Showing Compound Card for Dibutyl phthalate (CDB000591)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:45:29 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000591
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Dibuthyl 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 dibutyl esterChEBI
Benzene-O-dicarboxylic acid di-N-butyl esterChEBI
Benzenedicarboxylic acid dibutyl esterChEBI
Butyl phthalateChEBI
DBPChEBI
Di-N-butyl phthalateChEBI
Dibutyl 1,2-benzenedicarboxylateChEBI
Dibutyl O-phthalateChEBI
Dibutyl-O-phthalateChEBI
N-Butyl phthalateChEBI
O-Benzenedicarboxylic acid dibutyl esterChEBI
Phthalic acid di-N-butyl esterChEBI
Phthalic acid dibutyl esterChEBI
1,2-Benzenedicarboxylate dibutyl esterGenerator
Benzene-O-dicarboxylate di-N-butyl esterGenerator
Benzenedicarboxylate dibutyl esterGenerator
Butyl phthalic acidGenerator
Di-N-butyl phthalic acidGenerator
Dibutyl 1,2-benzenedicarboxylic acidGenerator
Dibutyl O-phthalic acidGenerator
Dibutyl-O-phthalic acidGenerator
N-Butyl phthalic acidGenerator
O-Benzenedicarboxylate dibutyl esterGenerator
Phthalate di-N-butyl esterGenerator
Phthalate dibutyl esterGenerator
Dibutyl phthalic acidGenerator
Di N butyl phthalateMeSH
Phthalate, butylMeSH
Phthalate, di-N-butylMeSH
Phthalate, dibutylMeSH
1,2-Benzenedicarboxylic acid, 1,2-dibutyl esterHMDB
1,2-Benzenedicarboxylic acid, dibutyl esterHMDB
Araldite 502HMDB
Benzene-O-dicarboxylic acid, di-N-butyl esterHMDB
Benzenedicarboxylic acid, dibutyl esterHMDB
BUFAHMDB
Celluflex DPBHMDB
DBP (Ester)HMDB
Di-N-butyl phthalate (dbup)HMDB
Di-N-butylester kyseliny ftaloveHMDB
Di-N-butylorthophthalateHMDB
Dibutyl 1, 2-benzenedicarboxylateHMDB
Dibutyl ester OF 1,2-benzenedicarboxylic acidHMDB
Dibutyl phthalatedHMDB
Dibutyl-1,2-benzenedicarboxylateHMDB
Dibutyl-phthalateHMDB
Dibutyll phthalateHMDB
DibutylphthatlateHMDB
ElaolHMDB
Ergoplast FDBHMDB
Ersoplast fdaHMDB
Genoplast bHMDB
Hatcol DBPHMDB
Hexaplas m/bHMDB
Kodaflex DBPHMDB
Morflex 240HMDB
N-ButylphthalateHMDB
O-Benzenedicarboxylic acid, dibutyl esterHMDB
ortho-Dibutyl phthalateHMDB
Phthalic acid, dibutyl esterHMDB
Polycizer DBPHMDB
Rapidcelltrade markpHMDB
RC Plasticizer DBPHMDB
Staflex DBPHMDB
Uniflex DBPHMDB
Unimoll DBHMDB
Uniplex 150HMDB
Witcizer 300HMDB
Dibutylphthalic acidGenerator
Chemical FormulaC16H22O4
Average Molecular Weight278.34
Monoisotopic Molecular Weight278.1518
IUPAC Name1,2-dibutyl benzene-1,2-dicarboxylate
Traditional Namedibutyl-phthalate
CAS Registry Number84-74-2
SMILES
CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC
InChI Identifier
InChI=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
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling Point340 °CWikipedia
Water Solubility0.011 mg/mL at 25 °CNot Available
logP4.50Not Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialSDHA5p15P31040 details
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrialSDHB1p36.1-p35P21912 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrialSDHB1p36.1-p35P21912 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033244
DrugBank IDDB13716
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011261
KNApSAcK IDC00053140
Chemspider ID13837319
KEGG Compound IDC14214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibutyl_phthalate
METLIN IDNot Available
PubChem Compound3026
PDB IDNot Available
ChEBI ID34687
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 ]

Enzymes

Enzyme Details
1. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular weight:
72690.975
Enzyme Details
2. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHB
Uniprot ID:
P21912
Molecular weight:
31629.365