Terephthalic acid (CHEM008910)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:54:52 UTC
Update Date2016-11-09 01:13:53 UTC
Accession NumberCHEM008910
Identification
Common NameTerephthalic acid
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass166.131 g/mol
Monoisotopic Mass166.027 g/mol
CAS Registry Number100-21-0
IUPAC Namebenzene-1,4-dicarboxylic acid
Traditional Nameterephthalic acid
SMILESOC(=O)C1=CC=C(C=C1)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udj-1960000000-c2ce285b39dcfaade068Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-9500000000-6b6ec61e945c382eed89Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-6900000000-1a7e017001fe0602a248Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-4900000000-95e39c2780c93f2f98fdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-1960000000-c2ce285b39dcfaade068Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-1960000000-27e0381620f64e37fcadSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-1900000000-a84aff968bc81936616cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8290000000-755c4a3b1fe10891e0bcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0900000000-95fdf5f4fdee61197dc8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00b9-9800000000-2b52539a11193ccec082Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00b9-8900000000-197587f1e6a9e594c5b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-014j-9500000000-aafffbb19047f4caf673Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-b445c3bf5a9a7a5579fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-63c35cbaa3dcd73735c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-4900000000-2e7d3b96b81c41872945Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9300000000-2d9c49fdd3573a453a1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00fr-9000000000-999fd340fed30a63e4ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-b445c3bf5a9a7a5579fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-63c35cbaa3dcd73735c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-4900000000-2e7d3b96b81c41872945Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-df1f4a76d59c66d5070dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-9000000000-999fd340fed30a63e4ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00di-0900000000-b7eddea80c1efd3740d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-00di-4900000000-395fdb86c134d67a782bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-0900000000-8eabec3ef384835097efSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00di-0900000000-a28fdef9c1c00d45c3ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-0900000000-17c7a2e06ddf58f100a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-384b938e005844d386b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-736a9cc29426a85f2dbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4900000000-be05d9e5afe70d40b269Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-eaf8e1fadaf0331df52fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2900000000-69d77e7980f3f93873c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9700000000-23275ad46308b76fb7c9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002428
FooDB IDFDB023000
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDTEREPHTHALATE
METLIN ID6676
PDB IDNot Available
Wikipedia LinkTerephthalic_acid
Chemspider ID7208
ChEBI ID15702
PubChem Compound ID7489
Kegg Compound IDC06337
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24101250
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24473302
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24527803
4. Emerson, 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.
5. Emerson, 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. Kim YH, Park JH, Hong SH, Koh JY: Nonproteolytic neuroprotection by human recombinant tissue plasminogen activator. Science. 1999 Apr 23;284(5414):647-50.
12. 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.
13. Tremaine LM, Quebbemann AJ: The renal handling of terephthalic acid. Toxicol Appl Pharmacol. 1985 Jan;77(1):165-74.
14. 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.
15. 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.
16. Gappa-Fahlenkamp H, Lewis RS: Improved hemocompatibility of poly(ethylene terephthalate) modified with various thiol-containing groups. Biomaterials. 2005 Jun;26(17):3479-85.