Di(n-octyl) phthalate (T3D3641)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-12-03 19:55:12 UTC
Update Date2014-12-24 20:26:16 UTC
Accession NumberT3D3641
Identification
Common NameDi(n-octyl) phthalate
ClassSmall Molecule
DescriptionDi(n-octyl) 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)
Compound Type
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,2-Benzenedicarbonic acid, dioctyl ester
1,2-Benzenedicarboxylic acid 1,2-dioctyl ester
1,2-Benzenedicarboxylic acid dioctyl ester
Benzenedicarboxylic acid di-n-octyl ester
Bis(n-octyl) phthalate
Di(N-octyl) phthalate
Di(N-octyl) phthalic acid
Dicapryl phthalate
Dinopol nop
Dioctyl 1, 2-benzenedicarboxylate
Dioctyl 1,2-benzenedicarboxylate
Dioctyl o-benzenedicarboxylate
Dioctyl o-phthalate
Dioctyl phthalate
N-octyl phthalate
O-benzenedicarboxylic acid dioctyl ester
Octyl phthalate
Phthalic acid di-n-octyl ester
Phthalic acid dioctyl ester
Chemical FormulaC24H38O4
Average Molecular Mass390.556 g/mol
Monoisotopic Mass390.277 g/mol
CAS Registry Number117-84-0
IUPAC Name1,2-dioctyl benzene-1,2-dicarboxylate
Traditional Namedioctyl phthalate
SMILESCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC
InChI IdentifierInChI=1S/C24H38O4/c1-3-5-7-9-11-15-19-27-23(25)21-17-13-14-18-22(21)24(26)28-20-16-12-10-8-6-4-2/h13-14,17-18H,3-12,15-16,19-20H2,1-2H3
InChI KeyInChIKey=MQIUGAXCHLFZKX-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
StateSolid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point25°C
Boiling PointNot Available
Solubility2.2e-05 mg/mL at 25°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
logP7.76ALOGPS
logP8.18ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity114.66 m³·mol⁻¹ChemAxon
Polarizability49.42 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-8972000000-5a8ecf0088a627f42da02021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-1900000000-9fb6b4325e699a139e0a2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0002-1900000000-7f7c28506e01f823a8622020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-03dm-0695000000-e99f47f201a13a40b1f72020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0002-0900000000-c6b9df5b2ccfb027d2e72020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0002-1900000000-189af9ebde1fa2a63bbb2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 39V, positivesplash10-00mk-0940000000-c497796373d4621cef322020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0002-0920000000-7b595b4b420c49195e5f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0109000000-a1cc0d131cb45cdb5da52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0006-0009000000-8f771fd98c406d48ea052020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-0006-0009000000-7980d3a8e284191d41142020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-0006-0009000000-13e55575d97403874b132020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0006-0109000000-26a4c9c86313a465e01b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-0006-0219000000-2ebc75da8abc7ef0d7db2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-0006-0529000000-2384ab77d02e03f317892020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-01oy-0935000000-266187a492dfd4e879b22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-01ow-0922000000-72c6d82d5a21a25e73b52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-01ot-0910000000-e8ec512e9a495a136bef2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0292-1910000000-83c7fb949679846346d92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-00kb-1900000000-a83f8e32cd1cff4d27572020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0339000000-01cb26c1b4d0ce8f22982016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4932000000-7be96c0f73af9bf207a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9600000000-0b98763c4b9ac3814a832016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0139000000-c8348cc26c6fdd13ff9b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0592000000-0ca1afb6532b1a5077a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02os-1910000000-175224683dd2f0783f282016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-5910000000-06ec4da7fbd2cda38bc02014-09-20View Spectrum
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. (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: 13000 mg/kg (Oral, Mouse) (5) LD50: 73 500 mg/kg (Dermal, Guinea pig) (3)
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’. (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 ID8346
ChEMBL IDCHEMBL1409747
ChemSpider ID8043
KEGG IDC14227
UniProt IDNot Available
OMIM ID
ChEBI ID17747
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3641.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. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  4. Wikipedia. Phthalate. Last Updated 22 November 2009. [Link]
  5. EPA/Office of Pollution Prevention and Toxics (2007). High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans: Phthalate Esters Category, Diethyl phthalate (84-66-2). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Nuclear receptor subfamily 1 group I member 2
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.65 uMATG_PXRE_CISAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]