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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2022-03-07 02:49:12 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 saltMeSH, HMDB
Phthalic acid, disodium saltMeSH, HMDB
Phthalic acid, monobarium saltMeSH, HMDB
Phthalic acid, monopotassium saltMeSH, HMDB
Phthalic acid, sodium saltMeSH, HMDB
Potassium hydrogen phthalateMeSH, HMDB
Phthalic acid, copper saltMeSH, HMDB
Phthalic acid, monocalcium saltMeSH, HMDB
Phthalic acid, monoruthenium saltMeSH, HMDB
Phthalic acid, potassium saltMeSH, HMDB
Phthalic acid, potassium, sodium saltMeSH, HMDB
Phthalic acid, monoiron (2+) saltMeSH, HMDB
Phthalic acid, monolead (2+) saltMeSH, HMDB
Phthalic acid, monosodium saltMeSH, HMDB
Phthalic acidGenerator
Disodium phthalateMeSH
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 - 230 °CNot Available
Boiling Point132.00 to 133.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility7.01 mg/mL at 25 °CNot Available
LogP0.73HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.21931661259
DarkChem[M-H]-129.40331661259
DeepCCS[M+H]+133.88230932474
DeepCCS[M-H]-130.05430932474
DeepCCS[M-2H]-167.27630932474
DeepCCS[M+Na]+142.81530932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.532859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.232859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-130.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O2700.6Standard polar33892256
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O1443.9Standard non polar33892256
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O1640.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phthalic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O1674.4Semi standard non polar33892256
Phthalic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1699.0Semi standard non polar33892256
Phthalic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O1909.2Semi standard non polar33892256
Phthalic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2133.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phthalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0910000000-13ae6bbb9f0d5dcc636c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phthalic acid EI-B (Non-derivatized)splash10-0zor-9500000000-e5ec33e3312a4a87ea392017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phthalic acid EI-B (Non-derivatized)splash10-0002-0910000000-b0d922c04c2f5dd6e4c72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phthalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-13ae6bbb9f0d5dcc636c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phthalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-9308910720abd784ba332017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-5900000000-68084b3e65fcd1cea8562017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phthalic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8390000000-d238ce57194d1385d9192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-0900000000-0f913d45c1daa36501382012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kf-9400000000-ba393489337831b167f02012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9000000000-998fd73fa45b918fbbd42012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-473374d725e62e2c60ef2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-00fr-4900000000-863cf771373d1802f7d02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-004i-9200000000-acf56d82f3969fd63b3b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9100000000-c03297cff4e455fc9a562012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00di-9000000000-88a6558d781ff1f9c6c52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-473374d725e62e2c60ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOFsplash10-00fr-4900000000-863cf771373d1802f7d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9200000000-9b673ed6e8d6d73b74b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9100000000-c03297cff4e455fc9a562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-88a6558d781ff1f9c6c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 20V, Negative-QTOFsplash10-004i-9000000000-79444e6f1e1cad82c9af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 10V, Negative-QTOFsplash10-00fr-7900000000-69919220fe286719b1542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 40V, Negative-QTOFsplash10-004i-9000000000-f8cd37ad5a7de3510c1c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 35V, Positive-QTOFsplash10-0002-0900000000-0bf84650c197f00d2d4b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 35V, Negative-QTOFsplash10-00di-0900000000-9e9de7b1b9755cbc0c832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phthalic acid 30V, Negative-QTOFsplash10-00di-0900000000-17c7a2e06ddf58f100a32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 10V, Positive-QTOFsplash10-014i-0900000000-544e377d1efe0d8040f22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 20V, Positive-QTOFsplash10-014j-0900000000-88ea8f2e083f769b4ecc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 40V, Positive-QTOFsplash10-0pb9-6900000000-f4a09894e4cd81ff485e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 10V, Negative-QTOFsplash10-014i-0900000000-e9d3605c3e0f232735dc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 20V, Negative-QTOFsplash10-00xr-2900000000-f0bd93b089cec9e1caf22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phthalic acid 40V, Negative-QTOFsplash10-00b9-9700000000-699743d9f7786056612c2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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
    • Analysis of 30 no...
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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB02746
Phenol Explorer Compound IDNot Available
FooDB IDFDB010566
KNApSAcK IDC00055600
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
MarkerDB IDNot Available
Good Scents IDrw1451041
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. 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. 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 ]
  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 ]