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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=C(C=CC=C1)C(=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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://ec.europa.eu/health/ph_risk/committees/sccp/documents/out168_en.pdf http://www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2014/11/WC500177736.pdf https://www.ncbi.nlm.nih.gov/pubmed/20943248 https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/diethyl_phthalate_508.pdf http://www.cir-safety.org/sites/default/files/phth_online.pdf http://www.meti.go.jp/english/report/downloadfiles/gED0308e.pdf

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

Curator's Comment: CNS effects only occurred in exposed workers after 6 to 7 years of chronic exposure to phthalates.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
0.84 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Biodegradation of phthalate esters by two bacteria strains.
2004 Apr
Environmental remediation by an integrated microwave/UV illumination technique. 8. Fate of carboxylic acids, aldehydes, alkoxycarbonyl and phenolic substrates in a microwave radiation field in the presence of TiO2 particles under UV irradiation.
2004 Apr 1
Tableting of Eudragit RS and propranolol hydrochloride solid dispersion: effect of particle size, compaction force, and plasticizer addition on drug release.
2004 Aug
Suppression by phthalates of the calcium signaling of human nicotinic acetylcholine receptors in human neuroblastoma SH-SY5Y cells.
2004 Aug 5
Temporal variability of urinary phthalate metabolite levels in men of reproductive age.
2004 Dec
Estimated exposure to phthalates in cosmetics and risk assessment.
2004 Dec
Temperature-dependent micellar structures in poly(styrene-b-isoprene) diblock copolymer solutions near the critical micelle temperature.
2004 Dec 8
Adsorption of phthalates by activated sludge and its biopolymers.
2004 Jul
Occurrence of phthalates and musk fragrances in indoor air and dust from apartments and kindergartens in Berlin (Germany).
2004 Jun
New methodology for the determination of phthalate esters, bisphenol A, bisphenol A diglycidyl ether, and nonylphenol in commercial whole milk samples.
2004 Jun 16
[Analysis of the phthalates in cosmetics by capillary gas chromatography].
2004 May
Medications as a source of human exposure to phthalates.
2004 May
Ethanol and diethyl phthalate: vehicle effects in the local lymph node assay.
2004 May-Jun
Biodegradable films of partly branched poly(l-lactide)-co-poly(epsilon-caprolactone) copolymer: modulation of phase morphology, plasticization properties and thermal depolymerization.
2004 May-Jun
Unequivocal estrogen receptor-binding affinity of phthalate esters featured with ring hydroxylation and proper alkyl chain size.
2004 Nov 1
The association between asthma and allergic symptoms in children and phthalates in house dust: a nested case-control study.
2004 Oct
Conflict of estrogenic activity by various phthalates between in vitro and in vivo models related to the expression of Calbindin-D9k.
2005 Apr
Evidence of interaction between polychlorinated biphenyls and phthalates in relation to human sperm motility.
2005 Apr
Multivariate optimization of a solid-phase microextraction method for the analysis of phthalate esters in environmental waters.
2005 Apr 22
Charge limits on droplets during evaporation.
2005 Apr 26
Direct quantitative analysis of phthalate esters as micro-contaminants in cleanroom air and wafer surfaces by auto-thermal desorption--gas chromatography--mass spectrometry.
2005 Apr 8
Decrease in anogenital distance among male infants with prenatal phthalate exposure.
2005 Aug
Controlled release of furosemide from the ethylene-vinyl acetate matrix.
2005 Aug 11
Human monitoring of phthalates and risk assessment.
2005 Aug 27
The toxic effect of phthalate esters on immune responses of giant freshwater prawn (Macrobrachium rosenbergii) via oral treatment.
2005 Aug 30
Kinetic analysis of the transformation of phthalate esters in a series of stoichiometric reactions in anaerobic wastes.
2005 Dec
The ugly side of beauty products.
2005 Jan
Urinary phthalate metabolites and biomarkers of reproductive function in young men.
2005 Jul
Gene expression profiling following in utero exposure to phthalate esters reveals new gene targets in the etiology of testicular dysgenesis.
2005 Jul
Adsorption of phthalic acid and its esters onto high-area activated carbon-cloth studied by in situ UV-spectroscopy.
2005 Jun 30
Anaerobic degradation of diethyl phthalate, di-n-butyl phthalate, and di-(2-ethylhexyl) phthalate from river sediment in Taiwan.
2005 Mar
Application of solid-phase microextraction to in vitro skin permeation experiments: example using diethyl phthalate.
2005 Mar
Biodegradation of an endocrine-disrupting chemical, di-2-ethylhexyl phthalate, by Bacillus subtilis No. 66.
2005 Mar
An in vivo bioassay for detecting antiandrogens using humanized transgenic mice coexpressing the tetracycline-controlled transactivator and human CYP1B1 gene.
2005 May-Jun
Personal care product use predicts urinary concentrations of some phthalate monoesters.
2005 Nov
The occurrence and removal of phthalates in a trickle filter STW.
2005 Nov
Oxidative degradation of diethyl phthalate by photochemically-enhanced Fenton reaction.
2005 Nov 11
Separation and determination of phthalates by micellar electrokinetic chromatography.
2005 Nov 18
Pressure dependence of the glass temperature in supercooled liquids.
2005 Oct
Phthalates in indoor dust and their association with building characteristics.
2005 Oct
Damming the flow of drugs into drinking water.
2005 Oct
Are EDCs blurring issues of gender?
2005 Oct
Bioavailability of phthalate congeners to earthworms (Eisenia fetida) in artificially contaminated soils.
2005 Sep
Human exposure to phthalates via consumer products.
2006 Feb
Human breast milk contamination with phthalates and alterations of endogenous reproductive hormones in infants three months of age.
2006 Feb
Biodegradable periodontal intrapocket device containing metronidazole and amoxycillin: formulation and characterisation.
2006 Jan
Validity of anogenital distance as a marker of in utero phthalate exposure.
2006 Jan
Orientation polarization from faster motions in the ultraviscous and glassy diethyl phthalate and its entropy.
2006 Jan 28
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Modelling MSW decomposition under landfill conditions considering hydrolytic and methanogenic inhibition.
2006 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Diethyl phthalate (DEP) in concentrations of 2 percent in petrolatum was nonirritating in 48-hour closed patch tests.
2% in petrolatum
Route of Administration: Transdermal
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
Created
by admin
on Fri Dec 15 15:15:18 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:18 UTC 2023
Record UNII
UF064M00AF
Record Status Validated (UNII)
Record Version
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Name Type Language
Diethyl phthalate
EP   HSDB   II   INCI   MART.   USP-RS   VANDF  
INCI  
Official Name English
PHTHALIC ACID ETHYL ESTER [MI]
Common Name English
PHTHALIC ACID ETHYL ESTER
MI  
Systematic Name English
NSC-8905
Code English
DIETHYL PHTHALATE [USP-RS]
Common Name English
ETHYL PHTHALATE
WHO-DD  
Systematic Name English
1,2-BENZENEDICARBOXYLIC ACID, DIETHYL ESTER
Common Name English
DIETHYL PHTHALATE [VANDF]
Common Name English
O-PHTHALIC ACID, DIETHYL ESTER
Common Name English
DIETHYL PHTHALATE [II]
Common Name English
DIETHYL PHTHALATE [MART.]
Common Name English
Ethyl phthalate [WHO-DD]
Common Name English
DIETHYL PHTHALATE [EP MONOGRAPH]
Common Name English
DIETHYL PHTHALATE [INCI]
Common Name English
DIETHYL PHTHALATE [HSDB]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128947
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
CFR 21 CFR 175.320
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NCI_THESAURUS C152072
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Code System Code Type Description
CAS
84-66-2
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY
CHEBI
34698
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PRIMARY
DAILYMED
UF064M00AF
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY
MESH
C007379
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PRIMARY
SMS_ID
100000076095
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PRIMARY
ChEMBL
CHEMBL388558
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PRIMARY
HSDB
926
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PRIMARY
MERCK INDEX
m8753
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PRIMARY Merck Index
WIKIPEDIA
DIETHYL PHTHALATE
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY
FDA UNII
UF064M00AF
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-550-6
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PRIMARY
RS_ITEM_NUM
1193505
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PRIMARY
EVMPD
SUB11901MIG
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PRIMARY
NCI_THESAURUS
C76749
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PRIMARY
PUBCHEM
6781
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PRIMARY
NSC
8905
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PRIMARY
EPA CompTox
DTXSID7021780
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY
RXCUI
1362921
Created by admin on Fri Dec 15 15:15:18 UTC 2023 , Edited by admin on Fri Dec 15 15:15:18 UTC 2023
PRIMARY RxNorm
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ACTIVE MOIETY