Di(2-ethylhexyl)phthalate (CHEM000072)

Record Information
Version1.0
Creation Date2009-03-06 18:58:02 UTC
Update Date2026-08-22 04:09:29 UTC
Accession NumberCHEM000072
Identification
Common NameDi(2-ethylhexyl)phthalate
ClassSmall 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
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Benzenedicarboxylic acid bis(2-ethylhexyl) esterChEBI
2-Ethylhexyl phthalateChEBI
Bis(2-ethylhexyl) O-phthalateChEBI
Bis(2-ethylhexyl)phthalateChEBI
Bis(ethylhexyl) phthalateChEBI
DEHPChEBI
Di(2-ethylhexyl) O-phthalateChEBI
Di(2-ethylhexyl)orthophthalateChEBI
Di(ethylhexyl) phthalateChEBI
Di-iso-octyl phthalateChEBI
Di-sec-octyl phthalateChEBI
Diethylhexyl phthalateChEBI
Dioctyl phthalateChEBI
Octyl phthalateChEBI
Phthalic acid bis(2-ethylhexyl) esterChEBI
Phthalic acid di(2-ethylhexyl) esterChEBI
1,2-Benzenedicarboxylate bis(2-ethylhexyl) esterGenerator
2-Ethylhexyl phthalic acidGenerator
Bis(2-ethylhexyl) O-phthalic acidGenerator
Bis(2-ethylhexyl)phthalic acidGenerator
Bis(ethylhexyl) phthalic acidGenerator
Di(2-ethylhexyl) O-phthalic acidGenerator
Di(2-ethylhexyl)orthophthalic acidGenerator
Di(ethylhexyl) phthalic acidGenerator
Di-iso-octyl phthalic acidGenerator
Di-sec-octyl phthalic acidGenerator
Diethylhexyl phthalic acidGenerator
Dioctyl phthalic acidGenerator
Octyl phthalic acidGenerator
Phthalate bis(2-ethylhexyl) esterGenerator
Phthalate di(2-ethylhexyl) esterGenerator
Di(2-ethylhexyl)phthalic acidGenerator
Di-2-ethylhexylphthalateMeSH
Phthalate, diethylhexylMeSH
Di 2 ethylhexylphthalateMeSH
Phthalate, dioctylMeSH
Chemical FormulaC24H38O4
Average Molecular Mass390.556 g/mol
Monoisotopic Mass390.277 g/mol
CAS Registry Number117-81-7
IUPAC Name1,2-bis(2-ethylhexyl) benzene-1,2-dicarboxylate
Traditional Nameetalon
SMILESCCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC
InChI IdentifierInChI=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 KeyBJQHLKABXJIVAM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColoress liquid.
Experimental Properties
PropertyValue
Melting Point-55°C
Boiling Point385°C
Solubility0.00027 mg/mL at 25 °C [DEFOE,DL et al. (1990)]
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP7.07ALOGPS
logP8.03ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity114.4 m³·mol⁻¹ChemAxon
Polarizability46.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityMonoethylhexylphthalate (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)
MetabolismDEHP 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 ValuesLD50: 33.9 g/kg (Oral, Rabbit) (8) LD50: 10 g/kg (Dermal, Guinea pig) (8) LD50: 30.7 g/kg (Intraperitoneal, Rat) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesDEHP 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 LevelIntermediate Oral: 0.1 mg/kg/day (3) Chronic Oral: 0.06 mg/kg/day (3)
Health EffectsChronic 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)
SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (2)
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
External Links
DrugBank IDNot Available
HMDB IDHMDB0249243
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00035576
BiGG IDNot Available
BioCyc IDBIS2-ETHYLHEXYLPHTHALATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBis(2-ethylhexyl)_phthalate
Chemspider ID21106505
ChEBI ID17747
PubChem Compound IDNot Available
Kegg Compound IDC03690
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12963402
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16874505
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17286146
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19211671
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19840837
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28199414
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28763719