U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C24H38O4
Molecular Weight 390.5561
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIETHYLHEXYL PHTHALATE

SMILES

CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC

InChI

InChIKey=BJQHLKABXJIVAM-UHFFFAOYSA-N
InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C24H38O4
Molecular Weight 390.5561
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Diethylhexyl phthalate (Di-2-ethylhexyl phthalate, DEHP), the most frequently occurring plasticiser in medical equipment manufactured from polymers of vinyl chloride, forms about 40% w/w of tubes and containers used for storing blood and for haemodialysis. The plasticiser leaches out into liquids with lipid contents, although it is very sparingly soluble in purely aqueous solutions. On infusion of 2-3 1 of stored blood, up to 200 mg DEHP may be transferred to the patient, while much higher quantities may be given during dialysis, which is moreover often repeated frequently over long periods. The acute toxicity of DEHP is very low (greater than 20 g/kg as LD50 in rats), and the ester is rapidly metabolised to products which are excreted in the urine and bile; chronic toxicity from the levels of dosage obtaining is thus very improbable. Carcenogenicity has never been demonstrable in animals, while teratological effects are of a very low order. The uses of DEHP fall into two major categories: polymer uses (e.g. consumer products such as footwear, shower curtains and toys, medical devices and commercial/industrial uses) and non-polymer uses (e.g. dielectric fluids, paints, adhesives and inks). Non-polymer uses represent less than 5% of the total DEHP used in the USA. Approximately 45% of total consumption of DEHP in the USA is for plasticizing various industrial and commercial products. Industrial and commercial uses of DEHP include resilient flooring, wall covering, roofing, aluminium foil coating/laminating, paper coating, extrudable moulds and profiles, electronic component parts, and wire and cable coating and jacketing. Medical devices comprise approximately 25% of total manufacturing use of DEHP in the USA. Medical devices that contain DEHP include PVC sheet materials such as intravenous bags, and tubing used in a variety of medical applications.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Role of oxidative stress in germ cell apoptosis induced by di(2-ethylhexyl)phthalate.
2002-08-01
Comparison of embryotoxicity of ESBO and phthalate esters using an in vitro battery system.
2002-08
Interactive effects of benzo(a)pyrene and cadmium and effects of di(2-ethylhexyl) phthalate on antioxidant and peroxisomal enzymes and peroxisomal volume density in the digestive gland of mussel Mytilus galloprovincialis Lmk.
2002-07-10
Preparation of samples for gas chromatography/mass spectrometry analysis of phthalate and adipate esters in plasma and beverages by steam distillation and extraction.
2002-06-27
Bax expression protects yeast plasma membrane against ethanol-induced permeabilization.
2002-06-19
Migration of phthalates from PVC toys into saliva simulant by dynamic extraction.
2002-06
Prediction of compound signature using high density gene expression profiling.
2002-06
Effect of a peroxisome proliferator on 3 beta-hydroxysteroid dehydrogenase.
2002-04-26
Effects of in utero linuron exposure on rat Wolffian duct development.
2002-04-17
Assessment of carcinogenicity of di(2-ethylhexyl)phthalate in a short-term assay using Xpa-/- and Xpa-/-/p53+/- mice.
2002-04-13
Elucidation of the toxic mechanism of the plasticizers, phthalic acid esters, putative endocrine disrupters: effects of dietary di(2-ethylhexyl)phthalate on the metabolism of tryptophan to niacin in rats.
2002-04
Particle size analysis of radioactive aerosols formed by irradiation of argon using 65 MeV quasi-monoenergetic neutrons.
2002-04
Leaching of diethylhexyl phthalate from polyvinyl chloride bags into intravenous etoposide solution.
2002-04
Protecting patients from toxins in plastic. Are you aware of the health hazards posed by DEHP?
2002-04
The association between biomarker-based exposure estimates for phthalates and demographic factors in a human reference population.
2002-04
Prediction of rodent nongenotoxic carcinogenesis: evaluation of biochemical and tissue changes in rodents following exposure to nine nongenotoxic NTP carcinogens.
2002-04
Effect of endocrine disrupters on immune responses in vitro.
2002-03-01
Occurrence of phthalates and bisphenol A and F in the environment.
2002-03
DI-(2-ethylhexyl) phthalate-induced cell proliferation is involved in the inhibition of gap junctional intercellular communication and blockage of apoptosis in mouse Sertoli cells.
2002-03
Testicular toxicity of di-(2-ethylhexyl)phthalate in young Sprague-Dawley rats.
2002-02-28
Effect of dialkyl phthalates on the degranulation and Ca2+ response of RBL-2H3 mast cells.
2002-02-01
Minimize exposure to DEHP.
2002-02
Characterization of the adipose tissue atrophy induced by peroxisome proliferators in mice.
2002-02
Phthalate and alkyl phenol concentrations in soil following applications of inorganic fertiliser or sewage sludge to pasture and potential rates of ingestion by grazing ruminants.
2002-02
Phthalate esters detected in various water samples and biodegradation of the phthalates by microbes isolated from river water.
2002-02
A case of contact urticaria syndrome due to di(2-ethylhexyl) phthalate (DOP) in work clothes.
2002-01
Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats.
2002-01
A regionally segmented national scale multimedia contaminant fate model for Canada with GIS data input and display.
2002
A comparative study of cytotoxic effects of N-ethyl-N-nitrosourea, adriamycin, and mono-(2-ethylhexyl)phthalate on mouse primordial germ cells.
2002
Di-(2-ethylhexyl) phthalate possesses an adjuvant effect in a subcutaneous injection model with BALB/c mice.
2001-12-15
Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes.
2001-12
A biomarker approach to measuring human dietary exposure to certain phthalate diesters.
2001-12
Reversibility and persistence of di-2-ethylhexyl phthalate (DEHP)- and phenobarbital-induced hepatocellular changes in rodents.
2001-12
Operational reversibility is a key aspect of carcinogenesis.
2001-12
Aromatic dental monomers affect the activity of cholesterol esterase.
2001-11-26
Differential effects of non-genotoxic carcinogens and proliferating agents on cell growth, survival and apoptosis in hepatic cells in vitro.
2001-11-09
From the Food and Drug Administration.
2001-11-07
New risk for newborns.
2001-11
Comparative study of the leachability of di(2-ethylhexyl) phthalate and tri(2-ethylhexyl) trimellitate from haemodialysis tubing.
2001-10-23
Further evidence for the involvement of inhibition of cell proliferation and development in thymic and splenic atrophy induced by the peroxisome proliferator perfluoroctanoic acid in mice.
2001-10-15
[Migrants from disposable gloves and residual acrylonitrile].
2001-10
[Residual chemicals in silicone rubber products for food contact use].
2001-10
The effects of polyvinyl chloride and polyolefin blood bags on red blood cells stored in a new additive solution.
2001-10
Current progress in isolation and characterization of toxins isolated from Pfiesteria piscicida.
2001-10
Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription.
2001-10
Modulation of rat Leydig cell steroidogenic function by di(2-ethylhexyl)phthalate.
2001-10
Quantitative proteomic analysis of mouse liver response to the peroxisome proliferator diethylhexylphthalate (DEHP).
2001-09
[Residual chemicals in natural rubber products for food contact use].
2001-06
Hazardous organic matters in municipal sewage sludge in Taiwan.
2001
Tg.AC genetically altered mouse: assay working group overview of available data.
2001
Patents

Sample Use Guides

In vivo treatment regimens were: (i) female rats, 12 000 p.p.m. Diethylhexyl phthalate (DEHP) in the diet for 30 days; (ii) female rats, 12 000 p.p.m. in the diet for 30 days, followed by 500 mg/kg DEHP by gavage 2 h before sacrifice; (iii) male rats, 500 mg/kg DEHP by gavage 2, 12, 24, or 48 h before sacrifice; and (iv) male rats, 150 mg/kg/day by gavage for 14 days.
Route of Administration: Oral
In Vitro Use Guide
In vitro conditions were 0.1, 1.0 and 10.0 mM Diethylhexyl phthalate (DEHP) in the human hepatocyte cultures for 18 h. Primary cultures of human hepatocytes were prepared from freshly discarded surgical material and exposed to the same concentration of DEHP.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:45 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:45 GMT 2025
Record UNII
C42K0PH13C
Record Status Validated (UNII)
Record Version
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Name Type Language
DIETHYLHEXYL PHTHALATE
INCI  
INCI  
Official Name English
DEHP
MI  
Preferred Name English
DI(2-ETHYLHEXYL)PHTHALATE
Systematic Name English
NSC-17069
Code English
DIOCTYLPHTHALATE [II]
Common Name English
DI(2-ETHYLHEXYL) PHTHALATE
Systematic Name English
BIS(2-ETHYLHEXYL)PHTHALATE [HSDB]
Common Name English
PLASTIC ADDITIVE 14
USP-RS  
Common Name English
DIOCTYLPHTHALATE
II  
Systematic Name English
DI-2-ETHYLHEXYL PHTHALATE
Common Name English
DEHP [MI]
Common Name English
BIS(2-ETHYLHEXYL PHTHALATE)-
Common Name English
PLASTIC ADDITIVE 14 [USP-RS]
Common Name English
DI(2-ETHYLHEXYL)PHTHALATE [IARC]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 295200
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
Code System Code Type Description
NSC
17069
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
EVMPD
SUB169666
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PRIMARY
HSDB
339
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID5020607
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PRIMARY
CHEBI
17747
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
NCI_THESAURUS
C44341
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
FDA UNII
C42K0PH13C
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
CAS
117-81-7
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PRIMARY
MERCK INDEX
m4138
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
204-211-0
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
PUBCHEM
8343
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
RS_ITEM_NUM
1545056
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
DAILYMED
C42K0PH13C
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
WIKIPEDIA
BIS(2-ETHYLHEXYL) PHTHALATE
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
MESH
D004051
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY
SMS_ID
100000159486
Created by admin on Mon Mar 31 17:47:45 GMT 2025 , Edited by admin on Mon Mar 31 17:47:45 GMT 2025
PRIMARY