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Bis(2-ethylhexyl) phthalate

CAS# 117-81-7

Bis(2-ethylhexyl) phthalate

2D Structure

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Bis(2-ethylhexyl) phthalate

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Chemical Properties of Bis(2-ethylhexyl) phthalate

Cas No. 117-81-7 SDF Download SDF
PubChem ID 8343 Appearance Oil
Formula C24H38O4 M.Wt 390.6
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility DMSO : 150 mg/mL (384.06 mM; Need ultrasonic)
Chemical Name bis(2-ethylhexyl) benzene-1,2-dicarboxylate
SMILES CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC
Standard InChIKey BJQHLKABXJIVAM-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Bis(2-ethylhexyl) phthalate

The heartwood of Pterocarpus angolensis

Biological Activity of Bis(2-ethylhexyl) phthalate

DescriptionBis(2-ethylhexyl) phthalate (DEHP) is a compound widely used in plastics technology to impart flexibility to rigid polymers, DEHP has oral toxicity during pregnancy and suckling in the Long-Evans rat.It can induce antiandrogenic effects in Spague-Dawley (SD) rats.
TargetsAndrogen Receptor
In vitro

Influence of lipid type on bis (2-ethylhexyl)phthalate (DEHP) leaching from infusion line sets in parenteral nutrition.[Pubmed: 21868720]

JPEN J Parenter Enteral Nutr. 2011 Nov;35(6):770-5.

Bis(2-ethylhexyl)phthalate (or DEHP) is widely used in polyvinyl chloride (PVC) tubings for its good plasticizing properties. Because it is not covalently bound to the plastic matrix, it is able to escape from PVC during the infusion of the lipid emulsions used in parenteral nutrition (PN). This creates a vector through which it can enter into contact with the patient via the nutrition admixtures infused. This study was designed to assess the potential role of the type of lipids used in PN admixtures on the quantity of DEHP leached out from PVC-based tubings.
METHODS AND RESULTS:
PVC-based infusion lines, 6 commercially available lipid emulsions, and their oil base components were left in direct contact, and the amount of DEHP leached was measured by liquid chromatography. After a 24-hour exposure period, DEHP migration varied significantly (P = .0000152) according to lipid type. The olive oil-based emulsion Clinoleic leached the most DEHP (65.8 µg/mL intravenous fat emulsion), followed by the fish oil-based emulsion Omegaven (37.8 µg/mL). The soybean oil-based emulsions Intralipid, Medialipide, Lipidem, and Structolipid showed comparable performances, with DEHP leaching rates into the emulsion measured at 27.3, 27.8, 23.6, and 19.6 µg/mL, respectively. Results from the same experiments run on pure-form oils (soybean oil, olive oil, coconut oil, and cod liver oil) confirmed the influence of lipid type on DEHP leaching.
CONCLUSIONS:
The major DEHP leaching caused by olive oil-based emulsions raises cause for concern because DEHP presents distinctive toxic effects, including an increased risk of cholestasis.

Food packaging and bisphenol A and bis(2-ethyhexyl) phthalate exposure: findings from a dietary intervention.[Pubmed: 21450549]

Environ Health Perspect. 2011 Jul;119(7):914-20.

Bisphenol A (BPA) and Bis(2-ethylhexyl) phthalate (DEHP) are high-production-volume chemicals used in plastics and resins for food packaging. They have been associated with endocrine disruption in animals and in some human studies. Human exposure sources have been estimated, but the relative contribution of dietary exposure to total intake has not been studied empirically. To evaluate the contribution of food packaging to exposure, we measured urinary BPA and phthalate metabolites before, during, and after a "fresh foods" dietary intervention.
METHODS AND RESULTS:
We selected 20 participants in five families based on self-reported use of canned and packaged foods. Participants ate their usual diet, followed by 3 days of "fresh foods" that were not canned or packaged in plastic, and then returned to their usual diet. We collected evening urine samples over 8 days in January 2010 and composited them into preintervention, during intervention, and postintervention samples. We used mixed-effects models for repeated measures and Wilcoxon signed-rank tests to assess change in urinary levels across time. Urine levels of BPA and DEHP metabolites decreased significantly during the fresh foods intervention [e.g., BPA geometric mean (GM), 3.7 ng/mL preintervention vs. 1.2 ng/mL during intervention; mono-(2-ethyl-5-hydroxy hexyl) phthalate GM, 57 ng/mL vs. 25 ng/mL]. The intervention reduced GM concentrations of BPA by 66% and DEHP metabolites by 53-56%. Maxima were reduced by 76% for BPA and 93-96% for DEHP metabolites.
CONCLUSIONS:
BPA and DEHP exposures were substantially reduced when participants' diets were restricted to food with limited packaging.

Bis-(2-ethylhexyl) phthalate, an ubiquitous environmental contaminant.[Pubmed: 3994287]

Ann Clin Lab Sci. 1985 Mar-Apr;15(2):140-51.

Bis-(2-ethylhexyl) phthalate (DEHP) is the most commonly used plasticizing agent for the widely used plastic polyvinylchloride (PVC). Consequently, this compound is found everywhere in the environment of civilization, where it is in frequent contact with every person. Blood storage bags and tubing, food wrappers, and many children's toys contain appreciable amounts of DEHP. Given this frequency of exposure, the toxic potential of the compound has become a major concern. Many workers have demonstrated its exceedingly low acute toxicity, while results from chronic exposure studies have been mixed. However, in 1982 the National Toxicology Program reported a significantly increased incidence of hepatocellular carcinoma in rats and mice exposed to high doses of DEHP over a period of two years. The significance of these studies remains in question. Bis-(2-ethylhexyl) phthalate is metabolized extensively by mammals, but reports of the direct study of the toxic effects of its metabolites are few.
CONCLUSIONS:
Efficient methods for analysis of biological samples for DEHP are available, but they are complicated by the constant presence of this compound as a contaminant.

Protocol of Bis(2-ethylhexyl) phthalate

Animal Research

Bis-(2-ethylexhyl) phthalate impairs spermatogenesis in zebrafish (Danio rerio).[Pubmed: 24011190]

Reprod Biol. 2013 Sep;13(3):195-202.

Bis-(2-ethylhexyl) phthalate (DEHP) is a widely used industrial additive for increasing plastic flexibility. Its metabolites are known to exert toxic effects on reproduction and development of mammals. The aim of this study was to evaluate the effects of environmentally relevant concentrations of DEHP (0.2 and 20 μg/L) on the reproductive biology of adult male zebrafish (Danio rerio).
METHODS AND RESULTS:
The effects of DEHP and 17β-ethynylestradiol (a positive control) were determined after one or three weeks of exposure by TUNEL assay, histomorphometric analysis and evaluation of reproductive performance. DEHP impaired reproduction in zebrafish by inducing a mitotic arrest during spermatogenesis, increasing DNA fragmentation in sperm cells and markedly reducing embryo production (up to 90%).
CONCLUSIONS:
In conclusion, relatively short-term exposure to environmentally relevant concentrations of DEHP is able to alter spermatogenesis and affect reproduction in zebrafish.

Bis(2-ethylhexyl) phthalate Dilution Calculator

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Preparing Stock Solutions of Bis(2-ethylhexyl) phthalate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5602 mL 12.8008 mL 25.6016 mL 51.2033 mL 64.0041 mL
5 mM 0.512 mL 2.5602 mL 5.1203 mL 10.2407 mL 12.8008 mL
10 mM 0.256 mL 1.2801 mL 2.5602 mL 5.1203 mL 6.4004 mL
50 mM 0.0512 mL 0.256 mL 0.512 mL 1.0241 mL 1.2801 mL
100 mM 0.0256 mL 0.128 mL 0.256 mL 0.512 mL 0.64 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Bis(2-ethylhexyl) phthalate

Influence of lipid type on bis (2-ethylhexyl)phthalate (DEHP) leaching from infusion line sets in parenteral nutrition.[Pubmed:21868720]

JPEN J Parenter Enteral Nutr. 2011 Nov;35(6):770-5.

BACKGROUND: Bis(2-ethylhexyl)phthalate (or DEHP) is widely used in polyvinyl chloride (PVC) tubings for its good plasticizing properties. Because it is not covalently bound to the plastic matrix, it is able to escape from PVC during the infusion of the lipid emulsions used in parenteral nutrition (PN). This creates a vector through which it can enter into contact with the patient via the nutrition admixtures infused. This study was designed to assess the potential role of the type of lipids used in PN admixtures on the quantity of DEHP leached out from PVC-based tubings. METHODS: PVC-based infusion lines, 6 commercially available lipid emulsions, and their oil base components were left in direct contact, and the amount of DEHP leached was measured by liquid chromatography. RESULTS: After a 24-hour exposure period, DEHP migration varied significantly (P = .0000152) according to lipid type. The olive oil-based emulsion Clinoleic leached the most DEHP (65.8 microg/mL intravenous fat emulsion), followed by the fish oil-based emulsion Omegaven (37.8 microg/mL). The soybean oil-based emulsions Intralipid, Medialipide, Lipidem, and Structolipid showed comparable performances, with DEHP leaching rates into the emulsion measured at 27.3, 27.8, 23.6, and 19.6 microg/mL, respectively. Results from the same experiments run on pure-form oils (soybean oil, olive oil, coconut oil, and cod liver oil) confirmed the influence of lipid type on DEHP leaching. CONCLUSION: The major DEHP leaching caused by olive oil-based emulsions raises cause for concern because DEHP presents distinctive toxic effects, including an increased risk of cholestasis.

Food packaging and bisphenol A and bis(2-ethyhexyl) phthalate exposure: findings from a dietary intervention.[Pubmed:21450549]

Environ Health Perspect. 2011 Jul;119(7):914-20.

BACKGROUND: Bisphenol A (BPA) and Bis(2-ethylhexyl) phthalate (DEHP) are high-production-volume chemicals used in plastics and resins for food packaging. They have been associated with endocrine disruption in animals and in some human studies. Human exposure sources have been estimated, but the relative contribution of dietary exposure to total intake has not been studied empirically. OBJECTIVES: To evaluate the contribution of food packaging to exposure, we measured urinary BPA and phthalate metabolites before, during, and after a "fresh foods" dietary intervention. METHODS: We selected 20 participants in five families based on self-reported use of canned and packaged foods. Participants ate their usual diet, followed by 3 days of "fresh foods" that were not canned or packaged in plastic, and then returned to their usual diet. We collected evening urine samples over 8 days in January 2010 and composited them into preintervention, during intervention, and postintervention samples. We used mixed-effects models for repeated measures and Wilcoxon signed-rank tests to assess change in urinary levels across time. RESULTS: Urine levels of BPA and DEHP metabolites decreased significantly during the fresh foods intervention [e.g., BPA geometric mean (GM), 3.7 ng/mL preintervention vs. 1.2 ng/mL during intervention; mono-(2-ethyl-5-hydroxy hexyl) phthalate GM, 57 ng/mL vs. 25 ng/mL]. The intervention reduced GM concentrations of BPA by 66% and DEHP metabolites by 53-56%. Maxima were reduced by 76% for BPA and 93-96% for DEHP metabolites. CONCLUSIONS: BPA and DEHP exposures were substantially reduced when participants' diets were restricted to food with limited packaging.

Bis-(2-ethylexhyl) phthalate impairs spermatogenesis in zebrafish (Danio rerio).[Pubmed:24011190]

Reprod Biol. 2013 Sep;13(3):195-202.

Bis-(2-ethylhexyl) phthalate (DEHP) is a widely used industrial additive for increasing plastic flexibility. Its metabolites are known to exert toxic effects on reproduction and development of mammals. The aim of this study was to evaluate the effects of environmentally relevant concentrations of DEHP (0.2 and 20 mug/L) on the reproductive biology of adult male zebrafish (Danio rerio). The effects of DEHP and 17beta-ethynylestradiol (a positive control) were determined after one or three weeks of exposure by TUNEL assay, histomorphometric analysis and evaluation of reproductive performance. DEHP impaired reproduction in zebrafish by inducing a mitotic arrest during spermatogenesis, increasing DNA fragmentation in sperm cells and markedly reducing embryo production (up to 90%). In conclusion, relatively short-term exposure to environmentally relevant concentrations of DEHP is able to alter spermatogenesis and affect reproduction in zebrafish.

Bis-(2-ethylhexyl) phthalate, an ubiquitous environmental contaminant.[Pubmed:3994287]

Ann Clin Lab Sci. 1985 Mar-Apr;15(2):140-51.

Bis-(2-ethylhexyl) phthalate (DEHP) is the most commonly used plasticizing agent for the widely used plastic polyvinylchloride (PVC). Consequently, this compound is found everywhere in the environment of civilization, where it is in frequent contact with every person. Blood storage bags and tubing, food wrappers, and many children's toys contain appreciable amounts of DEHP. Given this frequency of exposure, the toxic potential of the compound has become a major concern. Many workers have demonstrated its exceedingly low acute toxicity, while results from chronic exposure studies have been mixed. However, in 1982 the National Toxicology Program reported a significantly increased incidence of hepatocellular carcinoma in rats and mice exposed to high doses of DEHP over a period of two years. The significance of these studies remains in question. Bis-(2-ethylhexyl) phthalate is metabolized extensively by mammals, but reports of the direct study of the toxic effects of its metabolites are few. Efficient methods for analysis of biological samples for DEHP are available, but they are complicated by the constant presence of this compound as a contaminant.

Description

Bis(2-ethylhexyl) phthalate is an endogenous metabolite.

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