Diacetyl

Diacetyl[1]
Names
Preferred IUPAC name
Butane-2,3-dione
Other names
Diacetyl
Biacetyl
Dimethyl diketone
2,3-Diketobutane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.428
KEGG
UNII
Properties
C4H6O2
Molar mass 86.09 g·mol−1
Appearance Yellowish green liquid
Density 0.990 g/mL at 15 °C
Melting point −2 to −4 °C (28 to 25 °F; 271 to 269 K)
Boiling point 88 °C (190 °F; 361 K)
200 g/L (20 °C)
Hazards
Main hazards Harmful, flammable
Safety data sheet External MSDS
R-phrases (outdated) R10 R22 R36 R37 R38
S-phrases (outdated) S9 S16 S33
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diacetyl (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow/green liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. Diacetyl occurs naturally in alcoholic beverages and is added to some foods to impart its buttery flavor.

Chemical structure

A distinctive feature of diacetyl (and other 1,2-diketones) is the long C–C bond linking the carbonyl centers. This bond distance is about 1.54 Å, compared to 1.45 Å for the corresponding C–C bond in 1,3-butadiene. The elongation is attributed to repulsion between the polarized carbonyl carbon centers.[2]

Occurrence

Diacetyl arises naturally as a byproduct of fermentation. In some fermentative bacteria, it is formed via the thiamine pyrophosphate-mediated condensation of pyruvate and acetyl CoA.[3] Sour (cultured) cream, cultured buttermilk, and cultured butter are produced by inoculating pasteurized cream or milk with a lactic starter culture, churning (agitating) and holding the milk until a desired pH drop (or increase in acidity) is attained. Cultured cream, cultured butter, and cultured buttermilk owe their tart flavour to lactic acid bacteria and their buttery aroma and taste to diacetyl.[4]

Production

Diacetyl is produced industrially by dehydrogenation of 2,3-butanediol. Acetoin is an intermediate.[5]

Applications

In food products

Diacetyl and acetoin are two compounds that give butter its characteristic taste. Because of this, manufacturers of artificial butter flavoring, margarines or similar oil-based products typically add diacetyl and acetoin (along with beta-carotene for the yellow color) to make the final product butter-flavored, because it would otherwise be relatively tasteless.[6]

In alcoholic beverages

At low levels, diacetyl contributes a slipperiness to the feel of the alcoholic beverage in the mouth. As levels increase, it imparts a buttery or butterscotch flavor.

In some styles of beer (e.g. in most beers produced in Britain and Ireland, such as India Pale Ale), the presence of diacetyl can be acceptable or desirable at low or, in some cases, moderate levels. In other styles, its presence is considered a flaw or undesirable.[7]

Diacetyl is produced during fermentation as a byproduct of valine synthesis, when yeast produces α-acetolactate, which escapes the cell and is spontaneously decarboxylated into diacetyl. The yeast then absorbs the diacetyl, and reduces the ketone groups to form acetoin and 2,3-butanediol.

Beer sometimes undergoes a "diacetyl rest", in which its temperature is raised slightly for two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavor it imparts.[8] Diacetyl is present in some chardonnays known as "butter bombs", although there is a trend back toward the more traditional French styles.[9]

Concentrations from 0.005 mg/L to 1.7 mg/L were measured in chardonnay wines, and the amount needed for the flavor to be noticed is at least 0.2 mg/L.[10][11]

Other

1-Hexanol and diacetyl are strong inhibitors of the CO2-sensitive neurons in the Drosophila melanogaster fruit fly and the Culex mosquito, a vector of several deadly diseases.[12] Fruit flies tend to avoid CO2, but exhaled CO2 is the main attractant for the Culex.[13]

Safety

Worker safety

United States

The United States National Institute for Occupational Safety and Health has suggested diacetyl, when used in artificial butter flavoring (as used in many consumer foods), may be hazardous when heated and inhaled over a long period.

Workers in several factories that manufacture artificial butter flavoring have been diagnosed with bronchiolitis obliterans, a rare and serious disease of the lungs. The cases found have been mainly in young, healthy, nonsmoking males. As with other end-stage lung diseases, transplantation is currently the most viable treatment option. However, lung transplant rejection is very common and happens to be another setting in which bronchiolitis obliterans is known to occur.

The disease has been called "popcorn worker's lung" because it was first seen in former workers of a microwave popcorn factory in Missouri,[14] but NIOSH refers to it by the more general term "flavorings-related lung disease".[14] It has also been called "flavorings-related bronchiolitis obliterans"[14] or diacetyl-induced bronchiolitis obliterans.[15] People who work with flavorings that include diacetyl are at risk for flavorings-related lung disease, including those who work in popcorn factories, restaurants, other snack food factories, bakeries, candy factories, margarine and cooking spread factories, and coffee processing facilities.[16]

In 2006, the International Brotherhood of Teamsters and the United Food and Commercial Workers petitioned the U.S. OSHA to promulgate an emergency temporary standard to protect workers from the deleterious health effects of inhaling diacetyl vapors.[17] The petition was followed by a letter of support signed by more than 30 prominent scientists.[18] The matter is under consideration. On January 21, 2009, OSHA issued an advance notice of proposed rulemaking for regulating exposure to diacetyl.[19] The notice requests respondents to provide input regarding adverse health effects, methods to evaluate and monitor exposure, the training of workers. That notice also solicited input regarding exposure and health effects of acetoin, acetaldehyde, acetic acid and furfural.[20]

Two bills in the California Legislature seek to ban the use of diacetyl.[21][22][23]

A 2010 U.S. OSHA Safety and Health Information Bulletin and companion Worker Alert recommend employers use safety measures to avoid exposing employees to the potentially deadly effects of butter flavorings and other flavoring substances containing diacetyl or its substitutes.[24]

A preliminary in vitro study, published in 2012, suggests that diacetyl may exacerbate the effects of beta-amyloid aggregation, a process linked to Alzheimer's disease.[25] Research in rats and mice has shown that diacetyl can damage the airway and damage cells that line the airway.[16]

In 2015 there were allegations that the health of workers who roast coffee is threatened by diacetyl.[26][27]

Consumer safety

In 2007, the Flavor and Extract Manufacturers Association recommended reducing diacetyl in butter flavorings.[28] Manufacturers of butter flavored popcorn including Pop Weaver, Trail's End, and ConAgra Foods (maker of Orville Redenbacher's and Act II) began removing diacetyl as an ingredient from their products.[29][30]

In 2012, Wayne Watson, a regular microwavable popcorn consumer for years, was awarded US$7.27 million in damages from a federal jury in Denver, which decided his lung disease was caused by the chemicals in microwave popcorn and that the popcorn's manufacturer, Gilster-Mary Lee Corporation, and the grocery store that sold it should have warned him of its dangers.[31][32][33]

European Union Regulation

The European Commission has declared diacetyl is legal for use as a flavouring substance in all EU states.[34] As a diketone, diacetyl is included in the EU's flavouring classification Flavouring Group Evaluation 11 (FGE.11). A Scientific Panel of the EU Commission evaluated six flavouring substances (not including diacetyl) from FGE.11 in 2004.[35] As part of this study, the panel reviewed available studies on several other flavourings in FGE.11, including diacetyl. Based on the available data, the panel reiterated the finding that there were no safety concerns for diacetyl's use as a flavouring.

In 2007, the European Food Safety Authority (EFSA), the EU's food safety regulatory body, stated its scientific panel on food additives and flavourings (AFC) was evaluating diacetyl along with other flavourings as part of a larger study. "The experts of the EFSA AFC panel and its working group on food additives will look at this issue to see if new scientific evidence is available that may require further actions. If the experts conclude that consumer exposure to diacetyl can reach levels well above those considered as safe and, that a possible health risk for consumers cannot be excluded when inhaling diacetyl, EFSA will give priority to the re-evaluation of this substance and provide detailed scientific advice."[36]

Electronic cigarettes

A 2014 publication found that diacetyl was present in samples of many sweet-flavored electronic cigarette liquids, though at levels 100 times lower than that of tobacco smoke.[37] According to that research, diacetyl is approved for food use, but is associated with respiratory disease when inhaled. The study concluded that diacetyl is an avoidable risk for electronic cigarette liquid, and measures could be taken by the industry to eliminate its usage, without limiting availability of flavors. In 2015, another test of 51 purpose-selected liquids found diacetyl at trace levels or higher in 39 of the liquids.[38]

See also

References

  1. ↑ Merck Index (11th ed.). p. 2946.
  2. ↑ Eriks, K.; Hayden, T. D.; Yang, S. Hsi; Chan, I. Y. (1983). "Crystal and molecular structure of biacetyl (2,3-butanedione), (H3CCO)2, at −12 and −100 °C". J. Am. Chem. Soc. 105 (12): 3940–3942. doi:10.1021/ja00350a032.
  3. ↑ Speckman, R. A.; Collins, E. B. (1968). "Diacetyl biosynthesis in Streptococcus diacetilactis and Leuconostoc citrovorum". J. Bacteriol. 95 (1): 174–80. PMC 251989 Freely accessible. PMID 5636815.
  4. ↑ Jay, James M. Modern Food Microbiology (6th ed.). p. 120.
  5. ↑ Siegel, H.; Eggersdorfer, M. (2005), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
  6. ↑ Pavia; et al. Introduction to Organic Laboratory Techniques (4th ed.). ISBN 978-0-495-28069-9.
  7. ↑ "Beer Judge Certification Program style guidelines". Beer Judge Certification Program.
  8. ↑ "Diacetyl". E. coli Metabolome Database. ECMDB. Retrieved 20 October 2013.
  9. ↑ "Trends in Chardonnay". Sonoma-Cutrer Vineyards. Retrieved December 2, 2015.
  10. ↑ Nielsen, J. C.; Richelieu, M. (February 1999). "Control of flavor development in wine during and after malolactic fermentation by Oenococcus oeni". Appl. Environ. Microbiol. 65 (2): 740–5. PMC 91089 Freely accessible. PMID 9925610.
  11. ↑ Martineau, B.; Henick-Kling, T.; Acree, T. (1995). "Reassessment of the Influence of Malolactic Fermentation on the Concentration of Diacetyl in Wines". Am. Soc. Enol. Vitic. 46 (3): 385–8.
  12. ↑ "Discovery Of Natural Odors Could Help Develop Mosquito Repellents". Science Daily.
  13. ↑ Turner; et al. (2011). "Ultra-prolonged activation of CO2-sensing neurons disorients mosquitoes". Nature. 474: 87–91. PMC 3150595 Freely accessible. PMID 21637258. doi:10.1038/nature10081.
  14. 1 2 3 Levy, Barry S.; Wegman, David H.; Baron, Sherry L.; Sokas, Rosemary K., eds. (2011). Occupational and environmental health recognizing and preventing disease and injury (6th ed.). New York: Oxford University Press. p. 414. ISBN 9780199750061. Retrieved June 23, 2015.
  15. ↑ Committee to Review the Respiratory Diseases Research Program, Board on Environmental Studies and Toxicology, Division on Earth and Life Studies, National Research Council and Institute of Medicine of the National Academies (2008). Respiratory diseases research at NIOSH : reviews of research programs of the National Institute for Occupational Safety and Health. Washington, D.C.: National Academies Press. p. 139. ISBN 9780309118736. Retrieved June 23, 2015.
  16. 1 2 "CDC - Flavorings-Related Lung Disease: Exposures to Flavoring Chemicals - NIOSH Workplace Safety and Health Topic". www.cdc.gov. Retrieved October 22, 2015.
  17. ↑ "UFCW and Teamsters' Petition to OSHA" (PDF). Defending Science.
  18. ↑ "Scientists' Letter to Secretary Chao" (PDF). Defending Science.
  19. ↑ Federal Register, January 21, 2009 issue
  20. ↑ "OSHA begins rule on diacetyl". Chemical & Engineering News. 87 (4): 24. January 26, 2009.
  21. ↑ Flavoring-Factory Illnesses Raise Inquiries, New York Times, May 6, 2007.
  22. ↑ SB 456 Senate Bill - Bill Analysis
  23. ↑ AB 514 Assembly Bill - Bill Analysis.
  24. ↑ OSHA Recommends Safety Measures to Protect Workers from Diacetyl Exposure, EHS Today, December 10, 2010.
  25. ↑ More, Swati S.; Vartak, Ashish P.; Vince, Robert (2012). "The Butter Flavorant, Diacetyl, Exacerbates β-Amyloid Cytotoxicity". Chemical Research in Toxicology. 25: 120706140246003. doi:10.1021/tx3001016.
  26. ↑ "Coffee roasters' health at risk from chemical compound, air samples suggest". Journal Sentinel. June 20, 2015.
  27. ↑ "Obliterative Bronchiolitis in Workers in a Coffee-Processing Facility — Texas, 2008–2012". Morbidity and Mortality Weekly Report. Centers for Disease Control and Protection. 62 (16): 305–307. April 26, 2013.
  28. ↑ "Comments of the Flavor and Extract Manufacturers Association of the United States on New Information on Butter Flavored Microwave Popcorn" (PDF) (press release). FEMA.
  29. ↑ Weaver Popcorn Company. Press Release: Pop Weaver introduces first microwave popcorn with flavoring containing no diacetyl Archived September 28, 2007, at the Wayback Machine.
  30. ↑ ConAgra Foods Press Release ConAgra Foods press release announcing removal of added diacetyl
  31. ↑ ABC News: 'Popcorn Lung' Lawsuit Nets $7.2M Award
  32. ↑ NewsFeed Researcher: 'Popcorn Lung' Lawsuit Nets $7.2M Award
  33. ↑ Mark Jaffe (September 21, 2012). "Centennial man with "popcorn lung" disease gets $7.3 million award". The Denver Post. Archived from the original on September 22, 2012. Retrieved September 22, 2012.
  34. ↑ http://www.fsai.ie/legislation/food/eu_docs/Flavourings/Dir99.217.pdf Archived November 19, 2007, at the Wayback Machine.
  35. ↑ "Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission" (PDF). The EFSA Journal. 166: 1–44. 2004.
  36. ↑ Europe takes 'wait-and-see' stance on diacetyl flavouring. Oct 2007
  37. ↑ Farsalinos, Konstantinos (September 1, 2014). "Evaluation of electronic cigarette liquids and aerosol for the presence of selected inhalation toxins". Nicotine Tob. Res. online: 168–174. doi:10.1093/ntr/ntu176. Retrieved September 12, 2014.
  38. ↑ Flavoring Chemicals in E-Cigarettes: Diacetyl, 2,3-Pentanedione, and Acetoin in a Sample of 51 Products, Including Fruit-, Candy-, and Cocktail-Flavored E-Cigarettes
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