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 2578

PubMed

Title	Date	PubMed
Drug release from and mechanical properties of press-coated tablets with hydroxypropylmethylcellulose acetate succinate and plasticizers in the outer shell.	2001 Apr 17	11292540
Study of novel rosin-based biomaterials for pharmaceutical coating.	2002	12916925
Cytocompatibility of new phthalate ester-free tissue conditioners in vitro.	2002 Jun	12238781
Influence of plasticizer type and coat level on Surelease film properties.	2002 Nov	12503523
Effect of plasticizer on the dynamic surface tension and the free volume of Eudragit systems.	2002 Sep 5	12204567
[Examination of sex-hormonal activity of some additives for PVDC film].	2003 Oct	14733137
Evaluation of the film-forming property of hydrogenated rosin.	2003 Sep	14570308
Medications as a source of human exposure to phthalates.	2004 May	15121520
Temporary restorative resins using non-phthalate ester plasticizers.	2005 Aug	16005797
Influence of formulation and process parameters on the release characteristics of ethylcellulose sustained-release mini-matrices produced by hot-melt extrusion.	2008 May	18036793
Removal of pharmaceuticals from water: using liquid-core microcapsules as a novel approach.	2010 Apr	20163817
Curing of aqueous polymeric film coatings: Importance of the coating level and type of plasticizer.	2010 Feb	19895886
Rapid identification of additives in poly(vinyl chloride) lid gaskets by direct analysis in real time ionisation and single-quadrupole mass spectrometry.	2010 Jan	19957297
Development of a gas chromatographic/mass spectrometric method for determination of phthalates in oily foods.	2010 Jan-Feb	20334193
The use of dynamic mechanical analysis (DMA) to evaluate plasticization of acrylic polymer films under simulated gastrointestinal conditions.	2010 Nov	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 Sep	20631051

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

FEMA NO. 2373

Code

English

DIBUTYL 1,8-OCTANEDICARBOXYLATE

Systematic Name

English

PX-404

Code

English

DIBUTYL SEBACATE [INCI]

Common Name

English

DIBUTYL SEBACATE [MART.]

Common Name

English

DIBUTYL DECANEDIOATE

Systematic Name

English

DIBUTYL SEBACATE [USP-RS]

Common Name

English

NSC-3893

Code

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