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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2020-02-26 21:23:46 UTC
HMDB IDHMDB0002056
Secondary Accession Numbers
  • HMDB02056
Metabolite Identification
Common NameMonoisobutyl phthalic acid
DescriptionMonoisobutyl phthalic acid is a phthalate metabolite that has been found in human meconium and in semen (PMID: 16970347 ), saliva (PMID: 15995852 ), and urine (PMID: 15113553 ). Phthalate esters are a family of multifunctional compounds widely used as plasticizers, solvents, or additives in many diverse products such as poly(vinyl chloride) (PVC) materials, pharmaceuticals and medical devices, pesticides, lubricants, and personal care products. Humans have been exposed to phthalates through the manufacture, ubiquitous use, and disposal of PVC materials and other phthalate-containing products. (PMID: 16970347 ).
Structure
Data?1582752226
Synonyms
ValueSource
1,2-Benzenedicarboxylic acid, mono(2-methylpropyl) esterChEBI
2-(Isobutoxycarbonyl)benzoic acidChEBI
Isobutyl hydrogen phthalateChEBI
MIBPChEBI
mono-Iso-butyl phthalateChEBI
Phthalic acid, monoisobutyl esterChEBI
1,2-Benzenedicarboxylate, mono(2-methylpropyl) esterGenerator
2-(Isobutoxycarbonyl)benzoateGenerator
Isobutyl hydrogen phthalic acidGenerator
mono-Iso-butyl phthalic acidGenerator
Phthalate, monoisobutyl esterGenerator
Monoisobutyl phthalateGenerator
Monoisobutyl phthalic acidChEBI
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name2-[(2-methylpropoxy)carbonyl]benzoic acid
Traditional NameMIBP
CAS Registry Number30833-53-5
SMILES
CC(C)COC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C12H14O4/c1-8(2)7-16-12(15)10-6-4-3-5-9(10)11(13)14/h3-6,8H,7H2,1-2H3,(H,13,14)
InChI KeyRZJSUWQGFCHNFS-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
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP2.38ALOGPS
logP2.88ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.08 m³·mol⁻¹ChemAxon
Polarizability22.83 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]+151.69831661259
DarkChem[M-H]-148.58131661259
DeepCCS[M+H]+147.45630932474
DeepCCS[M-H]-144.09330932474
DeepCCS[M-2H]-180.59330932474
DeepCCS[M+Na]+156.13130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Monoisobutyl phthalic acidCC(C)COC(=O)C1=CC=CC=C1C(O)=O2752.5Standard polar33892256
Monoisobutyl phthalic acidCC(C)COC(=O)C1=CC=CC=C1C(O)=O1718.7Standard non polar33892256
Monoisobutyl phthalic acidCC(C)COC(=O)C1=CC=CC=C1C(O)=O1797.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monoisobutyl phthalic acid,1TMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1788.6Semi standard non polar33892256
Monoisobutyl phthalic acid,1TBDMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2014.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-4910000000-ac2484b74eb5cfd5b6902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6390000000-4ca9de5bf766a991b3dc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoisobutyl phthalic acid LC-ESI-QFT , negative-QTOFsplash10-0089-0930000000-d249a5cd21193a8a3cd22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoisobutyl phthalic acid LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-13d64e3eb0a1e3e235be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoisobutyl phthalic acid 35V, Negative-QTOFsplash10-0089-0930000000-3a306e5ce6ca6a0e91272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoisobutyl phthalic acid 35V, Positive-QTOFsplash10-0002-0900000000-b4a2e5d94dccaced84c12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Positive-QTOFsplash10-0ab9-6690000000-8f32418bd6ccde0549c02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Positive-QTOFsplash10-0a4i-9720000000-286cdd7561a043eef3d02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Positive-QTOFsplash10-0a4i-9500000000-6c3aca6817c2db6bb8042016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Negative-QTOFsplash10-00di-1790000000-2d20ca2ec96d849863212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Negative-QTOFsplash10-0100-2910000000-46c6c191f37b2782021a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Negative-QTOFsplash10-00di-6900000000-0d9a0ca1ebdbc964dac02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Positive-QTOFsplash10-0a4j-0940000000-827565da796a34bbd6b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Positive-QTOFsplash10-052b-1900000000-bfe543859b406a2dae922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Positive-QTOFsplash10-0a4i-2900000000-8cb1cf43ad6057fc27c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Negative-QTOFsplash10-00b9-0930000000-2a9d225bebcec6f946292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Negative-QTOFsplash10-004i-6910000000-2ae4c65b2cf89d2dde5a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Negative-QTOFsplash10-004i-9200000000-c321d909ae49bc32f15a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0022 (0.0-0.0044) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.0805 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00379 (0.00346-0.00415) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00672 (0.00600-0.00758) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022820
KNApSAcK IDNot Available
Chemspider ID83306
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92272
PDB IDNot Available
ChEBI ID90038
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKe, Changying. Esterification synthesis of diisobutyl phthalate. Huaxue Shijie (1986), 27(10), 440-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Silva MJ, Reidy JA, Samandar E, Herbert AR, Needham LL, Calafat AM: Detection of phthalate metabolites in human saliva. Arch Toxicol. 2005 Nov;79(11):647-52. Epub 2005 Jul 2. [PubMed:15995852 ]
  2. Silva MJ, Slakman AR, Reidy JA, Preau JL Jr, Herbert AR, Samandar E, Needham LL, Calafat AM: Analysis of human urine for fifteen phthalate metabolites using automated solid-phase extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 5;805(1):161-7. [PubMed:15113553 ]
  3. Kato K, Silva MJ, Needham LL, Calafat AM: Quantifying phthalate metabolites in human meconium and semen using automated off-line solid-phase extraction coupled with on-line SPE and isotope-dilution high-performance liquid chromatography--tandem mass spectrometry. Anal Chem. 2006 Sep 15;78(18):6651-5. [PubMed:16970347 ]