Showing Compound Card for Dioctyl phthalate (CDB005768)

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Record Information
Version1.0
Created at2020-04-27 16:53:48 UTC
Updated at2021-01-04 18:49:14 UTC
CannabisDB IDCDB005768
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDioctyl phthalate
DescriptionDioctyl phthalate or Di(n-octyl) phthalate or DOP, also known as diethylhexyl phthalate or DEHP is a dialkylated derivative of phthalate in which two n-octyl groups have been replaced by hydrogen atoms of carboxyl groups. Dioctyl phthalate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. It is also classified as a diester of phthalic acid and the branched-chain 2-ethylhexanol. Dioctyl phthalate or DEHP exists as a colorless, odorless oily liquid that is slightly soluble in water. Industrially, due to its suitable properties and the low cost, DEHP is widely used as a plasticizer in manufacturing of articles made of PVC (polyvinylchloride). Plastics may contain 1% to 40% of DEHP. It is also used as a hydraulic fluid and as a dielectric fluid in capacitors. DEHP is also used as a solvent in glowsticks. DEHP is a component of many household items, including tablecloths, floor tiles, shower curtains, garden hoses, rainwear, dolls, toys, shoes, medical tubing, furniture upholstery, and swimming pool liners. DEHP is an indoor air pollutant in homes and schools. Common exposures come from the use of DEHP as a fragrance carrier in cosmetics, personal care products, laundry detergents, colognes, scented candles, and air fresheners. The most common exposure to DEHP comes through food with an average consumption of 0.25 milligrams per day. When DEHP is ingested intestinal lipases convert it to MEHP (mono-ethylhexyl phthalate), which then is absorbed. MEHP is suspected to have an obesogenic effect. DEHP, along with other phthalates, is believed to cause endocrine disruption in males, through its action as an androgen antagonist. Di(n-octyl) phthalate or DEHP has been found in a small number of plants such as kohlrabis. It has also been found as a contaminant in milk, cream, butter and cheese (PMID: 7926171 ). Dioctyl phthalate is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Bis(N-octyl) phthalateKegg
Dioctyl 1,2-benzenedicarboxylateKegg
Bis(N-octyl) phthalic acidGenerator
Dioctyl 1,2-benzenedicarboxylic acidGenerator
Dioctyl phthalic acidGenerator
Phthalate, dioctylMeSH
Phthalate, diethylhexylMeSH
Di-2-ethylhexylphthalateMeSH
Bis(2-ethylhexyl)phthalateMeSH
Di(2-ethylhexyl)phthalateMeSH
DEHPMeSH
Di 2 ethylhexylphthalateMeSH
Diethylhexyl phthalateMeSH
Di(N-octyl) phthalic acidGenerator
Chemical FormulaC24H38O4
Average Molecular Weight390.56
Monoisotopic Molecular Weight390.277
IUPAC Name1,2-dioctyl benzene-1,2-dicarboxylate
Traditional Namedioctyl phthalate
CAS Registry Number117-84-0
SMILES
CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC
InChI Identifier
InChI=1S/C24H38O4/c1-3-5-7-9-11-15-19-27-23(25)21-17-13-14-18-22(21)24(26)28-20-16-12-10-8-6-4-2/h13-14,17-18H,3-12,15-16,19-20H2,1-2H3
InChI KeyMQIUGAXCHLFZKX-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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point−50 °CWikipedia
Boiling Point385 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.76ALOGPS
logP8.18ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity114.66 m³·mol⁻¹ChemAxon
Polarizability49.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-5910000000-06ec4da7fbd2cda38bc02014-09-20View Spectrum
Predicted GC-MSDioctyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03e9-8972000000-5a8ecf0088a627f42da0Spectrum
Predicted GC-MSDioctyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-1900000000-9fb6b4325e699a139e0a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0002-1900000000-7f7c28506e01f823a8622020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-03dm-0695000000-e99f47f201a13a40b1f72020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0002-0900000000-c6b9df5b2ccfb027d2e72020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0002-1900000000-189af9ebde1fa2a63bbb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 39V, positivesplash10-00mk-0940000000-c497796373d4621cef322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0002-0920000000-7b595b4b420c49195e5f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0109000000-a1cc0d131cb45cdb5da52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0006-0009000000-8f771fd98c406d48ea052020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-0006-0009000000-7980d3a8e284191d41142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-0006-0009000000-13e55575d97403874b132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0006-0109000000-26a4c9c86313a465e01b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-0006-0219000000-2ebc75da8abc7ef0d7db2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-0006-0529000000-2384ab77d02e03f317892020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-01oy-0935000000-266187a492dfd4e879b22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-01ow-0922000000-72c6d82d5a21a25e73b52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-01ot-0910000000-e8ec512e9a495a136bef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0292-1910000000-83c7fb949679846346d92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-00kb-1900000000-a83f8e32cd1cff4d27572020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0339000000-01cb26c1b4d0ce8f22982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4932000000-7be96c0f73af9bf207a02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9600000000-0b98763c4b9ac3814a832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0139000000-c8348cc26c6fdd13ff9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0592000000-0ca1afb6532b1a5077a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02os-1910000000-175224683dd2f0783f282016-08-03View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004316
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14227
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBis(2-ethylhexyl) phthalate
METLIN IDNot Available
PubChem Compound8346
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Sharman M, Read WA, Castle L, Gilbert J: Levels of di-(2-ethylhexyl)phthalate and total phthalate esters in milk, cream, butter and cheese. Food Addit Contam. 1994 May-Jun;11(3):375-85. doi: 10.1080/02652039409374236. [PubMed:7926171 ]