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Chemical Compound Review

phthals     phthalic acid

Synonyms: Alizarinate, Phthalinate, Naphthalinate, Sunftal 20, Pathalic acid, ...
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Disease relevance of phthalic acid


Psychiatry related information on phthalic acid


High impact information on phthalic acid


Chemical compound and disease context of phthalic acid


Biological context of phthalic acid


Anatomical context of phthalic acid


Associations of phthalic acid with other chemical compounds


Gene context of phthalic acid

  • Biochemical analysis in a second group of subjects confirmed that phthalic acid lesions produced a large decrease in basolateral amygdaloid ChAT, but had little effect on cortical ChAT activity [25].
  • In our recent experiments, we found that mouse pregnane X receptor (PXR) interacted with suppressor for gal1 (SUG1), a component of the proteasome, in a progesterone-dependent manner, but that endocrine-disrupting chemicals (EDCs), phthalic acid and nonylphenol, which activated PXR-mediated transcription, did not enhance this interaction [26].
  • This novel insecticide mode of action seems to be restricted to specific RyR subtypes because the phthalic acid diamides reported here had almost no effect on mammalian type 1 ryanodine receptors [27].
  • Mutagenicity of phthalic acid was evaluated by employing dominant lethal mutation and sperm head abnormality assays in male Swiss albino mice [19].
  • Di-n-butylphthalate (DBP) is a phthalic acid ester used as a plasticizer and solvent [28].

Analytical, diagnostic and therapeutic context of phthalic acid

  • In contrast to the hepatocytes, which extensively metabolized MEHP to a variety of products in 1 hr, the testicular cell cultures were apparently unable to metabolize MEHP (beyond a slight hydrolysis to phthalic acid by Sertoli cells) in 18-24 hr [29].
  • Substituted benzylic alcohols were enantioresolved by the chiral phthalic acid method as follows; 1) esterification of racemic alcohols with chiral phthalic acid, 2) separation of a diastereomeric mixture of the esters formed by HPLC on silica gel, and 3) recovery of enantiopure alcohols from the separated esters [30].
  • The polymerization of HEMA in the presence of NPG was studied by adding various amounts of water and/or 4-(2-methacryloyloxyethoxycarbonyl) phthalic acid (4-MET) and evaluated using differential scanning calorimetry (DSC) [31].
  • Influence of plasticizer-free CAPD bags and tubings on serum, urine, and dialysate levels of phthalic acid esters in CAPD patients [32].
  • The absolute configurations of chiral phthalic acid esters of benzylic alcohols were unambiguously determined by the X-ray crystallography using the campharsultam moiety as the internal standard of absolute configuration [30].


  1. Enhancement of the mutagenicity of amino acid pyrolysates by phthalate esters. Sato, T., Nagase, H., Sato, K., Niikawa, M., Kito, H. Environ. Mol. Mutagen. (1994) [Pubmed]
  2. Generation of anticalins with specificity for a nonsymmetric phthalic acid ester. Mercader, J.V., Skerra, A. Anal. Biochem. (2002) [Pubmed]
  3. Molecular characterization of a phenanthrene degradation pathway in Mycobacterium vanbaalenii PYR-1. Stingley, R.L., Khan, A.A., Cerniglia, C.E. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  4. Developmental toxicity evaluation of phthalic acid, one of the metabolites of phthalic acid esters, in rats. Ema, M., Miyawaki, E., Harazono, A., Kawashima, K. Toxicol. Lett. (1997) [Pubmed]
  5. Concentrations of urinary phthalate metabolites are associated with increased waist circumference and insulin resistance in adult U.S. males. Stahlhut, R.W., van Wijngaarden, E., Dye, T.D., Cook, S., Swan, S.H. Environ. Health Perspect. (2007) [Pubmed]
  6. Phthalic acid amygdalopetal lesion of the nucleus basalis magnocellularis induces reversible memory deficits in rats. Power, A.E., McGaugh, J.L. Neurobiology of learning and memory. (2002) [Pubmed]
  7. Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription. Masuyama, H., Hiramatsu, Y., Kunitomi, M., Kudo, T., MacDonald, P.N. Mol. Endocrinol. (2000) [Pubmed]
  8. Determination of ethyl sulfate - a marker for recent ethanol consumption - in human urine by CE with indirect UV detection. Esteve-Turrillas, F.A., Bicker, W., L??mmerhofer, M., Keller, T., Lindner, W. Electrophoresis (2006) [Pubmed]
  9. Nonylphenol induces the death of neural stem cells due to activation of the caspase cascade and regulation of the cell cycle. Kudo, C., Wada, K., Masuda, T., Yonemura, T., Shibuya, A., Fujimoto, Y., Nakajima, A., Niwa, H., Kamisaki, Y. J. Neurochem. (2004) [Pubmed]
  10. Novel cyclic templates of alpha-MSH give highly selective and potent antagonists/agonists for human melanocortin-3/4 receptors. Kavarana, M.J., Trivedi, D., Cai, M., Ying, J., Hammer, M., Cabello, C., Grieco, P., Han, G., Hruby, V.J. J. Med. Chem. (2002) [Pubmed]
  11. Isolation and identification of the reaction product of alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase. Maruyama, K. J. Biochem. (1979) [Pubmed]
  12. Anti-tumor promoting action of phthalic acid mono-n-butyl ester cupric salt, a biomimetic superoxide dismutase. Yamamoto, S., Nakadate, T., Aizu, E., Kato, R. Carcinogenesis (1990) [Pubmed]
  13. Characterization of quinolinic acid phosphoribosyltransferase in human blood and observations in Huntington's disease. Foster, A.C., Schwarcz, R. J. Neurochem. (1985) [Pubmed]
  14. Kinetic study of the hydrolysis of phthalic anhydride and aryl hydrogen phthalates. Andrés, G.O., Granados, A.M., de Rossi, R.H. J. Org. Chem. (2001) [Pubmed]
  15. Carcinogenic potential of phthalic acid esters and related compounds: structure-activity relationships. Kluwe, W.M. Environ. Health Perspect. (1986) [Pubmed]
  16. Determination of phthalic acid, mono-(2-ethylhexyl) phthalate and di-(2-ethylhexyl) phthalate in human plasma and in blood products. Shintani, H. J. Chromatogr. (1985) [Pubmed]
  17. Effects of phthalic acid esters on the liver and thyroid. Hinton, R.H., Mitchell, F.E., Mann, A., Chescoe, D., Price, S.C., Nunn, A., Grasso, P., Bridges, J.W. Environ. Health Perspect. (1986) [Pubmed]
  18. Cholinergic activation of the basolateral amygdala regulates unlearned freezing behavior in rats. Power, A.E., McGaugh, J.L. Behav. Brain Res. (2002) [Pubmed]
  19. Germ cell mutagenicity of phthalic acid in mice. Jha, A.M., Singh, A.C., Bharti, M. Mutat. Res. (1998) [Pubmed]
  20. Assay of inorganic sulfate in biologic fluids by nonsuppressed (single-column) ion chromatography. Morris, M.E., Levy, G. Anal. Biochem. (1988) [Pubmed]
  21. Biodegradation of phthalic acid esters in river water and activated sludge. Saeger, V.W., Tucker, E.S. Appl. Environ. Microbiol. (1976) [Pubmed]
  22. Metabolism of butyl benzyl phthalate by Gordonia sp. strain MTCC 4818. Chatterjee, S., Dutta, T.K. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  23. Analysis of mono- and diesters of o-phthalic acid by solid-phase extractions with polystyrene-divinylbenzene-based polymers. Jonsso, S., Borén, H. Journal of chromatography. A. (2002) [Pubmed]
  24. The renal handling of terephthalic acid. Tremaine, L.M., Quebbemann, A.J. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  25. Nucleus basalis lesions: implication of basoamygdaloid cholinergic pathways in memory. Mallet, P.E., Beninger, R.J., Flesher, S.N., Jhamandas, K., Boegman, R.J. Brain Res. Bull. (1995) [Pubmed]
  26. Ligands have various potential effects on the degradation of pregnane X receptor by proteasome. Masuyama, H., Inoshita, H., Hiramatsu, Y., Kudo, T. Endocrinology (2002) [Pubmed]
  27. Phthalic acid diamides activate ryanodine-sensitive Ca2+ release channels in insects. Ebbinghaus-Kintscher, U., Luemmen, P., Lobitz, N., Schulte, T., Funke, C., Fischer, R., Masaki, T., Yasokawa, N., Tohnishi, M. Cell Calcium (2006) [Pubmed]
  28. Pharmacokinetics of monobutylphthalate, the active metabolite of di-n-butylphthalate, in pregnant rats. Kremer, J.J., Williams, C.C., Parkinson, H.D., Borghoff, S.J. Toxicol. Lett. (2005) [Pubmed]
  29. Mono-2-ethylhexyl phthalate, a metabolite of di-(2-ethylhexyl) phthalate, causally linked to testicular atrophy in rats. Albro, P.W., Chapin, R.E., Corbett, J.T., Schroeder, J., Phelps, J.L. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  30. Enantioresolution by the chiral phthalic acid method: absolute configurations of substituted benzylic alcohols. Kosaka, M., Watanabe, M., Harada, N. Chirality. (2000) [Pubmed]
  31. Effects of water and carboxylic acid monomer on polymerization of HEMA in the presence of N-phenylglycine. Imai, Y., Suzuki, A. Dental materials : official publication of the Academy of Dental Materials. (1994) [Pubmed]
  32. Influence of plasticizer-free CAPD bags and tubings on serum, urine, and dialysate levels of phthalic acid esters in CAPD patients. Mettang, T., Pauli-Magnus, C., Alscher, D.M., Kirchgessner, J., Wodarz, R., Rettenmeier, A.W., Kuhlmann, U. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (2000) [Pubmed]
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