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MedKoo Cat#: 558639 | Name: Isophthalic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isophthalic acid is an intermediate for high performance unsaturated polyesters, resins for coatings, high solids paints, gel coats and modifier of polyethylene terephthalate for bottles.

Chemical Structure

Isophthalic acid
Isophthalic acid
CAS#121-91-5

Theoretical Analysis

MedKoo Cat#: 558639

Name: Isophthalic acid

CAS#: 121-91-5

Chemical Formula: C8H6O4

Exact Mass: 166.0266

Molecular Weight: 166.13

Elemental Analysis: C, 57.84; H, 3.64; O, 38.52

Price and Availability

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25g USD 250.00 2 Weeks
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Synonym
Isophthalic acid; Isophthalic acid; Acide isophtalique;
IUPAC/Chemical Name
1,3-Benzenedicarboxylic acid
InChi Key
QQVIHTHCMHWDBS-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H6O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
SMILES Code
O=C(C1=CC=CC(C(O)=O)=C1)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Isophthalic acid is an intermediate for high performance unsaturated polyesters, resins for coatings, high solids paints, gel coats and modifier of polyethylene terephthalate for bottles.
In vitro activity:
Sonication treatment of the initial mixture of compounds and the nature of the counter anion were found to be critical factors for the supramolecular assembly of the metal/click-TIA complexes and, hence, for the formation of stable and homogeneous metallogels. The gel materials have been characterized with a variety of techniques including infrared, rheology, UV-vis spectroscopy, powder X-ray diffraction, and scanning electron microscopy. Reference: ACS Omega. 2019 Jan 28;4(1):2111-2117. https://pubmed.ncbi.nlm.nih.gov/31459459/
In vivo activity:
By modulating the metal centers to adjust the coordination surroundings of the products, two mixed-linker coordination polymers [Cu2(L)(biz)(OH)]·H2O (1) and [Zn(HL)(biz)] (2) (H3L = 5-(4-carboxybenzyloxy)isophthalic acid, biz = benzimidazole), have been produced under mild hydrothermal conditions. To develop new candidates for the acute oral mucositis during orthodontic process, the acute oral mucositis rat model was constructed and the enzyme linked immunosorbent assay (ELISA) was used to find out the release levels of inflammatory cytokines Tumor Necrosis Factor-α (TNF-α) and Interleukin-1β (IL-1β). All the results in this research indicated the much more excellent treatment activity of compound 1 than 2 on the acute oral mucositis. Reference: J Oleo Sci. 2020;69(9):1051-1059. https://pubmed.ncbi.nlm.nih.gov/32879196/

Preparing Stock Solutions

The following data is based on the product molecular weight 166.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Häring M, Nandi SK, Rodríguez-López J, Haldar D, Martín VS, Lozano-Gorrín AD, Saldías C, Díaz DD. 5-(1H-1,2,3-Triazol-5-yl)isophthalic Acid: A Versatile Ligand for the Synthesis of New Supramolecular Metallogels. ACS Omega. 2019 Jan 28;4(1):2111-2117. doi: 10.1021/acsomega.8b03292. PMID: 31459459; PMCID: PMC6647994. 2. Makeiff DA, Cho JY, Smith B, Carlini R, Godbert N. Self-Assembly of Alkylamido Isophthalic Acids toward the Design of a Supergelator: Phase-Selective Gelation and Dye Adsorption. Gels. 2022 May 5;8(5):285. doi: 10.3390/gels8050285. PMID: 35621583; PMCID: PMC9140382. 3. Ren J, Du Z, Lin J, Chen Z, Feng X. Two Mixed-ligand Coordination Polymers: Treatment Activity on Acute Oral Mucositis during Orthodontic Process by Reducing Inflammatory Response. J Oleo Sci. 2020;69(9):1051-1059. doi: 10.5650/jos.ess20087. PMID: 32879196.
In vitro protocol:
1. Häring M, Nandi SK, Rodríguez-López J, Haldar D, Martín VS, Lozano-Gorrín AD, Saldías C, Díaz DD. 5-(1H-1,2,3-Triazol-5-yl)isophthalic Acid: A Versatile Ligand for the Synthesis of New Supramolecular Metallogels. ACS Omega. 2019 Jan 28;4(1):2111-2117. doi: 10.1021/acsomega.8b03292. PMID: 31459459; PMCID: PMC6647994. 2. Makeiff DA, Cho JY, Smith B, Carlini R, Godbert N. Self-Assembly of Alkylamido Isophthalic Acids toward the Design of a Supergelator: Phase-Selective Gelation and Dye Adsorption. Gels. 2022 May 5;8(5):285. doi: 10.3390/gels8050285. PMID: 35621583; PMCID: PMC9140382.
In vivo protocol:
1. Ren J, Du Z, Lin J, Chen Z, Feng X. Two Mixed-ligand Coordination Polymers: Treatment Activity on Acute Oral Mucositis during Orthodontic Process by Reducing Inflammatory Response. J Oleo Sci. 2020;69(9):1051-1059. doi: 10.5650/jos.ess20087. PMID: 32879196.
1: Khaneghah AM, Limbo S, Shoeibi S, Mazinani S. HPLC study of migration of terephthalic acid and isophthalic acid from PET bottles into edible oils. J Sci Food Agric. 2014 Aug;94(11):2205-9. doi: 10.1002/jsfa.6540. Epub 2014 Jan 31. PubMed PMID: 24343590. 2: He YC, Wu YD, Pan XH, Ma CL. Biosynthesis of terephthalic acid, isophthalic acid and their derivatives from the corresponding dinitriles by tetrachloroterephthalonitrile-induced Rhodococcus sp. Biotechnol Lett. 2014 Feb;36(2):341-7. doi: 10.1007/s10529-013-1367-3. Epub 2013 Oct 8. PubMed PMID: 24101250. 3: Murray NH, Biros SM, LaDuca RL. Crystal structure of [propane-1,3-diylbis(piperidine-4,1-di-yl)]bis-[(pyridin-4-yl)methanone]-isophtha lic acid (1/1). Acta Crystallogr Sect E Struct Rep Online. 2014 Oct 4;70(Pt 11):298-300. doi: 10.1107/S1600536814021679. eCollection 2014 Nov 1. PubMed PMID: 25484727; PubMed Central PMCID: PMC4257304. 4: Chen TH, Wang L, Trueblood JV, Grassian VH, Cohen SM. Poly(isophthalic acid)(ethylene oxide) as a Macromolecular Modulator for Metal-Organic Polyhedra. J Am Chem Soc. 2016 Aug 3;138(30):9646-54. doi: 10.1021/jacs.6b04971. Epub 2016 Jul 22. PubMed PMID: 27400759. 5: Ago H, Okimoto N, Kanaoka Y, Morimoto G, Ukita Y, Saino H, Taiji M, Miyano M. A leukotriene C4 synthase inhibitor with the backbone of 5-(5-methylene-4-oxo-4,5-dihydrothiazol-2-ylamino) isophthalic acid. J Biochem. 2013 May;153(5):421-9. doi: 10.1093/jb/mvt007. Epub 2013 Jan 31. PubMed PMID: 23378248; PubMed Central PMCID: PMC3635087. 6: Nilov D, Kucheryavy P, Walker V, Kidd C, Kolesnichenko VL, Goloverda GZ. Synthesis of 5-Substituted Derivatives of Isophthalic Acid as Non-Polymeric Amphiphilic Coating for Metal Oxide Nanoparticles. Tetrahedron Lett. 2014 Sep 3;55(36):5078-5081. PubMed PMID: 25152545; PubMed Central PMCID: PMC4138530. 7: Wang J, Jia C, Feng X, Yuan W. A new one-dimensional coordination polymer of 5-(1,3-dioxo-4,5,6,7-tetraphenylisoindolin-2-yl)isophthalic acid with manganese. Acta Crystallogr C Struct Chem. 2015 Sep;71(Pt 9):759-62. doi: 10.1107/S2053229615014217. Epub 2015 Aug 6. PubMed PMID: 26322606. 8: Bardak F, Karaca C, Bilgili S, Atac A, Mavis T, Asiri AM, Karabacak M, Kose E. Conformational, electronic, and spectroscopic characterization of isophthalic acid (monomer and dimer structures) experimentally and by DFT. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Aug 5;165:33-46. doi: 10.1016/j.saa.2016.03.050. Epub 2016 Apr 5. PubMed PMID: 27107533. 9: Lim IT, Choi KY. Self-assembly of a 1D hydrogen-bonded polymer from a hexamethyltetraaza macrocyclic nickel(II) complex and isophthalic acid. Molecules. 2013 Jun 6;18(6):6608-19. doi: 10.3390/molecules18066608. PubMed PMID: 23743887. 10: Saş EB, Kurt M, Can M, Okur S, İçli S, Demiç S. Structural investigation of a self-assembled monolayer material 5-[(3-methylphenyl) (phenyl) amino] isophthalic acid for organic light-emitting devices. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:307-17. doi: 10.1016/j.saa.2014.05.021. Epub 2014 May 20. PubMed PMID: 24954755. 11: Liu F, Zhang JJ, Lei MY, Zhang QF. A two-dimensional cadmium(II) coordination polymer based on 5-(pyridin-4-yl)isophthalic acid: poly[[tetraaquabis[μ₃-5-(pyridin-4-yl)isophthalato]dicadmium(II)] pentahydrate]. Acta Crystallogr C Struct Chem. 2015 Sep;71(Pt 9):834-8. doi: 10.1107/S2053229615015612. Epub 2015 Aug 27. PubMed PMID: 26322618. 12: Acharyya SS, Ghosh S, Bal R. Fabrication of three dimensional (3D) hierarchical Ag/WO3 flower-like catalyst materials for the selective oxidation of m-xylene to isophthalic acid. Chem Commun (Camb). 2015 Apr 7;51(27):5998-6001. doi: 10.1039/c5cc00351b. Epub 2015 Mar 5. PubMed PMID: 25740057. 13: Vetter A, Seichter W, Weber E. 5-(Naphthalen-1-yl)isophthalic acid-dimethyl sulfoxide-water (2/1/2). Acta Crystallogr Sect E Struct Rep Online. 2013 May 18;69(Pt 6):o912-3. doi: 10.1107/S1600536813012361. Print 2013 Jun 1. PubMed PMID: 23795084; PubMed Central PMCID: PMC3685065. 14: Zhang R, Gong Q, Emge TJ, Banerjee D, Li J. Design and synthesis of new 1D and 2D R-isophthalic acid-based coordination polymers (R = hydrogen or bromine). Chimia (Aarau). 2013;67(6):393-6. doi: 10.2533/chimia.2013.393. PubMed PMID: 23945098. 15: Devereux M, McCann M, Leon V, Geraghty M, McKee V, Wikaira J. Synthesis and Biological Activity of Manganese (II) Complexes of Phthalic and Isophthalic Acid: X-Ray Crystal Structures of [Mn(ph)(Phen)(2)(H(2)O)]. 4H(2)O, [Mn(Phen)(2)(H(2)O)(2)](2)(Isoph)(2)(Phen). 12H(2)O and {[Mn(Isoph)(bipy)](4). 2.75biby}(n)(phH(2) = Phthalic Acid; isoph = Isophthalic Acid; phen = 1,10-Phenanthroline; bipy = 2,2-Bipyridine). Met Based Drugs. 2000;7(5):275-88. doi: 10.1155/MBD.2000.275. PubMed PMID: 18475957; PubMed Central PMCID: PMC2365232. 16: Panda T, Kundu T, Banerjee R. Structural isomerism leading to variable proton conductivity in indium(III) isophthalic acid based frameworks. Chem Commun (Camb). 2013 Jul 14;49(55):6197-9. doi: 10.1039/c3cc41939h. PubMed PMID: 23732259. 17: Si YX, Yin SJ, Park D, Chung HY, Yan L, Lü ZR, Zhou HM, Yang JM, Qian GY, Park YD. Tyrosinase inhibition by isophthalic acid: kinetics and computational simulation. Int J Biol Macromol. 2011 May 1;48(4):700-4. doi: 10.1016/j.ijbiomac.2011.02.015. Epub 2011 Mar 1. PubMed PMID: 21371502. 18: Üstündağ Z, Cağlayan MO, Güzel R, Pişkin E, Solak AO. A novel Surface Plasmon Resonance enhanced Total Internal Reflection Ellipsometric application: electrochemically grafted isophthalic acid nanofilm on gold surface. Analyst. 2011 Apr 7;136(7):1464-71. doi: 10.1039/c0an00410c. Epub 2011 Feb 14. PubMed PMID: 21321683. 19: Zhu M, Su SQ, Song XZ, Hao ZM, Song SY, Zhang HJ. Spin canting magnetization in a 3D Cu(II) complex based on molybdate oxide cluster and 5-triazole isophthalic acid. Dalton Trans. 2012 Nov 21;41(43):13267-70. doi: 10.1039/c2dt31649h. PubMed PMID: 23023724. 20: Kwack SJ, Lee BM. Comparative Cytotoxicity and Sperm Motility Using a Computer-Aided Sperm Analysis System (CASA) for Isomers of Phthalic Acid, a Common Final Metabolite of Phthalates. J Toxicol Environ Health A. 2015;78(16):1038-50. doi: 10.1080/15287394.2015.1067503. Epub 2015 Aug 7. PubMed PMID: 26252616.