Record Information |
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Version | 2.0 |
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Created at | 2006-05-22 14:17:53 UTC |
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Updated at | 2024-09-17 15:41:37 UTC |
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NP-MRD ID | NP0000290 |
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Natural Product DOI | https://doi.org/10.57994/2995 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Terephthalic acid |
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Description | Terephthalic 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. |
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Structure | OC(=O)C1=CC=C(C=C1)C(O)=O InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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Synonyms | Value | Source |
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1,4-Benzenedicarboxylic acid | ChEBI | p-Benzenedicarboxylic acid | ChEBI | Para-benzenedicarboxylic acid | ChEBI | TPA | ChEBI | 1,4-Benzenedicarboxylate | Generator | p-Benzenedicarboxylate | Generator | Para-benzenedicarboxylate | Generator | Terephthalate | Generator | Benzene-p-dicarboxylate | HMDB | Benzene-p-dicarboxylic acid | HMDB | Kyselina terftalova | HMDB | p-Dicarboxybenzene | HMDB | p-Phthalate | HMDB | p-Phthalic acid | HMDB | p-Phthelate | HMDB | p-Phthelic acid | HMDB | Disodium terephthalate | HMDB | Terephthalic acid | KEGG |
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Chemical Formula | C8H6O4 |
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Average Mass | 166.1308 Da |
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Monoisotopic Mass | 166.02661 Da |
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IUPAC Name | benzene-1,4-dicarboxylic acid |
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Traditional Name | terephthalic acid |
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CAS Registry Number | 100-21-0 |
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SMILES | OC(=O)C1=CC=C(C=C1)C(O)=O |
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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) |
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InChI Key | KKEYFWRCBNTPAC-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-27 | View Spectrum |
| Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | P-phthalic acid and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | > 300 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.015 mg/mL at 20 °C | Not Available | LogP | 2.00 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Tremaine LM, Quebbemann AJ: The renal handling of terephthalic acid. Toxicol Appl Pharmacol. 1985 Jan;77(1):165-74. [PubMed:3966238 ]
- 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 ]
- 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 ]
- 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 ]
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