Phthalic acid mono-2-ethylhexyl ester (Synonyms: MEHP, Mono-2-ethylhexyl Phthalate) |
Catalog No.GC36902
One-Click Copy Product Info
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Phthalic acid mono-2-ethylhexyl ester, a major bioactive metabolite of diethylhexyl phthalate (DEHP), exhibiting anti-estrogenic (IC50=125μM) and anti-androgenic effects (IC50=736μM).
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 4376-20-9
Sample solution is provided at 25 µL, 10mM.
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Phthalic acid mono-2-ethylhexyl ester, a major bioactive metabolite of diethylhexyl phthalate (DEHP), exhibiting anti-estrogenic (IC50=125μM) and anti-androgenic effects (IC50=736μM) [1]. Phthalic acid mono-2-ethylhexyl ester impairs DNA methylation, histone modifications and levels of miRNAs and lncRNAs induce alterations in several placental functions[2]. Phthalic acid mono-2-ethylhexyl ester has been widely used to decrease estradiol and progesterone production in preovulatory granulosa cells[3].
In vitro, Phthalic acid mono-2-ethylhexyl ester treatment for 72h significantly inhibited the viability of TK6 cells, with an IC50 value of 80μM[4]. Treatment with 100μM Phthalic acid mono-2-ethylhexyl ester for 24 hours significantly increased the triglyceride levels in HepG2 cells, upregulated the expression of SREBP-1c and ChREBP genes, and enhanced the protein expressions of ChREBP1, ACC, FAS and SCD[5]. Treatment with 200μM Phthalic acid mono-2-ethylhexyl ester for 24 hours significantly inhibited the invasion of HTR-8/SVneo cells and activated the PPARγ pathway[6]. Phthalic acid mono-2-ethylhexyl ester (100μM; 36h) induced apoptosis in p53-silenced L02 cells, along with the up-regulations of Fas and FasL proteins as well as increased the Bax/Bcl-2 ratio and Caspase 3, 8, and 9 activities[7].
In vivo, Phthalic acid mono-2-ethylhexyl ester was administered to pregnant female mice for 24 hours by intragastric administration (360mg/kg; twice daily; at 08:30 and 18:30, respectively), which resulted in the loss of germ cells in the testes of the fetal mice, and the apoptosis rate significantly increased[8].
References:
[1] Kim D H, Park C G, Kim S H, et al. The effects of mono-(2-ethylhexyl) phthalate (MEHP) on human estrogen receptor (hER) and androgen receptor (hAR) by YES/YAS in vitro assay[J]. Molecules, 2019, 24(8): 1558.
[2] Martínez-Razo L D, Martínez-Ibarra A, Vázquez-Martínez E R, et al. The impact of Di-(2-ethylhexyl) Phthalate and Mono (2-ethylhexyl) Phthalate in placental development, function, and pathophysiology[J]. Environment International, 2021, 146: 106228.
[3] Reinsberg J, Wegener-Toper P, van der Ven K, et al. Effect of mono-(2-ethylhexyl) phthalate on steroid production of human granulosa cells[J]. Toxicology and applied pharmacology, 2009, 239(1): 116-123.
[4] Rosado-Berrios C A, Vélez C, Zayas B. Mitochondrial permeability and toxicity of diethylhexyl and monoethylhexyl phthalates on TK6 human lymphoblasts cells[J]. Toxicology in Vitro, 2011, 25(8): 2010-2016.
[5] Bai J, He Z, Li Y, et al. Mono-2-ethylhexyl phthalate induces the expression of genes involved in fatty acid synthesis in HepG2 cells[J]. Environmental Toxicology and Pharmacology, 2019, 69: 104-111.
[6] Gao F, Hu W, Li Y, et al. Mono-2-ethylhexyl phthalate inhibits human extravillous trophoblast invasion via the PPARγ pathway[J]. Toxicology and applied pharmacology, 2017, 327: 23-29.
[7] Yang G, Zhang W, Qin Q, et al. Mono (2‐ethylhexyl) phthalate induces apoptosis in p53‐silenced L02 cells via activation of both mitochondrial and death receptor pathways[J]. Environmental Toxicology, 2015, 30(10): 1178-1191.
[8] Muczynski V, Cravedi J P, Lehraiki A, et al. Effect of mono-(2-ethylhexyl) phthalate on human and mouse fetal testis: In vitro and in vivo approaches[J]. Toxicology and applied pharmacology, 2012, 261(1): 97-104.
| Cell experiment [1]: | |
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Cell lines |
Human TK6 lymphoblast cells |
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Preparation Method |
The human TK6 lymphoblast cells were cultured in RPMI 1640 medium containing 10% fetal bovine serum until confluence. The cell culture was conducted under conditions of 37°C and 5% CO2. TK6 cells were cultured at a density of 1×106 cells per 3.5ml of medium in 25cm2 culture flasks. Cells were exposed to different concentrations of Phthalic acid mono-2-ethylhexyl ester (10, 50, 100, 200, 300, 400, and 500μM) for 24, 48, and 72 hours, respectively. Cell viability was determined by trypan blue exclusion. |
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Reaction Conditions |
10, 50, 100, 200, 300, 400, and 500μM; 24, 48, and 72h |
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Applications |
Phthalic acid mono-2-ethylhexyl ester treatment inhibited cell viability of TK6 lymphoblast cells in a dose- and time-dependent manner. |
| Animal experiment [2]: | |
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Animal models |
C57Bl/6 mice |
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Preparation Method |
C57Bl/6 mice were housed under controlled photoperiod conditions (lights on 08:00–20:00) with ad libitum access to tap water and a soy and alfalfa-free breeding diet. Male mice were caged with females overnight and the day following overnight mating was counted as 0.5 days post coitum (dpc). 720mg/kg Phthalic acid mono-2-ethylhexyl ester was administered by oral gavage (360mg/kg twice a day at 08:30 and 18:30) to pregnant females at 13.5dpc for 24h. Pregnant mice were then killed by cervical dislocation at 14.5dpc, fetuses quickly removed and dissected under a binocular microscope. Extract the testicles from the male mouse fetal testis for analysis. |
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Dosage form |
360mg/kg twice a day for 24h; p.o. |
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Applications |
Phthalic acid mono-2-ethylhexyl ester treatment loss of germ cells in the mouse fetal testis. |
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References: |
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| Cas No. | 4376-20-9 | SDF | |
| Synonyms | MEHP, Mono-2-ethylhexyl Phthalate | ||
| Canonical SMILES | O=C(O)C1=CC=CC=C1C(OCC(CC)CCCC)=O | ||
| Formula | C16H22O4 | M.Wt | 278.34 |
| Solubility | Water: 100 mg/mL (359.27 mM); DMSO: ≥ 100 mg/mL (359.27 mM) | Storage | Store at -20°C |
| 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. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.5927 mL | 17.9636 mL | 35.9273 mL |
| 5 mM | 718.5 μL | 3.5927 mL | 7.1855 mL |
| 10 mM | 359.3 μL | 1.7964 mL | 3.5927 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Working concentration: mg/ml;
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 saline, 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.
Quality Control & SDS
- View current batch:
- Purity: >96.00% Appearance: <25°C Solid,>27°C Liquid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 10 reference(s) in Google Scholar.)