2.02012-08-09 09:16:16 -06002015-09-13 15:15:33 -0600ECMDB21446M2MDB001841DiacetylDiacetyl is a natural by-product of secondary or malolactic fermentation. It is also a product of butanoate metabolism. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. It has a buttery aroma. Beer sometimes undergoes a diacetyl rest, which entails waiting 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. 2,3-Butadione2,3-Butandione2,3-Butanedione2,3-Diketobutane2,3-Dioxobutane2,3-Dioxobutane, butadioneAcetoacetaldehydeBiacetylButadioneButan-2,3-dioneButane-2,3-dioneButanedioneButanedione [UN2346]Dimethyl diketoneDimethyl glyoxalDimethylglyoxalC4H6O286.089286.036779436butane-2,3-dionediacetyl431-03-8CC(=O)C(C)=OInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3QSJXEFYPDANLFS-UHFFFAOYSA-NLiquidCytoplasmlogp0.07logs0.18solubility1.29e+02 g/lmelting_point-2.4 oClogp0.4pka_strongest_acidic15.98pka_strongest_basic-8.3iupacbutane-2,3-dioneaverage_mass86.0892mono_mass86.036779436smilesCC(=O)C(C)=OformulaC4H6O2inchiInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3inchikeyQSJXEFYPDANLFS-UHFFFAOYSA-Npolar_surface_area34.14refractivity21.54polarizability8.41rotatable_bond_count1acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::CMs2617Specdb::CMs28533Specdb::CMs29319Specdb::CMs99812Specdb::CMs99813Specdb::CMs163696Specdb::EiMs49Specdb::NmrOneD2384Specdb::NmrOneD3078Specdb::NmrOneD286375Specdb::NmrOneD286376Specdb::NmrOneD286377Specdb::NmrOneD286378Specdb::NmrOneD286379Specdb::NmrOneD286380Specdb::NmrOneD286381Specdb::NmrOneD286382Specdb::NmrOneD286383Specdb::NmrOneD286384Specdb::NmrOneD286385Specdb::NmrOneD286386Specdb::NmrOneD286387Specdb::NmrOneD286388Specdb::NmrOneD286389Specdb::NmrOneD286390Specdb::NmrOneD286391Specdb::NmrOneD286392Specdb::NmrOneD286393Specdb::NmrOneD286394Specdb::MsMs2286Specdb::MsMs2287Specdb::MsMs2288Specdb::MsMs5923Specdb::MsMs5924Specdb::MsMs20762Specdb::MsMs20763Specdb::MsMs20764Specdb::MsMs21026Specdb::MsMs21027Specdb::MsMs21028Specdb::MsMs22313Specdb::MsMs22314Specdb::MsMs22315Specdb::MsMs22577Specdb::MsMs22578Specdb::MsMs22579Specdb::MsMs2231735Specdb::MsMs2232430Specdb::MsMs2234174Specdb::MsMs2234790Specdb::MsMs2466189Specdb::MsMs2466190Specdb::MsMs2466191Specdb::MsMs2495861HMDB03407650630C0074116583Diacetylvan der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Mehta RC, Hogan TF, Mardmomen S, Ma JK: Chromatographic studies of mitomycin C degradation in albumin microspheres. J Chromatogr. 1988 Sep 9;430(2):341-9.3148622Hayes BK, Varki A: O-acetylation and de-O-acetylation of sialic acids. Sialic acid esterases of diverse evolutionary origins have serine active sites and essential arginine residues. J Biol Chem. 1989 Nov 15;264(32):19443-8.2509478Lombardo D, Campese D, Multigner L, Lafont H, De Caro A: On the probable involvement of arginine residues in the bile-salt-binding site of human pancreatic carboxylic ester hydrolase. Eur J Biochem. 1983 Jun 15;133(2):327-33.6852044Espinosa-Mansilla A, Duran-Meras I, Salinas F: High-performance liquid chromatographic-fluorometric determination of glyoxal, methylglyoxal, and diacetyl in urine by prederivatization to pteridinic rings. Anal Biochem. 1998 Jan 15;255(2):263-73.9451513Ostap EM: 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23(4):305-8.12630704Sokolchik I, Tanabe T, Baldi PF, Sze JY: Polymodal sensory function of the Caenorhabditis elegans OCR-2 channel arises from distinct intrinsic determinants within the protein and is selectively conserved in mammalian TRPV proteins. J Neurosci. 2005 Jan 26;25(4):1015-23.15673683Sohaskey CD, Barbour AG: Esterases in serum-containing growth media counteract chloramphenicol acetyltransferase activity in vitro. Antimicrob Agents Chemother. 1999 Mar;43(3):655-60.10049283Peretti E, Karlaganis G, Lauterburg BH: Acetylation of acetylhydrazine, the toxic metabolite of isoniazid, in humans. Inhibition by concomitant administration of isoniazid. J Pharmacol Exp Ther. 1987 Nov;243(2):686-9.3681700Xu, Ping; Chen, Hong; Du, Yi; Chen, Wanqiu; Xiao, Zijun. Method of preparation diacetyl by oxidization. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.http://hmdb.ca/system/metabolites/msds/000/002/988/original/HMDB03407.pdf?1358463221