20 and 200 mg/kg treated groups and seminiferous tubule degeneration was observed in the 200 mg/kg treated group. Our study demonstrated the adverse effects of TBEP on male reproductive function in rats.
Toxicokinetic of Tris(2-butoxyethyl) phosphate (TBOEP) in humans following single oral administration
Arch Toxicol 2018 Feb;92(2):651-660.PMID:28956089DOI:10.1007/s00204-017-2078-7.
Tris(2-butoxyethyl) phosphate (TBOEP; 20 µg/kg b.w.) was orally administered to three female and three male volunteers. In urine samples collected for 39 h three metabolites of TBOEP were quantitated. bis(2-butoxyethyl) phosphate (BBOEP), tris(2-(3-hydroxy)butoxyethyl) phosphate (OH-TBOEP), bis(2-butoxyethyl)-(2-hydroxyethyl) phosphate (BBOEHEP) were observed in all urine samples within the first 7 h with highest concentration for BBOEHEP. C max of OH-TBOEP was in the range of 2-4 h and t 1/2 was between 1.5 and 6.1 h. Similar results were obtained for BBOEHEP. In contrast BBOEP showed several maxima within 25 h and, therefore, no toxicokinetic data were calculated. As proof of concept 54 urine samples of children staying at day-care centers in Germany were analysed for all 3 biomarkers. Only BBOEP and BBOEHEP were detected in about 80% of the samples with a median of 0.16 µg/l for BBOEP and 0.18 µg/l for BBOEHEP. A recalculation of daily intake (DI) based on BBOEHEP resulted in a clear undercut of the current reference dose of 50 µg/kg per day. As observed in other studies a calculation of the DI based on the dust concentrations and oral uptake of 20 mg of dust for 8 h for young children results in considerably higher DI but would also not exceed the RfD.
In vitro biotransformation of Tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum
Toxicol Appl Pharmacol 2015 Apr 15;284(2):246-53.PMID:25681655DOI:10.1016/j.taap.2015.01.021.
Tris(2-butoxyethyl) phosphate (TBOEP) is a plasticizer present in indoor dust, reaching levels of several micrograms per gram. Such levels could lead to significant daily exposure of adults and children. Currently, no toxicokinetic data are available to estimate TBOEP clearance in humans after uptake and therefore, one objective of this study was to investigate intrinsic clearance of TBOEP by human liver microsome (HLM) and serum enzymes. Another objective was to generate information to identify and prioritize several metabolites of TBOEP for investigation of human exposure by biomonitoring. 1D and 2D-NMR methodologies were successfully applied on a mixture of the metabolites to confirm the structure of 3-HO-TBOEP (bis(2-butoxyethyl) 3-hydroxyl-2-butoxyethyl phosphate) and to tentatively assign structures to 1-HO-TBOEP and 2-HO-TBOEP. HO-TBOEP isomers and bis(2-butoxyethyl) phosphate (BBOEP), bis(2-butoxyethyl) hydroxyethyl phosphate (BBOEHEP) were further monitored by liquid chromatography-tandem mass spectrometry. Rates of formation of BBOEHEP and HO-TBOEP metabolites by liver enzymes were best described by the Michaelis-Menten model. Apparent Km values for BBOEHEP, 3-HO-TBOEP, and sum of 1- and 2-HO-TBOEP isomer formation were 152, 197 and 148μM, respectively. Apparent Vmax values for the formation of BBOEHEP, 3-HO-TBOEP, and the sum of 1- and 2-HO-TBOEP isomers were 2560, 643, and 254pmol/min/mg protein, respectively. No detectable formation of BBOEP occurred with liver or serum enzymes. Our findings indicate that intrinsic clearance of TBOEP is mainly catalyzed by oxidative enzymes in the liver and that its major in vitro metabolite is BBOEHEP. These findings can be applied in human biomonitoring studies and risk assessment.
Meta-omics elucidates key degraders in a bacterial Tris(2-butoxyethyl) phosphate (TBOEP)-degrading enrichment culture
Water Res 2023 Apr 15;233:119774.PMID:36848852DOI:10.1016/j.watres.2023.119774.
Organophosphate esters (OPEs) are emerging contaminants of growing concern, and there is limited information about the bacterial transformation of OPEs. In this study, we investigated the biotransformation of Tris(2-butoxyethyl) phosphate (TBOEP), a frequently detected alkyl-OPE by a bacterial enrichment culture under aerobic conditions. The enrichment culture degraded 5 mg/L TBOEP following the first-order kinetics with a reaction rate constant of 0.314 h-1. TBOEP was mainly degraded via ether bond cleavage, evidenced by the production of bis(2-butoxyethyl) hydroxyethyl phosphate, 2-butoxyethyl bis(2-hydroxyethyl) phosphate, and 2-butoxyethyl (2-hydroxyethyl) hydrogen phosphate. Other transformation pathways include terminal oxidation of the butoxyethyl group and phosphoester bond hydrolysis. Metagenomic sequencing generated 14 metagenome-assembled genomes (MAGs), showing that the enrichment culture primarily consisted of Gammaproteobacteria, Bacteroidota, Myxococcota, and Actinobacteriota. One MAG assigned to Rhodocuccus ruber strain C1 was the most active in the community, showing upregulation of various monooxygenase, dehydrogenase, and phosphoesterase genes throughout the degradation process, and thus was identified as the key degrader of TBOEP and the metabolites. Another MAG affiliated with Ottowia mainly contributed to TBOEP hydroxylation. Our results provided a comprehensive understanding of the bacterial TBOEP degradation at community level.