2.0 2012-05-31 13:58:11 -0600 2015-09-13 12:56:12 -0600 ECMDB03243 M2MDB000484 Acetoin Acetoin is a chemical compound with the formula C4H8O2. It is a colourless or pale yellow to green yellow liquid with a pleasant buttery odour. It is used as a food flavoring and a fragrance. Acetoin is a product of fermentation. It is a component of the butanediol cycle in E. coli. Escherichia coli pyruvate oxidase (POXEC) requires FAD both for the oxidative decarboxylation of pyruvate to acetate and CO2 and for the formation of acetoin from pyruvate and acetaldehyde. [PMID:8424670] (R)-2-acetoin (R)-3-hydroxy-2-butanone (R)-3-hydroxybutan-2-one (R)-acetoin (R)-dimethylketol 1-Hydroxyethyl methyl ketone 2,3-Butanolone 2-Acetoin 2-Butanol-3-one 2-Hydroxy-3-butanone 2-Hydroxy-3-oxobutane 3-Hydroxy-2-Butanone 3-Hydroxy-2-butanone (acetoin) 3-Hydroxybutan-2-one 3-Hydroxyl-2-butanone Acetoine Acetyl methyl carbinol Acetylmethyl-Methanol B-oxobutane Beta-Oxobutane Dimethylketol β-Oxobutane C4H8O2 88.1051 88.0524295 3-hydroxybutan-2-one acetoin 513-86-0 CC(O)C(C)=O InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 ROWKJAVDOGWPAT-UHFFFAOYSA-N Liquid Cytoplasm Periplasm logp -0.66 ALOGPS logs 0.73 ALOGPS solubility 4.73e+02 g/l ALOGPS melting_point 15 oC logp -0.14 ChemAxon pka_strongest_acidic 13.72 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac 3-hydroxybutan-2-one ChemAxon average_mass 88.1051 ChemAxon mono_mass 88.0524295 ChemAxon smiles CC(O)C(C)=O ChemAxon formula C4H8O2 ChemAxon inchi InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 ChemAxon inchikey ROWKJAVDOGWPAT-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 22.39 ChemAxon polarizability 9.14 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20865 Specdb::CMs 29430 Specdb::CMs 38554 Specdb::CMs 99801 Specdb::CMs 132900 Specdb::CMs 140634 Specdb::EiMs 1627 Specdb::NmrOneD 1939 Specdb::NmrOneD 3890 Specdb::NmrOneD 4163 Specdb::NmrOneD 135420 Specdb::NmrOneD 135421 Specdb::NmrOneD 135422 Specdb::NmrOneD 135423 Specdb::NmrOneD 135424 Specdb::NmrOneD 135425 Specdb::NmrOneD 135426 Specdb::NmrOneD 135427 Specdb::NmrOneD 135428 Specdb::NmrOneD 135429 Specdb::NmrOneD 135430 Specdb::NmrOneD 135431 Specdb::NmrOneD 135432 Specdb::NmrOneD 135433 Specdb::NmrOneD 135434 Specdb::NmrOneD 135435 Specdb::NmrOneD 135436 Specdb::NmrOneD 135437 Specdb::NmrOneD 135438 Specdb::NmrOneD 135439 Specdb::NmrOneD 166336 Specdb::NmrOneD 166562 Specdb::MsMs 2218 Specdb::MsMs 2219 Specdb::MsMs 2220 Specdb::MsMs 5865 Specdb::MsMs 7067 Specdb::MsMs 7068 Specdb::MsMs 7069 Specdb::MsMs 13739 Specdb::MsMs 13740 Specdb::MsMs 13741 Specdb::MsMs 2252531 Specdb::MsMs 2253939 Specdb::MsMs 2290713 Specdb::MsMs 2290714 Specdb::MsMs 2290715 Specdb::MsMs 2644881 Specdb::MsMs 2644882 Specdb::MsMs 2644883 Specdb::NmrTwoD 1874 HMDB03243 21105851 C00466 Acetoin Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van 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. 17765195 Winder, 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. 18331064 Bertagnolli, B. L., Hager, L. P. (1993). "Role of flavin in acetoin production by two bacterial pyruvate oxidases." Arch Biochem Biophys 300:364-371. 8424670 Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. 3275321 Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. 2758593 Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73. 2589871 Otsuka M, Ohmori S: Simple and sensitive determination of diacetyl and acetoin in biological samples and alcoholic drinks by gas chromatography with electron-capture detection. J Chromatogr. 1992 Jun 10;577(2):215-20. 1400754 http://hmdb.ca/system/metabolites/msds/000/002/826/original/HMDB03243.pdf?1358461989 Pyruvate dehydrogenase [cytochrome] P07003 POXB_ECOLI poxB http://ecmdb.ca/proteins/P07003.xml