Phthalic acid mono-2-ethylhexyl ester

目录号: GC36902纯度: >96.00%同义词: 邻苯二甲酸单乙基己基酯,MEHP

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

规格	价格	库存	数量
50mg	¥310.00	现货	1
100mg	¥480.00	现货	1
10mM (in 1mL DMSO)	¥340.00	现货	1

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183(7):1867-1883 (2020)
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产品描述 Description

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.

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]。

实验参考方法 Experimental Reference Method

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: [1] 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. [2] 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.

产品文档 Product Documents

批次：Purity:>96.00%

化学性质Chemical Properties

CAS 号

4376-20-9

同义词

邻苯二甲酸单乙基己基酯,MEHP

SMILES

O=C(O)C1=CC=CC=C1C(OCC(CC)CCCC)=O

分子式

C₁₆H₂₂O₄

分子量

278.34 g/mol

溶解性

Water: 100 mg/mL (359.27 mM); DMSO: ≥ 100 mg/mL (359.27 mM)

保存条件

Store at -20°C

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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。
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