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Chemical Compound Review

Hacac     pentane-2,4-dione

Synonyms: ACAC, Acetoacetone, Pentanedione, Acetylacetone, CHEMBL191625, ...
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Disease relevance of ACAC

  • The toxicity of acetylacetone has been demonstrated in various studies [1].
  • Acetylacetone-cleaving enzyme Dke1: a novel C-C-bond-cleaving enzyme from Acinetobacter johnsonii [1].
  • The potential energy surfaces of the C-O cleavage, rotational isomerization, keto-enolic tautomerization, and dehydration reactions of acetylacetone in the lowest triplet and ground states have been determined using the complete active space self-consistent field and density functional theory methods [2].
  • Plant tumour producing Agrobacterium tumefaciens is effectively inhibited in vitro by the complex [VO(ACTSC-Na)(acac)]H2O (ACTSC-H2 = condensation product of acetylacetone and thiosemicarbazide) [3].

High impact information on ACAC


Chemical compound and disease context of ACAC


Biological context of ACAC


Anatomical context of ACAC


Associations of ACAC with other chemical compounds


Gene context of ACAC

  • The addition of acetyl acetone can potentially be used to assess the total potential of P450c17 to catalyze andien-beta synthase activity in vitro [16].
  • The developmental toxicity of 2,4-Pentanedione (2,4-PD; CAS No. 123-54-6), a widely used industrial chemical, was investigated by vapour exposure, because of its widespread use, and potential for human exposure [21].
  • 2,4-Pentanedione did not react with Arg residues of RTX-III even after 100 hr incubation [22].
  • The results obtained by the present method show good correlation with those obtained by the glycerol kinase method (correlation coefficient, 0.989) or the acetylacetone method (correlation coefficient, 0.979) [23].
  • THF:H2O (v/v) and hydrogen peroxide (0.082 mol/L) provided maximum yield of polymer (21.2% weight conversion of styrene to polystyrene) with 2,4-pentanedione as initiator [24].

Analytical, diagnostic and therapeutic context of ACAC


  1. Acetylacetone-cleaving enzyme Dke1: a novel C-C-bond-cleaving enzyme from Acinetobacter johnsonii. Straganz, G.D., Glieder, A., Brecker, L., Ribbons, D.W., Steiner, W. Biochem. J. (2003) [Pubmed]
  2. Theoretical studies of the photochemical dynamics of acetylacetone: isomerzation, dissociation, and dehydration reactions. Chen, X.B., Fang, W.H., Phillips, D.L. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  3. Antimicrobial, insect sterilizing and ovicidal activity of some oxo-vanadium(IV) and oxo-vanadium(V) complexes. Datta, S., Banerjee, P., Banerjee, R.D., Sarkar, G.M., Saha, S.K., Dey, K., Maiti, R.K., Sen, S.K., Bhar, J.K. Agents Actions (1982) [Pubmed]
  4. Evaluation of ascorbic acid in protecting labile folic acid derivatives. Wilson, S.D., Horne, D.W. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  5. Alteration of actin-tropomyosin interaction in 2,4-pentanedione-treated rabbit skeletal myofibrils. el-Saleh, S.C., Potter, J.D., Solaro, R.J. J. Biol. Chem. (1986) [Pubmed]
  6. Modification of Lys-237 on actin by 2,4-pentanedione. Alteration of the interaction of actin with tropomyosin. El-Saleh, S.C., Thieret, R., Johnson, P., Potter, J.D. J. Biol. Chem. (1984) [Pubmed]
  7. Ultrafast dynamics of 2E state formation in Cr(acac)3. Juban, E.A., McCusker, J.K. J. Am. Chem. Soc. (2005) [Pubmed]
  8. Clinical comparison of indium-111 acetylacetone and indium-111 tropolone granulocytes. Schauwecker, D.S., Burt, R.W., Park, H.M., Mock, B.H., Witt, R.M., Tobolski, M.M., Wellman, H.N. J. Nucl. Med. (1986) [Pubmed]
  9. A novel beta-diketone-cleaving enzyme from Acinetobacter johnsonii: acetylacetone 2,3-oxygenase. Straganz, G., Brecker, L., Weber, H.J., Steiner, W., Ribbons, D.W. Biochem. Biophys. Res. Commun. (2002) [Pubmed]
  10. Dominant lethal assay of 2,4-pentanedione vapor in Fischer 344 rats. Tyl, R.W., Ballantyne, B., Fisher, L.C., Tarasi, D.J., Dodd, D.E. Toxicology and industrial health. (1989) [Pubmed]
  11. Acute intravenous and inhalation pharmacokinetics of 2,4-pentanedione in the Fischer 344 rat. Frantz, S.W., Ballantyne, B., Leung, H.W. Toxicology and industrial health. (1998) [Pubmed]
  12. Free radical formation in the oxidation of malondialdehyde and acetylacetone by peroxidase enzymes. Mottley, C., Robinson, R.E., Mason, R.P. Arch. Biochem. Biophys. (1991) [Pubmed]
  13. Preparation of amorphous aluminum oxide-hydroxide nanoparticles in amphiphilic silicone-based copolymer microemulsions. Berkovich, Y., Aserin, A., Wachtel, E., Garti, N. Journal of colloid and interface science. (2002) [Pubmed]
  14. Quantitative determination of phenelzine in human fluids by gas chromatography with nitrogen specific detection. Lichtenwalner, M., McMullin, M., Hardy, D., Rieders, F. Journal of analytical toxicology. (1988) [Pubmed]
  15. Evaluation of complicating osteomyelitis with Tc-99m MDP, In-111 granulocytes, and Ga-67 citrate. Schauwecker, D.S., Park, H.M., Mock, B.H., Burt, R.W., Kernick, C.B., Ruoff, A.C., Sinn, H.J., Wellman, H.N. J. Nucl. Med. (1984) [Pubmed]
  16. Effect of phospholipids and organic solvents on the formation of 5,16-androstadien-3 beta-ol from pregnenolone in adrenal and testicular microsomes. Meadus, W.J., Squires, E.J. Steroids (1995) [Pubmed]
  17. Binding of 113mIn ion to human erythrocytes. Kämpfer, I., Nissler, K. Biomed. Biochim. Acta (1986) [Pubmed]
  18. Oxidation of acetylacetone catalyzed by horseradish peroxidase in the absence of hydrogen peroxide. Rodrigues, A.P., da Fonseca, L.M., de Faria Oliveira, O.M., Brunetti, I.L., Ximenes, V.F. Biochim. Biophys. Acta (2006) [Pubmed]
  19. Modification of arginine and lysine in proteins with 2,4-pentanedione. Gilbert, H.F., O'Leary, M.H. Biochemistry (1975) [Pubmed]
  20. Chemical modification of the bifunctional human serum pseudocholinesterase. Effect on the pseudocholinesterase and aryl acylamidase activities. Boopathy, R., Balasubramanian, A.S. Eur. J. Biochem. (1985) [Pubmed]
  21. An evaluation of the developmental toxicity of 2,4-pentanedione in the Fischer 344 rat by vapour exposure. Tyl, R.W., Ballantyne, B., Pritts, I.M., Garman, R.H., Fisher, L.C., France, K.A., McNeil, D.J. Toxicology and industrial health. (1990) [Pubmed]
  22. Modification of arginine in sea anemone toxin RTX-III from Radianthus macrodactylus. Mahnir, V.M., Kozlovskaya, E.P., Elyakov, G.B. Toxicon (1989) [Pubmed]
  23. A simple colorimetric method for determination of serum triglycerides with lipoprotein lipase and glycerol dehydrogenase. Sugiura, M., Oikawa, T., Hirano, K., Maeda, H., Yoshimura, H., Sugiyama, M., Kuratsu, T. Clin. Chim. Acta (1977) [Pubmed]
  24. Enzyme-mediated free radical polymerization of styrene. Singh, A., Ma, D., Kaplan, D.L. Biomacromolecules (2000) [Pubmed]
  25. Development of an analytical method for beryllium in airborne dust by micellar electrokinetic chromatography. Takaya, M. Journal of chromatography. A. (1999) [Pubmed]
  26. Improving mass spectrometric sequencing of arginine-containing peptides by derivatization with acetylacetone. Dikler, S., Kelly, J.W., Russell, D.H. Journal of mass spectrometry : JMS. (1997) [Pubmed]
  27. HPLC assay for guanidine salts based on pre-column derivatization with acetylacetone. Palaitis, W., Curran, J.R. Journal of chromatographic science. (1984) [Pubmed]
  28. Tautomer interconversion of 2,4-pentanedione during gas chromatography on an oxidized cyano-modified capillary column. Skrdla, P.J., Antonucci, V., Lindemann, C. Journal of chromatographic science. (2001) [Pubmed]
  29. Spectrophotometric and liquid chromatographic determination of dopamine from pharmaceutical preparations using acetyl acetone as derivatizing reagent. Khuhawar, M., Rajper, A., Rind, F. Pakistan journal of pharmaceutical sciences (2006) [Pubmed]
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