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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 15:59:08 UTC
Update Date2021-10-13 05:41:22 UTC
HMDB IDHMDB0013835
Secondary Accession Numbers
  • HMDB13835
Metabolite Identification
Common NameDiisobutyl phthalate
DescriptionDiisobutyl phthalate, also known as DIBP or hexaplas m/1b, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Diisobutyl phthalate is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes). This could make diisobutyl phthalate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Diisobutyl phthalate.
Structure
Data?1582753147
Synonyms
ValueSource
1,2-Benzenedicarboxylic acid bis(2-methylpropyl) esterChEBI
1,2-Benzenedicarboxylic acid di(2-methylpropyl) esterChEBI
1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) esterChEBI
Bis(2-methylpropyl) phthalateChEBI
Di(i-butyl)phthalateChEBI
Di-2-methylpropyl phthalateChEBI
Di-iso-butyl phthalateChEBI
DIBPChEBI
Isobutyl phthalateChEBI
Isobutyl-O-phthalateChEBI
Phthalic acid, diisobutyl esterChEBI
1,2-Benzenedicarboxylate bis(2-methylpropyl) esterGenerator
1,2-Benzenedicarboxylate di(2-methylpropyl) esterGenerator
1,2-Benzenedicarboxylate, 1,2-bis(2-methylpropyl) esterGenerator
Bis(2-methylpropyl) phthalic acidGenerator
Di(i-butyl)phthalic acidGenerator
Di-2-methylpropyl phthalic acidGenerator
Di-iso-butyl phthalic acidGenerator
Isobutyl phthalic acidGenerator
Isobutyl-O-phthalic acidGenerator
Phthalate, diisobutyl esterGenerator
Diisobutyl phthalic acidGenerator
1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) esterHMDB
1,2-Benzenedicarboxylic acid, di(2-methylpropyl) esterHMDB
Diisobutyl phthalate (acd/name 4.0)HMDB
Diisobutylester kyseliny ftaloveHMDB
Hexaplas m/1bHMDB
Kodaflex dibpHMDB
Di-(2-methylpropyl)-phthalic acidHMDB
Chemical FormulaC16H22O4
Average Molecular Weight278.3435
Monoisotopic Molecular Weight278.151809192
IUPAC Name1,2-bis(2-methylpropyl) benzene-1,2-dicarboxylate
Traditional Namediisobutyl phthalate
CAS Registry Number84-69-5
SMILES
CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C
InChI Identifier
InChI=1S/C16H22O4/c1-11(2)9-19-15(17)13-7-5-6-8-14(13)16(18)20-10-12(3)4/h5-8,11-12H,9-10H2,1-4H3
InChI KeyMGWAVDBGNNKXQV-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point296.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.0062 mg/mL at 24 °CNot Available
LogP4.11Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.98ALOGPS
logP4.47ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity77.6 m³·mol⁻¹ChemAxon
Polarizability31.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.26931661259
DarkChem[M-H]-164.42231661259
DeepCCS[M+H]+170.90830932474
DeepCCS[M-H]-168.5530932474
DeepCCS[M-2H]-201.43630932474
DeepCCS[M+Na]+177.00130932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+168.432859911
AllCCS[M+Na]+169.232859911
AllCCS[M-H]-170.132859911
AllCCS[M+Na-2H]-170.532859911
AllCCS[M+HCOO]-171.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Diisobutyl phthalateCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C2584.3Standard polar33892256
Diisobutyl phthalateCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C1930.0Standard non polar33892256
Diisobutyl phthalateCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C1929.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-2900000000-abec18892ce4da3756e02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-4910000000-f91f01037e6da27fb89b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-0910000000-3ed563f6a8676b13ac032017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate CI-B (Non-derivatized)splash10-0002-0950000000-6650563a272a276c29862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-2900000000-abec18892ce4da3756e02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-4910000000-f91f01037e6da27fb89b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate EI-B (Non-derivatized)splash10-0002-0910000000-3ed563f6a8676b13ac032018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diisobutyl phthalate CI-B (Non-derivatized)splash10-0002-0950000000-6650563a272a276c29862018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diisobutyl phthalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5190000000-3cdee427d414b0b974692017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diisobutyl phthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diisobutyl phthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-5910000000-eb47d6296ed23011b3fc2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 30V, Positive-QTOFsplash10-0a4j-2920000000-a259b42b28bed64bb35f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 90V, Positive-QTOFsplash10-066r-4900000000-fe89b1519d0396eeeadc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 90V, Positive-QTOFsplash10-002b-9800000000-b81075221fc6e80606652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 75V, Positive-QTOFsplash10-0a4i-2900000000-f6cf8e89556ba7e548f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 15V, Positive-QTOFsplash10-0002-4910000000-b006f036bf41476aaf6b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 30V, Positive-QTOFsplash10-052b-4920000000-d5ac27f5087499ebf6ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 60V, Positive-QTOFsplash10-0a4j-1900000000-9c0a0dff37933669808f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 45V, Positive-QTOFsplash10-0a4j-2900000000-2dfca5014fcf109f03ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 45V, Positive-QTOFsplash10-0a4j-2900000000-c3375f5918c308c461ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 15V, Positive-QTOFsplash10-052b-2910000000-cb35fe1c0bce4c9e72332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diisobutyl phthalate 60V, Positive-QTOFsplash10-0a4j-1900000000-8ddb46ee566aac676de92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 10V, Positive-QTOFsplash10-0a6r-6090000000-3922a463577bdefc01fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 20V, Positive-QTOFsplash10-0a4i-9130000000-c092263dab19ba0396662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 40V, Positive-QTOFsplash10-0a4i-9300000000-58a47be1f5ce3c753e352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 10V, Negative-QTOFsplash10-004i-1090000000-c6c63d84e32a57928a032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 20V, Negative-QTOFsplash10-00b9-2490000000-2038c67ef03d4059d4ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 40V, Negative-QTOFsplash10-00di-5910000000-107418e7a1be51abc14c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 10V, Negative-QTOFsplash10-004i-0090000000-95d4efbe59d9e89a80aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 20V, Negative-QTOFsplash10-00b9-0960000000-a314d50d660b210ec0282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 40V, Negative-QTOFsplash10-00fr-3900000000-7c951a251ddbba9bbdff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 10V, Positive-QTOFsplash10-0a6r-0290000000-6399bc22b0dbd3431dbe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 20V, Positive-QTOFsplash10-052b-1930000000-a64f6ab167b9b42bc0352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diisobutyl phthalate 40V, Positive-QTOFsplash10-0a4l-7910000000-99d19de0de10b8aa156d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004315
KNApSAcK IDC00055801
Chemspider ID6524
KEGG Compound IDC15205
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiisobutyl_phthalate
METLIN IDNot Available
PubChem Compound6782
PDB IDNot Available
ChEBI ID79053
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1309191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available