Bis(2-methoxyethyl) phthalate (T3D0194)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-03-06 18:58:15 UTC
Update Date2014-12-24 20:21:18 UTC
Accession NumberT3D0194
Identification
Common NameBis(2-methoxyethyl) phthalate
ClassSmall Molecule
DescriptionBis(2-methoxyethyl) phthalate (DMEP) is a specialty plasticiser, used in cellulose ester plastics, and can also be used as a solvent. This compound can form peroxides. (2)
Compound Type
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Ester
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1,2-Benzenedicarboxylic acid, butyl methyl ester
2-O-butyl 1-O-methyl benzene-1,2-dicarboxylate
Bis(2-methoxyethyl) phthalic acid
Butyl methyl phthalate
Methyl butyl phthalate
Phthalic acid, butyl methyl ester
Chemical FormulaC13H16O4
Average Molecular Mass236.264 g/mol
Monoisotopic Mass236.105 g/mol
CAS Registry Number34006-76-3
IUPAC Name1-butyl 2-methyl benzene-1,2-dicarboxylate
Traditional Name1-butyl 2-methyl phthalate
SMILESCCCCOC(=O)C1=CC=CC=C1C(=O)OC
InChI IdentifierInChI=1S/C13H16O4/c1-3-4-9-17-13(15)11-8-6-5-7-10(11)12(14)16-2/h5-8H,3-4,9H2,1-2H3
InChI KeyInChIKey=XXFSYINDUHLBIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceLight coloured, clear liquid, with a mild aromatic odour. (2)
Experimental Properties
PropertyValue
Melting Point-40°C
Boiling Point340 °C
Solubility0.9 g/L (20°C)
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP3.04ALOGPS
logP3.3ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity63.98 m³·mol⁻¹ChemAxon
Polarizability24.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-2390000000-dc2c00bf7e71ba8edabe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9630000000-f8eac707f0f12faacbdb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7900000000-66c60c4b1ff43775def32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1390000000-d28ca178746f6508eef32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-1920000000-6f1427fc3f3c3ed3c9442016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0550-3900000000-f397c5b548a96c9fe56e2016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityPhthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (1)
MetabolismIn pregnant rat, DMEP rapidly undergoes hydrolysis to 2-methoxyethanol (2-ME) and mono-2-methoxyethyl phthalate (MMEP). 2-ME is then oxidised to methoxyacetic acid (MAA). The rat foetus has little or no ability to hydrolyse DMEP to the monoester and intact DMEP is rapidly transferred across the placenta into the foetus. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBis(2-methoxyethyl) phthalate (DMEP) is a specialty plasticizer, used in cellulose ester plastics, and can also be used as a solvent. (2)
Minimum Risk LevelNot Available
Health EffectsPhthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (1)
SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID36655
ChEMBL IDNot Available
ChemSpider ID33674
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBis(2-methoxyethyl) phthalate
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wilson VS, Blystone CR, Hotchkiss AK, Rider CV, Gray LE Jr: Diverse mechanisms of anti-androgen action: impact on male rat reproductive tract development. Int J Androl. 2008 Apr;31(2):178-87. doi: 10.1111/j.1365-2605.2007.00861.x. [18315717 ]
  2. National Industrial Chemicals Notification and Assessment Scheme (NICNAS) (2007). Human Health Hazard Assessment for Bis(2-methoxyethyl) Phthalate (DMEP). [Link]
  3. Wikipedia. Phthalate. Last Updated 22 November 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available