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Record Information
Version3.6
Creation Date2012-09-11 17:57:30 UTC
Update Date2013-06-30 06:18:20 UTC
HMDB IDHMDB33244
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. 1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester
  2. 1,2-Benzenedicarboxylic acid, dibutyl ester
  3. Araldite 502
  4. Benzene-O-dicarboxylic acid di-N-butyl ester
  5. Benzene-O-dicarboxylic acid, di-N-butyl ester
  6. Benzenedicarboxylic acid, dibutyl ester
  7. BUFA
  8. Butyl phthalate
  9. Celluflex DPB
  10. DBP (ester)
  11. Di N butyl phthalate
  12. Di-N-butyl phthalate
  13. Di-N-butyl phthalate (dbup)
  14. Di-N-butylester kyseliny ftalove
  15. Di-N-butylorthophthalate
  16. Dibutyl 1, 2-benzenedicarboxylate
  17. Dibutyl 1,2-benzenedicarboxylate
  18. Dibutyl ester of 1,2-benzenedicarboxylic acid
  19. Dibutyl O-phthalate
  20. Dibutyl phthalate
  21. Dibutyl phthalated
  22. Dibutyl-1,2-benzenedicarboxylate
  23. Dibutyl-O-phthalate
  24. Dibutyl-Phthalate
  25. Dibutyll phthalate
  26. Dibutylphthatlate
  27. Elaol
  28. Ergoplast FDB
  29. Ersoplast fda
  30. Genoplast b
  31. Hatcol DBP
  32. Hexaplas m/b
  33. Kodaflex DBP
  34. Morflex 240
  35. N-Butyl phthalate
  36. N-Butylphthalate
  37. O-Benzenedicarboxylic acid, dibutyl ester
  38. Ortho-dibutyl phthalate
  39. Palatinol c
  40. Palatinol DBP
  41. Phthalate, butyl
  42. Phthalate, di-N-butyl
  43. Phthalate, dibutyl
  44. Phthalic acid di-N-butyl ester
  45. Phthalic acid dibutyl ester
  46. Phthalic acid, dibutyl ester
  47. Polycizer DBP
  48. Rapidcelltrade markp
  49. RC plasticizer DBP
  50. Staflex DBP
  51. Uniflex DBP
  52. Unimoll DB
  53. Uniplex 150
  54. Witcizer 300
Chemical FormulaC16H22O4
Average Molecular Weight278.3435
Monoisotopic Molecular Weight278.151809192
IUPAC Name1,2-dibutyl benzene-1,2-dicarboxylate
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassPhthalic Acid and Derivatives
Other Descriptors
  • Insect repellents(KEGG)
  • Organic Compounds
  • Phthalates(KEGG)
  • phthalate ester(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
Direct Parento-Phthalic Acid and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Cosmetic
  • Plant
  • Toxin/Pollutant
Biofunction
  • Nutrient
Application
  • Laboratory Chemical
Cellular locations
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0112 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 Area52.6ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity77.86ChemAxon
Polarizability32.15ChemAxon
Spectra
Spectra1D NMR
Biological Properties
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011261
KNApSAcK IDNot Available
Chemspider ID13837319
KEGG Compound IDC14214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibutyl_phthalate
NuGOwiki LinkHMDB33244
Metagene LinkHMDB33244
METLIN IDNot Available
PubChem Compound3026
PDB IDNot Available
ChEBI ID535597
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.