Diisononyl phthalate (CHEM002617)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (32)XML
Record Information
Version1.0
Creation Date2009-12-03 21:16:18 UTC
Update Date2026-08-22 07:00:40 UTC
Accession NumberCHEM002617
Identification
Common NameDiisononyl phthalate
ClassSmall Molecule
DescriptionDiisononyl phthalate (C26H42O4) is an exogenous organic compound with an average molecular weight of 418.61 g/mol. It exists as a liquid at room temperature. Diisononyl phthalate belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. Industrially, this compound is utilized as a plasticizer, a fragrance, and an adhesion/cohesion promoter. In the context of plastics, it is used in polyurethane, acrylonitrile butadiene styrene, and polyvinyl chloride. It is present in ethylene-vinyl acetate and polystyrene, and it is released in polyethylene terephthalate and polypropylene. Its presence in high-density polyethylene remains inconclusive, while it has not been detected in polyamide or polycarbonate. Exposure to diisononyl phthalate can occur through oral, inhalation, and touch routes. It is found in or released from four recorded sources: drinking water, indoor air, food contact materials, and amplifiers within electrical and electronic equipment. At a molecular level, the compound interacts with seven recorded protein targets, including peroxisome proliferator-activated receptor alpha (PPARA), peroxisome proliferator-activated receptor delta (PPARD), nuclear receptor subfamily 1 group I member 2 (NR1I2), and nuclear receptor subfamily 1 group I member 3 (NR1I3).
Contaminant Sources
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Diisononyl phthalic acidGenerator
Chemical FormulaC26H42O4
Average Molecular Mass418.609 g/mol
Monoisotopic Mass418.308 g/mol
CAS Registry Number28553-12-0
IUPAC Namebis(3,5,5-trimethylhexyl) benzene-1,2-dicarboxylate
Traditional Name1,2-bis(3,5,5-trimethylhexyl) phthalate
SMILESCC(CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)CC(C)(C)C)CC(C)(C)C
InChI IdentifierInChI=1S/C26H42O4/c1-19(17-25(3,4)5)13-15-29-23(27)21-11-9-10-12-22(21)24(28)30-16-14-20(2)18-26(6,7)8/h9-12,19-20H,13-18H2,1-8H3
InChI KeyGDJOUZYAIHWDCA-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
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-48°C
Boiling Point244-252 °C
Solubility0.0002 mg/mL at 20°C
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP7.35ALOGPS
logP8.15ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity123.4 m³·mol⁻¹ChemAxon
Polarizability49.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-1341900000-8fae2759c0389f328598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3941100000-b470e7aab79ee905171eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9720000000-c802b37798844f00029bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0230900000-f5e0c667dfa6da82d68bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r7-0690200000-a281232f9fc43bad46b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0101-1910000000-4eee141b544d2758f592Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
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. (2)
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. (3)
Toxicity ValuesLD50: >40000 mg/kg (Oral, Rat) (1) LD50: >9750 mg/kg (Intraperitoneal, Mouse) (1) LC50: >4.4 mg/L over 4 hours (Inhalation, Rat) (1)
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. (4)
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’. (2)
SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiisononyl phthalate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID34277
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available