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Chemical Compound Review

biacetyl     butane-2,3-dione

Synonyms: diacetyl, Butanedione, Lopac-D-3634, Biacetyl; BDM, CCRIS 827, ...
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Disease relevance of biacetyl

  • Regional myocardium function was measured during a selective intracoronary infusion of 2,3-butanedione monoxime (BDM), a specific inhibitor of actin-myosin coupling, in the control state (10 pigs) and in a protocol of a 51-minute coronary occlusion followed by reperfusion (40 pigs) [1].
  • Five heart groups (cold) were perfused with AVP, D-ARG, L-ARG, L-NAME, or nothing (control), but after 2 hours they were perfused at low flow for 22 hours at 3.7 degrees C and again for 3 hours at 37.5 degrees C. ADE, butanedione monoxime, and NP were given for cardioprotection before, during, and after hypothermia [2].
  • The role of contracture in the manifestation of calcium paradox-induced damage was examined using 2,3-butanedione monoxime (BDM) to inhibit myofibrillar activity [3].
  • Cleaving Xenopus embryos and parthenogenetically activated eggs treated with 2,3-butanedione monoxime (BDM) undergo a dramatic large-scale torsion, with the cortex of the animal hemisphere shearing in an exclusively counterclockwise direction past the vegetal cortex [4].
  • Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue [5].
  • Exposure to an agent during diacetyl production appears to be responsible for causing bronchiolitis obliterans syndrome in chemical process operators, consistent with the suspected role of diacetyl in downstream food production [6].

Psychiatry related information on biacetyl

  • Controlled clinical evaluation of diacetyl morphine for treatment of intractable opiate dependence [7].
  • The determination of diacetyl permits the detection of microbial growth in the processing of citrus fruit before the appearance of other organoleptic, chemical or microbiological changes [8].
  • The biosensor could be used to determine diacetyl concentration within the range from 0.1 microgram/mL to 0.5 microgram/mL and the response time was less than two minutes, and its performance was stable within 9 days [9].

High impact information on biacetyl

  • Chemical modification with 2,3-butanedione in borate buffer indicates that nine of ten glycolytic enzymes studied contain arginyl residues at their active sites [10].
  • In apicomplexan parasites, actin-disrupting drugs and the inhibitor of myosin heavy chain ATPase, 2,3-butanedione monoxime, have been shown to interfere with host cell invasion by inhibiting parasite gliding motility [11].
  • Cells lacking MyoB (myoA(-)/B(-), and myoB(-) cells) and wild-type cells treated with the myosin inhibitor butanedione monoxime accumulated a plasma membrane marker and biotinylated surface proteins on intracellular endocytic vacuoles [12].
  • In addition, the involvement of myosin-based cytoskeleton in uropod formation and ICAM-3 redistribution in response to chemokines was suggested by the prevention of this phenomenon with the myosin-disrupting agent butanedione monoxime [13].
  • Maintenance of such cell-cell contact structures critically depended on the contractility of actin cytoskeleton, as inhibition of contractility with serum-free medium or 2,3-butanedione 2-monoxime (BDM) resulted in loss of strand formation [14].

Chemical compound and disease context of biacetyl


Biological context of biacetyl

  • Chemotaxis toward one such odorant, diacetyl (butanedione), requires the function of a seven-transmembrane receptor protein encoded by the odr-10 gene [20].
  • In separate hearts (n = 8), costs (basal metabolism and excitation-contraction coupling) were estimated by use of 2,3-butanedione monoxime [21].
  • Although their specific effects are difficult to quantitate, other LAB metabolic products such as hydrogen peroxide and diacetyl can also contribute to the overall antibiosis and preservative potential of these products [22].
  • The polarization and homotypic cell aggregation induced through CD43 was prevented by butanedione monoxime, indicating the involvement of myosin cytoskeleton in these phenomena [23].
  • Interestingly, the myosin-disrupting drug butanedione monoxime inhibited the redistribution of CD43 induced by the specific MoAb, whereas the stimulation of cell adhesion induced by engagement of CD43 was preserved in the presence of this drug [24].

Anatomical context of biacetyl


Associations of biacetyl with other chemical compounds

  • Conversely, treatment of cells on firm substrates with myosin inhibitors 2,3-butanedione monoxime or KT5926 caused the reduction of both vinculin and phosphotyrosine at adhesion sites [30].
  • We found that modification with butanedione of four arginine residues in the HMW kininogen molecule prevented bradykinin release, which results from cleavage of HMW kininogen [31].
  • Phytomonas iPDH and R. eutropha ADH are able to use a wide range of substrates with similar Km values such as primary and secondary alcohols, diols, and aldehydes, as well as ketones such as acetone, diacetyl, and acetoin [32].
  • When both NAD and NADP were present, the butanedione effect was completely abolished, thus suggesting the possible presence of arginyl residues at the nucleotide binding site of the NADPH leads to NAD transhydrogenase enzyme [33].
  • The results imply that P34H and diacetyl reductase (EC ) are identical to l-xylulose reductase (EC ), which is involved in the uronate cycle of glucose metabolism, and the unique localization of the enzyme in kidney suggests that it has a role other than in general carbohydrate metabolism [34].

Gene context of biacetyl

  • Yeast hexokinase PII is rapidly inactivated (assayed at pH 8.0) by either butanedione in borate buffer or phenylglyoxal, reagents which are highly selective for the modification of arginyl residues [35].
  • Cytochalasin B or butanedione monoxime blocked the contraction, which suggested that both actin filaments and myosin ATPase activity were required for the contraction [36].
  • Correspondingly elevated levels of ILV5 transcript in strain WM56 compared to the control (i.e. non-tandem) parental strain led to increased amounts of encoded acetohydroxyacid reductoisomerase as evidenced by significantly lower diacetyl production [37].
  • These findings suggest that one, or both, of the two arginyl residues which appear to be unique to the active sites of the mammalian CA III isozymes are modified by butanedione [38].
  • Towards diacetyl-less brewers' yeast. Influence of ilv2 and ilv5 mutations [39].

Analytical, diagnostic and therapeutic context of biacetyl


  1. Selective inhibition of the contractile apparatus. A new approach to modification of infarct size, infarct composition, and infarct geometry during coronary artery occlusion and reperfusion. Garcia-Dorado, D., Théroux, P., Duran, J.M., Solares, J., Alonso, J., Sanz, E., Munoz, R., Elizaga, J., Botas, J., Fernandez-Avilés, F. Circulation (1992) [Pubmed]
  2. Effects of L-arginine and N omega-nitro-L-arginine methyl ester on cardiac perfusion and function after 1-day cold preservation of isolated hearts. Stowe, D.F., Boban, M., Roerig, D.L., Chang, D., Palmisano, B.W., Bosnjak, Z.J. Circulation (1997) [Pubmed]
  3. Contracture and the calcium paradox in the rat heart. Daly, M.J., Elz, J.S., Nayler, W.G. Circ. Res. (1987) [Pubmed]
  4. Intrinsic chiral properties of the Xenopus egg cortex: an early indicator of left-right asymmetry? Danilchik, M.V., Brown, E.E., Riegert, K. Development (2006) [Pubmed]
  5. Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue. Epperly, B.R., Dekker, E.E. J. Biol. Chem. (1989) [Pubmed]
  6. Bronchiolitis obliterans syndrome in chemical workers producing diacetyl for food flavorings. van Rooy, F.G., Rooyackers, J.M., Prokop, M., Houba, R., Smit, L.A., Heederik, D.J. Am. J. Respir. Crit. Care Med. (2007) [Pubmed]
  7. Controlled clinical evaluation of diacetyl morphine for treatment of intractable opiate dependence. Drucker, E., Vlahov, D. Lancet (1999) [Pubmed]
  8. Use of polarography as a quality-control method for determining diacetyl in citrus and vegetable juices, yoghurt and butter. Esteve, M.J., Frígola, A., Rodrigo, M.C., Rodrigo, M. Food additives and contaminants. (2002) [Pubmed]
  9. Studies on biosensor to determine diacetyl. Zhang, J., Yu, D., Sha, C., Xi, X., Peng, W., Tang, W., Chen, Y. Chin. J. Biotechnol. (1999) [Pubmed]
  10. Arginyl residues: anion recognition sites in enzymes. Riordan, J.F., McElvany, K.D., Borders, C.L. Science (1977) [Pubmed]
  11. Toxoplasma gondii myosins B/C: one gene, two tails, two localizations, and a role in parasite division. Delbac, F., Sänger, A., Neuhaus, E.M., Stratmann, R., Ajioka, J.W., Toursel, C., Herm-Götz, A., Tomavo, S., Soldati, T., Soldati, D. J. Cell Biol. (2001) [Pubmed]
  12. A myosin I is involved in membrane recycling from early endosomes. Neuhaus, E.M., Soldati, T. J. Cell Biol. (2000) [Pubmed]
  13. Chemokines regulate cellular polarization and adhesion receptor redistribution during lymphocyte interaction with endothelium and extracellular matrix. Involvement of cAMP signaling pathway. del Pozo, M.A., Sánchez-Mateos, P., Nieto, M., Sánchez-Madrid, F. J. Cell Biol. (1995) [Pubmed]
  14. Dynamics of contacts between lamellae of fibroblasts: essential role of the actin cytoskeleton. Gloushankova, N.A., Krendel, M.F., Alieva, N.O., Bonder, E.M., Feder, H.H., Vasiliev, J.M., Gelfand, I.M. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  15. D-Serine dehydratase from Escherichia coli. Essential arginine residue at the pyridoxal 5'-phosphate binding site. Kazarinoff, M.N., Snell, E.E. J. Biol. Chem. (1976) [Pubmed]
  16. Esterases in serum-containing growth media counteract chloramphenicol acetyltransferase activity in vitro. Sohaskey, C.D., Barbour, A.G. Antimicrob. Agents Chemother. (1999) [Pubmed]
  17. Total recovery of heart grafts of non-heart-beating donors after 3 hours of hypothermic coronary oxygen persufflation preservation in an orthotopic pig transplantation model. Yotsumoto, G., Jeschkeit-Schubbert, S., Funcke, C., Kuhn-Régnier, F., Fischer, J.H. Transplantation (2003) [Pubmed]
  18. Cloning, expression, and characterization of the Lactococcus lactis pfl gene, encoding pyruvate formate-lyase. Arnau, J., Jørgensen, F., Madsen, S.M., Vrang, A., Israelsen, H. J. Bacteriol. (1997) [Pubmed]
  19. Characterization of the genes of the 2,3-butanediol operons from Klebsiella terrigena and Enterobacter aerogenes. Blomqvist, K., Nikkola, M., Lehtovaara, P., Suihko, M.L., Airaksinen, U., Stråby, K.B., Knowles, J.K., Penttilä, M.E. J. Bacteriol. (1993) [Pubmed]
  20. The Caenorhabditis elegans seven-transmembrane protein ODR-10 functions as an odorant receptor in mammalian cells. Zhang, Y., Chou, J.H., Bradley, J., Bargmann, C.I., Zinn, K. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  21. Rapid shortening during relaxation increases activation and improves systolic performance. Watkins, M.W., Higashiyama, A., Chen, Z., LeWinter, M.M. Circulation (1996) [Pubmed]
  22. Antagonistic activities of lactic acid bacteria in food and feed fermentations. Lindgren, S.E., Dobrogosz, W.J. FEMS Microbiol. Rev. (1990) [Pubmed]
  23. CD43 interacts with moesin and ezrin and regulates its redistribution to the uropods of T lymphocytes at the cell-cell contacts. Serrador, J.M., Nieto, M., Alonso-Lebrero, J.L., del Pozo, M.A., Calvo, J., Furthmayr, H., Schwartz-Albiez, R., Lozano, F., González-Amaro, R., Sánchez-Mateos, P., Sánchez-Madrid, F. Blood (1998) [Pubmed]
  24. Regulatory role of CD43 leukosialin on integrin-mediated T-cell adhesion to endothelial and extracellular matrix ligands and its polar redistribution to a cellular uropod. Sánchez-Mateos, P., Campanero, M.R., del Pozo, M.A., Sánchez-Madrid, F. Blood (1995) [Pubmed]
  25. Mechanisms of reoxygenation injury in cultured ventricular myocytes. Quaife, R.A., Kohmoto, O., Barry, W.H. Circulation (1991) [Pubmed]
  26. Reconstitution of purified brown adipose tissue mitochondria uncoupling protein: demonstration of separate identity of nucleotide binding and proton translocation sites by chemical probes. Katiyar, S.S., Shrago, E. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  27. Protection of human left ventricular myocardium from cutting injury with 2,3-butanedione monoxime. Mulieri, L.A., Hasenfuss, G., Ittleman, F., Blanchard, E.M., Alpert, N.R. Circ. Res. (1989) [Pubmed]
  28. Nerve growth factor stimulates the accumulation of beta1 integrin at the tips of filopodia in the growth cones of sympathetic neurons. Grabham, P.W., Goldberg, D.J. J. Neurosci. (1997) [Pubmed]
  29. Two large families of chemoreceptor genes in the nematodes Caenorhabditis elegans and Caenorhabditis briggsae reveal extensive gene duplication, diversification, movement, and intron loss. Robertson, H.M. Genome Res. (1998) [Pubmed]
  30. Cell locomotion and focal adhesions are regulated by substrate flexibility. Pelham, R.J., Wang, Y. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  31. Role of arginine residues in the coagulant activity of high molecular weight kininogen. Chang, J.J., Scott, C.F., Colman, R.W. Blood (1986) [Pubmed]
  32. The multifunctional isopropyl alcohol dehydrogenase of Phytomonas sp. could be the result of a horizontal gene transfer from a bacterium to the trypanosomatid lineage. Molinas, S.M., Altabe, S.G., Opperdoes, F.R., Rider, M.H., Michels, P.A., Uttaro, A.D. J. Biol. Chem. (2003) [Pubmed]
  33. Oxidation of NADPH by submitochondrial particles from beef heart in complete absence of transhydrogenase activity from NADPH to NAD. Djavadi-Ohaniance, L., Hatefi, H. J. Biol. Chem. (1975) [Pubmed]
  34. Molecular characterization of mammalian dicarbonyl/L-xylulose reductase and its localization in kidney. Nakagawa, J., Ishikura, S., Asami, J., Isaji, T., Usami, N., Hara, A., Sakurai, T., Tsuritani, K., Oda, K., Takahashi, M., Yoshimoto, M., Otsuka, N., Kitamura, K. J. Biol. Chem. (2002) [Pubmed]
  35. Role of arginyl residues in yeast hexokinase PII. Borders, C.L., Cipollo, K.L., Jorkasky, J.F., Neet, K.E. Biochemistry (1978) [Pubmed]
  36. Calyculin-A, an inhibitor for protein phosphatases, induces cortical contraction in unfertilized sea urchin eggs. Asano, Y., Mabuchi, I. Cell Motil. Cytoskeleton (2001) [Pubmed]
  37. Tandem integration of multiple ILV5 copies and elevated transcription in polyploid yeast. Mithieux, S.M., Weiss, A.S. Yeast (1995) [Pubmed]
  38. Activation of mammalian skeletal-muscle carbonic anhydrase III by arginine modification. Tashian, R.E., Johansen, J.T., Christiansen, E., Chegwidden, W.R. Biosci. Rep. (1984) [Pubmed]
  39. Towards diacetyl-less brewers' yeast. Influence of ilv2 and ilv5 mutations. Gjermansen, C., Nilsson-Tillgren, T., Petersen, J.G., Kielland-Brandt, M.C., Sigsgaard, P., Holmberg, S. J. Basic Microbiol. (1988) [Pubmed]
  40. Contraction uncoupling with butanedione monoxime versus low calcium or high potassium solutions on flow and contractile function of isolated hearts after prolonged hypothermic perfusion. Stowe, D.F., Boban, M., Graf, B.M., Kampine, J.P., Bosnjak, Z.J. Circulation (1994) [Pubmed]
  41. The role of active site arginines of sorghum NADP-malate dehydrogenase in thioredoxin-dependent activation and activity. Schepens, I., Ruelland, E., Miginiac-Maslow, M., Le Maréchal, P., Decottignies, P. J. Biol. Chem. (2000) [Pubmed]
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