Mono(2-ethyl-5-hydroxyhexyl) phthalate
Based on 1 Customer Validation
Mono (2-ethyl-5-hydroxyhexyl) phthalate (MEHHP) is a biomarker for human exposure to DEHP (HY-B1945). By activating the tryptophan-kynurenine-aryl hydrocarbon receptor (AhR) pathway, mono (2-ethyl-5-hydroxyhexyl) phthalate significantly increases the viability of primary uterine leiomyoma cells and reduces cell apoptosis. Mono (2-ethyl-5-hydroxyhexyl) phthalate correlates with decreased sperm DNA damage. Mono (2-ethyl-5-hydroxyhexyl) phthalate can be used in studies related to uterine leiomyoma.
For research use only. We do not sell to patients.
- Purity : 99.03%
- CAS No.: 40321-99-1
- Formula: C16H22O5
- Molecular Weight:294.34
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Storage:
Store at room temperature 3 years.
In solvent -80°C, 2 years , -20°C, 1 year
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
In Vitro
Mono(2-ethyl-5-hydroxyhexyl) phthalate (0.16-16 μM; 48-72 h) enhances the viability and reduces the apoptosis level of primary human uterine leiomyoma smooth muscle cells, with the most significant effect observed at the moderate dose of 1.6 μM[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 48 h) significantly reduces the apoptotic cell population in primary human uterine leiomyoma smooth muscle cells[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 72 h) causes a slight, statistically insignificant increase in the proportion of primary human uterine leiomyoma smooth muscle cells in the S phase[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 24 h) significantly increases the nuclear localization level of AHR in primary human uterine leiomyoma smooth muscle cells, which is comparable to that induced by the potent AHR agonist TCDD[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 8 h) significantly upregulates the mRNA levels of CYP1A1, CYP1B1, AHR, SLC7A5 and SLC7A8 in primary human uterine leiomyoma smooth muscle cells, and (1.6 μM; 24 h) significantly upregulates the mRNA level of TDO2 in these cells[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 72 h) significantly increases the cellular levels of tryptophan and kynurenine in primary human uterine leiomyoma smooth muscle cells[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 24 h) significantly increases the protein level of SLC7A5 in primary human uterine leiomyoma smooth muscle cells[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 72 h) enhances the viability and reduces the apoptosis level of primary human uterine leiomyoma smooth muscle cells, and these effects can be abolished by small interfering RNA (siRNA)-mediated knockdown of aryl hydrocarbon receptor (AHR) or treatment with the AHR antagonist CH223191[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 72 h) increases the viability and reduces the apoptosis level of primary human uterine leiomyoma smooth muscle cells, while siRNA-mediated knockdown of the tryptophan transporters SLC7A5 and SLC7A8 abrogates these effects[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (1.6 μM; 72 h) increases the viability and reduces the apoptosis level of primary human uterine leiomyoma smooth muscle cells, while siRNA-mediated knockdown of the tryptophan catabolic enzyme TDO2 significantly attenuates these effects[1].
Mono(2-ethyl-5-hydroxyhexyl) phthalate (0.16-16 μM; 48-72 h) does not increase the viability of primary human uterine myometrial smooth muscle cells, and its anti-apoptotic effect is weaker or different compared with that in uterine leiomyoma cells[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
Chemical Information
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CAS No. 40321-99-1
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Appearance Liquid (Density: 1.160±0.06 g/cm3)
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Molecular Weight 294.34
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Formula C16H22O5
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Color Colorless to light yellow
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SMILES
O=C(C1=CC=CC=C1C(O)=O)OCC(CC)CCC(O)C
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Synonyms
MEHHP
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Store at room temperature 3 years
In solvent -80°C 2 years -20°C 1 year
Solvent & Solubility
In Vitro:
DMSO : 100 mg/mL (339.74 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (8.49 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocols
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Genotoxicity/Mutagenicity Study
The bacterial reverse mutation assay detects point mutations that restore amino-acid prototrophy in auxotrophic Salmonella typhimurium or Escherichia coli tester strains; after exposure to a test article, mutagenic activity is read out as an increased number of revertant colonies on minimal agar compared with the vehicle control. The assay uses tester strains with different mutation targets so that base-substitution and frameshift mutagens can be detected, and testing is performed with and without exogenous mammalian metabolic activation because some chemicals require biotransformation to become mutagenic.
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Cell Viability Determination by MTT Colorimetric Assay
The following protocol uses the MTT colorimetric assay as a classic literature-established method for assessing cell viability/metabolic activity in cultured mammalian cells. MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] is reduced by metabolically active cells to a colored formazan product; the amount of formazan is quantified spectrophotometrically and provides an indirect measure of metabolically active viable cells. Importantly, MTT reduction reflects cellular oxidoreductase/metabolic activity rather than an absolute direct count of living cells, so changes in cellular metabolism can alter the signal independently of cell number.
Purity & Documentation
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Data Sheet (274 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Iizuka T, et al. Mono-(2-ethyl-5-hydroxyhexyl) phthalate promotes uterine leiomyoma cell survival through tryptophan-kynurenine-AHR pathway activation. Proc Natl Acad Sci U S A. 2022;119(47):e2208886119. [Content Brief]
[2]. Hauser R, et al. Urinary phthalate metabolites and semen quality: a review of a potential biomarker of susceptibility. Int J Androl. 2008;31(2):112-117. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 3.3974 mL | 16.9872 mL | 33.9743 mL | 84.9358 mL |
| 5 mM | 0.6795 mL | 3.3974 mL | 6.7949 mL | 16.9872 mL | |
| 10 mM | 0.3397 mL | 1.6987 mL | 3.3974 mL | 8.4936 mL | |
| 15 mM | 0.2265 mL | 1.1325 mL | 2.2650 mL | 5.6624 mL | |
| 20 mM | 0.1699 mL | 0.8494 mL | 1.6987 mL | 4.2468 mL | |
| 25 mM | 0.1359 mL | 0.6795 mL | 1.3590 mL | 3.3974 mL | |
| 30 mM | 0.1132 mL | 0.5662 mL | 1.1325 mL | 2.8312 mL | |
| 40 mM | 0.0849 mL | 0.4247 mL | 0.8494 mL | 2.1234 mL | |
| 50 mM | 0.0679 mL | 0.3397 mL | 0.6795 mL | 1.6987 mL | |
| 60 mM | 0.0566 mL | 0.2831 mL | 0.5662 mL | 1.4156 mL | |
| 80 mM | 0.0425 mL | 0.2123 mL | 0.4247 mL | 1.0617 mL | |
| 100 mM | 0.0340 mL | 0.1699 mL | 0.3397 mL | 0.8494 mL |
Mono(2-ethyl-5-hydroxyhexyl) phthalate Related Classifications
HY-133677 Related Classifications
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