Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2019-11-26 03:03:49 UTC
Primary IDFDB010566
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhthalic acid
DescriptionPhthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. Phthalic acid is used mainly in the form of the anhydride to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many other useful products. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. Phthalate is an environmental chemical of heightened public concern because reports of its potential risk to male reproductive health (PMID 16804814), being significantly associated with reduced sperm concentration to pesticide concentration in men's urine (PMID 16804812). Within the reproductive tract, the male is exquisitely vulnerable to the effects of anti-androgens during development due the reliance on the synthesis and action of androgens for the masculinization of the male reproductive tract. The ability of phthalates to suppress androgen synthesis during development and to induce testicular dysgenesis together with cryptorchidism and hypospadias has raised considerable concern. (PMID 15016950) [HMDB].
CAS Number88-99-3
Structure
Thumb
Synonyms
SynonymSource
1,2-Benzenedicarboxylic acidChEBI
O-Benzenedicarboxylic acidChEBI
Ortho-phthalic acidChEBI
O-Phthalic acidKegg
1,2-BenzenedicarboxylateGenerator
O-BenzenedicarboxylateGenerator
Ortho-phthalateGenerator
O-PhthalateGenerator
PhthalateGenerator
AlizarinateHMDB
Alizarinic acidHMDB
M 2HMDB
NaphthalinateHMDB
Naphthalinic acidHMDB
O-CarboxybenzoateHMDB
O-Carboxybenzoic acidHMDB
O-DicarboxybenzeneHMDB
PhthalinateHMDB
Phthalinic acidHMDB
Sunftal 20HMDB
Phthalic acid, dipotassium saltHMDB
Phthalic acid, disodium saltHMDB
Phthalic acid, monobarium saltHMDB
Phthalic acid, monopotassium saltHMDB
Phthalic acid, sodium saltHMDB
Potassium hydrogen phthalateHMDB
Phthalic acid, copper saltHMDB
Phthalic acid, monocalcium saltHMDB
Phthalic acid, monoruthenium saltHMDB
Phthalic acid, potassium saltHMDB
Phthalic acid, potassium, sodium saltHMDB
Phthalic acid, monoiron (2+) saltHMDB
Phthalic acid, monolead (2+) saltHMDB
Phthalic acid, monosodium saltHMDB
Phthalic acidGenerator
Disodium phthalateMeSH
Naphthalinic acid?db_source
ortho-PhthalateGenerator
ortho-Phthalic acidChEBI
Phthalic acid, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility3.12 g/LALOGPS
logP1.22ALOGPS
logP1.29ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.57 m³·mol⁻¹ChemAxon
Polarizability14.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H6O4
IUPAC namebenzene-1,2-dicarboxylic acid
InChI IdentifierInChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChI KeyXNGIFLGASWRNHJ-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=CC=C1C(O)=O
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
Classification
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • 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

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.84%; H 3.64%; O 38.52%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhthalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-13ae6bbb9f0d5dcc636cSpectrum
GC-MSPhthalic acid, non-derivatized, GC-MS Spectrumsplash10-0zor-9500000000-e5ec33e3312a4a87ea39Spectrum
GC-MSPhthalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-b0d922c04c2f5dd6e4c7Spectrum
GC-MSPhthalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-13ae6bbb9f0d5dcc636cSpectrum
GC-MSPhthalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-9308910720abd784ba33Spectrum
Predicted GC-MSPhthalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014j-5900000000-68084b3e65fcd1cea856Spectrum
Predicted GC-MSPhthalic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8390000000-d238ce57194d1385d919Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-0f913d45c1daa3650138Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9400000000-ba393489337831b167f0Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-998fd73fa45b918fbbd4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-473374d725e62e2c60efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00fr-4900000000-863cf771373d1802f7d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9200000000-acf56d82f3969fd63b3bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9100000000-c03297cff4e455fc9a56Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-88a6558d781ff1f9c6c5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-473374d725e62e2c60efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-4900000000-863cf771373d1802f7d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-9b673ed6e8d6d73b74b4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-c03297cff4e455fc9a56Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-88a6558d781ff1f9c6c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-544e377d1efe0d8040f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-88ea8f2e083f769b4eccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-6900000000-f4a09894e4cd81ff485eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e9d3605c3e0f232735dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2900000000-f0bd93b089cec9e1caf2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9700000000-699743d9f7786056612cSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID992
ChEMBL IDCHEMBL1045
KEGG Compound IDC01606
Pubchem Compound ID1017
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02746
HMDB IDHMDB02107
CRC / DFC (Dictionary of Food Compounds) IDFDK47-M:FDK47-M
EAFUS IDNot Available
Dr. Duke IDO-PHTHALIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPHT
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).