Di-n-hexyl phthalate (CHEM002622)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-12-04 03:29:32 UTC
Update Date2026-04-17 18:32:08 UTC
Accession NumberCHEM002622
Identification
Common NameDi-n-hexyl phthalate
ClassSmall Molecule
DescriptionDi-n-hexyl 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)
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant 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
ValueSource
Dihexyl 1,2-benzenedicarboxylateKegg
Dihexyl phthalateKegg
Dihexyl 1,2-benzenedicarboxylic acidGenerator
Dihexyl phthalic acidGenerator
Di-N-hexyl phthalic acidGenerator
Phthalic acid dihexyl esterMeSH
Chemical FormulaC20H30O4
Average Molecular Mass334.450 g/mol
Monoisotopic Mass334.214 g/mol
CAS Registry Number84-75-3
IUPAC Name1,2-dihexyl benzene-1,2-dicarboxylate
Traditional Namedi-n-hexyl phthalate
SMILESCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC
InChI IdentifierInChI=1S/C20H30O4/c1-3-5-7-11-15-23-19(21)17-13-9-10-14-18(17)20(22)24-16-12-8-6-4-2/h9-10,13-14H,3-8,11-12,15-16H2,1-2H3
InChI KeyKCXZNSGUUQJJTR-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 Descriptors
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 Point-58°C
Boiling PointNot Available
Solubility5e-05 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.00039 g/LALOGPS
logP6.28ALOGPS
logP6.41ChemAxon
logS-5.9ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity96.26 m³·mol⁻¹ChemAxon
Polarizability39.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9460000000-ca815da48e56acefe225Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-006t-2900000000-d639a38dc5a7fece4c0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-01b9-7900000000-4c14e15fa86aeb68fd45Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-006t-2900000000-903acf8162ec62253b09Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0002-0900000000-de0d2b0a25bd619b72dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0900000000-9cbb8ae426e35be18cf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0002-0900000000-828c2acfd33489c50593Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-bba4a0cd565847d4d706Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4049000000-8316032be71d5a779d44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9031000000-ead16b0dc4835f67b52dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9100000000-05c553e1eaef77622608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1039000000-0232e872834e9e529afaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1492000000-849ec7febfb5db3605b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-060s-4920000000-424736b08a8d2610c17fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0379000000-9a6cb7a2de60dde9343dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-3921000000-f969e59f583680bf29afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9410000000-d96aed445d5e61b9f5f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0059000000-be2d5aec655f6103f2dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gj-0892000000-e4f68bfca92f1979034fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-1900000000-2933513aeba376465388Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-8900000000-bef175f60de778e77c81Spectrum
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 ValuesLD50: 20000 mg/kg (Dermal, Rabbit) (4) LD50: 29600 mg/kg (Oral, Rat) (4)
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0251287
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID6528
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC14504
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available