Diisohexyl phthalate (T3D3647)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-12-03 21:14:41 UTC
Update Date2014-12-24 20:26:17 UTC
Accession NumberT3D3647
Identification
Common NameDiisohexyl phthalate
ClassSmall Molecule
DescriptionDiisohexyl phthalate is a phthalate ester. Phthalate esters are esters of phthalic acid and are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are hazardous due to their ability to act as endocrine disruptors. They are being phased out of many products in the United States and European Union due to these health concerns. (3)
Compound Type
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,2-Benzenedicarboxylic acid diisohexyl ester
bis(4-methyl-2-pentyl) phthalate
Bis(4-methylpentyl) 1,2-benzenedicarboxylate
Bis(4-methylpentyl) phthalate
Carboxylic ester
DIIsohexyl phthalate
Diisohexyl phthalic acid
Phthalic acid di(4-methylpentyl) ester
Phthalic acid dIIsohexyl ester
Chemical FormulaC20H30O4
Average Molecular Mass334.450 g/mol
Monoisotopic Mass334.214 g/mol
CAS Registry Number146-50-9
IUPAC Name1,2-bis(4-methylpentyl) benzene-1,2-dicarboxylate
Traditional Namediisohexyl phthalate
SMILESCC(C)CCCOC(=O)C1=CC=CC=C1C(=O)OCCCC(C)C
InChI IdentifierInChI=1S/C20H30O4/c1-15(2)9-7-13-23-19(21)17-11-5-6-12-18(17)20(22)24-14-8-10-16(3)4/h5-6,11-12,15-16H,7-10,13-14H2,1-4H3
InChI KeyInChIKey=ALEROMXYYSQFLX-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
  • 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
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility2.49e-05 mg/mL at 25°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP5.52ALOGPS
logP6.09ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity96.16 m³·mol⁻¹ChemAxon
Polarizability40 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-000i-4059000000-8ed2b77f061126c1a7a72016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9141000000-59d23d82143f4e60b37a2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9210000000-f41c3339579977cf42222016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1039000000-bf35683fb435306a1c6b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1492000000-d23b6e619f1f8d905fd32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-060s-4910000000-46a2de10e4ec6ce726d62016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-6900000000-12191b33856c91867da12014-09-20View 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)
MetabolismPhthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPhthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (3)
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 ID8970
ChEMBL IDNot Available
ChemSpider ID8623
KEGG IDC02391
UniProt IDNot Available
OMIM ID
ChEBI ID33308
BioCyc IDO-ACETYLCARNITINE
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3647.pdf
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. Wittassek M, Angerer J: Phthalates: metabolism and exposure. Int J Androl. 2008 Apr;31(2):131-8. Epub 2007 Dec 7. [18070048 ]
  3. Wikipedia. Phthalate. Last Updated 22 November 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available