Diacetyl

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Diacetyl^[1]

IUPAC name	2,3-Butanedione
Other names	Diacetyl Biacetyl
Identifiers
CAS number	[431-03-8]
PubChem	650
SMILES	CC(=O)C(C)=O
Properties
Molecular formula	C₄H₆O₂
Molar mass	86.0892 g/mol
Appearance	Yellowish green liquid
Density	0.990 g/mL at 15 °C
Melting point	-2 to -4 °C
Boiling point	88 °C
Solubility in water	Soluble in 4 parts
Hazards
MSDS	External MSDS
Main hazards	Harmful, flammable
R-phrases	R10 R22 R36 R37 R38
S-phrases	S9 S16 S33
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Diacetyl (IUPAC systematic name: butanedione or 2,3-butanedione) is a natural byproduct of fermentation. 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 a buttery flavor.

1 In food products
2 In alcoholic beverages
3 Safety
4 See also
5 References
6 External links

[edit] In food products

Diacetyl, along with acetoin, is one of the compounds that gives butter its characteristic taste. Because of this, manufacturers of margarines or similar oil based products typically add diacetyl and acetoin (along with beta carotene for the yellow color) to the final product, which would otherwise be tasteless.^[2]

[edit] In alcoholic beverages

At low levels in alcoholic beverages, it contributes a slipperiness to the feel of the beer or wine in the mouth. As levels increase, it imparts a buttery or butterscotch flavor (butterscotch itself may be devoid of diacetyl).

It is produced during fermentation as a byproduct of valine synthesis. During this synthesis 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, relatively flavorless compounds.

Beer sometimes undergoes a diacetyl rest, which entails elevating temperature 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 flavors it imparts. It is present in many California chardonnays known as "Butter Bombs," although there is a growing trend back toward the more traditional French styles.^{[citation needed]}

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.^[3]^[4]

[edit] Safety

[edit] Worker safety

The United States National Institute for Occupational Safety and Health has suggested that 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, non-smoking males. There are no known cures for bronchiolitis obliterans except for lung transplantation.

While several authorities have called the disease "Popcorn Worker's Lung," a more accurate term suggested by other doctors may be more appropriate, since the disease can occur in any industry working with diacetyl: diacetyl-induced bronchiolitis obliterans.

After the workers filed a lawsuit against the manufacturers, the United States Environmental Protection Agency began an investigation into the chemical properties of microwave popcorn butter flavoring. In March 2004, former microwave popcorn plant employee Eric Peoples, of Joplin, Missouri, was awarded $20 million for permanent lung-injuries sustained while on the job.^[5] On July 19, 2005, jurors awarded $2.7 million to another popcorn plant worker in Missouri for his claim of diacetyl-induced respiratory problems.^[6]

On July 26, 2006, the International Brotherhood of Teamsters and the United Food and Commercial Workers petitioned the U.S. Occupational Safety and Health Administration to promulgate an emergency temporary standard to protect workers from the deleterious health effects of inhaling diacetyl vapors.^[7] The petition was followed by a letter of support signed by more than thirty prominent scientists.^[8] The matter is under consideration.

There are currently two bills in the California Legislature to ban the use of diacetyl.^[9]^[10]^[11]

[edit] Consumer safety

Dr. Cecile Rose, pulmonary specialist at Denver's National Jewish Medical and Research Center, in a letter, warned federal agencies or regulators that consumers, not just factory workers, are in danger of suffering the fatal popcorn lung disease from buttery flavoring fumes in microwave popcorn. David Michaels of the George Washington University School of Public Health first published Rose's letter on his blog.^[12]^[13] However, the only sample data known-to-date is the case where a consumer, who ate at least two bags of buttery microwave popcorn daily for 10 years, became diagnosed with the same disease affecting workers exposed to the substance, bronchiolitis obliterans.^[14] His lung problems were linked to breathing the vapors; although rare, the reported man's kitchen also had diacetyl levels comparable to those in popcorn plants.^[15]

The Flavor and Extract Manufacturers on September 4, 2007, recommended reduction of diacetyl in butter flavorings. The Weaver Popcorn Company of Indianapolis has replaced the butter flavoring with a new ingredient.^[16] Weaver makes the Trail's End brand of popcorn sold by the Boy Scouts of America. A ConAgra spokesperson has said it will do the same in a year,^[17] and is working to remove the ingredient from its popcorn products. ^[18]

In a Reuters story dated September 5, 2007, writer Julie Steenhuysen quoted the spokeswoman for ConAgra Foods Inc, maker of Orville Redenbacher and Act II microwave popcorn brands, saying "it will drop diacetyl from its butter-flavored microwave popcorn in the near future." ^[19]

[edit] EU regulation

The EU Commission has declared that diacetyl is legal for use as a flavouring substance in all EU states. ^[20] As a diketone, diacetyl falls with 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.^[21] As part of this study, the Panel reviewed available studies on several other flavourings in FEG.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. As a result of the Panel's 2004 study, acetylacetone (FL 07.191) was found to be genotoxic in vitro and in vivo, and was therefore deleted from the register of permitted flavouring substances.^[22] Recently, the European Food Safety Authority (EFSA), the EU's food safety regulatory body, stated that that 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."^[23]