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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2020-02-26 21:23:49 UTC
HMDB IDHMDB0002107
Secondary Accession Numbers
  • HMDB02107
Metabolite Identification
Common 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 ).
Structure
Data?1582752229
Synonyms
ValueSource
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
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Namebenzene-1,2-dicarboxylic acid
Traditional Namephthalic acid
CAS Registry Number88-99-3
SMILES
OC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.01 mg/mL at 25 °CNot Available
LogP0.73HANSCH,C ET AL. (1995)
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0910000000-13ae6bbb9f0d5dcc636cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zor-9500000000-e5ec33e3312a4a87ea39Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0910000000-b0d922c04c2f5dd6e4c7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-13ae6bbb9f0d5dcc636cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-9308910720abd784ba33Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-5900000000-68084b3e65fcd1cea856Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8390000000-d238ce57194d1385d919Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-0f913d45c1daa3650138Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9400000000-ba393489337831b167f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-998fd73fa45b918fbbd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-473374d725e62e2c60efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00fr-4900000000-863cf771373d1802f7d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9200000000-acf56d82f3969fd63b3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9100000000-c03297cff4e455fc9a56Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-88a6558d781ff1f9c6c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-473374d725e62e2c60efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-4900000000-863cf771373d1802f7d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-9b673ed6e8d6d73b74b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-c03297cff4e455fc9a56Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-88a6558d781ff1f9c6c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-544e377d1efe0d8040f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-88ea8f2e083f769b4eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-6900000000-f4a09894e4cd81ff485eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e9d3605c3e0f232735dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2900000000-f0bd93b089cec9e1caf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9700000000-699743d9f7786056612cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified2.179 (0.211-21.573) nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0397 +/- 0.0623 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0841 +/- 0.0878 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.146 +/- 0.00566 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.174 +/- 0.499 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0638 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified75.3 (27.5-109.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified30.5 (22.8-98.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified31.4 +/- 23.7 uMAdult (>18 years old)BothHemodialysis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified2.116 +/- 0.589 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. Pollack GM, Buchanan JF, Slaughter RL, Kohli RK, Shen DD: Circulating concentrations of di(2-ethylhexyl) phthalate and its de-esterified phthalic acid products following plasticizer exposure in patients receiving hemodialysis. Toxicol Appl Pharmacol. 1985 Jun 30;79(2):257-67. [PubMed:4002227 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB02746
Phenol Explorer Compound IDNot Available
FooDB IDFDB010566
KNApSAcK IDNot Available
Chemspider ID992
KEGG Compound IDC01606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalic_acid
METLIN ID6489
PubChem Compound1017
PDB IDNot Available
ChEBI ID29069
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSchep, Raymond Albert. Production of carboxylic acid. Brit. UK Pat. Appl. (1979), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lapinskas PJ, Brown S, Leesnitzer LM, Blanchard S, Swanson C, Cattley RC, Corton JC: Role of PPARalpha in mediating the effects of phthalates and metabolites in the liver. Toxicology. 2005 Feb 1;207(1):149-63. [PubMed:15590130 ]
  2. 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 ]
  3. Hurst CH, Waxman DJ: Activation of PPARalpha and PPARgamma by environmental phthalate monoesters. Toxicol Sci. 2003 Aug;74(2):297-308. Epub 2003 Jun 12. [PubMed:12805656 ]
  4. Hauser R: The environment and male fertility: recent research on emerging chemicals and semen quality. Semin Reprod Med. 2006 Jul;24(3):156-67. [PubMed:16804814 ]
  5. Swan SH: Does our environment affect our fertility? Some examples to help reframe the question. Semin Reprod Med. 2006 Jul;24(3):142-6. [PubMed:16804812 ]
  6. Fisher JS: Environmental anti-androgens and male reproductive health: focus on phthalates and testicular dysgenesis syndrome. Reproduction. 2004 Mar;127(3):305-15. [PubMed:15016950 ]