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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-10-23 19:03:56 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
Thumb
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
Monoisobutyl phthalateGenerator
2-(Isobutoxycarbonyl)benzoateGenerator
Isobutyl hydrogen phthalic acidGenerator
mono-iso-Butyl phthalic acidGenerator
Phthalate, monoisobutyl esterGenerator
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
DescriptionThis compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted 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:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP2.38ALOGPS
logP2.88ChemAxon
logS-2.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-4910000000-ac2484b74eb5cfd5b690View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6390000000-4ca9de5bf766a991b3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0089-0930000000-d249a5cd21193a8a3cd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-13d64e3eb0a1e3e235beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-6690000000-8f32418bd6ccde0549c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9720000000-286cdd7561a043eef3d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-6c3aca6817c2db6bb804View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1790000000-2d20ca2ec96d84986321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0100-2910000000-46c6c191f37b2782021aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-6900000000-0d9a0ca1ebdbc964dac0View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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
METLIN IDNot Available
PubChem Compound92272
PDB IDNot Available
ChEBI ID90038
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 ]