T3DB: Dibutyl decanedioate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2014-09-11 05:18:50 UTC

Update Date

2014-12-24 20:26:58 UTC

Accession Number

T3D4842

Identification

Common Name

Dibutyl decanedioate

Class

Small Molecule

Description

Dibutyl decanedioate is a flavouring ingredient used in fruit food flavouring.

Compound Type

Ester
Ether
Flavouring Agent
Food Additive
Food Toxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Bis(N-butyl) sebacate
Bis(N-butyl)sebacate
Butyl sebacate
DBS
Decanedioic acid, 1,10-dibutyl ester
Decanedioic acid, dibutyl ester
Di(N-butyl) sebacate
Di-N-butyl sebacate
Di-N-butyl-sebacate
Di-N-butylsebacate
Dibutyl 1,8-octanedicarboxylate
Dibutyl decanedioic acid
Dibutyl sebacate
Dibutyl sebacate (NF)
Dibutyl sebacinate
Dibutylester kyseliny sebakove
FEMA 2373
Kodaflex DBS
Monoplex DBS
N-Butyl sebacate
Plasthall DBS
Polycizer DBS
Reomol DBS
Sebacic acid dibutyl ester
Sebacic acid, dibutyl ester
Staflex DBS
Uniflex DBS

Chemical Formula

C₁₈H₃₄O₄

Average Molecular Mass

314.460 g/mol

Monoisotopic Mass

314.246 g/mol

CAS Registry Number

109-43-3

IUPAC Name

1,10-dibutyl decanedioate

Traditional Name

dibutyl sebacate

SMILES

CCCCOC(=O)CCCCCCCCC(=O)OCCCC

InChI Identifier

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

InChI Key

InChIKey=PYGXAGIECVVIOZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	12 °C
Boiling Point	Not Available
Solubility	0.04 mg/mL at 20 °C
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.74	ALOGPS
logP	5.21	ChemAxon
logS	-5.3	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	17	ChemAxon
Refractivity	88.43 m³·mol⁻¹	ChemAxon
Polarizability	39.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052p-7910000000-ddef7e520d4682270616	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014l-0269000000-ea80f1079920fdbba712	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052p-7910000000-ddef7e520d4682270616	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014l-0269000000-ea80f1079920fdbba712	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvl-9750000000-477103a747cc0a1a93cd	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0930000000-a7ea0c9209b5ce68b0f9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9000000000-b565e48548642f8a520e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3900000000-145ffebe938009b15cef	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4149000000-0870e45363ff44545748	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9220000000-dc89dfce1cadee632f81	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6f35a7219c6047e78ad	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dr-3169000000-ba6ba99fe86e72b131a5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c09-5792000000-faf43c5c50ed3f9e04d5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9630000000-82b5379885f65dbea1fe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2459000000-f63b9e73240ee08b7743	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-9781000000-24a905363d14be44015a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-3970773affbaeebbc00f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-6ff89dbb05113fef5787	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dr-0395000000-ce2f6d0e0c348c460428	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-1960000000-cbdf4381b889639adfce	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9730000000-9cf5ac14e673701613db	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Peroxisome proliferator-activated receptor alpha

General Function:: Zinc ion binding
Specific Function:: Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:: PPARA
Uniprot ID:: Q07869
Molecular Weight:: 52224.595 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	2.91 uM	ATG_PPARa_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. Steroid hormone receptor ERR1

General Function:: Zinc ion binding
Specific Function:: Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
Gene Name:: ESRRA
Uniprot ID:: P11474
Molecular Weight:: 45509.11 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	5.5 uM	ATG_ERRa_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Dibutyl decanedioate (T3D4842)

Structure for T3D4842: Dibutyl decanedioate

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References