DIBUTYL PHTHALATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H22O4
Molecular Weight	278.3435
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DOIRQSBPFJWKBE-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H22O4
Molecular Weight	278.3435
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://echa.europa.eu/documents/10162/f36205a8-df0a-4e94-8763-2a6a02f0228c | https://www.epa.gov/sites/production/files/2016-09/documents/dibutyl-phthalate.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12731275 | https://www.ncbi.nlm.nih.gov/pubmed/27581038 | https://www.ncbi.nlm.nih.gov/pubmed/15587163

Dibutyl phthalate (DBP) is used to help make plastics soft and flexible. It is used in shower curtains, raincoats, food wraps, bowls, car interiors, vinyl fabrics, floor tiles, and other products. Animal studies have reported developmental and reproductive effects from oral exposure. Dibutyl phthalate (DBP) is classified as a substance toxic to reproduction. No information is available on the carcinogenic effects of dibutyl phthalate in humans or animals. Treatment with dibutyl phthalate enhanced Aryl Hydrocarbon Receptor mRNA expression, which was reflected by the increased AhR protein level. ERα, ERβ, and PPARγ antagonists stimulated DBP-induced caspase-3 and LDH activities. AhR is involved in DBP-induced apoptosis and neurotoxicity, while the ERs and PPARγ signaling pathways are impaired by the phthalate. In vitro test showed that DBP killed all Demodex mites within 1 hour. Dibutyl phthalate emulsion is promising to be developed as a safe, effective therapeutic medicament on demodicidosis.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Demodicidosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12571942 https://www.ncbi.nlm.nih.gov/pubmed/15587163	Curative		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Effect of dibutyl phthalate on demodicidosis].	2001	12571942
Binding of protegrin-1 to Pseudomonas aeruginosa and Burkholderia cepacia.	2002	11980587
Elucidation of the toxic mechanism of the plasticizers, phthalic acid esters, putative endocrine disrupters: effects of dietary di(2-ethylhexyl)phthalate on the metabolism of tryptophan to niacin in rats.	2002 Apr	12036039
The association between biomarker-based exposure estimates for phthalates and demographic factors in a human reference population.	2002 Apr	11940459
Effect of photo-irradiation on hardness of soft lining materials for denture base.	2002 Aug	12220341
Phthalates in underground waters of the Zagreb area.	2002 Aug	12187530
Comparison of embryotoxicity of ESBO and phthalate esters using an in vitro battery system.	2002 Aug	12110284
Antiandrogenic effects of dibutyl phthalate and its metabolite, monobutyl phthalate, in rats.	2002 Dec	12634449
Occurrence and microbial degradation of phthalate esters in Taiwan river sediments.	2002 Dec	12489726
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.	2002 Dec	12460799
A butyrylcholinesterase in the early development of the brine shrimp (Artemia salina) larvae: a target for phthalate ester embryotoxicity?	2002 Dec 13	12459190
Purging effect of dibutyl phthalate on leukemia cells involves fas independent activation of caspase-3/CPP32 protease.	2002 Dec 5	12213287
Combined treatment with 4-(N-methyl-N-nitrosamino)-1- (3-pyridyl)-1-butanone and dibutyl phthalate enhances ozone-induced genotoxicity in B6C3F1 mice.	2002 Jul	12110630
Application of on-line solid-phase extraction-gas chromatography-mass spectrometry to the determination of endocrine disruptors in water samples.	2002 Jul 19	12187982
[Levels of phthalates and adipates in processed foods and migration of di-isononyl adipate from polyvinyl chloride film into foods].	2002 Jun	12238159
Oxidative DNA damage in male Wistar rats exposed to di-n-butyl phthalate.	2002 Jun 14	12079616
A perchlorate-selective membrane electrode based on a Cu(II) complex of the ligand 1,4,8,11-tetra(n-octyl)-1,4,8,11-tetraazacyclotetradecane.	2002 Mar	11996365
Occurrence of phthalates and bisphenol A and F in the environment.	2002 Mar	11996333
Coated-wire copper(II)-selective electrode based on phenylglyoxal-alpha-monoxime ionophore.	2002 Mar	11941444
Preparation of samples for gas chromatography/mass spectrometry analysis of phthalate and adipate esters in plasma and beverages by steam distillation and extraction.	2002 May-Jun	12083265
[Determination of natural gas by gas chromatography with external standard-area normalization method].	2002 Nov	12683016
Adjuvant effect of di-n-butyl-, di-n-octyl-, di-iso-nonyl- and di-iso-decyl phthalate in a subcutaneous injection model using BALB/c mice.	2002 Nov	12570034
Supercritical fluid extraction of potential migrants from paper and board intended for use as food packaging materials.	2002 Nov 15	12463369
Effects of phthalate esters on actin cytoskeleton of Py1a rat osteoblasts.	2002 Oct	12371133
Potentiometric determination of fentanyl in pharmaceutical formulations.	2002 Oct 15	12367692
Regulation of inhibin beta chains and follistatin mRNA levels during rat hepatocyte growth induced by the peroxisome proliferator di-n-butyl phthalate.	2002 Sep	12230121
Evaluation of a 15-day screening assay using intact male rats for identifying antiandrogens.	2002 Sep	12215663
Pediatric and young adult exposure to chemiluminescent glow sticks.	2002 Sep	12197797
Generation of anticalins with specificity for a nonsymmetric phthalic acid ester.	2002 Sep 15	12419339
Numerical chromosomal aberrations in the early life-history stages of a marine tubeworm, Pomatoceros lamarckii (Polychaeta: Serpulidae).	2002 Sep 24	12127734
The phthalate diesters DEHP and DBP do not induce lauric acid hydroxylase activity in rainbow trout.	2002 Sep-Dec	12408651
Environmental estrogens interact with and modulate the properties of plasma sex steroid-binding proteins in juvenile Atlantic salmon (Salmo salar).	2002 Sep-Dec	12408638
NTP Center for the Evaluation of Risks to Human Reproduction: phthalates expert panel report on the reproductive and developmental toxicity of di-n-butyl phthalate.	2002 Sep-Oct	12406493
Estimated daily intake of plasticizers in 1-week duplicate diet samples following regulation of DEHP-containing PVC gloves in Japan.	2003 Apr	12775472
Effects of dibutyl phthalate in male rabbits following in utero, adolescent, or postpubertal exposure.	2003 Apr	12655036
In vitro modulation of common carp (Cyprinus carpio L.) phagocytic cells by Di-n-butyl phthalate and Di-2-ethylhexyl phthalate.	2003 Apr 10	12657487
Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane.	2003 Apr 14	12695059
A simple and reproducible testing method for dialkyl phthalate migration from polyvinyl chloride products into saliva simulant.	2003 Feb	12749191
Effect of DBP/DEHP in vegetable planted soil on the quality of capsicum fruit.	2003 Feb	12688494
Ion-selective electrodes based on metalloporphyrins for gibberellic acid determination in agricultural products.	2003 Feb	12610702
[Estrogenic activity of some environmental chemicals].	2003 Jan	12731275
Development and application of a generalized physiologically based pharmacokinetic model for multiple environmental contaminants.	2003 Jan	12503743
Biodegradation of phthalate esters during the mesophilic anaerobic digestion of sludge.	2003 Jul	12738281
Quantitative changes in gene expression in fetal rat testes following exposure to di(n-butyl) phthalate.	2003 Jun	12700402
Estrogenic activity of tissue conditioners in vitro.	2003 Jun	12686300
Effects and toxicity of phthalate esters to hemocytes of giant freshwater prawn, Macrobrachium rosenbergii.	2003 Jun 19	12763673
Toxicity of di-(2-ethylhexyl) phthalate on the anaerobic digestion of wastewater sludge.	2003 Mar	12598190
Opposing mechanisms of NADPH-cytochrome P450 oxidoreductase regulation by peroxisome proliferators.	2003 Mar 15	12623126
Changes in peroxisome proliferator-activated receptor gamma-regulated gene expression and inhibin/activin-follistatin system gene expression in rat testis after an administration of di-n-butyl phthalate.	2003 Mar 3	12565198
Aggregate exposures of nine preschool children to persistent organic pollutants at day care and at home.	2003 May	12743613

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:15:21 UTC 2023` Edited by `admin` on `Fri Dec 15 15:15:21 UTC 2023`
Record UNII	2286E5R2KE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIBUTYL PHTHALATE

Official Name

English

DIBUTYL PHTHALATE [EP MONOGRAPH]

Common Name

English

HEXAPLAS M/B

Brand Name

English

DI-N-BUTYL PHTHALATE

Common Name

English

STAFLEX DBP

Brand Name

English

MONOCIZER DBP

Brand Name

English

DIBUTYL PHTHALATE [II]

Common Name

English

ERGOPLAST FDB

Brand Name

English

DIBUTYL PHTHALATE [MART.]

Common Name

English

DIBUTYL 1,2-BENZENEDICARBOXYLATE

Systematic Name

English

PLASTHALL DBP

Brand Name

English

DIBUTYL PHTHALATE [USP-RS]

Common Name

English

CORFLEX 440

Brand Name

English

RUIFENG VP 201

Brand Name

English

Butyl phthalate [WHO-DD]

Common Name

English

DIBUTYL PHTHALATE [INCI]

Common Name

English

HATCO DBP

Brand Name

English

UNIMOLL DB

Brand Name

English

DIBUTYL PHTHALATE [MI]

Common Name

English

WITCIZER 300

Brand Name

English

DIBUTYLPHTHALATE

Systematic Name

English

YH-1BD2

Brand Name

English

VESTINOL C

Brand Name

English

KODAFLEX DBP

Brand Name

English

BUTYL PHTHALATE

Common Name

English

PALATINOL C

Brand Name

English

GENOPLAST B

Brand Name

English

POLYCIZER DBP

Brand Name

English

DIBUTYL PHTHALATE [HSDB]

Common Name

English

VP-201

Brand Name

English

NSC-6370

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C152072