Human Metabolome Database Version 3.5

Showing metabocard for Dibutyl phthalate (HMDB33244)

Record Information
Version 3.5
Creation Date 2012-09-11 11:57:30 -0600
Update Date 2013-06-30 00:18:20 -0600
HMDB ID HMDB33244
Secondary Accession Numbers None
Metabolite Identification
Common Name Dibutyl phthalate
Description Dibutyl 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C16H22O4
Average Molecular Weight 278.3435
Monoisotopic Molecular Weight 278.151809192
IUPAC Name 1,2-dibutyl benzene-1,2-dicarboxylate
Traditional IUPAC Name dibutyl-phthalate
CAS Registry Number 84-74-2
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 Key DOIRQSBPFJWKBE-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Phthalic Acid and Derivatives
Other Descriptors
  • Insect repellents(KEGG)
  • Organic Compounds
  • Phthalates(KEGG)
  • phthalate ester(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
Direct Parent o-Phthalic Acid and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Cosmetic
  • Plant
  • Toxin/Pollutant
Biofunction
  • Nutrient
Application
  • Laboratory Chemical
Cellular locations
  • Membrane
Physical Properties
State Not Available
Experimental Properties
Property Value Reference
Melting Point 35 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0112 mg/mL at 25 °C Not Available
LogP 4.50 Not Available
Predicted Properties
Property Value Source
LogP 4.53 ALOGPS
LogP 4.63 ChemAxon
LogS -4.67 ALOGPS
pKa (strongest basic) -6.7 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 52.6 A2 ChemAxon
Rotatable Bond Count 10 ChemAxon
Refractivity 77.86 ChemAxon
Polarizability 32.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011261
KNApSAcK ID Not Available
Chemspider ID 13837319 Link_out
KEGG Compound ID C14214 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Dibutyl_phthalate Link_out
NuGOwiki Link HMDB33244 Link_out
Metagene Link HMDB33244 Link_out
METLIN ID Not Available
PubChem Compound 3026 Link_out
PDB ID Not Available
ChEBI ID 535597 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  15. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.