Showing Compound Card for Diethyl Phthalate (CDB000592)

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Record Information
Version1.0
Created at2020-03-19 00:45:33 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000592
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDiethyl Phthalate
DescriptionDiethyl phthalate, also known as 1,2-diethyl phthalate or DEP, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Diethyl phthalate is hydrolyzed to its monoester derivative by diethyl phthalic acid hydrolase. Diethyl phthalate is a potentially toxic compound. It is a clear liquid at room temperature, and it is only slightly denser than liquid water. When burned, DEP produces toxic gases. Many organic molecules are soluble in it and it is therefore often used to bind cosmetics and fragrances. It is industrially used as a plasticizer, detergent bases and aerosol sprays. Diethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of a catalytic amount of concentrated sulfuric acid. Diethyl phthalate, and other phthalates, are often reported as components of natural products extracts. However, due to their high solubility in organic solvents (e.g. ethanol, ethers, dichloromethane, and benzene) they are most likely a contaminant analyte, introduced into the sample through the use of plastics during sample preparation or from contaminated solvents, especially in gas chromatography analyses. Diethyl phtalate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2-Benzenedicarboxylic acid diethyl esterChEBI
1,2-Diethyl phthalateChEBI
DEPChEBI
Diethyl 1,2-benzenedicarboxylateChEBI
Diethyl benzene-1,2-dicarboxylateChEBI
Diethyl O-phthalateChEBI
Ethyl phthalateChEBI
O-Benzenedicarboxylic acid diethyl esterChEBI
O-Bis(ethoxycarbonyl)benzeneChEBI
Phthalic acid diethyl esterChEBI
PhthalsaeurediaethylesterChEBI
1,2-Benzenedicarboxylate diethyl esterGenerator
1,2-Diethyl phthalic acidGenerator
Diethyl 1,2-benzenedicarboxylic acidGenerator
Diethyl benzene-1,2-dicarboxylic acidGenerator
Diethyl O-phthalic acidGenerator
Ethyl phthalic acidGenerator
O-Benzenedicarboxylate diethyl esterGenerator
Phthalate diethyl esterGenerator
Diethyl phthalateGenerator
Diethyl phthalic acidGenerator
Chemical FormulaC12H14O4
Average Molecular Weight222.24
Monoisotopic Molecular Weight222.0892
IUPAC Name1,2-diethyl benzene-1,2-dicarboxylate
Traditional Namediethyl phthalate
CAS Registry NumberNot Available
SMILES
CCOC(=O)C1=CC=CC=C1C(=O)OCC
InChI Identifier
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
InChI KeyFLKPEMZONWLCSK-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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.6ALOGPS
logP2.69ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity59.61 m³·mol⁻¹ChemAxon
Polarizability23.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-2900000000-c0f3a0df2bad7bb63a1a2014-09-20View Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-002b-1900000000-503cf95871c5904aff71Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004i-0930000000-7086cd5850c044d82e6aSpectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-4412971f705146d2fd1fSpectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004j-0910000000-3da30560fd9393855d42Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-417398cedfbfc7e8f2c4Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-40ef56b72df55d26c8ceSpectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-002b-1900000000-503cf95871c5904aff71Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004i-0930000000-7086cd5850c044d82e6aSpectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-4412971f705146d2fd1fSpectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004j-0910000000-3da30560fd9393855d42Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-417398cedfbfc7e8f2c4Spectrum
GC-MSDiethyl Phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-40ef56b72df55d26c8ceSpectrum
Predicted GC-MSDiethyl Phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-4900000000-95f8663192d5c11641bbSpectrum
Predicted GC-MSDiethyl Phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiethyl Phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-7950000000-17006e6795e6cbb4bcf72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9810000000-2c960e7f0228478b05762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9600000000-4bf131a7544bb092312a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9400000000-2a69601f610fdcd4f4772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-9200000000-19d7f94c7af5b78aca582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0100-9100000000-744178d47d141e29f10c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-c4fa127cbd14a64144de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-136161f75c32091bf1802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004j-0900000000-8845fcd110c6da94d5542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-70f0da44ec73bc26362c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-a7761aec74b20d2eb58d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-f41b5fc7349bff1654072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-1900000000-fea3964d97a7809c1bcf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xs-4900000000-ac8b2ce4bcb6a6724cf32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9200000000-4d7079f620d5ad4e4a282017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-06f59bdd387a43c568862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-23fb179d6576972a10d32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-adbdc25fa7d0fdb4f8682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-0900000000-3a6c7d7f9113fed591742021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0590000000-19c4c903328f99b0457d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-0930000000-1634c3a90c28e33287ee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-e4a1aeacabe307c975722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0390000000-6eb1e81609a1c2b23bf82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2960000000-3743338637ef15aafeea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0092-4900000000-9ae1ef130a13535ace142016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0094660
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00042472
Chemspider IDNot Available
KEGG Compound IDC14175
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethyl_phthalate
METLIN IDNot Available
PubChem Compound6781
PDB IDNot Available
ChEBI ID34698
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]