diacetyl

Summary

Summary: Carrier of aroma of butter, vinegar, coffee, and other foods.

Top Publications

  1. Nadal I, Rico J, Perez Martinez G, Yebra M, Monedero V. Diacetyl and acetoin production from whey permeate using engineered Lactobacillus casei. J Ind Microbiol Biotechnol. 2009;36:1233-7 pubmed publisher
    The capability of Lactobacillus casei to produce the flavor-related compounds diacetyl and acetoin from whey permeate has been examined by a metabolic engineering approach. An L...
  2. Kovacic P, Cooksy A. Role of diacetyl metabolite in alcohol toxicity and addiction via electron transfer and oxidative stress. Arch Toxicol. 2005;79:123-8 pubmed
    ..Metabolism affords mainly acetic acid via acetaldehyde. A minor metabolite, diacetyl (an alpha-dicarbonyl), arises from the aldehyde...
  3. Ostap E. 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23:305-8 pubmed
    ..Therefore, BDM is not a general inhibitor of the myosin ATPase. BDM has a broad effect on many non-myosin proteins (many uncharacterized), and thus should not be used in whole-cell experiments as a myosin inhibitor. ..
  4. Keller H, Zadeh A, Eggli P. Localised depletion of polymerised actin at the front of Walker carcinosarcoma cells increases the speed of locomotion. Cell Motil Cytoskeleton. 2002;53:189-202 pubmed
    ..They are best compatible with a cortical contraction/frontal expansion model, but they are not compatible with models implying that actin polymerisation or actomyosin contraction at the front drive locomotion of the cells studied...
  5. Sengupta P, Chou J, Bargmann C. odr-10 encodes a seven transmembrane domain olfactory receptor required for responses to the odorant diacetyl. Cell. 1996;84:899-909 pubmed
    ..We show that the C. elegans odr-10 gene is likely to encode a receptor for the odorant diacetyl. odr-10 mutants have a specific defect in chemotaxis to diacetyl, one of several odorants detected by the AWA ..
  6. Mathews J, Watson S, Snyder R, Burgess J, Morgan D. Reaction of the butter flavorant diacetyl (2,3-butanedione) with N-α-acetylarginine: a model for epitope formation with pulmonary proteins in the etiology of obliterative bronchiolitis. J Agric Food Chem. 2010;58:12761-8 pubmed publisher
    The butter flavorant diacetyl (2,3-butanedione) is implicated in causing obliterative bronchiolitis in microwave popcorn plant workers...
  7. García Quintáns N, Repizo G, Martin M, Magni C, Lopez P. Activation of the diacetyl/acetoin pathway in Lactococcus lactis subsp. lactis bv. diacetylactis CRL264 by acidic growth. Appl Environ Microbiol. 2008;74:1988-96 pubmed publisher
    ..a fermentative microorganism, which cometabolizes glucose and citrate to yield aroma compounds through the diacetyl/acetoin biosynthetic pathway. Our previous results have shown that under acidic growth Lactococcus bv...
  8. Le Bars D, Yvon M. Formation of diacetyl and acetoin by Lactococcus lactis via aspartate catabolism. J Appl Microbiol. 2008;104:171-7 pubmed
    To verify whether diacetyl can be produced by Lactococcus lactis via amino acid catabolism, and to investigate the impact of the pH on the conversion. Resting cells of L...
  9. Prakki A, Tallury P, Mondelli R, Kalachandra S. Influence of additives on the properties of Bis-GMA/Bis-GMA analog comonomers and corresponding copolymers. Dent Mater. 2007;23:1199-204 pubmed
    ..Use of novel comonomer systems with the addition of aldehyde and diketone functional groups would improve dental resin composite properties. ..

More Information

Publications62

  1. Birkenhauer J, Oliver J. Use of diacetyl to reduce the load of Vibrio vulnificus in the Eastern oyster, Crassostrea virginica. J Food Prot. 2003;66:38-43 pubmed
    ..conducted in our laboratory have examined various generally recognized as safe compounds and have determined that diacetyl, a component of butter, is among the most effective of these compounds in reducing loads of V...
  2. Swindell S, Benson K, Griffin H, Renault P, Ehrlich S, Gasson M. Genetic manipulation of the pathway for diacetyl metabolism in Lactococcus lactis. Appl Environ Microbiol. 1996;62:2641-3 pubmed
    b>Diacetyl is an important food flavor compound produced by certain strains of citrate-metabolizing lactic acid bacteria. Citrate is converted to pyruvate, from which diacetyl is produced via intermediate alpha-acetolactate...
  3. Boyde T, Rahmatullah M. Optimization of conditions for the colorimetric determination of citrulline, using diacetyl monoxime. Anal Biochem. 1980;107:424-31 pubmed
  4. Farman G, Tachampa K, Mateja R, Cazorla O, Lacampagne A, de Tombe P. Blebbistatin: use as inhibitor of muscle contraction. Pflugers Arch. 2008;455:995-1005 pubmed
  5. Lockey J, Hilbert T, Levin L, Ryan P, White K, Borton E, et al. Airway obstruction related to diacetyl exposure at microwave popcorn production facilities. Eur Respir J. 2009;34:63-71 pubmed publisher
    ..Butter flavourings including diacetyl have been associated with these findings...
  6. Kreiss K, Gomaa A, Kullman G, Fedan K, Simoes E, Enright P. Clinical bronchiolitis obliterans in workers at a microwave-popcorn plant. N Engl J Med. 2002;347:330-8 pubmed
    ..outcomes by analyzing the rates of symptoms and abnormalities according to current and cumulative exposure to diacetyl, the predominant ketone in artificial butter flavoring and in the air at the plant...
  7. Thum T, Borlak J. Butanedione monoxime increases the viability and yield of adult cardiomyocytes in primary cultures. Cardiovasc Toxicol. 2001;1:61-72 pubmed
    ..05%) when BDM was added to the isolation and cultivation buffer. The results obtained with BDM warrant further investigation into its cytoprotective potential during ischemia and damage to the cytoskeleton. ..
  8. Bartowsky E, Henschke P. The 'buttery' attribute of wine--diacetyl--desirability, spoilage and beyond. Int J Food Microbiol. 2004;96:235-52 pubmed
    The diketone, diacetyl, is a major flavour metabolite produced by lactic acid bacteria (LAB)...
  9. Morgan D, Flake G, Kirby P, Palmer S. Respiratory toxicity of diacetyl in C57BL/6 mice. Toxicol Sci. 2008;103:169-80 pubmed publisher
    b>Diacetyl, a component of artificial butter flavoring, is a potential etiological agent of obliterative bronchiolitis (OB); however, the toxic dose and mechanisms of toxicity remain controversial...
  10. Li L, Wang Y, Zhang L, Ma C, Wang A, Tao F, et al. Biocatalytic production of (2S,3S)-2,3-butanediol from diacetyl using whole cells of engineered Escherichia coli. Bioresour Technol. 2012;115:111-6 pubmed publisher
    ..Whole cells of the recombinant E. coli was used to produce (2S,3S)-2,3-BD from diacetyl. Under optimal conditions, high-optical-purity (2S,3S)-2,3-BD (purity >99%) was obtained with concentrations ..
  11. Lee M, Lin S, Ohara T, Omichi C, Okuyama Y, Chudin E, et al. Effects of diacetyl monoxime and cytochalasin D on ventricular fibrillation in swine right ventricles. Am J Physiol Heart Circ Physiol. 2001;280:H2689-96 pubmed
    Whether or not the excitation-contraction (E-C) uncoupler diacetyl monoxime (DAM) and cytochalacin D (Cyto D) alter the ventricular fibrillation (VF) activation patterns is unclear...
  12. Li Y, Ye H, Du M, Zhang Y, Ye B, Pu Y, et al. Induction of chemotaxis to sodium chloride and diacetyl and thermotaxis defects by microcystin-LR exposure in nematode Caenorhabditis elegans. J Environ Sci (China). 2009;21:971-9 pubmed
    ..In the present study, we provided evidence to indicate the neurotoxicity on chemotaxis to NaCl and diacetyl, and thermotaxis from MC-LR exposure to C. elegans...
  13. Kobayashi K, Kusaka K, Takahashi T, Sato K. Method for the simultaneous assay of diacetyl and acetoin in the presence of alpha-acetolactate: application in determining the kinetic parameters for the decomposition of alpha-acetolactate. J Biosci Bioeng. 2005;99:502-7 pubmed
    A simultaneous assay method for diacetyl and acetoin was developed to investigate the formation of diacetyl during the brewing of alcoholic beverages...
  14. Duong C, Strack L, Futschik M, Katou Y, Nakao Y, Fujimura T, et al. Identification of Sc-type ILV6 as a target to reduce diacetyl formation in lager brewers' yeast. Metab Eng. 2011;13:638-47 pubmed publisher
    b>Diacetyl causes an unwanted buttery off-flavor in lager beer. It is spontaneously generated from ?-acetolactate, an intermediate of yeast's valine biosynthesis released during the main beer fermentation...
  15. Guo T, Kong J, Zhang L, Zhang C, Hu S. Fine tuning of the lactate and diacetyl production through promoter engineering in Lactococcus lactis. PLoS ONE. 2012;7:e36296 pubmed publisher
    ..For fine tuning of the distribution of glycolytic flux at the pyruvate branch from lactate to diacetyl and balancing the production of the two metabolites under aerobic conditions, a constitutive promoter library was ..
  16. Hugenholtz J, Kleerebezem M, Starrenburg M, Delcour J, de Vos W, Hols P. Lactococcus lactis as a cell factory for high-level diacetyl production. Appl Environ Microbiol. 2000;66:4112-4 pubmed
    We report the engineering of Lactococcus lactis for the efficient conversion of sugar into diacetyl by combining NADH-oxidase overproduction and alpha-acetolactate decarboxylase inactivation...
  17. Passerini D, Laroute V, Coddeville M, Le Bourgeois P, Loubiere P, Ritzenthaler P, et al. New insights into Lactococcus lactis diacetyl- and acetoin-producing strains isolated from diverse origins. Int J Food Microbiol. 2013;160:329-36 pubmed publisher
    ..lactis biovar diacetylactis strains are used in the dairy industry for generating acetoin and notably diacetyl which imparts a high level of buttery flavor notes...
  18. Monnet C, Aymes F, Corrieu G. Diacetyl and alpha-acetolactate overproduction by Lactococcus lactis subsp. lactis biovar diacetylactis mutants that are deficient in alpha-acetolactate decarboxylase and have a low lactate dehydrogenase activity. Appl Environ Microbiol. 2000;66:5518-20 pubmed
    ..biovar diacetylactis strains are utilized in several industrial processes for producing the flavoring compound diacetyl or its precursor alpha-acetolactate...
  19. Cox Ganser J, Ganser G, Saito R, Hobbs G, Boylstein R, Hendricks W, et al. Correcting diacetyl concentrations from air samples collected with NIOSH method 2557. J Occup Environ Hyg. 2011;8:59-70 pubmed publisher
    b>Diacetyl (2,3-butanedione), a diketone chemical used to impart a buttery taste in many flavoring mixtures, has been associated with bronchiolitis obliterans in several industrial settings...
  20. Ui S, Takusagawa Y, Sato T, Ohtsuki T, Mimura A, Ohkuma M, et al. Production of L-2,3-butanediol by a new pathway constructed in Escherichia coli. Lett Appl Microbiol. 2004;39:533-7 pubmed
    ..To rectify this situation, we attempted to produce L-BD from diacetyl (DA) by producing simultaneous expression of diacetyl reductase (DAR) and L-2,3-butanediol dehydrogenase (BDH) ..
  21. Kusunoki K, Ogata T. Construction of self-cloning bottom-fermenting yeast with low vicinal diketone production by the homo-integration of ILV5. Yeast. 2012;29:435-42 pubmed publisher
    The vicinal diketones (VDK), such as diacetyl and 2,3-pentandione, impart an unpleasant butter-like flavour to beer...
  22. Kim T, Materna B, Prudhomme J, Fedan K, Enright P, Sahakian N, et al. Industry-wide medical surveillance of California flavor manufacturing workers: Cross-sectional results. Am J Ind Med. 2010;53:857-65 pubmed publisher
    ..from six companies included younger age, Hispanic ethnicity, liquid and powder production work, greater company diacetyl usage, and having a coworker with obstruction. Severity of obstruction was related to tenure...
  23. Otsuka M, Harada N, Itabashi T, Ohmori S. Blood and urinary levels of ethanol, acetaldehyde, and C4 compounds such as diacetyl, acetoin, and 2,3-butanediol in normal male students after ethanol ingestion. Alcohol. 1999;17:119-24 pubmed
    ..The student with the inactive form of ALDH2 was flushed and his levels of 2,3-butanediol and acetaldehyde in blood and urine were found to be the highest...
  24. Gao C, Zhang L, Xie Y, Hu C, Zhang Y, Li L, et al. Production of (3S)-acetoin from diacetyl by using stereoselective NADPH-dependent carbonyl reductase and glucose dehydrogenase. Bioresour Technol. 2013;137:111-5 pubmed publisher
    ..carbonyl reductase (Gox0644) from Gluconobacter oxydans DSM 2003 was confirmed to have a good ability to reduce diacetyl (DA) to produce (3S)-AC. In this work, the NADPH-dependent carbonyl reductase was expressed and purified...
  25. Prakki A, Cilli R, Mondelli R, Kalachandra S. In vitro wear, surface roughness and hardness of propanal-containing and diacetyl-containing novel composites and copolymers based on bis-GMA analogs. Dent Mater. 2008;24:410-7 pubmed
    ..The findings correlate with additives ability to improve degree of conversion of some composites/copolymers thereby enhancing mechanical properties. ..
  26. Zeppa G, Conterno L, Gerbi V. Determination of organic acids, sugars, diacetyl, and acetoin in cheese by high-performance liquid chromatography. J Agric Food Chem. 2001;49:2722-6 pubmed
    ..and hippuric), some free fatty acids (formic, acetic, propionic, butyric, isobutyric, valeric, and isovaleric), diacetyl, and acetoin were separated on an Aminex HPX-87H column using a simple isocratic HPLC method and identified by ..
  27. Hubbs A, Goldsmith W, Kashon M, Frazer D, Mercer R, Battelli L, et al. Respiratory toxicologic pathology of inhaled diacetyl in sprague-dawley rats. Toxicol Pathol. 2008;36:330-44 pubmed publisher
    ..b>Diacetyl, an alpha-diketone, is a major component of these vapors...
  28. Flagg T, Cazorla O, Remedi M, Haim T, Tones M, Bahinski A, et al. Ca2+-independent alterations in diastolic sarcomere length and relaxation kinetics in a mouse model of lipotoxic diabetic cardiomyopathy. Circ Res. 2009;104:95-103 pubmed publisher
  29. Dasari S, Kölling R. Cytosolic localization of acetohydroxyacid synthase Ilv2 and its impact on diacetyl formation during beer fermentation. Appl Environ Microbiol. 2011;77:727-31 pubmed publisher
    b>Diacetyl (2,3-butanedione) imparts an unpleasant "butterscotch-like" flavor to alcoholic beverages such as beer, and therefore its concentration needs to be reduced below the sensory threshold before packaging...
  30. Gao J, Xu Y, Li F, Ding G. Production of S-acetoin from diacetyl by Escherichia coli transformant cells that express the diacetyl reductase gene of Paenibacillus polymyxa ZJ-9. Lett Appl Microbiol. 2013;57:274-81 pubmed publisher
    ..In the current work, a gene encoding diacetyl reductase (DAR) from a Paenibacillus polymyxa strain ZJ-9 was cloned and expressed in Escherichia coli...
  31. van Rooy F, Rooyackers J, Prokop M, Houba R, Smit L, Heederik D. Bronchiolitis obliterans syndrome in chemical workers producing diacetyl for food flavorings. Am J Respir Crit Care Med. 2007;176:498-504 pubmed
    ..at risk of developing bronchiolitis obliterans associated with exposure to butter flavoring volatiles, including diacetyl. To investigate the risk of bronchiolitis obliterans for chemical workers producing diacetyl, with exposure to ..
  32. Matsuura T, Endo S, Iwamoto R, Takahashi H, Ichinose M. Developmental changes in chemotactic response and choice of two attractants, sodium acetate and diacetyl, in the nematode Caenorhabditis elegans. Comp Biochem Physiol A Mol Integr Physiol. 2007;147:920-7 pubmed
    ..behavior of the nematode Caenorhabditis elegans to chemical attractants, water-soluble sodium acetate and odorant diacetyl, was investigated using nematodes at various developmental stages to examine the effects of postembryonic ..
  33. Prakki A, Pereira P, Kalachandra S. Effect of propionaldehyde or 2,3-butanedione additives on the mechanical properties of Bis-GMA analog-based composites. Dent Mater. 2009;25:26-32 pubmed publisher
    ..The findings correlate with the ability of additives to improve degree of conversion of some composite systems thereby enhancing mechanical properties. ..
  34. Wang Y, Li L, Ma C, Gao C, Tao F, Xu P. Engineering of cofactor regeneration enhances (2S,3S)-2,3-butanediol production from diacetyl. Sci Rep. 2013;3:2643 pubmed publisher
    ..Introduction of FDH resulted in higher (2S,3S)-2,3-BD concentration, productivity and yield from diacetyl, and large increase in the intracellular NADH concentration...
  35. Egilman D, Schilling J, Menendez L. A proposal for a safe exposure level for diacetyl. Int J Occup Environ Health. 2011;17:122-34 pubmed
    b>Diacetyl is a naturally occurring compound that has been used in concentrated form as a food additive, particularly in butter flavorings...
  36. Baker L, Wolk R, Choi B, Watkins S, Plan P, Shah A, et al. Effects of mechanical uncouplers, diacetyl monoxime, and cytochalasin-D on the electrophysiology of perfused mouse hearts. Am J Physiol Heart Circ Physiol. 2004;287:H1771-9 pubmed
    Chemical uncouplers diacetyl monoxime (DAM) and cytochalasin D (cyto-D) are used to abolish cardiac contractions in optical studies, yet alter intracellular Ca(2+) concentration ([Ca(2+)](i)) handling and vulnerability to arrhythmias in a ..
  37. Oliver T, Dembo M, Jacobson K. Separation of propulsive and adhesive traction stresses in locomoting keratocytes. J Cell Biol. 1999;145:589-604 pubmed
  38. Morris J, Hubbs A. Inhalation dosimetry of diacetyl and butyric acid, two components of butter flavoring vapors. Toxicol Sci. 2009;108:173-83 pubmed publisher
    ..The goal of the current study was to characterize inhalation dosimetric patterns of diacetyl and butyric acid, two components of BFV, and to develop a hybrid computational fluid dynamic-physiologically ..
  39. Temprana C, Duarte E, Taira M, Lamy M, del Valle Alonso S. Structural characterization of photopolymerizable binary liposomes containing diacetylenic and saturated phospholipids. Langmuir. 2010;26:10084-92 pubmed publisher
    ..A model explaining lipids rearrangement is proposed for this partially polymerized system. ..
  40. Sathaye A, Bursac N, Sheehy S, Tung L. Electrical pacing counteracts intrinsic shortening of action potential duration of neonatal rat ventricular cells in culture. J Mol Cell Cardiol. 2006;41:633-41 pubmed
    ..These effects produce a steadier functional phenotype that may be beneficial for electrophysiological studies. ..
  41. Zalán Z, Hudáček J, Tóth Markus M, Husová E, Solichová K, Hegyi F, et al. Sensorically and antimicrobially active metabolite production of Lactobacillus strains on Jerusalem artichoke juice. J Sci Food Agric. 2011;91:672-9 pubmed publisher
    ..25-1.77 mg L(-1) ), mannitol (0.06-3.24 g L(-1) ), acetoin and diacetyl production of strains varies not only according to the species but also from strain to strain, which will be ..
  42. Qin H, Kay M, Chattipakorn N, Redden D, Ideker R, Rogers J. Effects of heart isolation, voltage-sensitive dye, and electromechanical uncoupling agents on ventricular fibrillation. Am J Physiol Heart Circ Physiol. 2003;284:H1818-26 pubmed
    ..dye di-4-ANEPPS, and six more episodes were mapped after exposure to the electromechanical uncoupling agents diacetyl monoxime (DAM; 20 mmol/l, n = 6) or cytochalasin D (CytoD; 10 micromol/l, n = 6)...
  43. Shiono Y, Fujita Y, Oka S, Yamazaki Y. ATPase inhibitors suppress actinomycin D-induced apoptosis in leukemia cells. Anticancer Res. 2002;22:2907-11 pubmed
    ..Since geldanamycin and radicicol are specific inhibitors of the ATPase in HSP90, the present result implies that ATPase activity in HSP90 plays some role in this apoptosis. ..
  44. Singh S, Pandey V, Naaz H, Dwivedi U. Phylogenetic analysis, molecular modeling, substrate-inhibitor specificity, and active site comparison of bacterial, fungal, and plant heme peroxidases. Biotechnol Appl Biochem. 2012;59:283-94 pubmed publisher
    ..Phenylglyoxal, 1,2-cyclohexanedione, and 2,3-butanedione were found to be most potent inhibitors of bacterial, fungal, and plant peroxidases, respectively...
  45. Saltman A, Aksehirli T, Valiunas V, Gaudette G, Matsuyama N, Brink P, et al. Gap junction uncoupling protects the heart against ischemia. J Thorac Cardiovasc Surg. 2002;124:371-6 pubmed
    ..This protection is not a direct result of a decrease in developed pressure before a prolonged ischemic period nor is it achieved through a mechanism involving the adenosine triphosphate-dependent potassium channel. ..
  46. Esteve M, Frigola A, Rodrigo M, Rodrigo M. Use of polarography as a quality-control method for determining diacetyl in citrus and vegetable juices, yoghurt and butter. Food Addit Contam. 2002;19:519-23 pubmed
    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...
  47. Habazettl H, Voigtlander J, Leiderer R, Messmer K. Efficacy of myocardial initial reperfusion with 2,3 butanedione monoxime after cardioplegic arrest is time-dependent. Cardiovasc Res. 1998;37:684-90 pubmed
    ..Thus, contraction uncoupling during initial reperfusion by BDM or similarly acting drugs may prove a viable technique to reduce myocardial reperfusion damage in patients undergoing open heart surgery. ..
  48. Kindig C, Stary C, Hogan M. Effect of dissociating cytosolic calcium and metabolic rate on intracellular PO2 kinetics in single frog myocytes. J Physiol. 2005;562:527-34 pubmed
  49. Fann M, Davies A, Varadhachary A, Kuroda T, Sevier C, Tsuchiya T, et al. Identification of two essential arginine residues in UhpT, the sugar phosphate antiporter of Escherichia coli. J Membr Biol. 1998;164:187-95 pubmed
    ..Accordingly, by virtue of their locations at the entrance to this pathway, we speculate that R46 and R275 function in establishing substrate specificity. ..
  50. Ma X, Du C, Zheng J, Chen X. [Studies on chemical constituents of Gaultheria leucocarpa var. Yunnanensis (Franch.) T. Z. Hsu & R. C. Fang]. Zhongguo Zhong Yao Za Zhi. 2001;26:844-5 pubmed
    ..To separate and identify the chemical constituents of the aerial part of Gaultheria leucocarpa var. yunnanensis...
  51. Zhou R, Watson C, Fu C, Yao X, Forte J. Myosin II is present in gastric parietal cells and required for lamellipodial dynamics associated with cell activation. Am J Physiol Cell Physiol. 2003;285:C662-73 pubmed
    ..However, myosin II plays an important role in regulating lamellipodial dynamics and cortical actomyosin associated with parietal cell activation. ..
  52. Wang X, Hou Z, Lu W, Chen F, Zheng X. Identification of 2,3-butanedione monoxime hydrogenation products by gas chromatography-mass spectrometry in an ion trap mass spectrometer. J Chromatogr A. 1999;855:341-7 pubmed
  53. Fernández García E, Carbonell M, Nunez M. Volatile fraction and sensory characteristics of Manchego cheese. 1. Comparison of raw and pasteurized milk cheese. J Dairy Res. 2002;69:579-93 pubmed
    ..b>Diacetyl was positively correlated with the aroma attribute 'toasted' and negatively correlated with aroma quality in PM ..