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Record Information
Creation Date2006-05-22 14:17:34 UTC
Update Date2016-02-11 01:05:15 UTC
Secondary Accession NumbersNone
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 ).
Isobutyl hydrogen phthalateHMDB
mono-iso-Butyl phthalateHMDB
Monoisobutyl phthalateHMDB
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name2-[(2-methylpropoxy)carbonyl]benzoic acid
Traditional NameMIBP
CAS Registry Number30833-53-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Benzoate ester
  • Benzylether
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.79 mg/mLALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.08 m3·mol-1ChemAxon
Polarizability22.83 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
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...
UrineDetected and Quantified0.00672 (0.00600-0.00758) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022820
KNApSAcK IDNot Available
Chemspider ID83306
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02056
Metagene LinkHMDB02056
METLIN IDNot Available
PubChem Compound92272
PDB IDNot Available
ChEBI IDNot Available
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. [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. [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. [16970347 ]