ContaminantDB: 2-Butenedioic acid (2Z)-, bis(2-ethylhexyl) ester

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 03:17:51 UTC

Update Date

2016-11-09 01:14:09 UTC

Accession Number

CHEM010174

Identification

Common Name

2-Butenedioic acid (2Z)-, bis(2-ethylhexyl) ester

Class

Small Molecule

Description

Dioctyl maleate is a chemical compound with the molecular formula C20H36O4. It is often called DOM in the chemical industry even though the octyl is not straight chained but branched. It is manufactured by reacting 2-ethylhexanol with maleic anhydride and an esterification catalyst. This is a key intermediate raw material in the production of DOSS surfactants, including the pharmaceutical drug docusate (dioctyl sodium sulfosuccinate).. The DOSS molecule is formed by reacting a metal (usually sodium) bisulfite across the vinylic double bond of the dioctyl maleate thus forming an ionic species.

Contaminant Sources

HPV EPA Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bis(2-ethylhexyl) maleic acid	Generator

Chemical Formula

C₂₀H₃₆O₄

Average Molecular Mass

340.504 g/mol

Monoisotopic Mass

340.261 g/mol

CAS Registry Number

142-16-5

IUPAC Name

1,4-bis(2-ethylhexyl) (2Z)-but-2-enedioate

Traditional Name

di-2-ethylhexyl maleate

SMILES

[H]\C(=C(/[H])C(=O)OCC(CC)CCCC)C(=O)OCC(CC)CCCC

InChI Identifier

InChI=1S/C20H36O4/c1-5-9-11-17(7-3)15-23-19(21)13-14-20(22)24-16-18(8-4)12-10-6-2/h13-14,17-18H,5-12,15-16H2,1-4H3/b14-13-

InChI Key

ROPXFXOUUANXRR-YPKPFQOOSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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

Not Available

Cellular Locations

Not Available

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

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00017 g/L	ALOGPS
logP	6.72	ALOGPS
logP	6.76	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-6.5	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	16	ChemAxon
Refractivity	98.44 m³·mol⁻¹	ChemAxon
Polarizability	40.76 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1926000000-b5e93702eaf71b1a80d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4910000000-a6564aeb081740dca8e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9300000000-e4116dac3f715116a3b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-1469000000-f95e0abdcbd193133ff3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0571-6973000000-016330d26ed879956a07	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9510000000-6db229daa1d0ebeca589	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)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dioctyl maleate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5365125

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

2-Butenedioic acid (2Z)-, bis(2-ethylhexyl) ester (CHEM010174)

Structure for CHEM010174: 2-Butenedioic acid (2Z)-, bis(2-ethylhexyl) ester