ContaminantDB: Di(2-ethylhexyl)phthalate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (17)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:02 UTC

Update Date

2026-03-31 19:50:48 UTC

Accession Number

CHEM000072

Identification

Common Name

Di(2-ethylhexyl)phthalate

Class

Small Molecule

Description

Di(2-ethylhexyl) phthlate (DEHP) is a manufactured chemical that is commonly added to plastics to make them flexible. DEHP exposure is generally low and not harmful, but increased exposures resulting from intravenous fluids delivered through plastic tubing or ingesting contaminated foods or water may have toxic effects. This is of particular concern since DEHP is known to leach into liquid that come in contact with DEHP containing plastic. (5, 6)

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
IARC Carcinogens General
IARC Carcinogens Group 2B
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Sludge Chemicals
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cosmetic Toxin
Ester
Ether
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Phthalate
Plasticizer
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid bis(2-ethylhexyl) ester	ChEBI
2-Ethylhexyl phthalate	ChEBI
Bis(2-ethylhexyl) O-phthalate	ChEBI
Bis(2-ethylhexyl)phthalate	ChEBI
Bis(ethylhexyl) phthalate	ChEBI
DEHP	ChEBI
Di(2-ethylhexyl) O-phthalate	ChEBI
Di(2-ethylhexyl)orthophthalate	ChEBI
Di(ethylhexyl) phthalate	ChEBI
Di-iso-octyl phthalate	ChEBI
Di-sec-octyl phthalate	ChEBI
Diethylhexyl phthalate	ChEBI
Dioctyl phthalate	ChEBI
Octyl phthalate	ChEBI
Phthalic acid bis(2-ethylhexyl) ester	ChEBI
Phthalic acid di(2-ethylhexyl) ester	ChEBI
1,2-Benzenedicarboxylate bis(2-ethylhexyl) ester	Generator
2-Ethylhexyl phthalic acid	Generator
Bis(2-ethylhexyl) O-phthalic acid	Generator
Bis(2-ethylhexyl)phthalic acid	Generator
Bis(ethylhexyl) phthalic acid	Generator
Di(2-ethylhexyl) O-phthalic acid	Generator
Di(2-ethylhexyl)orthophthalic acid	Generator
Di(ethylhexyl) phthalic acid	Generator
Di-iso-octyl phthalic acid	Generator
Di-sec-octyl phthalic acid	Generator
Diethylhexyl phthalic acid	Generator
Dioctyl phthalic acid	Generator
Octyl phthalic acid	Generator
Phthalate bis(2-ethylhexyl) ester	Generator
Phthalate di(2-ethylhexyl) ester	Generator
Di(2-ethylhexyl)phthalic acid	Generator
Di-2-ethylhexylphthalate	MeSH
Phthalate, diethylhexyl	MeSH
Di 2 ethylhexylphthalate	MeSH
Phthalate, dioctyl	MeSH

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Mass

390.556 g/mol

Monoisotopic Mass

390.277 g/mol

CAS Registry Number

117-81-7

IUPAC Name

1,2-bis(2-ethylhexyl) benzene-1,2-dicarboxylate

Traditional Name

etalon

SMILES

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

InChI Identifier

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

InChI Key

BJQHLKABXJIVAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

diester (CHEBI:17747 )
phthalate ester (CHEBI:17747 )
Phthalates (C03690 )
a small molecule (BIS2-ETHYLHEXYLPHTHALATE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

plasticiser

Biological Roles

Chemical Roles

apoptosis inhibitor

Physical Properties

State

Liquid

Appearance

Coloress liquid.

Experimental Properties

Property	Value
Melting Point	-55°C
Boiling Point	385°C
Solubility	0.00027 mg/mL at 25 °C [DEFOE,DL et al. (1990)]

Predicted Properties

Property	Value	Source
Water Solubility	0.00011 g/L	ALOGPS
logP	7.07	ALOGPS
logP	8.03	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	114.4 m³·mol⁻¹	ChemAxon
Polarizability	46.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gj-9662000000-c432a8bae07e4e643f0a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1900000000-dc95460619515b5dbe34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-1900000000-7f58b09d9a09115d50d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-3900000000-4cf9588dd18494f8bc0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1900000000-dd5c1792ab0a30677ce0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1938000000-bed181109e4a3e91f837	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-6921000000-b4344c35d612bc17ddc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9500000000-e24dbff2067b6ec540ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0139000000-d6f0ae6354823d53d277	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01s9-1795000000-ef9c4c2be7f658c2365a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-8910000000-15311b666bb1947a607d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0029000000-bf1e8a3b2dd1fdde61af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-6895000000-8780cbef3b20a660d7b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e2caedd1b33f644d6c58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0119000000-1a244e7da4535cd00101	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0210-0593000000-a86dc559ea4ececf0808	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00vi-0920000000-278951b964848b052980	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-8910000000-e26c8df30ee051bd4c48	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (7) ; inhalation (7) ; dermal (7)

Mechanism of Toxicity

Monoethylhexylphthalate (MEHP), one of the major metabolites of DEHP, induces peroxisome proliferation by activating peroxisome proliferator activated receptors. This is believed to increase production of hydrogen peroxide by peroxisomes and enhance cell proliferation, leading to hepatotoxic and carcinogenic effects. MEHP is also believed to exhibit testicular toxicity by targeting and damaging the Sertoli cells. DEHP may act as an antiandrogen during a critical stage of reproductive tract differentiation by reducing testosterone in fetal males, hindering development. (5, 1)

Metabolism

DEHP is mainly absorbed via ingestion. It is hydrolyzed in the small intestine and absorbed as monoethylhexylphthalate (MEHP) and 2-ethylhexanol, then likely distributed to the adipose tissues and kidneys. MEHP is further metabolized via numerous oxidative reactions, resulting in the formation of 30 or more metabolites, some of which can be conjugated with glucuronic acid for excretion. Oxidation of 2-ethylhexanol primarily yields 2-ethylhexanoic acid and several keto acid derivatives. Most DEHP metabolites are excreted in the urine as glucuronide conjugates, while unmetabolized DEHP is excreted in the faeces. (5)

Toxicity Values

LD50: 33.9 g/kg (Oral, Rabbit) (8) LD50: 10 g/kg (Dermal, Guinea pig) (8) LD50: 30.7 g/kg (Intraperitoneal, Rat) (8)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (4)

Uses/Sources

DEHP is present in plastic products such as wall coverings, tablecloths, floor tiles, furniture upholstery, shower curtains, garden hoses, swimming pool liners, rainwear, baby pants, dolls, some toys, shoes, automobile upholstery and tops, packaging film and sheets, sheathing for wire and cable, medical tubing, and blood storage bags. (5)

Minimum Risk Level

Intermediate Oral: 0.1 mg/kg/day (3) Chronic Oral: 0.06 mg/kg/day (3)

Health Effects

Chronic and/or high levels of DEHP exposure may cause reproductive and developmental damage. This includes damaged sperm, delayed sexual maturity, and deficiencies in the development of male babies. DEHP may also cause liver and kidney damage, and is potentially carcinogenic. (5, 6)

Symptoms

Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (2)

Treatment

Not Available

Concentrations