butane-2,3-dione
Also known as 2,3-butadione, diacetyl, Butadione, Butan-2,3-dione, Dimethyl glyoxal, Acetoacetaldehyde, 2,3-butandione, Butanedione [UN2346]
Diacetyl ( ; IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacetyl occurs naturally in alcoholic beverages and some cheeses and is added as a flavoring to some foods to impart its buttery flavor. Chronic inhalation exposure to diacetyl fumes is a causative agent of the lung disease bronchiolitis obliterans, commonly known as "popcorn lung".
Research
3,786 papers- (R,R)-Butane-2,3-diol dehydrogenase from Bacillus clausii DSM 8716(T): Cloning and expression of the bdhA-gene, and initial characterization of enzyme.Journal of biotechnology · 2017
- Multiple effects of 2,3-butanedione monoxime.Pharmacology & toxicology · 1994
- Diacetyl-induced lung disease.Toxicological reviews · 2006
- Flavoring-related bronchiolitis obliterans.Current opinion in allergy and clinical immunology · 2007
- Does 2,3-butanedione monoxime inhibit nonmuscle myosin?Protoplasma · 2005
via PubMed
Article
14 sectionsContents
- Chemical structure
- Occurrence and biosynthesis
- Production
- Applications
- In food products
- Electronic cigarettes
- In alcoholic beverages
- Use as butter flavoring
- Butter-flavoring controversy
- Regulation
- See also
- References
- Further reading
- External links
Diacetyl ( ; IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacetyl occurs naturally in alcoholic beverages and some cheeses and is added as a flavoring to some foods to impart its buttery flavor. Chronic inhalation exposure to diacetyl fumes is a causative agent of the lung disease bronchiolitis obliterans, commonly known as "popcorn lung".
==Chemical structure== A distinctive feature of diacetyl (and other vicinal 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.