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Bis(2-ethylhexyl) phthalate

Katalog-Nr.GC38654

Bis(2-ethylhexyl)phthalat (Bis(2-ethylhexyl)phthalat) ist ein kÖrpereigener Metabolit.

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Bis(2-ethylhexyl) phthalate Chemische Struktur

Cas No.: 117-81-7

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Sample solution is provided at 25 µL, 10mM.

Description of Bis(2-ethylhexyl) phthalate

Bis(2-ethylhexyl) phthalate, commonly referred to as DEHP, is a synthetic compound primarily used as a plasticizer[1]. Exposure to Bis(2-ethylhexyl) phthalate can have various adverse effects on organisms, such as impaired reproduction and development, cancer, altered metabolism, and neurological and behavioral disorders[2].

In vitro, Bis(2-ethylhexyl) phthalate (50μM and 150μM; 48h) and MEHP induce glucose and lipid metabolic abnormalities in hepatocytes[3]. Bis(2-ethylhexyl) phthalate (0-80µM; 48h) significantly inhibited mouse TM3 Leydig cells viability and induced cell apoptosis[4].

In vivo, Bis(2-ethylhexyl) phthalate (5/10mg/kg/day; 16 weeks; p.o.) exposure elevates plasma glucose and disrupts hepatic lipid metabolism in mice[3]. Chronic, low-level exposure to Bis(2-ethylhexyl) phthalate (37µg/kg; 34 days; p.o.) enhances OVA-induced allergic lung inflammation in mice[5]. Prenatal exposure to Bis(2-ethylhexyl) phthalate (20 and 200μg/kg/day and 200, 500 and 750mg/kg/day; p.o.) disrupts ovarian function in a transgenerational manner in female mice[6].

References:
[1] Gaur K, Varshney H, Subhan I, Fatima J, Jyoti S, Siddique YH. Evaluation of Bis(2-ethylhexyl) phthalate toxicity on the third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ) Bg9. Food Chem Toxicol. 2024 Feb;184:114425.
[2] Martínez-Razo LD, Martínez-Ibarra A, Vázquez-Martínez ER, Cerbón M. The impact of Di-(2-ethylhexyl) Phthalate and Mono(2-ethylhexyl) Phthalate in placental development, function, and pathophysiology. Environ Int. 2021 Jan;146:106228.
[3] Wei X, Yang D, Zhang B, Fan X, Du H, Zhu R, Sun X, Zhao M, Gu N. Di-(2-ethylhexyl) phthalate increases plasma glucose and induces lipid metabolic disorders via FoxO1 in adult mice. Sci Total Environ. 2022 Oct 10;842:156815.
[4] Sun Y, Shen J, Zeng L, Yang D, Shao S, Wang J, Wei J, Xiong J, Chen J. Role of autophagy in di-2-ethylhexyl phthalate (DEHP)-induced apoptosis in mouse Leydig cells. Environ Pollut. 2018 Dec;243(Pt A):563-572.
[5] Tseng HH, Li CY, Wu ST, Su HH, Wong TH, Wu HE, Chang YW, Huang SK, Tsai EM, Suen JL. Di-(2-ethylhexyl) Phthalate Promotes Allergic Lung Inflammation by Modulating CD8α+ Dendritic Cell Differentiation via Metabolite MEHP-PPARγ Axis. Front Immunol. 2022 May 19;13:581854.
[6] Rattan S, Brehm E, Gao L, Niermann S, Flaws JA. Prenatal exposure to di(2-ethylhexyl) phthalate disrupts ovarian function in a transgenerational manner in female mice. Biol Reprod. 2018 Jan 1;98(1):130-145.

Protocol of Bis(2-ethylhexyl) phthalate

Cell experiment [1]:

Cell lines

Mouse TM3 Leydig cells

Preparation Method

TM3 cells were seeded at 1 × 104 cells per well in a 96-well plate and treated with the indicated concentrations of Bis(2-ethylhexyl) phthalate (0-80µM) in the presence or absence of N-Acetyl-L-cysteine (NAC) (5mM), or 3-Methyladenine (3-MA) (1mM) for 48h. Cell viability was determined by adding MTT (final concentration: 0.5 mg/mL), and the absorbance of the samples was measured at a wavelength of 570nm using a spectrophotometer.

Reaction Conditions

0-80µM; 48h

Applications

Bis(2-ethylhexyl) phthalate significantly inhibited mouse TM3 Leydig cells viability and induced cell apoptosis.
Animal experiment [2]:

Animal models

Female BALB/c mice (6–8 weeks of age)

Preparation Method

To mimic the exposure that humans typically encounter in daily life, female mice were administered a daily oral gavage of Bis(2-ethylhexyl) phthalate or MEHP at the human TDI dose determined by the EU Scientific Committee for Toxicity, Ecotoxicity, and the Environment , which is 37μg/kg BW, for a study period of 34 days. After the initial administration of phthalate for 20 consecutive days, the mice were immunized with OVA, to induce mild allergic lung inflammation. Control mice were orally administered 0.33% ethanol in corn oil, as a vehicle control.

Dosage form

37µg/kg; 34 days; p.o.

Applications

Chronic, low-level exposure to Bis(2-ethylhexyl) phthalate enhances OVA-induced allergic lung inflammation in mice.

References:
[1] Sun Y, Shen J, Zeng L, Yang D, Shao S, Wang J, Wei J, Xiong J, Chen J. Role of autophagy in di-2-ethylhexyl phthalate (DEHP)-induced apoptosis in mouse Leydig cells. Environ Pollut. 2018 Dec;243(Pt A):563-572.
[2] Tseng HH, Li CY, Wu ST, Su HH, Wong TH, Wu HE, Chang YW, Huang SK, Tsai EM, Suen JL. Di-(2-ethylhexyl) Phthalate Promotes Allergic Lung Inflammation by Modulating CD8?+ Dendritic Cell Differentiation via Metabolite MEHP-PPAR? Axis. Front Immunol. 2022 May 19;13:581854.
 

Chemical Properties of Bis(2-ethylhexyl) phthalate

Cas No. 117-81-7 SDF
Canonical SMILES O=C(C1=CC=CC=C1C(OCC(CC)CCCC)=O)OCC(CC)CCCC
Formula C24H38O4 M.Wt 390.56
Löslichkeit DMSO: 150 mg/mL (384.06 mM) Storage Store at -20°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Bis(2-ethylhexyl) phthalate

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.5604 mL 12.8021 mL 25.6043 mL
5 mM 512.1 μL 2.5604 mL 5.1209 mL
10 mM 256 μL 1.2802 mL 2.5604 mL
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Berechnen

In vivo Formulation Calculator (Clear solution) of Bis(2-ethylhexyl) phthalate

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.

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