Showing Compound Dibutyl phthalate (FDB011261)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:33 UTC

Update date

2020-09-17 15:35:02 UTC

Primary ID

FDB011261

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dibutyl phthalate

Description

Dibutyl 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 Number

84-74-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,2-Benzenedicarboxylic acid dibutyl ester	ChEBI
Benzene-O-dicarboxylic acid di-N-butyl ester	ChEBI
Benzenedicarboxylic acid dibutyl ester	ChEBI
Butyl phthalate	ChEBI
DBP	ChEBI
Di-N-butyl phthalate	ChEBI
Dibutyl 1,2-benzenedicarboxylate	ChEBI
Dibutyl O-phthalate	ChEBI
Dibutyl-O-phthalate	ChEBI
N-Butyl phthalate	ChEBI
O-Benzenedicarboxylic acid dibutyl ester	ChEBI
Phthalic acid di-N-butyl ester	ChEBI
Phthalic acid dibutyl ester	ChEBI
1,2-Benzenedicarboxylate dibutyl ester	Generator
Benzene-O-dicarboxylate di-N-butyl ester	Generator
Benzenedicarboxylate dibutyl ester	Generator
Butyl phthalic acid	Generator
Di-N-butyl phthalic acid	Generator
Dibutyl 1,2-benzenedicarboxylic acid	Generator
Dibutyl O-phthalic acid	Generator
Dibutyl-O-phthalic acid	Generator
N-Butyl phthalic acid	Generator
O-Benzenedicarboxylate dibutyl ester	Generator
Phthalate di-N-butyl ester	Generator
Phthalate dibutyl ester	Generator
Dibutyl phthalic acid	Generator
Di N butyl phthalate	MeSH
Phthalate, butyl	MeSH
Phthalate, di-N-butyl	MeSH
Phthalate, dibutyl	MeSH
1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester	HMDB
1,2-Benzenedicarboxylic acid, dibutyl ester	HMDB
Araldite 502	HMDB
Benzene-O-dicarboxylic acid, di-N-butyl ester	HMDB
Benzenedicarboxylic acid, dibutyl ester	HMDB
BUFA	HMDB
Celluflex DPB	HMDB
DBP (Ester)	HMDB
Di-N-butyl phthalate (dbup)	HMDB
Di-N-butylester kyseliny ftalove	HMDB
Di-N-butylorthophthalate	HMDB
Dibutyl 1, 2-benzenedicarboxylate	HMDB
Dibutyl ester OF 1,2-benzenedicarboxylic acid	HMDB
Dibutyl phthalated	HMDB
Dibutyl-1,2-benzenedicarboxylate	HMDB
Dibutyl-phthalate	HMDB
Dibutyll phthalate	HMDB
Dibutylphthatlate	HMDB
Elaol	HMDB
Ergoplast FDB	HMDB
Ersoplast fda	HMDB
Genoplast b	HMDB
Hatcol DBP	HMDB
Hexaplas m/b	HMDB
Kodaflex DBP	HMDB
Morflex 240	HMDB
N-Butylphthalate	HMDB
O-Benzenedicarboxylic acid, dibutyl ester	HMDB
ortho-Dibutyl phthalate	HMDB
Phthalic acid, dibutyl ester	HMDB
Polycizer DBP	HMDB
Rapidcelltrade markp	HMDB
RC Plasticizer DBP	HMDB
Staflex DBP	HMDB
Uniflex DBP	HMDB
Unimoll DB	HMDB
Uniplex 150	HMDB
Witcizer 300	HMDB
Dibutylphthalic acid	Generator
Benzene-o-dicarboxylic acid di-n-butyl ester	biospider
Benzene-o-dicarboxylic acid, di-n-butyl ester	biospider
DBP (ester)	biospider
Di n butyl phthalate	biospider
Di-n-butyl phthalate	biospider
Di-n-butyl phthalate (dbup)	biospider
Di-n-butylester kyseliny ftalove	biospider
Di-n-butylorthophthalate	biospider
Dibutyl ester of 1,2-benzenedicarboxylic acid	biospider
Dibutyl o-phthalate	biospider
Dibutyl phthalate	db_source
Dibutyl-o-phthalate	biospider
N-butyl phthalate	biospider
N-butylphthalate	biospider
O-benzenedicarboxylic acid, dibutyl ester	biospider
Ortho-dibutyl phthalate	biospider
Palatinol c	biospider
Palatinol DBP	biospider
Phthalate, di-n-butyl	biospider
Phthalate, dibutyl-	biospider
Phthalic acid di-n-butyl ester	biospider
RC plasticizer DBP	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	4.53	ALOGPS
logP	4.63	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	77.86 m³·mol⁻¹	ChemAxon
Polarizability	32.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H22O4

IUPAC name

1,2-dibutyl benzene-1,2-dicarboxylate

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

Isomeric SMILES

CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC

Average Molecular Weight

278.3435

Monoisotopic Molecular Weight

278.151809192

Classification

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

diester (CHEBI:34687 )
phthalate ester (CHEBI:34687 )
Insect repellents (C14214 )
Phthalates (C14214 )

Ontology

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Plant

Biological location:

Subcellular:

Role

Indirect biological role:

Teratogen

Environmental role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 69.04%; H 7.97%; O 22.99%	DFC
Melting Point	Mp ?35°	DFC
Boiling Point	Bp 340°	DFC
Experimental Water Solubility	0.0112 mg/mL at 25 oC	HOWARD,PH et al. (1985)
Experimental logP	4.50	ELLINGTON,JT & FLOYD,TL (1996)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d2020 1.05	DFC
Refractive Index	n25D 1.4915	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0002-3900000000-ecab0016129a96c4ece7	2014-09-20	View Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-964b3411de1f914de4da	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-97464fdc3b8040ec3d36	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-052b-0960000000-7a12a722da333ebed5e0	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-5900000000-bb309d93583ab774d1f9	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-964b3411de1f914de4da	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-97464fdc3b8040ec3d36	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-052b-0960000000-7a12a722da333ebed5e0	Spectrum
GC-MS	Dibutyl phthalate, non-derivatized, GC-MS Spectrum	splash10-0002-5900000000-bb309d93583ab774d1f9	Spectrum
Predicted GC-MS	Dibutyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-5190000000-8daed01d42925467217c	Spectrum
Predicted GC-MS	Dibutyl phthalate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0590000000-d7fd13586fba8d9bcbb8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-003r-0900000000-26a0280d411587ad0406	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-003r-0900000000-01dec35be5d4cb24d183	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00b9-1900000000-0a9f876d83f5cdff62be	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-6900000000-88c2bba04cf08d8a94e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9300000000-6e11d76c309a036870da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-24ad78f1c73dbed6290d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-2d5177b1586a4461b278	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-4516fb7c10721dc8cedb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0910000000-7702573da14ce44e4e73	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-78eaf490a7fb4d87b419	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-5c75cf8111466a2bd813	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-a0747aefa385c43d47b1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-1900000000-29635db4a2da5e62db7f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00xs-5900000000-02c97dee9727d0badc2e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9200000000-2b0820b30884f0f997a5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-5d4f80a8a661596a7cc8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-f45a033b5a30528756de	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-19ad0b11756e1ca9188a	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2090000000-80ca0d0b0000ed2e7f82	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9240000000-62634d519d04aa7360b1	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9500000000-7279733c1ed1974ee785	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1090000000-5c82ef4822a947c8f20b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-2590000000-eadc4a21565f062f1e5a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-5910000000-41f7de518636cfc255d9	2016-08-03	View Spectrum