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Record Information
Version4.0
Creation Date2006-05-22 14:17:53 UTC
Update Date2017-09-27 08:24:16 UTC
HMDB IDHMDB0002428
Secondary Accession Numbers
  • HMDB02428
Metabolite Identification
Common NameTerephthalic acid
DescriptionTerephthalic acid is one isomer of the three phthalic acids. It finds important use as a commodity chemical, principally as a starting compound for the manufacture of polyester (specifically PET), used in clothing and to make plastic bottles. It is also known as 1,4-benzenedicarboxylic acid, and it has the chemical formula C6H4(COOH)2. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
1,4-Benzenedicarboxylic acidChEBI
P-Benzenedicarboxylic acidChEBI
Para-benzenedicarboxylic acidChEBI
TPAChEBI
1,4-BenzenedicarboxylateGenerator
TerephthalateGenerator
P-BenzenedicarboxylateGenerator
Para-benzenedicarboxylateGenerator
Benzene-P-dicarboxylateHMDB
Benzene-P-dicarboxylic acidHMDB
Kyselina terftalovaHMDB
P-DicarboxybenzeneHMDB
P-PhthalateHMDB
P-Phthalic acidHMDB
P-PhthelateHMDB
P-Phthelic acidHMDB
Disodium terephthalateMeSH
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Namebenzene-1,4-dicarboxylic acid
Traditional Nameterephthalic acid
CAS Registry Number100-21-0
SMILES
OC(=O)C1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChI KeyKKEYFWRCBNTPAC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as p-phthalic acid and derivatives. These are compounds containing a benzene ring bearing a carboxylic acid group at ring carbon atoms 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-phthalic acid and derivatives
Alternative Parents
Substituents
  • Para_phthalic_acid
  • 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
Disposition

Biological Location:

  Biofluid and excreta:

  Cell and elements:

    Cell:

    Element:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 mg/mL at 20 °CNot Available
LogP2.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.29 g/LALOGPS
logP1.01ALOGPS
logP1.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.57 m³·mol⁻¹ChemAxon
Polarizability15.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udj-1960000000-c2ce285b39dcfaade068View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014j-9500000000-6b6ec61e945c382eed89View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014j-6900000000-1a7e017001fe0602a248View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014j-4900000000-95e39c2780c93f2f98fdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udj-1960000000-c2ce285b39dcfaade068View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udj-1960000000-27e0381620f64e37fcadView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0900000000-95fdf5f4fdee61197dc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00b9-9800000000-2b52539a11193ccec082View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00b9-8900000000-197587f1e6a9e594c5b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-014j-9500000000-aafffbb19047f4caf673View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-b445c3bf5a9a7a5579fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-63c35cbaa3dcd73735c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-4900000000-2e7d3b96b81c41872945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-2d9c49fdd3573a453a1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00fr-9000000000-999fd340fed30a63e4ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-b445c3bf5a9a7a5579fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-63c35cbaa3dcd73735c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-4900000000-2e7d3b96b81c41872945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-df1f4a76d59c66d5070dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-9000000000-999fd340fed30a63e4ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-384b938e005844d386b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-736a9cc29426a85f2dbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4900000000-be05d9e5afe70d40b269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-eaf8e1fadaf0331df52fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2900000000-69d77e7980f3f93873c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9700000000-23275ad46308b76fb7c9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Platelet
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected and Quantified5.01 +/- 1.19 uMAdult (>18 years old)Both
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified0.0785 +/- 0.0591 uMAdult (>18 years old)Male
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.72 +/- 1.60 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified0.546 +/- 0.381 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.94 +/- 1.61 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified3.95 +/- 1.89 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    UrineDetected and Quantified75.3 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified30.5 umol/mmol creatinineInfant (0-1 year old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023000
    KNApSAcK IDNot Available
    Chemspider ID7208
    KEGG Compound IDC06337
    BioCyc IDCPD-1943
    BiGG IDNot Available
    Wikipedia LinkTerephthalic acid
    METLIN ID6676
    PubChem Compound7489
    PDB IDNot Available
    ChEBI ID15702
    References
    Synthesis ReferenceEmerson, Wm. S.; Shafer, Theodore C.; Heimsch, Robert A. A study of the conversion of p-toluic acid to terephthalic acid with high-pressure oxygen. Journal of Organic Chemistry (1951), 16 1839-45.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
    2. Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
    3. Bot I, von der Thusen JH, Donners MM, Lucas A, Fekkes ML, de Jager SC, Kuiper J, Daemen MJ, van Berkel TJ, Heeneman S, Biessen EA: Serine protease inhibitor Serp-1 strongly impairs atherosclerotic lesion formation and induces a stable plaque phenotype in ApoE-/-mice. Circ Res. 2003 Sep 5;93(5):464-71. Epub 2003 Aug 14. [PubMed:12919945 ]
    4. Yepes M, Sandkvist M, Moore EG, Bugge TH, Strickland DK, Lawrence DA: Tissue-type plasminogen activator induces opening of the blood-brain barrier via the LDL receptor-related protein. J Clin Invest. 2003 Nov;112(10):1533-40. [PubMed:14617754 ]
    5. Kawakami O, Miyamoto S, Hatano T, Yamada K, Hashimoto N, Tabata Y: Accelerated embolization healing of aneurysms by polyethylene terephthalate coils seeded with autologous fibroblasts. Neurosurgery. 2005 May;56(5):1075-81; discussion 1075-81. [PubMed:15854257 ]
    6. Kim YH, Park JH, Hong SH, Koh JY: Nonproteolytic neuroprotection by human recombinant tissue plasminogen activator. Science. 1999 Apr 23;284(5414):647-50. [PubMed:10213688 ]
    7. Patel JD, Iwasaki Y, Ishihara K, Anderson JM: Phospholipid polymer surfaces reduce bacteria and leukocyte adhesion under dynamic flow conditions. J Biomed Mater Res A. 2005 Jun 1;73(3):359-66. [PubMed:15800952 ]
    8. Tremaine LM, Quebbemann AJ: The renal handling of terephthalic acid. Toxicol Appl Pharmacol. 1985 Jan;77(1):165-74. [PubMed:3966238 ]
    9. Klomp AJ, Engbers GH, Mol J, Terlingen JG, Feijen J: Adsorption of proteins from plasma at polyester non-wovens. Biomaterials. 1999 Jul;20(13):1203-11. [PubMed:10395389 ]
    10. Roald HE, Barstad RM, Bakken IJ, Roald B, Lyberg T, Sakariassen KS: Initial interactions of platelets and plasma proteins in flowing non-anticoagulated human blood with the artificial surfaces Dacron and PTFE. Blood Coagul Fibrinolysis. 1994 Jun;5(3):355-63. [PubMed:8075307 ]
    11. Gappa-Fahlenkamp H, Lewis RS: Improved hemocompatibility of poly(ethylene terephthalate) modified with various thiol-containing groups. Biomaterials. 2005 Jun;26(17):3479-85. [PubMed:15621237 ]