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Details

Stereochemistry ACHIRAL
Molecular Formula C12H14O4
Molecular Weight 222.2372
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Diethyl phthalate

SMILES

CCOC(=O)C1=CC=CC=C1C(=O)OCC

InChI

InChIKey=FLKPEMZONWLCSK-UHFFFAOYSA-N
InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C12H14O4
Molecular Weight 222.2372
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diethyl phthalate is a colourless liquid with a slight aromatic odour and low volatility. Diethyl phthalate is used as a plasticizer for cellulose ester plastic films and sheets (photographic, blister packaging, and tape applications) and moulded and extruded articles (consumer articles such as toothbrushes, automotive components, tool handles, and toys). Diethyl phthalate was reported as an ingredient in 67 cosmetic formulations. Diethyl phthalate is used as a component in insecticide sprays and mosquito repellents. Diethyl phthalate is likely to undergo biodegradation in the environment. General population exposure in the USA, as estimated from urinary concentrations of the monoester, was estimated to be 12 µg/kg body weight per day (median value). Dermally applied diethyl phthalate penetrates the skin and can be widely distributed in the body, but it does not accumulate in tissue. Diethyl phthalate has irritant effects on the eyes, skin, and mucous membranes and can lead to central nervous system (CNS) effects in exposed workers. The exposure to diethyl phthalates (DEP), a parent compound of the monoethyl phthalate (MEP) metabolite, may be associated with increased risk of BC (Odds Ratio of 2.20, p value for trend, p<0.003).

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.84 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
2% in petrolatum
Route of Administration: Transdermal
In Vitro Use Guide
The authors analysed the androgen receptor (AR) agonistic and antagonistic activity of phthalates using MDAkb2 human breast cancer cells, stably expressing an AR-responsive luciferase reporter gene, MMTV-luc. Antagonistic activity was assessed in competition against dihydrotestosterone (DHT) (0.5 nM). The androgenic activity is low or absent among the phthalates. A 70-80% inhibition of the DHT response was detected at the highest concentration of Diethyl phthalate (DEP) (625 uM). The calculated IC50 value for Diethyl phthalate was 515 uM.
Substance Class Chemical
Record UNII
UF064M00AF
Record Status Validated (UNII)
Record Version