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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-11-09 23:16:36 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. Based on a literature review very few articles have been published on Monomethyl phthalate.
Structure
Data?1582752231
Synonyms
ValueSource
Monomethyl phthalic acidGenerator
2-(Methoxycarbonyl)benzoateHMDB, Generator
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 esterMeSH, HMDB
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point82 - 84 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.13HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
logP10(1.5) g/LALOGPS
logP10(1.63) g/LChemAxon
logS10(-2) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.48231661259
DarkChem[M-H]-137.00931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Monomethyl phthalateCOC(=O)C1=CC=CC=C1C(O)=O2513.5Standard polar33892256
Monomethyl phthalateCOC(=O)C1=CC=CC=C1C(O)=O1430.3Standard non polar33892256
Monomethyl phthalateCOC(=O)C1=CC=CC=C1C(O)=O1578.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monomethyl phthalate,1TMS,isomer #1COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1596.3Semi standard non polar33892256
Monomethyl phthalate,1TBDMS,isomer #1COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C1808.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monomethyl phthalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rt-4900000000-7ecedc5a0ae37b95fb892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monomethyl phthalate GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9740000000-01768b5a1dd9f429bc592017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monomethyl phthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ufr-9400000000-0563d9ffe58f40e5046c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 45V, Positive-QTOFsplash10-01ot-0900000000-65098170b3784885cf3e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 60V, Positive-QTOFsplash10-0002-1900000000-eb93036cba5677f432e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 30V, Positive-QTOFsplash10-01ot-0900000000-6757db1ade89e1c39c0f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 15V, Positive-QTOFsplash10-01ot-0900000000-bfa80ccf09eb7547a4212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 75V, Positive-QTOFsplash10-00r2-6900000000-7e7becd99ce7a415a27a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 90V, Positive-QTOFsplash10-014j-9300000000-85d661af2d78119733282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 30V, Negative-QTOFsplash10-0a4i-0900000000-e16e03b30bfbb5c3e6f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 90V, Negative-QTOFsplash10-00b9-9400000000-d46f471c7dd86ce167d82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 75V, Negative-QTOFsplash10-00fu-9800000000-94470b2ac4d094b659562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 15V, Negative-QTOFsplash10-0a4i-0900000000-f0a6ee4ef8d00d6650662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 45V, Negative-QTOFsplash10-0a4i-0900000000-f5d8dcb50914d6dec34c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monomethyl phthalate 60V, Negative-QTOFsplash10-0abc-3900000000-4cbbe5ea3080e1835e8b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 10V, Positive-QTOFsplash10-001i-0900000000-a30afed48b4abca44a752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 20V, Positive-QTOFsplash10-001j-0900000000-6c900681bbe7b512eb7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 40V, Positive-QTOFsplash10-0a4i-3900000000-894c68b2baa026fb0ba02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 10V, Negative-QTOFsplash10-004i-0900000000-9ffa6bd1a11cb78d8eeb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 20V, Negative-QTOFsplash10-002r-0900000000-56be31444cf112d7c4a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 40V, Negative-QTOFsplash10-0udr-2900000000-bba5768c32c4e6274e8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 10V, Positive-QTOFsplash10-01ot-0900000000-cc0e0c22916327043a552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 20V, Positive-QTOFsplash10-052b-0900000000-782a28b988f8b2a279d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 40V, Positive-QTOFsplash10-0a4i-3900000000-3b0ed44720a2090fc9b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 10V, Negative-QTOFsplash10-004r-3900000000-6ec50e9028830ab6da822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 20V, Negative-QTOFsplash10-004i-9500000000-da5c1bf0509aad0449372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomethyl phthalate 40V, Negative-QTOFsplash10-004i-9000000000-79b57c4c262a25bff4312021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
MarkerDB IDNot Available
Good Scents 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 ]