DIBUTYL SEBACATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H34O4
Molecular Weight	314.4602
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC(=O)CCCCCCCCC(=O)OCCCC

InChI

InChIKey=PYGXAGIECVVIOZ-UHFFFAOYSA-N

InChI=1S/C18H34O4/c1-3-5-15-21-17(19)13-11-9-7-8-10-12-14-18(20)22-16-6-4-2/h3-16H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+109-43-3#permalink | https://www.ncbi.nlm.nih.gov/pubmed/12238781 | https://www.accessdata.fda.gov/scripts/fdcc/index.cfm?set=IndirectAdditives&id=DIOCTYLSEBACATE | https://www.ncbi.nlm.nih.gov/pubmed/12238781 |

Dibutyl sebacate (DBS) is an organic chemical which is mainly used as a plasticizer in the production of such plastics as cellulose acetate butyrate, cellulose acetate propionate, ethyl cellulose, polyvinyl butyral, polyvinyl chloride, polystyrene, and many synthetic rubbers and other plastics. It is used for plastics in the food packaging industry, in medical devices, and for pharmaceutical applications. It is classified as mildly toxic by ingestion in humans and has shown experimental reproductive effects in animals; however, it is also approved by the US-FDA as a food additive to be used with the minimum quantity needed to produce the intended effect.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The use of dynamic mechanical analysis (DMA) to evaluate plasticization of acrylic polymer films under simulated gastrointestinal conditions.	2010-11	20800682
pH-dependent permeation of amino acids through isolated ivy cuticles is affected by cuticular water sorption and hydration shell size of the solute.	2010-09	20631051
Removal of pharmaceuticals from water: using liquid-core microcapsules as a novel approach.	2010-04	20163817
Development of a gas chromatographic/mass spectrometric method for determination of phthalates in oily foods.	2010-03-26	20334193
Curing of aqueous polymeric film coatings: Importance of the coating level and type of plasticizer.	2010-02	19895886
Rapid identification of additives in poly(vinyl chloride) lid gaskets by direct analysis in real time ionisation and single-quadrupole mass spectrometry.	2010-01	19957297
Use of ethylcellulose to control chlorsulfuron leaching in a calcareous soil.	2009-04-08	19334760
Evaluation of injection moulding as a pharmaceutical technology to produce matrix tablets.	2009-01	18511248
Influence of the components of Kollicoat SR film on mechanical properties of floating pellets from the point of view of tableting.	2008-10	18972835
Physico-mechanical analysis of free ethyl cellulose films comprised with novel plasticizers of vitamin resources.	2008-05-22	18355993
Influence of formulation and process parameters on the release characteristics of ethylcellulose sustained-release mini-matrices produced by hot-melt extrusion.	2008-05	18036793
Colonic release and reduced intestinal tissue damage of coated tablets containing naproxen inclusion complex.	2008-02-28	17928177
Controlled-release formulations of cyromazine-lignin matrix coated with ethylcellulose.	2007-09-01	17763045
Tramadol extended-release in the management of chronic pain.	2007-06	18488071
Quinine sulphate pellets for flexible pediatric drug dosing: formulation development and evaluation of taste-masking efficiency using the electronic tongue.	2007-06	17267189
Stability-indicating methods for the determination of disopyramide phosphate.	2006-08-19	16915833
Compression and compaction properties of plasticised high molecular weight hydroxypropylmethylcellulose (HPMC) as a hydrophilic matrix carrier.	2006-03-27	16431049
Quantitative estimation of film forming polymer-plasticizer interactions by the Lorentz-Lorenz Law.	2006-03-09	16436320
Temporary restorative resins using non-phthalate ester plasticizers.	2005-08	16005797
Novel reactive perstraction system applied to the hydrolysis of penicillin G.	2005-07-20	15915512
Sorption in reconstituted waxes of homologous series of alcohol ethoxylates and n-alkyl esters and their effects on the mobility of 2,4-dichlorophenoxybutyric acid.	2005-04	15751010
Effects of accelerators on mobility of 14C-2,4-dichlorophenoxy butyric acid in plant cuticles depends on type and concentration of accelerator.	2005-03-23	15769158
A novel approach for the extraction of herbicides and pesticides from water using liquid-core microcapsules.	2004-09-20	15329931
Polymer blends used for the aqueous coating of solid dosage forms: importance of the type of plasticizer.	2004-09-14	15342176
Cytocompatibility and viscoelastic properties of phthalate ester-free tissue conditioners.	2004-09	15510874
Relationship between plasticizer content and tensile bond strength of soft denture liners to a denture base resin.	2004-06	15287552
Polymeric membrane electrodes with enhanced fluoride selectivity using Zr(IV)-porphyrins functioning as neutral carriers.	2004-05-10	18969407
Medications as a source of human exposure to phthalates.	2004-05	15121520
[Examination of sex-hormonal activity of some additives for PVDC film].	2003-10	14733137
Evaluation of the film-forming property of hydrogenated rosin.	2003-09	14570308
Novel type of in situ extraction: Use of solvent containing microcapsules for the bioconversion of 2-phenylethanol from L-phenylalanine by Saccharomyces cerevisiae.	2003-08-20	12800132
Enhanced film-forming properties for ethyl cellulose and starch acetate using n-alkenyl succinic anhydrides as novel plasticizers.	2003-08	12907287
Time-dependent mechanical properties of polymeric coatings used in rupturable pulsatile release dosage forms.	2003-07	12889780
Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane.	2003-04-14	12695059
Enhancement of 2-phenylethanol productivity by Saccharomyces cerevisiae in two-phase fed-batch fermentations using solvent immobilization.	2003-04-05	12569629
Novel bilirubin-based PVC calcium sensors.	2003-03	12675340
Formulation of enterosoluble microparticles for an acid labile protein.	2003-01-30	12553892
Polymerized rosin: novel film forming polymer for drug delivery.	2002-12-05	12433446
Influence of plasticizer type and coat level on Surelease film properties.	2002-11	12503523
Effect of plasticizer on the dynamic surface tension and the free volume of Eudragit systems.	2002-09-05	12204567
Cytocompatibility of new phthalate ester-free tissue conditioners in vitro.	2002-06	12238781
Drug release from Kollicoat SR 30D-coated nonpareil beads: evaluation of coating level, plasticizer type, and curing condition.	2002	12916952
Study of novel rosin-based biomaterials for pharmaceutical coating.	2002	12916925
Drug release from and mechanical properties of press-coated tablets with hydroxypropylmethylcellulose acetate succinate and plasticizers in the outer shell.	2001-04-17	11292540
Calculation of the dimensions of dosage forms with release controlled by diffusion for in vivo use.	2001-01	11154899

Patents

Sample Use Guides

In Vivo Use Guide

Dibutyl sebacate was selected as a plasticiser in the formulation of sustained-release matrix tablets. Dibutyl sebacate was added to a dichloromethane/EC solution and subsequently spray-dried, or was mixed as a liquid with EC powder. Hydrated tablets were evaluated by frequency sweep and creep rheological tests to correlate the results with drug release.

Route of Administration: Oral

In Vitro Use Guide

Dibutyl Sebacate (DBS) was diluted with dimethyl sulfoxide. Estrogenic activity was measured using a yeast two-hybrid system and a fluorescence polarization system within a concentration range of 10^-7 to 10^-3 M. Yeast strain Y190 was transformed with the pGBT9-receptors and pGAD424-coactivators using the lithium acetate method, and an S9 hepatic microsomal fraction was used to implement the mediating influence of metabolic bioactivation. DBS was tested for its ability to displaceflourescent non-steroid estrogen from the estrogen receptor. A threshold of B-galactosidase activity above 0.1, greater than 50% inhibition and a 1.5 fold increase in cell growth over controls was considered estrogenic activity. DBS showed the weakest cytotoxicity among tested compounds and an IC50 value for B-galactosidase that was higher than the applicable measurement range.

Name

Type

Language

DIBUTYL SEBACATE

Official Name

English

NSC-3893

Preferred Name

English

FEMA NO. 2373

Code

English

DIBUTYL 1,8-OCTANEDICARBOXYLATE

Systematic Name

English

PX-404

Code

English

DIBUTYL SEBACATE [MART.]

Common Name

English

DIBUTYL DECANEDIOATE

Systematic Name

English

DIBUTYL SEBACATE [USP-RS]

Common Name

English

DIBUTYL SEBACATE [HSDB]

Common Name

English

DIBUTYL SEBACATE [II]

Common Name

English

DIBUTYL SEBACATE [FHFI]

Common Name

English

DECANEDIOIC ACID, DIBUTYL ESTER

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 176.170