NP-MRD: Showing NP-Card for Terephthalic acid (NP0000290)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:53 UTC

Updated at

2025-02-11 15:48:59 UTC

NP-MRD ID

NP0000290

Natural Product DOI

https://doi.org/10.57994/2995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Terephthalic acid

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3   11                                                  
CONECT    2    1                                                            
CONECT    3    1    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   12                                                  
CONECT   10    9                                                            
CONECT   11    1                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
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

Chemical Formula

C₈H₆O₄

Average Mass

166.1308 Da

Monoisotopic Mass

166.02661 Da

IUPAC Name

benzene-1,4-dicarboxylic acid

Traditional Name

terephthalic acid

CAS Registry Number

100-21-0

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 Key

KKEYFWRCBNTPAC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cassia roxburghii	LOTUS Database	35616633
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pinus pinaster	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenedicarboxylic acid (CHEBI:15702 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
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).

Predicted Properties

Property	Value	Source
Water Solubility	2.29 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.29	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.57 m³·mol⁻¹	ChemAxon
Polarizability	15.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002428

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023000

KNApSAcK ID

Not Available

Chemspider ID

7208

KEGG Compound ID

C06337

BioCyc ID

TEREPHTHALATE

BiGG ID

Not Available

Wikipedia Link

Terephthalic_acid

METLIN ID

6676

PubChem Compound

7489

PDB ID

Not Available

ChEBI ID

15702

Good Scents ID

rw1285651

References

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 ]

Showing NP-Card for Terephthalic acid (NP0000290)

MOL for NP0000290 (Terephthalic acid)

3D MOL for NP0000290 (Terephthalic acid)

3D SDF for NP0000290 (Terephthalic acid)

3D-SDF for NP0000290 (Terephthalic acid)

PDB for NP0000290 (Terephthalic acid)

3D PDB for NP0000290 (Terephthalic acid)

SMILES for NP0000290 (Terephthalic acid)

INCHI for NP0000290 (Terephthalic acid)

Structure for NP0000290 (Terephthalic acid)

3D Structure for NP0000290 (Terephthalic acid)