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
Synonyms
SynonymSource
1,2-Benzenedicarboxylate dibutyl esterGenerator
1,2-Benzenedicarboxylic acid dibutyl esterChEBI
1,2-Benzenedicarboxylic acid, 1,2-dibutyl esterbiospider
1,2-Benzenedicarboxylic acid, dibutyl esterbiospider
Araldite 502biospider
Benzene-O-dicarboxylate di-N-butyl esterGenerator
Benzene-o-dicarboxylic acid di-n-butyl esterbiospider
Benzene-o-dicarboxylic acid, di-n-butyl esterbiospider
Benzenedicarboxylate dibutyl esterGenerator
Benzenedicarboxylic acid dibutyl esterChEBI
Benzenedicarboxylic acid, dibutyl esterbiospider
BUFAbiospider
Butyl phthalatebiospider
Butyl phthalic acidGenerator
Celluflex DPBbiospider
DBPChEBI
DBP (ester)biospider
Di n butyl phthalatebiospider
Di-n-butyl phthalatebiospider
Di-n-butyl phthalate (dbup)biospider
Di-N-butyl phthalic acidGenerator
Di-n-butylester kyseliny ftalovebiospider
Di-n-butylorthophthalatebiospider
Dibutyl 1, 2-benzenedicarboxylatebiospider
Dibutyl 1,2-benzenedicarboxylatebiospider
Dibutyl 1,2-benzenedicarboxylic acidGenerator
Dibutyl ester of 1,2-benzenedicarboxylic acidbiospider
Dibutyl o-phthalatebiospider
Dibutyl O-phthalic acidGenerator
Dibutyl phthalatedb_source
Dibutyl phthalatedbiospider
Dibutyl phthalic acidGenerator
Dibutyl-1,2-benzenedicarboxylatebiospider
Dibutyl-o-phthalatebiospider
Dibutyl-O-phthalic acidGenerator
Dibutyl-phthalateHMDB
Dibutyll phthalatebiospider
Dibutylphthatlatebiospider
Elaolbiospider
Ergoplast FDBbiospider
Ersoplast fdabiospider
Genoplast bbiospider
Hatcol DBPbiospider
Hexaplas m/bbiospider
Kodaflex DBPbiospider
Morflex 240biospider
N-butyl phthalatebiospider
N-Butyl phthalic acidGenerator
N-butylphthalatebiospider
O-Benzenedicarboxylate dibutyl esterGenerator
O-Benzenedicarboxylic acid dibutyl esterChEBI
O-benzenedicarboxylic acid, dibutyl esterbiospider
Ortho-dibutyl phthalatebiospider
Palatinol cbiospider
Palatinol DBPbiospider
Phthalate di-N-butyl esterGenerator
Phthalate dibutyl esterGenerator
Phthalate, butylbiospider
Phthalate, di-n-butylbiospider
Phthalate, dibutylbiospider
Phthalate, dibutyl-biospider
Phthalic acid di-n-butyl esterbiospider
Phthalic acid dibutyl esterbiospider
Phthalic acid, dibutyl esterbiospider
Polycizer DBPbiospider
Rapidcelltrade markpbiospider
RC plasticizer DBPbiospider
Staflex DBPbiospider
Uniflex DBPbiospider
Unimoll DBbiospider
Uniplex 150biospider
Witcizer 300biospider
Predicted PropertiesNot Available
Chemical FormulaC16H22O4
IUPAC name
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
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.04%; H 7.97%; O 22.99%DFC
Melting PointMp ?35°DFC
Boiling PointBp 340°DFC
Experimental Water Solubility0.0112 mg/mL at 25 oCHOWARD,PH et al. (1985)
Experimental logP4.50ELLINGTON,JT & FLOYD,TL (1996)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2020 1.05DFC
Refractive Indexn25D 1.4915DFC
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).