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Showing Compound Dibutyl phthalate (FDB011261)

Record Information
Version1.0
Creation date2010-04-08 22:09:33 UTC
Update date2020-09-17 15:35:02 UTC
Primary IDFDB011261
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDibutyl phthalate
DescriptionDibutyl phthalate, also known as DBP or butyl phthalic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is a paint tasting, colorless oil, although commercial samples are often yellow. Metabolism of dibutyl phthalate proceeds mainly by nonspecific esterases in the gastrointestinal tract, which hydrolyze one of the butyl ester bonds to yield mono-n-butyl phthalate, the primary toxic metabolite. Dibutyl phthalate is absorbed via oral, inhalation, and dermal routes. It is rapidly distributed and cleared from the body. Mono-butyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. Dibutyl phthalate is a potentially toxic compound. The most characteristic effect of dibutyl phthalate on mammals is testicular atrophy. Animal studies have shown that dibutyl phthalate can affect the reproductive ability by decreasing sperm count and causing birth defects. DBT has also exhibited toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting the succinate dehydrogenase. Adverse effects from dibutyl phthalate exposure have not yet been reported in humans. Dibutyl phthalate is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. DBP is also used as an ectoparasiticide. Dibutyl 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.
CAS Number84-74-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP4.53ALOGPS
logP4.63ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity77.86 m³·mol⁻¹ChemAxon
Polarizability32.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H22O4
IUPAC name1,2-dibutyl benzene-1,2-dicarboxylate
InChI IdentifierInChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3
InChI KeyDOIRQSBPFJWKBE-UHFFFAOYSA-N
Isomeric SMILESCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC
Average Molecular Weight278.3435
Monoisotopic Molecular Weight278.151809192
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-3900000000-ecab0016129a96c4ece72014-09-20View Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0a6s-0490000000-bb10c8ff49d65e9fbcfdSpectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-964b3411de1f914de4daSpectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-97464fdc3b8040ec3d36Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-052b-0960000000-7a12a722da333ebed5e0Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-bb309d93583ab774d1f9Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0a6s-0490000000-bb10c8ff49d65e9fbcfdSpectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-964b3411de1f914de4daSpectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-97464fdc3b8040ec3d36Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-052b-0960000000-7a12a722da333ebed5e0Spectrum
GC-MSDibutyl phthalate, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-bb309d93583ab774d1f9Spectrum
Predicted GC-MSDibutyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5190000000-8daed01d42925467217cSpectrum
Predicted GC-MSDibutyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0590000000-d7fd13586fba8d9bcbb82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-003r-0900000000-26a0280d411587ad04062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-003r-0900000000-01dec35be5d4cb24d1832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00b9-1900000000-0a9f876d83f5cdff62be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-6900000000-88c2bba04cf08d8a94e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9300000000-6e11d76c309a036870da2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-24ad78f1c73dbed6290d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-2d5177b1586a4461b2782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-4516fb7c10721dc8cedb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0910000000-7702573da14ce44e4e732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-78eaf490a7fb4d87b4192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-5c75cf8111466a2bd8132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-a0747aefa385c43d47b12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-1900000000-29635db4a2da5e62db7f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xs-5900000000-02c97dee9727d0badc2e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9200000000-2b0820b30884f0f997a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-5d4f80a8a661596a7cc82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-f45a033b5a30528756de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-19ad0b11756e1ca9188a2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2090000000-80ca0d0b0000ed2e7f822016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9240000000-62634d519d04aa7360b12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-7279733c1ed1974ee7852016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1090000000-5c82ef4822a947c8f20b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-2590000000-eadc4a21565f062f1e5a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-5910000000-41f7de518636cfc255d92016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13837319
ChEMBL IDCHEMBL272485
KEGG Compound IDC14214
Pubchem Compound ID3026
Pubchem Substance IDNot Available
ChEBI ID535597
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33244
CRC / DFC (Dictionary of Food Compounds) IDFDK47-M:GLG23-X
EAFUS IDNot Available
Dr. Duke IDDIBUTYL-PHTHALATE|PHTHALIC ACID DIBUTYL DIESTER
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1018721
SuperScent IDNot Available
Wikipedia IDDibutyl_phthalate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).