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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002428
Secondary Accession Numbers
  • HMDB0061917
  • HMDB02428
  • HMDB61917
Metabolite Identification
Common NameTerephthalic acid
DescriptionTerephthalic acid is a benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids. It is a conjugate acid of a terephthalate(1-). Terephthalic 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.
Structure
Data?1582752249
Synonyms
ValueSource
1,4-Benzenedicarboxylic acidChEBI
p-Benzenedicarboxylic acidChEBI
Para-benzenedicarboxylic acidChEBI
TPAChEBI
1,4-BenzenedicarboxylateGenerator
p-BenzenedicarboxylateGenerator
Para-benzenedicarboxylateGenerator
TerephthalateGenerator
Benzene-P-dicarboxylateHMDB
Benzene-P-dicarboxylic acidHMDB
Kyselina terftalovaHMDB
P-DicarboxybenzeneHMDB
P-PhthalateHMDB
P-Phthalic acidHMDB
P-PhthelateHMDB
P-Phthelic acidHMDB
Disodium terephthalateMeSH, HMDB
Terephthalic acidKEGG
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
Description Belongs to the class of organic compounds known as p-phthalic acid and derivatives. P-phthalic acid and derivatives 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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular 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)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+137.98331661259
DarkChem[M-H]-132.68331661259
DeepCCS[M+H]+132.68430932474
DeepCCS[M-H]-128.85730932474
DeepCCS[M-2H]-166.31630932474
DeepCCS[M+Na]+141.85530932474
AllCCS[M+H]+134.832859911
AllCCS[M+H-H2O]+130.432859911
AllCCS[M+NH4]+138.932859911
AllCCS[M+Na]+140.132859911
AllCCS[M-H]-130.832859911
AllCCS[M+Na-2H]-131.732859911
AllCCS[M+HCOO]-132.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Terephthalic acidOC(=O)C1=CC=C(C=C1)C(O)=O2750.0Standard polar33892256
Terephthalic acidOC(=O)C1=CC=C(C=C1)C(O)=O1323.1Standard non polar33892256
Terephthalic acidOC(=O)C1=CC=C(C=C1)C(O)=O1590.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Terephthalic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)C=C11771.4Semi standard non polar33892256
Terephthalic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C11847.7Semi standard non polar33892256
Terephthalic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)C=C12040.9Semi standard non polar33892256
Terephthalic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C12331.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Terephthalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udj-1960000000-c2ce285b39dcfaade0682014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized)splash10-014j-9500000000-6b6ec61e945c382eed892017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized)splash10-014j-6900000000-1a7e017001fe0602a2482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Terephthalic acid EI-B (Non-derivatized)splash10-014j-4900000000-95e39c2780c93f2f98fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Terephthalic acid GC-EI-TOF (Non-derivatized)splash10-0udj-1960000000-c2ce285b39dcfaade0682017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Terephthalic acid GC-EI-TOF (Non-derivatized)splash10-0udj-1960000000-27e0381620f64e37fcad2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terephthalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-1900000000-a84aff968bc81936616c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terephthalic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8290000000-755c4a3b1fe10891e0bc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terephthalic 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 - Terephthalic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-00di-0900000000-95fdf5f4fdee61197dc82012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00b9-9800000000-2b52539a11193ccec0822012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00b9-8900000000-197587f1e6a9e594c5b32012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-b445c3bf5a9a7a5579fc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-00di-0900000000-63c35cbaa3dcd73735c82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-00di-4900000000-2e7d3b96b81c418729452012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9300000000-2d9c49fdd3573a453a1b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00fr-9000000000-999fd340fed30a63e4dd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-b445c3bf5a9a7a5579fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOFsplash10-00di-0900000000-63c35cbaa3dcd73735c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOFsplash10-00di-4900000000-2e7d3b96b81c418729452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9300000000-df1f4a76d59c66d5070d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid LC-ESI-QQ , negative-QTOFsplash10-00fr-9000000000-999fd340fed30a63e4dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 75V, Negative-QTOFsplash10-00di-0900000000-b7eddea80c1efd3740d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 90V, Negative-QTOFsplash10-00di-4900000000-395fdb86c134d67a782b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 45V, Negative-QTOFsplash10-00di-0900000000-8eabec3ef384835097ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 60V, Negative-QTOFsplash10-00di-0900000000-a28fdef9c1c00d45c3ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 30V, Negative-QTOFsplash10-00di-0900000000-17c7a2e06ddf58f100a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid 15V, Negative-QTOFsplash10-00di-0900000000-b4922f6308065fd1b3a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terephthalic acid EI-B (JEOL JMS-AX-505-H) , Positive-QTOFsplash10-014j-9500000000-aafffbb19047f4caf6732012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terephthalic acid 10V, Negative-QTOFsplash10-014i-0900000000-eaf8e1fadaf0331df52f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terephthalic acid 20V, Negative-QTOFsplash10-00xr-2900000000-69d77e7980f3f93873c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terephthalic acid 40V, Negative-QTOFsplash10-00b9-9700000000-23275ad46308b76fb7c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terephthalic acid 10V, Negative-QTOFsplash10-01b9-0900000000-241ba3e5146fc0921af72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terephthalic acid 20V, Negative-QTOFsplash10-00b9-9700000000-861e35e1415e854c89f12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023000
KNApSAcK IDNot Available
Chemspider ID7208
KEGG Compound IDC06337
BioCyc IDTEREPHTHALATE
BiGG IDNot Available
Wikipedia LinkTerephthalic_acid
METLIN ID6676
PubChem Compound7489
PDB IDNot Available
ChEBI ID15702
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1285651
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 ]