Record Information
Version1.0
Creation date2011-09-21 01:54:35 UTC
Update date2018-05-29 01:54:44 UTC
Primary IDFDB029358
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMonoethylhexyl phthalic acid
DescriptionMonoethylhexyl phthalic acid (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP measured from the blood of pregnant women have been significantly associated with the decreased penis width, shorter anogenital distance, and the incomplete descent of testes of their newborn sons, replicating effects identified in animals. DEHP hydrolyzes to MEHP via the enzyme Bis(2-ethylhexyl)phthalate acylhydrolase(3.1.1.60)and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid. [HMDB]
CAS Number4376-20-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.36ALOGPS
logP4.66ChemAxon
logS-4.3ALOGPS
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 Count9ChemAxon
Refractivity77.49 m³·mol⁻¹ChemAxon
Polarizability30.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H22O4
IUPAC name2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid
InChI IdentifierInChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)
InChI KeyDJDSLBVSSOQSLW-UHFFFAOYSA-N
Isomeric SMILESCCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O
Average Molecular Weight278.3435
Monoisotopic Molecular Weight278.151809192
Classification
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

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-4900000000-af0f2c76a7c01b845a002014-09-20View Spectrum
GC-MSMonoethylhexyl phthalic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-2970000000-346112e2dd7eb2ef672fSpectrum
GC-MSMonoethylhexyl phthalic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-2970000000-346112e2dd7eb2ef672fSpectrum
Predicted GC-MSMonoethylhexyl phthalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-5920000000-6756fbba86aadca647ceSpectrum
Predicted GC-MSMonoethylhexyl phthalic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7392000000-fd40ccd8c52320562e5cSpectrum
Predicted GC-MSMonoethylhexyl phthalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-006t-0960000000-efbb62fb904150b613f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-006t-0960000000-bace63e54682391af6712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00kb-0910000000-77eed661ab413010d3542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00mk-0900000000-214bdb75cf5614522a032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00ai-0900000000-d636e4277afd375744d22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-0900000000-e6f221aefc0e24f648d52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002b-0900000000-d8cdf715271ec6e661b82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0059-0940000000-bbc0013de532edede4832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-004i-9100000000-d5a5ecd4f3c706f53a0f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00kb-0910000000-a2eba6e125597cb7530d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00b9-2900000000-1d8439ed7614ed7148222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-004i-9800000000-3f611dc53f826ce065362021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0790000000-972234c38f1e6baf99092016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4930000000-1ab987bce4973d4f07f42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-53028683cce560c7a65b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0490000000-44a004dad8099c4e00de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00w9-1940000000-8169435369a241584a632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-6900000000-56a7cc157be52d6494f32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-bf11acdb8d5f1fa06aa52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-2940000000-474dfefcab564610df5f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-0b315e8ad86892867d122021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-048ea11376b7fe3280072021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-5950000000-012e94386a547e3c0c232021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9410000000-a8dbecb62f34e602da892021-09-25View Spectrum
NMR
TypeDescriptionView
ChemSpider ID19208
ChEMBL IDCHEMBL1867438
KEGG Compound IDC03343
Pubchem Compound ID20393
Pubchem Substance IDNot Available
ChEBI ID17243
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13248
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference