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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:57:30 UTC
Update Date2019-07-23 06:12:55 UTC
HMDB IDHMDB0033244
Secondary Accession Numbers
  • HMDB33244
Metabolite 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Dibutyl phthalate may also exhibit weak estrogenic activity. Dibutyl phthalate is a faint tasting compound. Outside of the human body, Dibutyl phthalate is found, on average, in the highest concentration within kohlrabis. Dibutyl phthalate has also been detected, but not quantified in, cloves. This could make dibutyl phthalate a potential biomarker for the consumption of these foods. The most characteristic effect of Dibutyl phthalate is testicular atrophy. Dibutyl phthalate is a potentially toxic compound. The decreased amount of available iron results in a decrease in succinate dehydrogenase activity in the Sertoli cells. Metabolism of Dibutyl phthalate proceeds mainly by nonspecific esterases in the gastrointestinal tract, which hydrolyze of one butyl ester bond to yield mono-n-butyl phthalate, the primary toxic metabolite. Mono-Dibutyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. Dibutyl phthalate is absorbed via oral, inhalation, and dermal routes. However, animals studies have shown that Dibutyl phthalate can affect reproductive ability by decreasing sperm count and causing birth defects. It is rapidly distributed and cleared from the body. It has been shown to exhibit toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting succinate dehydrogenase. Adverse effects from Dibutyl phthalate exposure have not yet been reported in humans.
Structure
Data?1563862375
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
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 phthalateHMDB
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
Phthalate, butylHMDB
Phthalate, di-N-butylHMDB
Phthalate, dibutylHMDB
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 Weight278.3435
Monoisotopic Molecular Weight278.151809192
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 PointNot AvailableNot Available
Water Solubility0.011 mg/mL at 25 °CNot Available
LogP4.50Not Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-1910000000-964b3411de1f914de4daSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0910000000-97464fdc3b8040ec3d36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-052b-0960000000-7a12a722da333ebed5e0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-5900000000-bb309d93583ab774d1f9Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-1910000000-964b3411de1f914de4daSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0910000000-97464fdc3b8040ec3d36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-052b-0960000000-7a12a722da333ebed5e0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-5900000000-bb309d93583ab774d1f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5190000000-8daed01d42925467217cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0590000000-d7fd13586fba8d9bcbb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-003r-0900000000-26a0280d411587ad0406Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-003r-0900000000-01dec35be5d4cb24d183Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00b9-1900000000-0a9f876d83f5cdff62beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-6900000000-88c2bba04cf08d8a94e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9300000000-6e11d76c309a036870daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-24ad78f1c73dbed6290dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-2d5177b1586a4461b278Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-4516fb7c10721dc8cedbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0910000000-7702573da14ce44e4e73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-78eaf490a7fb4d87b419Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-5c75cf8111466a2bd813Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-a0747aefa385c43d47b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-1900000000-29635db4a2da5e62db7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xs-5900000000-02c97dee9727d0badc2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9200000000-2b0820b30884f0f997a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-5d4f80a8a661596a7cc8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-f45a033b5a30528756deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-19ad0b11756e1ca9188aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-c218819436377fba26c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0930000000-3ffd578a63631650756aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0920000000-f84bcb5ebbad7fcd0a80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-0b26194ced4d64df6a2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1090000000-5c82ef4822a947c8f20bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-2590000000-eadc4a21565f062f1e5aSpectrum
MSMass Spectrum (Electron Ionization)splash10-0002-3900000000-ecab0016129a96c4ece7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13716
Phenol Explorer Compound IDNot Available
FooDB IDFDB011261
KNApSAcK IDNot Available
Chemspider ID13837319
KEGG Compound IDC14214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibutyl_phthalate
METLIN IDNot Available
PubChem Compound3026
PDB IDNot Available
ChEBI ID34687
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  2. Gupta VK, Singh LP, Chandra S, Kumar S, Singh R, Sethi B: Anion recognition through amide-based dendritic molecule: a poly(vinyl chloride) based sensor for nitrate ion. Talanta. 2011 Aug 15;85(2):970-4. doi: 10.1016/j.talanta.2011.05.014. Epub 2011 May 12. [PubMed:21726726 ]
  3. Cirillo T, Fasano E, Castaldi E, Montuori P, Amodio Cocchieri R: Children's exposure to Di(2-ethylhexyl)phthalate and dibutylphthalate plasticizers from school meals. J Agric Food Chem. 2011 Oct 12;59(19):10532-8. doi: 10.1021/jf2020446. Epub 2011 Sep 19. [PubMed:21894916 ]
  4. Ito Y, Nakamura T, Yanagiba Y, Ramdhan DH, Yamagishi N, Naito H, Kamijima M, Gonzalez FJ, Nakajima T: Plasticizers May Activate Human Hepatic Peroxisome Proliferator-Activated Receptor alpha Less Than That of a Mouse but May Activate Constitutive Androstane Receptor in Liver. PPAR Res. 2012;2012:201284. doi: 10.1155/2012/201284. Epub 2012 Jun 20. [PubMed:22792086 ]
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  7. Fishman AI, Noskov AI, Stolov AA: Conformational mobility of small molecules in glass-forming solutions studied by FTIR spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jun;91:184-91. doi: 10.1016/j.saa.2012.01.060. Epub 2012 Feb 9. [PubMed:22381789 ]
  8. Tyagi S, Agarwal H, Ikram S: A polyvinylchloride-based cadmium ion-selective electrode using [Mo(2)(OAc)(2)(H(2)-calix[4]arene)] as an electroactive material. Water Sci Technol. 2010;62(11):2510-8. doi: 10.2166/wst.2010.774. [PubMed:21099036 ]
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  10. Dobrzynska MM, Tyrkiel EJ, Hernik A, Derezinska E, Goralczyk K, Ludwicki JK: [The effects of di-n-butyl phthalate on the somatic cells of laboratory mice]. Rocz Panstw Zakl Hig. 2010;61(1):13-9. [PubMed:20803895 ]
  11. Carran M, Shaw IC: New Zealand Malayan war veterans' exposure to dibutylphthalate is associated with an increased incidence of cryptorchidism, hypospadias and breast cancer in their children. N Z Med J. 2012 Jul 29;125(1358):52-63. [PubMed:22864157 ]
  12. Singh AK, Singh P: Determination of cerium ion by polymeric membrane and coated graphite electrode based on novel pendant armed macrocycle. Anal Chim Acta. 2010 Aug 24;675(2):170-80. doi: 10.1016/j.aca.2010.07.023. Epub 2010 Jul 21. [PubMed:20800729 ]
  13. van Ravenzwaay B, Coelho-Palermo Cunha G, Strauss V, Wiemer J, Leibold E, Kamp H, Walk T, Mellert W, Looser R, Prokoudine A, Fabian E, Krennrich G, Herold M: The individual and combined metabolite profiles (metabolomics) of dibutylphthalate and di(2-ethylhexyl)phthalate following a 28-day dietary exposure in rats. Toxicol Lett. 2010 Oct 5;198(2):159-70. doi: 10.1016/j.toxlet.2010.06.009. Epub 2010 Jun 23. [PubMed:20600714 ]
  14. Tyagi S, Agarwal H, Ikram S: Potentiometric polymeric membrane electrodes for mercury detection using calixarene ionophores. Water Sci Technol. 2010;61(3):693-704. doi: 10.2166/wst.2010.860. [PubMed:20150706 ]
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