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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-11-30 15:51:39 UTC
Update Date2020-11-09 23:18:51 UTC
HMDB IDHMDB0013247
Secondary Accession Numbers
  • HMDB13247
Metabolite Identification
Common NameMonobutylphthalate
DescriptionMonobutylphthalate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Monobutylphthalate has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make monobutylphthalate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Monobutylphthalate.
Structure
Data?1582753105
Synonyms
ValueSource
Monobutylphthalic acidGenerator
-N-Butyl-phthalateHMDB
2-(Butoxycarbonyl)benzoateHMDB
2-(Butoxycarbonyl)benzoic acidHMDB
Butyl hydrogen phthalateHMDB
mono-N-Butyl phthalateHMDB
MONOBUTYL phthalATEHMDB
Phthalic acid monobutyl esterHMDB
Phthalic acid, monobutyl esterHMDB
Monobutyl phthalate, copper (2+) saltHMDB
Monobutyl phthalate, potassium saltHMDB
Monobutyl phthalate, manganese (2+) saltHMDB
Monobutyl phthalate, sodium saltHMDB
Monobutyl phthalate, cobalt (2+) saltHMDB
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name2-(butoxycarbonyl)benzoic acid
Traditional Namemonobutyl phthalate
CAS Registry Number131-70-4
SMILES
CCCCOC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)
InChI KeyYZBOVSFWWNVKRJ-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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point73.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP2.48ALOGPS
logP2.96ChemAxon
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 Count6ChemAxon
Refractivity59.21 m³·mol⁻¹ChemAxon
Polarizability23.48 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]+151.2731661259
DarkChem[M-H]-148.09431661259
DeepCCS[M+H]+155.62430932474
DeepCCS[M-H]-151.77830932474
DeepCCS[M-2H]-188.55930932474
DeepCCS[M+Na]+164.43930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MonobutylphthalateCCCCOC(=O)C1=CC=CC=C1C(O)=O2860.9Standard polar33892256
MonobutylphthalateCCCCOC(=O)C1=CC=CC=C1C(O)=O1729.8Standard non polar33892256
MonobutylphthalateCCCCOC(=O)C1=CC=CC=C1C(O)=O1847.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monobutylphthalate,1TMS,isomer #1CCCCOC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1833.7Semi standard non polar33892256
Monobutylphthalate,1TBDMS,isomer #1CCCCOC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2058.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monobutylphthalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-4900000000-0bd4c8a90791996644362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monobutylphthalate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5190000000-8ce12e65fc5416eb63c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monobutylphthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-2900000000-8b540fe8b986d5e981d22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 75V, Negative-QTOFsplash10-00b9-9700000000-2002a92aa776f731f5472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 90V, Negative-QTOFsplash10-004i-9200000000-bab0e6b59be9a589fdf82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 45V, Negative-QTOFsplash10-00di-0900000000-3a6c7d7f9113fed591742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 60V, Negative-QTOFsplash10-00di-3900000000-a00fe976c698b4ed63252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 30V, Negative-QTOFsplash10-00di-0900000000-1a1e3d54f88fd157a5de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 15V, Negative-QTOFsplash10-00di-0910000000-70714079ed7e95d6ef742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 75V, Positive-QTOFsplash10-0umj-5900000000-82639734b79004580e2b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 90V, Positive-QTOFsplash10-0udj-7900000000-a0eea15924ac087b77f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 45V, Positive-QTOFsplash10-00ou-9800000000-3e69e882204361a9a2572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 60V, Positive-QTOFsplash10-00bc-3900000000-20330bc7cb80b4cf2ef22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 30V, Positive-QTOFsplash10-004i-0900000000-e14af552e9b8db2e93642021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monobutylphthalate 15V, Positive-QTOFsplash10-014i-9000000000-ed8d9d8c1adcba78ab3e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 10V, Negative-QTOFsplash10-00di-1690000000-7e0e4445918862b4b0632015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 20V, Negative-QTOFsplash10-01di-1910000000-ce84303eee04f3918d732015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 40V, Negative-QTOFsplash10-00xr-6900000000-6436ac077fdf043a99e22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 10V, Negative-QTOFsplash10-00fr-4950000000-9c4ed667a42f397ac54a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 20V, Negative-QTOFsplash10-004i-9700000000-55facdfeaed9d4e03bf62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 40V, Negative-QTOFsplash10-004i-9100000000-5f179b04881d205104732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 10V, Positive-QTOFsplash10-0ab9-2390000000-f41da427e765b1dd98712015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 20V, Positive-QTOFsplash10-0a4i-9740000000-cb5edfb11d260e7c31fd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 40V, Positive-QTOFsplash10-0a4i-9500000000-b49c31617c73e9b8576e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 10V, Positive-QTOFsplash10-052b-0950000000-d305caaad2e713bf407a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 20V, Positive-QTOFsplash10-0002-1900000000-b7daf95a5e27e75950282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monobutylphthalate 40V, Positive-QTOFsplash10-0a4i-3900000000-b4e189df4806c2a3f6a12021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00900 (0.00829-0.0977) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0144 (0.0127-0.0163) 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 IDFDB012951
KNApSAcK IDNot Available
Chemspider ID8257
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMonobutyl phthalate
METLIN IDNot Available
PubChem Compound8575
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Blount BC, Silva MJ, Caudill SP, Needham LL, Pirkle JL, Sampson EJ, Lucier GW, Jackson RJ, Brock JW: Levels of seven urinary phthalate metabolites in a human reference population. Environ Health Perspect. 2000 Oct;108(10):979-82. [PubMed:11049818 ]