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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-02-26 21:23:51 UTC
HMDB IDHMDB0002130
Secondary Accession Numbers
  • HMDB02130
Metabolite Identification
Common NameMonomethyl phthalate
DescriptionMonomethyl phthalate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Monomethyl phthalate is an extremely weak basic (essentially neutral) compound (based on its pKa). Monomethyl phthalate is a potentially toxic compound.
Structure
Data?1582752231
Synonyms
ValueSource
Monomethyl phthalic acidGenerator
2-(Methoxycarbonyl)benzoateHMDB
2-(Methoxycarbonyl)benzoic acidHMDB
Methyl hydrogen phthalateHMDB
Methyl phthalateHMDB
Monomethyl 1,2-benzenedicarboxylateHMDB
O-(Methoxycarbonyl)benzoateHMDB
O-(Methoxycarbonyl)benzoic acidHMDB
1,2-Benzenedicarboxylic acid monomethyl esterHMDB
Monomethyl phthalateMeSH
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name2-(methoxycarbonyl)benzoic acid
Traditional Namemethyl hydrogen phthalate
CAS Registry Number4376-18-5
SMILES
COC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C9H8O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-5H,1H3,(H,10,11)
InChI KeyFNJSWIPFHMKRAT-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
  • Methyl ester
  • 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:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82 - 84 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
logP1.5ALOGPS
logP1.63ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.34 m³·mol⁻¹ChemAxon
Polarizability16.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rt-4900000000-7ecedc5a0ae37b95fb89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9740000000-01768b5a1dd9f429bc59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a30afed48b4abca44a75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-6c900681bbe7b512eb7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-894c68b2baa026fb0ba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-9ffa6bd1a11cb78d8eebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0900000000-56be31444cf112d7c4a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-2900000000-bba5768c32c4e6274e8dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0ufr-9400000000-0563d9ffe58f40e5046cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.0172 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000628 (0.000546-0.000734) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00174 (0.00153-0.00198) 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 IDFDB022858
KNApSAcK IDNot Available
Chemspider ID19207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20392
PDB IDNot Available
ChEBI ID491486
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMedonos, Vladimir; Pasek, Josef; Ruzicka, Vlastimil. Preparation of methyl phthalate by addition of dimethyl ether to phthalic anhydride. Chemicky Prumysl (1957), 7 281-5.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Liang DW, Zhang T, Fang HH: Denitrifying degradation of dimethyl phthalate. Appl Microbiol Biotechnol. 2007 Feb;74(1):221-9. Epub 2006 Nov 10. [PubMed:17096122 ]