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Chemical Compound Review

ESEN     isobenzofuran-1,3-dione

Synonyms: Ftalanhydrid, Phthalandione, Vulkalent B, Wiltrol P, Retarder AK, ...
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Disease relevance of Phthalandione


High impact information on Phthalandione


Chemical compound and disease context of Phthalandione


Biological context of Phthalandione

  • Inhalation challenge of a subgroup of animals with phthalic anhydride dust did not elicit an immediate response, as measured by changes in respiratory frequency and plethysmograph pressure [1].
  • Under conditions of exposure where both chemicals elicited an IgG anti-hapten antibody response, only phthalic anhydride caused an increase in the serum concentration of IgE [10].
  • Exposure to PA was low in relation to the Occupational Exposure Standard (OES) [11].
  • Synthesis of 3beta-O-phthalic esters from betulinic acid and its esters and synthesis of phthalic esters from betulin and its monoacetates using classical acylation procedure with phthalic anhydride [12].
  • However, treatment with a non-carcinogen phthalic anhydride, also inhibits apoptosis while it does not superinduce ODC activity [13].

Anatomical context of Phthalandione

  • Topical application of DNCB and PA resulted in a similar lymphocyte proliferation, while application of TMA and TDI resulted in a 1.8-fold higher proliferation [14].
  • Both TMA (25% and 12.5% for sensitization and challenge, respectively) and PA (12.5% and 6.25% for sensitization and challenge, respectively) induced a Th2 response marked by an increasing production of IL-4 and IL-10 in the supernatants of ex vivo spleen cells cultured with concanavalin A and also of serum total IgE [15].
  • By using phthalic anhydride or tetrachlorophthalic anhydride conjugated to human serum albumin, a study was undertaken to determine whether histamine release from basophils or lymphocyte transformation correlated with clinical symptoms, circulating anhydride specific IgE, and skin test reactivity [16].

Associations of Phthalandione with other chemical compounds


Gene context of Phthalandione

  • In every experiment relatively low levels of IFN-gamma and IL-12 were elaborated by acid anhydride-activated LNC, with the exception of PA-stimulated LNC that displayed increased amounts of IL-12 in comparison with other acid anhydrides [20].
  • Furthermore, like TMA, phthalic anhydride preferentially induced IgG2b rather than IgG2a antibody [10].
  • SPE/LC/ESI/MS with phthalic anhydride derivatisation for the determination of alcohol ethoxylate surfactants in sewage influent and effluent samples [21].
  • In summary, the CAP and ML methods were found to be appropriate for routine diagnosis of specific IgE antibodies against the allergens HDI, MDI, TDI, and phthalic anhydride [22].
  • Twenty sera showed increased levels of diisocyanate-specific IgE antibodies, and five sera were phthalic anhydride positive [22].

Analytical, diagnostic and therapeutic context of Phthalandione


  1. Induction of type I hypersensitivity in guinea pigs after inhalation of phthalic anhydride. Sarlo, K., Clark, E.D., Ferguson, J., Zeiss, C.R., Hatoum, N. J. Allergy Clin. Immunol. (1994) [Pubmed]
  2. Mortality from lung cancer in an acetylene and phthalic anhydride plant. A case-referent study. Riboli, E., Bai, E., Berrino, F., Merisi, A. Scandinavian journal of work, environment & health. (1983) [Pubmed]
  3. A series of four cases of allergic contact dermatitis to phthalic anhydride/trimellitic anhydride/glycols copolymer in nail varnish. Gach, J.E., Stone, N.M., Finch, T.M. Contact Derm. (2005) [Pubmed]
  4. The characteristics of specific IgG to phthalic anhydride (PA)-albumin conjugate. Hatanaka, S., Imamura, I., Terazawa, Y., Kuroda, K., Endo, G. Industrial health. (1997) [Pubmed]
  5. Phthalic anhydride-induced occupational asthma. Wernfors, M., Nielsen, J., Schütz, A., Skerfving, S. Int. Arch. Allergy Appl. Immunol. (1986) [Pubmed]
  6. Allergy in long-term hemodialysis. II. Allergic and atopic patterns of a population of patients undergoing long-term hemodialysis. Bousquet, J., Maurice, F., Rivory, J.P., Skassa-Brociek, W., Florence, P., Chouzenoux, R., Mion, C., Michel, F.B. J. Allergy Clin. Immunol. (1988) [Pubmed]
  7. Clinical and immunologic evaluation of trimellitic anhydride-and phthalic anhydride-exposed workers using a questionnaire with comparative analysis of enzyme-linked immunosorbent and radioimmunoassay studies. Bernstein, D.I., Patterson, R., Zeiss, C.R. J. Allergy Clin. Immunol. (1982) [Pubmed]
  8. 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]
  9. Establishing clinical and immunologic criteria for diagnosis of occupational immunologic lung disease with phthalic anhydride and tetrachlorophthalic anhydride exposures as a model. Grammer, L.C., Harris, K.E., Chandler, M.J., Flaherty, D., Patterson, R. Journal of occupational medicine. : official publication of the Industrial Medical Association. (1987) [Pubmed]
  10. Divergent immune responses to respiratory and contact chemical allergens: antibody elicited by phthalic anhydride and oxazolone. Dearman, R.J., Kimber, I. Clin. Exp. Allergy (1992) [Pubmed]
  11. Exposure to acid anhydrides in three resin and one cushioned flooring manufacturing plants. van Tongeren, M.J., Barker, R.D., Gardiner, K., Harris, J.M., Venables, K.M., Taylor, A.J., Harrington, J.M. The Annals of occupational hygiene. (1995) [Pubmed]
  12. Synthesis of phthalates of betulinic acid and betulin with cytotoxic activity. Kvasnica, M., Sarek, J., Klinotova, E., Dzubak, P., Hajduch, M. Bioorg. Med. Chem. (2005) [Pubmed]
  13. Epigenetic events during the process of cell transformation induced by carcinogens (review). Nguyen-Ba, G., Vasseur, P. Oncol. Rep. (1999) [Pubmed]
  14. Assessment of preferential T-helper 1 or T-helper 2 induction by low molecular weight compounds using the local lymph node assay in conjunction with RT-PCR and ELISA for interferon-gamma and interleukin-4. Vandebriel, R.J., De Jong, W.H., Spiekstra, S.W., Van Dijk, M., Fluitman, A., Garssen, J., Van Loveren, H. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  15. Effect of Th2 cytokine antagonist treatments on chemical-induced allergic response in mice. Ban, M., Hettich, D. Journal of applied toxicology : JAT. (2005) [Pubmed]
  16. In vitro immunologic studies on a population of workers exposed to phthalic and tetrachlorophthalic anhydride. Flaherty, D.K., Gross, C.J., Winzenburger, P., Compas, M.B., McGarity, K., Tillman, E. Journal of occupational medicine. : official publication of the Industrial Medical Association. (1988) [Pubmed]
  17. Kinetics and products of photolysis and reaction with OH radicals of a series of aromatic carbonyl compounds. Wang, L., Arey, J., Atkinson, R. Environ. Sci. Technol. (2006) [Pubmed]
  18. Urine phthalate determinations as an index of occupational exposure to phthalic anhydride and di(2-ethylhexyl)phthalate. Liss, G.M., Albro, P.W., Hartle, R.W., Stringer, W.T. Scandinavian journal of work, environment & health. (1985) [Pubmed]
  19. Phthalic anhydride asthma. Chester, E.H., Schwartz, H.J., Payne, C.B., Greenstein, S. Clin. Allergy (1977) [Pubmed]
  20. Characterization in mice of the immunological properties of five allergenic acid anhydrides. Dearman, R.J., Warbrick, E.V., Humphreys, I.R., Kimber, I. Journal of applied toxicology : JAT. (2000) [Pubmed]
  21. SPE/LC/ESI/MS with phthalic anhydride derivatisation for the determination of alcohol ethoxylate surfactants in sewage influent and effluent samples. Sparham, C.J., Bromilow, I.D., Dean, J.R. Journal of chromatography. A. (2005) [Pubmed]
  22. Detection of specific IgE in isocyanate and phthalic anhydride exposed workers: comparison of RAST RIA, Immuno CAP System FEIA, and Magic Lite SQ. Mazur, G., Pethran, A. Allergy (1993) [Pubmed]
  23. Phthalic anhydride as an impurity in industrial atmospheres: assay in air samples by gas chromatography with electron-capture detection. Pfäffli, P. The Analyst. (1986) [Pubmed]
  24. Preparation, characterization and in vitro drug release of poly-epsilon-caprolactone and hydroxypropyl methylcellulose phthalate ketoprofen loaded microspheres. Guzman, M., Molpeceres, J., Garcia, F., Aberturas, M.R. Journal of microencapsulation. (1996) [Pubmed]
  25. In vitro demonstration of specific IgE in phthalic anhydride hypersensitivity. Maccia, C.A., Bernstein, I.L., Emmett, E.A., Brooks, S.M. Am. Rev. Respir. Dis. (1976) [Pubmed]
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