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
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
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 |
DescriptionCurator'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
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
Sources: http://www.cdc.gov/niosh/docs/81-123/pdfs/0213.pdf
Curator's Comment: CNS effects only occurred in exposed workers after 6 to 7 years of chronic exposure to phthalates.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20943248 |
0.84 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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Tableting of Eudragit RS and propranolol hydrochloride solid dispersion: effect of particle size, compaction force, and plasticizer addition on drug release. | 2004 Aug |
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Suppression by phthalates of the calcium signaling of human nicotinic acetylcholine receptors in human neuroblastoma SH-SY5Y cells. | 2004 Aug 5 |
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Temporal variability of urinary phthalate metabolite levels in men of reproductive age. | 2004 Dec |
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Estimated exposure to phthalates in cosmetics and risk assessment. | 2004 Dec |
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Temperature-dependent micellar structures in poly(styrene-b-isoprene) diblock copolymer solutions near the critical micelle temperature. | 2004 Dec 8 |
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Adsorption of phthalates by activated sludge and its biopolymers. | 2004 Jul |
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Occurrence of phthalates and musk fragrances in indoor air and dust from apartments and kindergartens in Berlin (Germany). | 2004 Jun |
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New methodology for the determination of phthalate esters, bisphenol A, bisphenol A diglycidyl ether, and nonylphenol in commercial whole milk samples. | 2004 Jun 16 |
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[Analysis of the phthalates in cosmetics by capillary gas chromatography]. | 2004 May |
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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 |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20943248
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
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admin
on
Edited
Fri Dec 15 15:15:18 UTC 2023
by
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on
Fri Dec 15 15:15:18 UTC 2023
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Record UNII |
UF064M00AF
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
128947
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CFR |
21 CFR 175.320
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NCI_THESAURUS |
C152072
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84-66-2
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34698
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UF064M00AF
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C007379
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100000076095
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CHEMBL388558
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926
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m8753
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DIETHYL PHTHALATE
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UF064M00AF
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201-550-6
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SUB11901MIG
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C76749
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6781
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DTXSID7021780
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1362921
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