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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-10-09 21:02:28 UTC
HMDB IDHMDB0002120
Secondary Accession Numbers
  • HMDB02120
Metabolite Identification
Common NameMonoethyl phthalate
DescriptionMonoethyl phthalate, also known as metp, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Monoethyl phthalate is an extremely weak basic (essentially neutral) compound (based on its pKa). Monoethyl phthalate is a potentially toxic compound. A phthalic acid monoester resulting from the condensation of one of the carboxy groups of phthalic acid with ethanol.
Structure
Data?1582752230
Synonyms
ValueSource
MEtPChEBI
Phthalic acid monoethyl esterChEBI
Phthalate monoethyl esterGenerator
Monoethyl phthalic acidGenerator
2-(Ethoxycarbonyl)benzoateHMDB
2-(Ethoxycarbonyl)benzoic acidHMDB
14C-Monoethyl phthalateMeSH, HMDB
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name2-(ethoxycarbonyl)benzoic acid
Traditional Name2-(ethoxycarbonyl)benzoic acid
CAS Registry Number2306-33-4
SMILES
CCOC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C10H10O4/c1-2-14-10(13)8-6-4-3-5-7(8)9(11)12/h3-6H,2H2,1H3,(H,11,12)
InChI KeyYWWHKOHZGJFMIE-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 Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available148.226http://allccs.zhulab.cn/database/detail?ID=AllCCS00001928
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP10(1.77) g/LALOGPS
logP10(1.99) g/LChemAxon
logS10(-2) g/LALOGPS
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 Count4ChemAxon
Refractivity50.09 m³·mol⁻¹ChemAxon
Polarizability18.96 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]+145.27431661259
DarkChem[M-H]-141.41831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Monoethyl phthalateCCOC(=O)C1=CC=CC=C1C(O)=O2621.8Standard polar33892256
Monoethyl phthalateCCOC(=O)C1=CC=CC=C1C(O)=O1529.0Standard non polar33892256
Monoethyl phthalateCCOC(=O)C1=CC=CC=C1C(O)=O1649.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monoethyl phthalate,1TMS,isomer #1CCOC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1656.0Semi standard non polar33892256
Monoethyl phthalate,1TBDMS,isomer #1CCOC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C1871.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl phthalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-9485da16793404440a4d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl phthalate GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-7950000000-df66d7e474b2aafe512b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl phthalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-3900000000-6be1b202beedc9e2f7bb2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , negative-QTOFsplash10-00dj-0900000000-7184720c787659f6ce3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , negative-QTOFsplash10-00dj-0900000000-7caa3692e7c497a561fe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-QFT , negative-QTOFsplash10-0007-0900000000-e3be2058874e4c54fcba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate 35V, Negative-QTOFsplash10-00dj-0900000000-7184720c787659f6ce3f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate 55V, Negative-QTOFsplash10-00dj-0900000000-7caa3692e7c497a561fe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate 35V, Negative-QTOFsplash10-0007-0900000000-e3be2058874e4c54fcba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-c1875e3853edd9c77c792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , positive-QTOFsplash10-006t-0900000000-ed9b6f54a127b19a848a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , positive-QTOFsplash10-002b-0900000000-680192921fe7c95759a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl phthalate LC-ESI-ITFT , positive-QTOFsplash10-002b-0900000000-2659d3b8194bd70238c32017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 10V, Negative-QTOFsplash10-0007-0900000000-c173a682384a3e4ce72e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 20V, Negative-QTOFsplash10-0005-1900000000-e831a6f904fea172c8132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 40V, Negative-QTOFsplash10-00fr-7900000000-ada3cc1476b2baa0c2222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 10V, Negative-QTOFsplash10-0002-0900000000-cdd9e8d7ae56c220b5652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 20V, Negative-QTOFsplash10-00b9-8900000000-5bb135ce61ef2c8625a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 40V, Negative-QTOFsplash10-004i-9000000000-71521d25edc345facd862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 10V, Positive-QTOFsplash10-0002-0900000000-bcac77a38e977b4d8e6f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 20V, Positive-QTOFsplash10-0002-0900000000-576d07318ff410e939e42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 40V, Positive-QTOFsplash10-0a4i-3900000000-0d79875f59bc643d940b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 10V, Positive-QTOFsplash10-000t-0900000000-b49a354bdefc4b90730e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 20V, Positive-QTOFsplash10-052b-0900000000-8d53a9c546f12ecf4e332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl phthalate 40V, Positive-QTOFsplash10-0a4i-1900000000-1c31c607d2c356d682bc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.471 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0570 (0.0522-0.0623) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0267 (0.0239-0.0299) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.009 umol/mmol creatinineAdult (>18 years old)BothPregnancy details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Huang PC, Kuo PL, Guo YL, Liao PC, Lee CC: Associations between urinary phthalate monoesters and thyroid hormones in pregnant women. Hum Reprod. 2007 Oct;22(10):2715-22. Epub 2007 Aug 17. [PubMed:17704099 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022852
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75318
PDB IDNot Available
ChEBI ID70973
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000378
Good Scents IDNot Available
References
Synthesis Referencev. Amann, Walter. Ethyl hydrogen phthalate. Monatshefte fuer Chemie (1915), 36 505-8.
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. Hauser R, Meeker JD, Singh NP, Silva MJ, Ryan L, Duty S, Calafat AM: DNA damage in human sperm is related to urinary levels of phthalate monoester and oxidative metabolites. Hum Reprod. 2007 Mar;22(3):688-95. Epub 2006 Nov 7. [PubMed:17090632 ]