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Record Information
Version4.0
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
Physiological effect

Health effect:

Disposition

Biological location:

Role

Industrial application:

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 Solubility1.81 g/LALOGPS
logP1.77ALOGPS
logP1.99ChemAxon
logS-2ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-9485da16793404440a4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-7950000000-df66d7e474b2aafe512bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00dj-0900000000-7184720c787659f6ce3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00dj-0900000000-7caa3692e7c497a561feSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0007-0900000000-e3be2058874e4c54fcbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-c1875e3853edd9c77c79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006t-0900000000-ed9b6f54a127b19a848aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-002b-0900000000-680192921fe7c95759a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-002b-0900000000-2659d3b8194bd70238c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bcac77a38e977b4d8e6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-576d07318ff410e939e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-0d79875f59bc643d940bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-c173a682384a3e4ce72eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-1900000000-e831a6f904fea172c813Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-7900000000-ada3cc1476b2baa0c222Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-3900000000-6be1b202beedc9e2f7bbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
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 ]