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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:57:30 UTC
Update Date2021-10-13 06:31:21 UTC
HMDB IDHMDB0033244
Secondary Accession Numbers
  • HMDB33244
Metabolite Identification
Common NameDibutyl phthalate
DescriptionDibutyl phthalate is found in cloves. DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide.
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
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 Weight278.3435
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling Point337.00 to 340.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.011 mg/mL at 25 °CNot Available
LogP4.50Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP10(4.53) g/LALOGPS
logP10(4.63) g/LChemAxon
logS10(-4.7) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.94631661259
DarkChem[M-H]-163.18631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized)splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-1910000000-964b3411de1f914de4da2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-0910000000-97464fdc3b8040ec3d362017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized)splash10-052b-0960000000-7a12a722da333ebed5e02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-5900000000-bb309d93583ab774d1f92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized)splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-1910000000-964b3411de1f914de4da2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-0910000000-97464fdc3b8040ec3d362018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized)splash10-052b-0960000000-7a12a722da333ebed5e02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized)splash10-0002-5900000000-bb309d93583ab774d1f92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibutyl phthalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5190000000-8daed01d42925467217c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibutyl phthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-3900000000-ecab0016129a96c4ece72014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-0590000000-d7fd13586fba8d9bcbb82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-003r-0900000000-26a0280d411587ad04062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-003r-0900000000-01dec35be5d4cb24d1832017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-00b9-1900000000-0a9f876d83f5cdff62be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-6900000000-88c2bba04cf08d8a94e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-9300000000-6e11d76c309a036870da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-9000000000-24ad78f1c73dbed6290d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-9000000000-2d5177b1586a4461b2782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOFsplash10-004i-9000000000-4516fb7c10721dc8cedb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-0002-0910000000-7702573da14ce44e4e732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-78eaf490a7fb4d87b4192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-5c75cf8111466a2bd8132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-a0747aefa385c43d47b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-006t-1900000000-29635db4a2da5e62db7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-00xs-5900000000-02c97dee9727d0badc2e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-014i-9200000000-2b0820b30884f0f997a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-5d4f80a8a661596a7cc82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-f45a033b5a30528756de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-19ad0b11756e1ca9188a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 10V, Positive-QTOFsplash10-056r-2090000000-80ca0d0b0000ed2e7f822016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 20V, Positive-QTOFsplash10-0a4i-9240000000-62634d519d04aa7360b12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 40V, Positive-QTOFsplash10-0a4i-9500000000-7279733c1ed1974ee7852016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 10V, Negative-QTOFsplash10-004i-1090000000-5c82ef4822a947c8f20b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 20V, Negative-QTOFsplash10-00fr-2590000000-eadc4a21565f062f1e5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibutyl phthalate 40V, Negative-QTOFsplash10-0600-5910000000-41f7de518636cfc255d92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kim H, Lee S, Ryu S, Choi HT: Decolorization of Remazol Brilliant Blue R by a purified laccase of Polyporus brumalis. Appl Biochem Biotechnol. 2012 Jan;166(1):159-64. doi: 10.1007/s12010-011-9412-y. Epub 2011 Nov 5. [PubMed:22057907 ]
  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 ]
  5. Simonsson C, Stenfeldt AL, Karlberg AT, Ericson MB, Jonsson CA: The pilosebaceous unit--a phthalate-induced pathway to skin sensitization. Toxicol Appl Pharmacol. 2012 Oct 1;264(1):114-20. doi: 10.1016/j.taap.2012.07.023. Epub 2012 Jul 27. [PubMed:22842015 ]
  6. Petersen JH, Jensen LK: Phthalates and food-contact materials: enforcing the 2008 European Union plastics legislation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Nov;27(11):1608-16. doi: 10.1080/19440049.2010.501825. [PubMed:20737341 ]
  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 ]
  9. Brucker-Davis F, Wagner-Mahler K, Bornebusch L, Delattre I, Ferrari P, Gal J, Boda-Buccino M, Pacini P, Tommasi C, Azuar P, Bongain A, Fenichel P: Exposure to selected endocrine disruptors and neonatal outcome of 86 healthy boys from Nice area (France). Chemosphere. 2010 Sep;81(2):169-76. doi: 10.1016/j.chemosphere.2010.06.068. [PubMed:20663538 ]
  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 ]
  15. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .