Phthalic acid mono-2-ethylhexyl ester
(Synonyms: 邻苯二甲酸单乙基己基酯,MEHP) 目录号 : GC36902
Phthalic acid mono-2-ethylhexyl ester是diethylhexyl phthalate (DEHP)的一种主要生物活性代谢物，具有抗雌激素（IC50=125μM）和抗雄激素作用（IC50=736μM）。
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 vivo, 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.
Phthalic acid mono-2-ethylhexyl ester是diethylhexyl phthalate (DEHP)的一种主要生物活性代谢物，具有抗雌激素（IC50=125μM）和抗雄激素作用（IC50=736μM）[1]。Phthalic acid mono-2-ethylhexyl ester会损害DNA甲基化、组蛋白修饰以及miRNA和lncRNA的水平，从而引起多种胎盘功能的改变[2]。Phthalic acid mono-2-ethylhexyl ester已被广泛用于降低排卵前颗粒细胞中雌二醇和孕酮的生成[3]。
在体外，Phthalic acid mono-2-ethylhexyl ester处理72小时显著抑制了TK6细胞的活力，IC50值为80μM[4]。用100μM的Phthalic acid mono-2-ethylhexyl ester处理24小时，显著提高了HepG2细胞中的甘油三酯水平，上调了SREBP-1c和ChREBP基因的表达，并提高了ChREBP1、ACC、FAS和SCD的蛋白表达[5]。用200μM的Phthalic acid mono-2-ethylhexyl ester处理24小时，显著抑制了HTR-8/SVneo细胞的侵袭并激活了PPARγ通路[6]。Phthalic acid mono-2-ethylhexyl ester（100μM；36小时）诱导了p53沉默的L02细胞凋亡，同时伴有Fas和FasL蛋白的上调，以及Bax/Bcl-2比值和Caspase 3、8、9活性的增加[7]。
在体内，对怀孕雌鼠进行24小时的胃内给药Phthalic acid mono-2-ethylhexyl ester（每日两次；分别在08:30和18:30给药；每次360mg/kg剂量），结果导致胎鼠睾丸中生殖细胞丢失，且细胞凋亡率显著增加[8]。
| Cell experiment [1]: | |
Cell lines | Human TK6 lymphoblast cells |
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. |
Reaction Conditions | 10, 50, 100, 200, 300, 400, and 500μM; 24, 48, and 72h |
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]: | |
Animal models | C57Bl/6 mice |
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. |
Dosage form | 360mg/kg twice a day for 24h; p.o. |
Applications | Phthalic acid mono-2-ethylhexyl ester treatment loss of germ cells in the mouse fetal testis. |
References: | |
| Cas No. | 4376-20-9 | SDF | |
| 别名 | 邻苯二甲酸单乙基己基酯,MEHP | ||
| Canonical SMILES | O=C(O)C1=CC=CC=C1C(OCC(CC)CCCC)=O | ||
| 分子式 | C16H22O4 | 分子量 | 278.34 |
| 溶解度 | Water: 100 mg/mL (359.27 mM); DMSO: ≥ 100 mg/mL (359.27 mM) | 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 | 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 |
| 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % 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。
Quality Control & SDS
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- Purity: >97.00%
- COA (Certificate Of Analysis)
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