ContaminantDB: Diisononyl phthalate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-12-03 21:16:18 UTC

Update Date

2026-03-31 19:12:31 UTC

Accession Number

CHEM002617

Identification

Common Name

Diisononyl phthalate

Class

Small Molecule

Description

Diisononyl 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. (4)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Diisononyl phthalic acid	Generator

Chemical Formula

C₂₆H₄₂O₄

Average Molecular Mass

418.609 g/mol

Monoisotopic Mass

418.308 g/mol

CAS Registry Number

28553-12-0

IUPAC Name

1,2-bis(3,5,5-trimethylhexyl) benzene-1,2-dicarboxylate

Traditional Name

1,2-bis(3,5,5-trimethylhexyl) phthalate

SMILES

CC(CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)CC(C)(C)C)CC(C)(C)C

InChI Identifier

InChI=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 Key

GDJOUZYAIHWDCA-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

plasticiser

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-48°C
Boiling Point	244-252 °C
Solubility	0.0002 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	0.00016 g/L	ALOGPS
logP	7.35	ALOGPS
logP	8.15	ChemAxon
logS	-6.4	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	14	ChemAxon
Refractivity	123.4 m³·mol⁻¹	ChemAxon
Polarizability	49.74 Å³	ChemAxon
Number of Rings	1	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	splash10-016r-1341900000-8fae2759c0389f328598	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3941100000-b470e7aab79ee905171e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9720000000-c802b37798844f00029b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0230900000-f5e0c667dfa6da82d68b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-0690200000-a281232f9fc43bad46b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0101-1910000000-4eee141b544d2758f592	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal (4)

Mechanism of Toxicity

Phthalate 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)

Metabolism

Phthalate 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 Values

LD50: >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 Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Phthalate 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 Level

Not Available

Health Effects

Phthalate 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)

Symptoms

Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (2)

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

Diisononyl phthalate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

34277

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

Diisononyl phthalate (CHEM002617)

Structure for CHEM002617: Diisononyl phthalate