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At least 19 recordsLinked to original sources
PubMed1970

Enzymatic removal of diacetyl from beer. II. Further studies on the use of diacetyl reductase.

Diacetyl removal from beer was studied with whole cells and crude enzyme extracts of yeasts and bacteria. Cells of Streptococcus diacetilactis 18-16 destroyed diacetyl in solutions at a rate almost equal to that achieved by the addition of whole yeast cells. Yeast cells impregnated in a diatomaceous earth filter bed removed all diacetyl from solutions percolated through the bed. Undialyzed crude enzyme extracts from yeast cells removed diacetyl very slowly from beer at its normal pH (4.1); at a pH of 5.0 or higher, rapid diacetyl removal was achieved. Dialyzed crude enzyme extracts from yeast cells were found to destroy diacetyl in a manner quite similar to that of diacetyl reductase from Aerobacter aerogenes, and both the bacterial and the yeast extracts were stimulated significantly by the addition of reduced nicotinamide adenine dinucleotide (NADH). Diacetyl reductase activity of four strains of A. aerogenes was compared; three of the strains produced enzyme with approximately twice the specific activity of the other strain (8724). Gel electrophoresis results indicated that at least three different NADH-oxidizing enzymes were present in crude extracts of diacetyl reductase. Sephadex-gel chromotography separated NADH oxidase from diacetyl reductase. It was also noted that ethyl alcohol concentrations approximately equivalent to those found in beer were quite inhibitory to diacetyl reductase.

Acetobacter↗
PubMed1988

Kinetics of the diacetyl and 2,3-pentanedione reduction by diacetyl reductase (alpha-diketone reductase (NAD)) from Staphylococcus aureus.

The kinetic mechanism of diacetyl and 2,3-pentanedione reduction by diacetyl reductase from Staphylococcus aureus was investigated. The shape of the primary double reciprocal plots, the product inhibition pattern, and the features of the inhibition by a substrate analogue (acetone) show that diacetyl is reduced via an Ordered Bi-Bi mechanism, and 2,3-pentanedione by an Ordered Bi-Bi or Theorell-Chance mechanism. NADH is the leading substrate in both reactions. Affinity constants for the coenzyme and the substrates and inhibition constants for NAD, acetoin, and acetone were also calculated. This enzyme has a high affinity for NADH; Km (31-50 microM) and Ks (20-27 microM) for this compound are around one-tenth of the NADH intracellular concentration. Therefore, it must operate in vivo saturated with the coenzyme. This condition is not adequate to play the role, formerly proposed for diacetyl reductases, of regulating the equilibrium between oxidized and reduced forms of pyridine-nucleotides.

Acetoin Dehydrogenase↗
PubMed2006

Diacetyl emissions and airborne dust from butter flavorings used in microwave popcorn production.

In microwave popcorn workers, exposure to butter flavorings has been associated with fixed obstructive lung disease resembling bronchiolitis obliterans. Inhalation toxicology studies have shown severe respiratory effects in rats exposed to vapors from a paste butter flavoring, and to diacetyl, a diketone found in most butter flavorings. To gain a better understanding of worker exposures, we assessed diacetyl emissions and airborne dust levels from butter flavorings used by several microwave popcorn manufacturing companies. We heated bulk samples of 40 different butter flavorings (liquids, pastes, and powders) to approximately 50 degrees C and used gas chromatography, with a mass selective detector, to measure the relative abundance of volatile organic compounds emitted. Air sampling was conducted for diacetyl and for total and respirable dust during the mixing of powder, liquid, or paste flavorings with heated soybean oil at a microwave popcorn plant. To further examine the potential for respiratory exposures to powders, we measured dust generated during different simulated methods of manual handling of several powder butter flavorings. Powder flavorings were found to give off much lower diacetyl emissions than pastes or liquids. The mean diacetyl emissions from liquids and pastes were 64 and 26 times larger, respectively, than the mean of diacetyl emissions from powders. The median diacetyl emissions from liquids and pastes were 364 and 72 times larger, respectively, than the median of diacetyl emissions from powders. Fourteen of 16 powders had diacetyl emissions that were lower than the diacetyl emissions from any liquid flavoring and from most paste flavorings. However, simulated handling of powder flavorings showed that a substantial amount of the airborne dust generated was of respirable size and could thus pose its own respiratory hazard. Companies that use butter flavorings should consider substituting flavorings with lower diacetyl emissions and the use of ventilation and enclosure engineering controls to minimize exposures. Until controls are fully implemented, companies should institute mandatory respiratory protection for all exposed workers.

Air Pollutants, Occupational↗
PubMed2002

Effects of diacetyl and carbon dioxide on spoilage microflora in ground beef.

The effect of CO2 and diacetyl, alone or in combination, on spoilage microflora in ground beef was determined. Ground beef was treated with 20, 30, or 40% CO2 for 22 days (study I); 20, 50, or 100 microg/g diacetyl for 26 days (study II); or a combination of 20% CO2 and 100 microglg diacetyl for 40 days (study III). Antimicrobial effectiveness was determined by aerobic plate counts (log10 CFU/g) using plate count agar (total aerobic bacteria), deMan Rogosa Sharpe (MRS) Lactobacillus agar (gram-positive bacteria), MacConkey agar (gram-negative bacteria), pH, and informal organoleptic assessments (by appearance and by odor). In study I, total bacteria and pH increased by day 4 in control meat samples. For all CO2 levels, gram-negative bacteria decreased and gram-positive bacteria increased compared with untreated controls. The pH remained constant for CO2-treated meat. Control samples had an off-odor and a brown appearance, while CO2-treated samples had no off-odor but did have a brown appearance. For samples treated with diacetyl (study II), spoilage was evident by day 7 for samples treated with 0, 20. and 50 microg/g diacetyl for all parameters examined. Ground beef treated with 100 microg/g diacetyl was spoiled on day 12. Diacetyl was detected (by odor) in samples that were treated with 100 microg/g diacetyl and had a brown appearance. Meat samples treated with the combination of CO2 and diacetyl (study III) showed that the addition of diacetyl did not have an additive effect on microbial growth. Combination-treated meat maintained a red appearance and no off-odor. Diacetyl and CO2 could be used in combination to maintain a red color and inhibit spoilage microorganisms.

Animals↗
PubMed2004

The 'buttery' attribute of wine--diacetyl--desirability, spoilage and beyond.

The diketone, diacetyl, is a major flavour metabolite produced by lactic acid bacteria (LAB). Of the LAB associated with wine, Oenococcus oeni is encouraged during the malolactic (ML) fermentation, a biodeacidification of wine during which the metabolism of diacetyl occurs. Diacetyl, which imparts a buttery aroma and flavour to many fermented foods and beverages, is a key flavour compound of most fermented dairy products. In wine, diacetyl has important stylistic implications. The biosynthesis of diacetyl is dependent upon citric acid metabolism and diacetyl is an intermediate metabolite which can be further reduced to acetoin and the alcohol, 2,3-butanediol. This review will focus on the sensory perception, metabolism, genetics and analysis of diacetyl during wine production. The extensive knowledge of diacetyl metabolism in dairy LAB is used to enhance the understanding of diacetyl metabolism of wine LAB. Factors which can effect the formation and concentration of diacetyl in wine are discussed. These include malolactic bacterial strain, wine chemical and physical parameters (pH, temperature, citric acid, sulfur dioxide, aeration) and the presence of yeast lees. Finally, the affects of other wine components, such as phenolics, are discussed.

Citric Acid↗
PubMed2006

Popcorn worker's lung: in vitro exposure to diacetyl, an ingredient in microwave popcorn butter flavoring, increases reactivity to methacholine.

Workers who inhale microwave popcorn butter flavorings experience decrements in lung function and can develop clinical bronchiolitis obliterans, i.e., "popcorn worker's lung" (Kreiss, K., Gomaa, A., Kullman, G., Fedan, K., Simoes, E.J., Enright, P.L., 2002. Clinical bronchiolitis obliterans in workers at a microwave-popcorn plant. N. Engl. J. Med. 347, 330-338.). In a rat inhalation model, vapors of an artificial butter flavoring damaged the epithelium of the upper and lower airways (Hubbs, A.F., Battelli, L.A., Goldsmith, W.T., Porter, D.W., Frazer, D., Friend, S., Schwegler-Berry, D., Mercer, R.R., Reynolds, J.S., Grote, A., Castranova, V., Kullman, G., Fedan, J.S., Dowdy, J., Jones, W.G., 2002. Necrosis of nasal and airway epithelium in rats inhaling vapors of artificial butter flavoring. Toxicol. Appl. Pharmacol. 185, 128-135.). Diacetyl, a butter flavoring component, is a major volatile ketone in the popcorn-processing workplace. We investigated the effects of diacetyl on epithelium of guinea pig isolated airway preparations and the effects of diacetyl in vitro on reactivity to bronchoactive agents. In the isolated, perfused trachea preparation, diacetyl added to the intraluminal (mucosal) bath elicited responses that began with contraction (threshold ca. 3 mM) and ended with relaxation. After a 4-h incubation with intraluminal diacetyl (3 mM), contractions to extraluminal (serosal) methacholine (MCh) were slightly increased; however, sensitivity to intraluminally (mucosally) applied MCh was increased by 10-fold. Relaxation responses of MCh (3 x 10(-7) M)-contracted tracheas to extraluminally applied terbutaline and intraluminally applied 120 mM KCl, to evoke epithelium-derived relaxing factor release, were unaffected by diacetyl. Exposure of the tracheal epithelium in Ussing chambers to diacetyl decreased transepithelial potential difference and resistance. These findings suggest that diacetyl exposure compromised epithelial barrier function, leading to hyperreactivity to mucosally applied MCh. The respiratory epithelium appears to serve as an initial target for the toxic effects of diacetyl in the airways.

Animals↗
PubMed1990

Purification and properties of two oxidoreductases catalyzing the enantioselective reduction of diacetyl and other diketones from baker's yeast.

The NADPH-linked diacetyl reductase system from the cytosolic fraction of Saccharomyces cerevisiae has been resolved into two oxidoreductases catalyzing irreversibly the enantioselective reduction of diacetyl (2,3-butanedione) to (S)- and (R)-acetoin (3-hydroxy-2-butanone) [so-called (S)- and (R)-diacetyl reductases] (EC 1.1.1.5) which have been isolated to apparent electrophoretical purity. The clean-up procedures comprising streptomycin sulfate treatment, Sephadex G-25 filtration, DEAE-Sepharose CL-6B column chromatography, affinity chromatography on Matrex Gel Red A and Superose 6 prep grade filtration led to 120-fold and 368-fold purifications, respectively. The relative molecular mass of the (R)-diacetyl reductase, estimated by means of HPLC filtration on Zorbax GF 250 and sodium dodecyl sulfate/polyacrylamide gel electrophoresis, was 36,000. The (R)-enzyme was most active at pH 6.4 and accepted in addition to diacetyl C5-, C6-2,3-diketones, 1,2-cyclohexanedione, 2-oxo aldehydes and short-chain 2- and 3-oxo esters as substrates. The enzyme was characterized by high enantioselectivity and regiospecificity. The Km values for diacetyl and 2,3-pentanedione were determined as 2.0 mM. The Mr of the (S)-diacetyl reductase was determined as 75,000 by means of HPLC filtration of Zorbax GF 250. The enzyme decomposed into subunits of Mr 48,000 and 24,000 on sodium dodecyl sulfate/polyacrylamide gel electrophoresis. The optimum pH was 6.9. The purified (S)-enzyme reduced stereospecifically a broad spectrum of substrates, comprising 2,3-, 2,4- and 2,5-diketones, 2-oxo aldehydes, 1,2-cyclohexanedione and methyl ketones as well as 3-, 4- and 5-oxo esters. The 2,3- and 2,4-diketones are transformed to the corresponding (S)-2-hydroxy ketones; 2,5-hexanedione, however, was reduced to (S,S)-2,5-hexanediol. The Km values for diacetyl and 2,3-pentanedione were estimated as 2.3 and 1.5 mM, respectively. Further characterization of the (S)-diacetyl reductase revealed that it is identical with the so-called '(S)-enzyme', involved in the enantioselective reduction of 3-, 4- and 5-oxo esters in baker's yeast.

Acetoin Dehydrogenase↗
PubMed2003

Use of diacetyl to reduce the load of Vibrio vulnificus in the Eastern oyster, Crassostrea virginica.

Vibrio vulnificus is a highly virulent human pathogen that occurs naturally among the microflora of oysters. This organism has two portals of entry into humans, one of which is ingestion. Oysters containing V. vulnificus consumed in a raw or undercooked state often serve as a vehicle for the transmission of this organism. Previous studies 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. vulnificus in oysters. The purpose of this study was to further examine the role of diacetyl, along with that of depuration, in reducing loads of V. vulnificus. Shellstock oysters were treated with various concentrations of diacetyl, and we found that many of the oysters ceased pumping when diacetyl was added. The data obtained in this study indicated that treatment with diacetyl is ineffective; however, any reduction in V. vulnificus numbers may be masked when groups of oysters, some of which may not have taken up diacetyl, are sampled. We then investigated the efficacy of diacetyl in lowering levels of V. vulnificus in shucked oysters. Diacetyl was found to significantly reduce the load of V. vulnificus in shucked oysters containing natural populations. Overall, it appears that treatment with diacetyl is ineffective for shellstock oysters, although it has potential for use in reducing loads of V. vulnificus in shucked oysters.

Animals↗
PubMed1996

Effect of propanal and diacetyl on quantity of remaining double bonds of chemically cured BisGMA/TEGDMA resins.

The aim of the present study was to determine the effect of propanal and diacetyl addition on the quantity of remaining double bonds of chemically cured dental resins. Propanal (propionaldehyde) or diacetyl (2,3-butanedione) was added to monomer mixtures, which were then made chemically curable. The monomer mixtures were varied with respect to content of propanal or diacetyl. Addition of propanal or diacetyl to chemically curable resins resulted in a decrease in the quantity of remaining double bonds from 19.6% to 1.9% and from 19.6% to 11.4%, respectively. A negative correlation of statistical significance was found between content of propanal and quantity of remaining double bonds, while the relationship between content of diacetyl and quantity of remaining double bonds was found not to be linear. Propanal was equally effective in reducing the quantity of remaining double bonds in chemically cured and in the light cured resins studied previously. As regards diacetyl, a more pronounced effect on quantity of remaining double bonds was noted for light cured resins as compared with chemically cured resins. The most likely common reaction mechanism of propanal and diacetyl seemed to be that of chain transfer reactions. Furthermore, analysis of the data indicated a possible additional photoinitiating function of diacetyl.

Aldehydes↗
PubMed1999

Effect of diacetyl on controlling Escherichia coli O157:H7 and Salmonella Typhimurium in the presence of starter culture in a laboratory medium and during meat fermentation.

Diacetyl is a flavor compound that possesses antimicrobial activity and is found in several dairy products. The effect of diacetyl on controlling the growth of two foodborne pathogens, Escherichia coli O157:H7 and Salmonella Typhimurium, when grown with Pediococcus acidilactici as a meat starter culture was evaluated in a laboratory medium and during salami fermentation. Diacetyl (50 ppm) added to each mixed culture system strongly inhibited the growth of E. coli O157:H7 and Salmonella Typhimurium in the laboratory medium (brain heart infusion, 2.3% of NaCl, 0.75% of dextrose) (P < 0.05). During meat fermentation, the growth of E. coli O157:H7 and Salmonella Typhimurium was inhibited significantly by addition of diacetyl (300 ppm) (P < 0.05) after 24 h fermentation. However, the acid production and growth of P. acidilactici were not affected by the addition of diacetyl (P > 0.05). After 24 h meat fermentation, about a 1.0-log CFU/g difference occurred in numbers of each foodborne pathogen mixed with P. acidilactici (P < 0.05) with and without 300 ppm diacetyl. Diacetyl and the acid produced by the meat starter culture reduced the growth of the two foodborne pathogens during salami fermentation. These results suggest that diacetyl can be used as a food ingredient during meat fermentation to control E. coli O157:H7 and Salmonella Typhimurium without harmful effects on the growth and acid production of P. acidilactici.

Animals↗
PubMed1973

Diacetyl, acetoin, and acetaldehyde production by mixed-species lactic starter cultures.

Citrate utilization and acetoin, diacetyl, acetaldehyde, and lactic acid production in milk at 21 C by five different mixed-strain starters, containing Streptococcus diacetilactis (D type), Leuconostoc (B type), and S. diacetilactis and Leuconostoc (BD type), were measured. BD and D cultures utilized citrate more rapidly and produced more diacetyl, acetoin, and acetaldehyde than B types. All cultures produced much more acetoin than diacetyl, with the BD and D cultures producing four to five times larger amounts of acetoin than the B cultures. Reduction of diacetyl and acetoin toward the end of the normal incubation period was characteristic of BD and D cultures, whereas a similar reduction of acetaldehyde was characteristic of BD and especially of B cultures. Continued incubation of B cultures beyond 17 h also resulted in reduction of diacetyl and acetoin. Addition of citrate to the milk retarded diacetyl and acetoin reduction. Mn(2+) had no effect on diacetyl production by a BD culture but increased citrate utilization and, as a consequence, caused greater diacetyl destruction in one of the B cultures.

Acetaldehyde↗
PubMed1988

Towards diacetyl-less brewers' yeast. Influence of ilv2 and ilv5 mutations.

During alcoholic fermentations, the off-flavour compound diacetyl is formed non-enzymatically from acetolactate leaking out from the cells. Acetolactate is an intermediate in the biosynthesis of valine. In beer fermentation, the amount of diacetyl is reduced to acceptable levels during maturation. A reduction of the time needed for maturation may be achieved by the use of a brewing yeast that produces less diacetyl. Saccharomyces cerevisiae laboratory strains with an inactive ilv2 gene can not form acetolactate, while ilv5 strains, blocked in the subsequent step, leak acetolactate in high amounts. Induction of recessive mutations in production strains of Saccharomyces carlsbergensis has not yet been achieved, as the yeast is polyploid and possibly a hybrid between S. cerevisiae and another Saccharomyces species. Thus, all chromosomes investigated so far are present in at least two genetically different versions. Genetic and molecular analysis has shown that the brewing yeast is structurally heterozygous for ILV2 and ILV5. Genetic modification of brewers' yeast to reduce diacetyl formation is being carried out by mutation of ILV2. Deletion mutations in both ILV2 alleles have been constructed in vitro to be used for gene replacement in the brewing strain. In addition, partial inactivation of the ILV2 function is carried out by selecting spontaneous dominant mutations resistant to the herbicide sulfometuron methyl. Among these mutants some produce only half the amount of diacetyl compared to the parental strain. An alternative way to reduce diacetyl production might be to increase the activity of the ILV5 gene product. Model experiments in S. cerevisiae show that the presence of the ILV5 gene on a 2-micron based multi-copy vector can reduce the diacetyl production by half.

Acetolactate Synthase↗
PubMed1982

Diacetyl: a new substrate in the overall reaction of the pyruvate dehydrogenase complex.

Pig heart pyruvate dehydrogenase complex (pyruvate: lipoamide oxidoreductase (decarboxylating and acceptor-acetylating), EC 1.2.4.1) catalyzes the decomposition of diacetyl to acetate, acetyl-CoA and produces reduced NAD+ with 1:1:1 stoichiometry. The reaction rate with diacetyl is approximately 7.1% of that with pyruvate. The Km value for diacetyl was found to be 0.46 mM. Acetoin and acetaldehyde inhibit the pyruvate dehydrogenase-catalyzed reaction of diacetyl with Ki values of 0.91 mM and 0.48 mM, respectively. Inhibition patterns show that they are competitive inhibitors versus diacetyl. Acetate, as product, does not inhibit the enzymatic decomposition of diacetyl. Diacetyl is not only an alternative substrate in the pyruvate dehydrogenase reaction, but a competitive inhibitor versus pyruvate with a Ki value of 0.43 mM.

Acetaldehyde↗
PubMed1984

Possibility of diacetyl and related compounds as the 4-carbon compound necessary for the formation of riboflavin in Ashbya gossypii.

The effects of various compounds (0.5%) involved in the butanediol and the glycolytic pathways on riboflavin formation in whole cells of Ashbya gossypii at rest were examined. The addition of acetate, glycerol and diacetyl inhibited riboflavin formation, while the addition of acetoin had no effect on it, and the addition of ethanol, 2,3-butanediol, pyruvic acid and glucose accelerated it. The relation of diacetyl and acetoin to riboflavin formation during resting cell incubation in the presence of 0.5% ethanol and various concentrations of 2,3-butanediol was examined. The results quantitatively revealed a precursor-product relation between riboflavin formation and the formation of diacetyl and acetoin. The results obtained provide evidence that a high flavinogenic agent, ethanol, was converted to acetaldehyde, pyruvic acid, acetoin and diacetyl in this order, that a week flavinogenic agent, 2,3-butanediol, was transferred to diacetyl through acetoin, and that the diacetyl produced can be utilized as the 4-carbon compound for riboflavin formation in the flavinogenic mold, Ashbya gossypii. It remains obscure whether diacetyl is enzymatically involved in riboflavin formation.

Acetaldehyde↗