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231:
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40:
1165:
1034:. 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.
31:
812:
873:
814:
1115:
In some styles of beer (e.g. in many beer styles produced in the United
Kingdom, such as stouts, English bitters, and Scottish ales), 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.
1217:
substance in all EU states. 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. As part of this study, the panel
1142:
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
1147:, deliberately promote the production of diacetyl because of the feel and flavor it imparts. Diacetyl is present in some chardonnays known as "butter bombs", although there is a trend back toward the more traditional French styles.
1218:
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.
606:
558:
1005:
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
1225:(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.
830:
732:
2163:. Links to studies on the health effects of diacetyl, and to a variety of related documents including the recent OSHA petition and the scientists' letter of support may be found here.
2023:
1944:
886:
724:
1259:
A 2010 U.S. OSHA Safety and Health
Information Bulletin and companion Worker Alert recommend employers use safety measures to minimize exposure to diacetyl or its substitutes.
2142:
1888:"Adopting a register of flavouring substances used in or on foodstuffs drawn up in application of Regulation (EC) No 2232/96 of the European Parliament and of the Council"
1478:
1966:
1150:
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.
815:
823:
1414:
2041:
1973:
1229:
419:
1912:"Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission"
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728:
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837:
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2020:
1967:"Comments of the Flavor and Extract Manufacturers Association of the United States on New Information on Butter Flavored Microwave Popcorn"
1936:
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1804:
2062:
1597:
1549:
949:
384:
2004:
716:
2172:
1584:
Committee on the Review of the Health
Effects of Electronic Nicotine Delivery Systems, National Academies of Sciences (2018).
1536:
Committee on the Review of the Health
Effects of Electronic Nicotine Delivery Systems, National Academies of Sciences (2018).
1222:
539:
1977:
2182:
2131:
712:
893:
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658:
317:
760:
597:
2217:
1671:
1563:
1159:
1080:
1019:
708:
348:
1107:. People nearby may be exposed to it in the exhaled aerosol at levels near the limit set for occupational exposure.
1091:
for the yellow color) to make the final product butter-flavored, because it would otherwise be relatively tasteless.
776:
592:
1410:
2038:
1911:
2212:
650:
238:
1317:
Eriks K, Hayden TD, Yang SH, Chan IY (1983). "Crystal and molecular structure of biacetyl (2,3-butanedione), (H
1282:
1182:
676:
1249:
756:
577:
39:
993:
groups, side-by-side). Diacetyl occurs naturally in alcoholic beverages and some cheeses and is added as a
582:
226:
118:
1262:
In 2016, diacetyl was banned in e-liquids/e-cigarettes in the EU under the EU Tobacco
Products Directive.
1241:
1023:
684:
188:
1894:
620:
587:
570:
1731:
1104:
736:
52:
1824:
1777:"Reassessment of the Influence of Malolactic Fermentation on the Concentration of Diacetyl in Wines"
1720:"Control of flavor development in wine during and after malolactic fermentation by Oenococcus oeni"
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1335:
1253:
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911:
772:
522:
442:
2059:"European Commission – Press Releases – 10 key changes for tobacco products sold in the EU"
1010:. The elongation is attributed to repulsion between the polarized carbonyl carbon centers.
748:
326:
2045:
2027:
2008:
1831:
1639:
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94:
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2178:
National
Institute for Occupational Safety and Health – Flavorings-Related Lung Disease
1051:
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17:
2001:
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1354:
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2100:
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1007:
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2002:
Pop Weaver introduces first microwave popcorn with flavoring containing no diacetyl
1198:
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or similar oil-based products typically add diacetyl and acetoin (along with
1462:
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994:
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337:
2137:
2108:
1865:
1663:
1607:
1559:
1537:
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1396:
2039:
OSHA Recommends Safety
Measures to Protect Workers from Diacetyl Exposure
1194:
1027:
990:
986:
836:
829:
822:
795:
642:
1339:
1168:
Butter-Vanilla flavor, a combination of butter flavor and vanilla flavor
2087:
Harber P, Saechao K, Boomus C (2006). "Diacetyl-induced lung disease".
1844:
Harber P, Saechao K, Boomus C (2006). "Diacetyl-induced lung disease".
1277:
1136:
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491:
277:
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1233:
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into diacetyl. The yeast then absorbs the diacetyl, and reduces the
863:
Except where otherwise noted, data are given for materials in their
630:
2155:
Scientists Urge
Secretary of Labor to Protect Workers from Diacetyl
265:
2159:
2147:
982:. It is a yellow liquid with an intensely buttery flavor. It is a
959:
301:
159:
117:
107:
1185:, a rare and life-threatening form of non-reversible obstructive
2021:
ConAgra Foods press release announcing removal of added diacetyl
1825:
Merriam-Webster
Medical Dictionary > bronchiolitis obliterans
1256:) began removing diacetyl as an ingredient from their products.
1186:
784:
646:
256:
1236:
flavorings. Manufacturers of butter flavored popcorn including
2138:
Preventing Lung Disease and Workers who Use or Make Flavorings
1177:
Chronic industrial exposure to diacetyl fumes, such as in the
932:
1079:
its characteristic taste. Because of this, manufacturers of
752:
353:
1937:"Europe takes 'wait-and-see' stance on diacetyl flavouring"
1411:"Scott Labs | Managing Diacetyl Production During MLF"
1119:
Diacetyl is produced during fermentation as a byproduct of
938:
923:
917:
920:
807:
1193:(small airway branches) are compressed and narrowed by
881:
506:−2 to −4 °C (28 to 25 °F; 271 to 269 K)
16:"Butanedione" redirects here. For 1,4-butanedione, see
1022:. In some fermentative bacteria, it is formed via the
1586:"Chapter 3: E-Cigarette Devices, Uses, and Exposures"
950:
929:
941:
935:
914:
2173:
NIOSH International Safety Card for 2,3-butanedione
2143:
A Case of Regulatory Failure – Popcorn Workers Lung
1538:"Chapter 5: Toxicology of E-Cigarette Constituents"
926:
1038:can be converted to lactic acid to make diacetyl.
135:
289:
1443:. Gaithersburg, Md: Aspen Publishers. pp.
811:
93:
1479:Ullmann's Encyclopedia of Industrial Chemistry
1181:production industry, has been associated with
1127:, which escapes the cell and is spontaneously
1099:Diacetyl is used as a flavoring agent in some
1775:Martineau B, Henick-Kling T, Acree T (1995).
1513:Introduction to Organic Laboratory Techniques
8:
1230:Flavor and Extract Manufacturers Association
1213:has declared diacetyl is legal for use as a
1018:Diacetyl arises naturally as a byproduct of
997:to some foods to impart its buttery flavor.
1588:. In Eaton DL, Kwan LY, Stratton K (eds.).
1540:. In Eaton DL, Kwan LY, Stratton K (eds.).
1590:Public Health Consequences of E-Cigarettes
1542:Public Health Consequences of E-Cigarettes
368:
229:
207:
22:
1751:
1718:Nielsen JC, Richelieu M (February 1999).
1544:. National Academies Press. p. 175.
1386:
325:
1592:. National Academies Press. p. 82.
1353:Speckman RA, Collins EB (January 1968).
1163:
2000:Weaver Popcorn Company. Press Release:
1293:
424:
389:
364:
1724:Applied and Environmental Microbiology
220:
1476:Siegel H, Eggersdorfer M. "Ketones".
1046:Diacetyl is produced industrially by
516:88 °C (190 °F; 361 K)
396:Key: QSJXEFYPDANLFS-UHFFFAOYSA-N
187:
167:
7:
1674:from the original on 20 October 2013
406:Key: QSJXEFYPDANLFS-UHFFFAOYAX
393:InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
280:
264:
1947:from the original on March 8, 2023
1515:(4th ed.). Cengage Learning.
403:InChI=1/C4H6O2/c1-3(5)4(2)6/h1-2H3
14:
1893:. 28 October 1996. Archived from
1232:recommended reducing diacetyl in
2101:10.2165/00139709-200625040-00006
1858:10.2165/00139709-200625040-00006
910:
871:
596:
591:
586:
581:
576:
454:
38:
29:
2169:, Washington Post, May 7, 2007.
2065:from the original on 2018-10-20
2048:, EHS Today, December 10, 2010.
1807:from the original on 2009-01-07
1614:from the original on 2018-11-18
1566:from the original on 2020-01-07
1417:from the original on 2022-07-05
1123:synthesis, when yeast produces
867:(at 25 °C , 100 kPa).
2167:Flavoring suspected in illness
1306:(11th ed.). p. 2946.
1223:European Food Safety Authority
540:Occupational safety and health
460:
448:
1:
1744:10.1128/AEM.65.2.740-745.1999
974:with the chemical formula (CH
2019:ConAgra Foods Press Release
1379:10.1128/JB.95.1.174-180.1968
1173:Butter-flavoring controversy
1075:are two compounds that give
2007:September 28, 2007, at the
1668:E. coli Metabolome Database
1357:Streptococcus diacetilactis
1160:Artificial butter flavoring
1081:artificial butter flavoring
1014:Occurrence and biosynthesis
2234:
1793:10.5344/ajev.1995.46.3.385
1355:"Diacetyl Biosynthesis in
1157:
1026:-mediated condensation of
15:
1834:Retrieved on August, 2010
1638:. Storey Books. pp.
861:
557:
537:
532:
496:0.990 g/mL at 15 °C
435:
415:
380:
77:
63:
51:
46:
37:
28:
2148:www.defendingscience.org
1488:10.1002/14356007.a15_077
1439:Modern Food Microbiology
1283:Bronchiolitis obliterans
1183:bronchiolitis obliterans
659:Precautionary statements
2157:, a press release from
1698:Sonoma-Cutrer Vineyards
1482:. Weinheim: Wiley-VCH.
1367:Journal of Bacteriology
1325:, at −12 and −100 °C".
1154:Use as butter flavoring
1694:"Trends in Chardonnay"
1361:Leuconostoc citrovorum
1169:
1111:In alcoholic beverages
1024:thiamine pyrophosphate
818:
2089:Toxicological Reviews
1900:on November 19, 2007.
1435:Jay, James M (2000).
1250:Orville Redenbacher's
1197:(scar tissue) and/or
1189:disease in which the
1167:
1105:electronic cigarettes
1095:Electronic cigarettes
817:
2160:defendingscience.org
1943:. October 31, 2007.
1781:Am. Soc. Enol. Vitic
1274:, a similar diketone
1139:and 2,3-butanediol.
1058:is an intermediate.
800:(fire diamond)
53:Preferred IUPAC name
1736:1999ApEnM..65..740N
1340:10.1021/ja00350a032
1211:European Commission
553:Harmful, flammable
523:Solubility in water
478: g·mol
149:Beilstein Reference
25:
2218:Conjugated ketones
2044:2010-12-21 at the
2026:2015-10-18 at the
1830:2017-08-01 at the
1170:
1001:Chemical structure
894:Infobox references
819:
23:
1972:(press release).
1941:foodnavigator.com
1649:978-0-88266-940-3
1632:Janson L (1996).
1522:978-0-495-28069-9
1511:Pavia DL (2006).
1334:(12): 3940–3942.
1328:J. Am. Chem. Soc.
1179:microwave popcorn
962:systematic name:
902:Chemical compound
900:
899:
850:Safety data sheet
621:Hazard statements
349:CompTox Dashboard
119:Interactive image
70:Dimethyl diketone
2225:
2213:Chemical hazards
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1314:
1308:
1307:
1298:
1067:In food products
972:organic compound
968:butane-2,3-dione
954:
948:
947:
944:
943:
940:
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931:
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528:200 g/L (20 °C)
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443:Chemical formula
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139:
121:
97:
72:2,3-Diketobutane
57:Butane-2,3-dione
42:
33:
26:
2233:
2232:
2228:
2227:
2226:
2224:
2223:
2222:
2188:
2187:
2183:IFIC – Diacetyl
2132:Toxicology data
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2086:
2082:
2080:Further reading
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1158:Main article:
1155:
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1129:decarboxylated
1125:α-acetolactate
1112:
1109:
1096:
1093:
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1052:2,3-butanediol
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865:standard state
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18:succinaldehyde
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2136:NIOSH Alert:
2135:
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2110:
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1983:on 2015-10-18
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1635:Brew Chem 101
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1089:beta-carotene
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1071:Diacetyl and
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1021:
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1008:1,3-butadiene
1000:
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856:External MSDS
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221:ECHA InfoCard
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27:
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2158:
2146:
2092:
2088:
2067:. Retrieved
2053:
2034:
2015:
1996:
1985:. Retrieved
1978:the original
1961:
1949:. Retrieved
1940:
1931:
1922:
1918:
1906:
1895:the original
1882:
1849:
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1839:
1820:
1809:. Retrieved
1784:
1780:
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1723:
1713:
1701:. Retrieved
1697:
1688:
1676:. Retrieved
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1627:
1616:. Retrieved
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1579:
1568:. Retrieved
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1419:. Retrieved
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1199:inflammation
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1062:Applications
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1020:fermentation
1017:
1004:
967:
963:
905:
904:
796:
612:
559:
549:Main hazards
538:
427:CC(=O)C(=O)C
302:RTECS number
189:ChEMBL365809
78:Identifiers
64:Other names
1951:December 4,
1846:Toxicol Rev
1703:December 2,
1303:Merck Index
1242:Trail's End
1191:bronchioles
964:butanedione
607:Signal word
543:(OHS/OSH):
483:Appearance
436:Properties
227:100.006.428
169:CHEBI:16583
2192:Categories
2069:2018-11-17
1987:2012-07-25
1811:2009-04-24
1678:20 October
1664:"Diacetyl"
1618:2018-11-17
1570:2019-11-30
1421:2022-07-11
1289:References
1248:(maker of
1238:Pop Weaver
1215:flavouring
1205:Regulation
1145:chardonnay
1085:margarines
1042:Production
1036:Malic acid
1032:acetyl CoA
571:Pictograms
471:Molar mass
327:K324J5K4HM
200:ChemSpider
106:3D model (
85:CAS Number
2198:Diketones
1670:. ECMDB.
995:flavoring
781:P403+P235
777:P403+P233
773:P370+P378
761:P333+P313
757:P332+P313
729:P304+P340
721:P302+P352
717:P301+P312
562:labelling
338:UN number
309:EK2625000
248:207-069-8
240:EC Number
24:Diacetyl
2117:42169510
2109:17288497
2063:Archived
2042:Archived
2024:Archived
2005:Archived
1945:Archived
1874:42169510
1866:17288497
1828:Archived
1805:Archived
1801:88263667
1672:Archived
1612:Archived
1608:29894118
1564:Archived
1560:29894118
1463:42692251
1415:Archived
1266:See also
1195:fibrosis
1103:used in
1028:pyruvate
987:diketone
970:) is an
906:Diacetyl
797:NFPA 704
533:Hazards
95:431-03-8
68:Biacetyl
66:Diacetyl
2208:Popcorn
2203:Flavors
2145:, from
1762:9925610
1732:Bibcode
1397:5636815
1278:Acetoin
1137:acetoin
1101:liquids
1073:acetoin
1056:Acetoin
984:vicinal
951:dy-yuh-
887:what is
885: (
492:Density
278:PubChem
154:605398
2115:
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1461:
1451:
1395:
1388:251989
1385:
1254:Act II
1244:, and
1234:butter
1133:ketone
1121:valine
1077:butter
882:verify
879:
852:(SDS)
613:Danger
476:86.090
420:SMILES
266:C00741
180:ChEMBL
137:B00164
129:3DMet
47:Names
2113:S2CID
1981:(PDF)
1970:(PDF)
1915:(PDF)
1898:(PDF)
1891:(PDF)
1870:S2CID
1797:S2CID
1753:91089
1640:64–67
989:(two
960:IUPAC
955:-tuhl
385:InChI
342:2346
160:ChEBI
108:JSmol
2105:PMID
1974:FEMA
1953:2023
1862:PMID
1758:PMID
1705:2015
1680:2013
1644:ISBN
1604:PMID
1594:ISBN
1556:PMID
1546:ISBN
1517:ISBN
1492:ISBN
1459:OCLC
1449:ISBN
1393:PMID
1359:and
1321:CCO)
1252:and
1209:The
1187:lung
1030:and
789:P501
785:P405
769:P363
765:P362
753:P330
749:P321
745:P314
741:P311
737:P310
713:P280
709:P272
705:P271
701:P270
697:P264
693:P261
689:P260
685:P243
681:P242
677:P241
673:P240
669:P233
665:P210
651:H373
647:H331
643:H318
639:H317
635:H315
631:H302
627:H225
318:UNII
257:KEGG
2097:doi
1923:166
1854:doi
1789:doi
1748:PMC
1740:doi
1484:doi
1445:120
1383:PMC
1375:doi
1336:doi
1332:105
1050:of
991:C=O
978:CO)
966:or
953:SEE
560:GHS
354:EPA
291:650
281:CID
209:630
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