ContaminantDB: Dibutyl phthalate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:59 UTC

Update Date

2026-03-31 18:32:24 UTC

Accession Number

CHEM000048

Identification

Common Name

Dibutyl phthalate

Class

Small Molecule

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.

Contaminant Sources

Clean Air Act Chemicals
Cosmetic Chemicals
ECHA Toxic for reproduction
EPA Endocrine Screening
FooDB Chemicals
HPV EPA Chemicals
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cosmetic Toxin
Ester
Ether
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Phthalate
Plasticizer
Pollutant

Chemical Structure

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

Synonyms

Value	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

Chemical Formula

C₁₆H₂₂O₄

Average Molecular Mass

278.344 g/mol

Monoisotopic Mass

278.152 g/mol

CAS Registry Number

84-74-2

IUPAC Name

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

Traditional Name

dibutyl-phthalate

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

plasticiser

Biological Roles

teratogenic agent

Chemical Roles

environmental contaminant

Physical Properties

State

Solid

Appearance

Colorless oily liquid.

Experimental Properties

Property	Value
Melting Point	35°C
Boiling Point	340 °C
Solubility	0.0112 mg/mL at 25°C

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-1910000000-964b3411de1f914de4da	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0910000000-97464fdc3b8040ec3d36	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-052b-0960000000-7a12a722da333ebed5e0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-5900000000-bb309d93583ab774d1f9	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-1910000000-964b3411de1f914de4da	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0910000000-97464fdc3b8040ec3d36	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-052b-0960000000-7a12a722da333ebed5e0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-5900000000-bb309d93583ab774d1f9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5190000000-8daed01d42925467217c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0590000000-d7fd13586fba8d9bcbb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-003r-0900000000-26a0280d411587ad0406	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-003r-0900000000-01dec35be5d4cb24d183	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00b9-1900000000-0a9f876d83f5cdff62be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-6900000000-88c2bba04cf08d8a94e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9300000000-6e11d76c309a036870da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-24ad78f1c73dbed6290d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-2d5177b1586a4461b278	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9000000000-4516fb7c10721dc8cedb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0910000000-7702573da14ce44e4e73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-78eaf490a7fb4d87b419	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-5c75cf8111466a2bd813	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-a0747aefa385c43d47b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-1900000000-29635db4a2da5e62db7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00xs-5900000000-02c97dee9727d0badc2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9200000000-2b0820b30884f0f997a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-5d4f80a8a661596a7cc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-f45a033b5a30528756de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-19ad0b11756e1ca9188a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2090000000-80ca0d0b0000ed2e7f82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9240000000-62634d519d04aa7360b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9500000000-7279733c1ed1974ee785	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1090000000-5c82ef4822a947c8f20b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-2590000000-eadc4a21565f062f1e5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-5910000000-41f7de518636cfc255d9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-3900000000-ecab0016129a96c4ece7	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (16) ; inhalation (16) ; dermal (16)

Mechanism of Toxicity

The most characteristic effect of di-n-butyl phthalate is testicular atrophy. Di-n-butyl phthalate exposure causes both the release of iron from hemoglobin and/or transferrin in the liver and spleen, and the subsequent depletion of iron in the blood and testes. The decreased amount of available iron results in a decrease in succinate dehydrogenase activity in the Sertoli cells. This results in disturbances in the energy transfer system between Sertoli cells and germ cells, which is required for the differentiation of male germ cells and their progression through the seminiferous epithelium and release as mature spermatozoa. Di-n-butyl phthalate may also exhibit weak estrogenic activity. It has been shown to exhibit toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting succinate dehydrogenase. (16, 1)

Metabolism

Di-n-butyl phthalate is absorbed via oral, inhalation, and dermal routes. It is rapidly distributed and cleared from the body. Metabolism of di-n-butyl 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-n-butyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. (16)

Toxicity Values

LD50: 3050 mg/kg (Intraperitoneal, Rat) (17) LD50: 720 mg/kg (Intravenous, Mouse) (17) LD50: 5289 mg/kg (Oral, Mouse) (17) LC50: 25 g/m3 over 2 hours (Inhalation, Mouse) (17)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Di-n-butyl phthalate is used to make plastics more flexible and is also in carpet backings, paints, glue, insect repellents, hair spray, nail polish, and rocket fuel. (16)

Minimum Risk Level

Not Available

Health Effects

Adverse effects from di-n-butyl phthalate exposure have not yet been reported in humans. However, animals studies have shown that di-n-butyl phthalate can affect reproductive ability by decreasing sperm count and causing birth defects. (16)

Symptoms

Skin contact with di-n-butyl phthalate may cause mild irritation. (16)

Treatment

Not Available

Concentrations