2.02012-05-31 13:58:11 -06002015-09-13 12:56:12 -0600ECMDB03243M2MDB000484AcetoinAcetoin 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)-dimethylketol1-Hydroxyethyl methyl ketone2,3-Butanolone2-Acetoin2-Butanol-3-one2-Hydroxy-3-butanone2-Hydroxy-3-oxobutane3-Hydroxy-2-Butanone3-Hydroxy-2-butanone (acetoin)3-Hydroxybutan-2-one3-Hydroxyl-2-butanoneAcetoineAcetyl methyl carbinolAcetylmethyl-MethanolB-oxobutaneBeta-OxobutaneDimethylketolβ-OxobutaneC4H8O288.105188.05242953-hydroxybutan-2-oneacetoin513-86-0CC(O)C(C)=OInChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3ROWKJAVDOGWPAT-UHFFFAOYSA-NLiquidCytoplasmPeriplasmlogp-0.66logs0.73solubility4.73e+02 g/lmelting_point15 oClogp-0.14pka_strongest_acidic13.72pka_strongest_basic-3.4iupac3-hydroxybutan-2-oneaverage_mass88.1051mono_mass88.0524295smilesCC(O)C(C)=OformulaC4H8O2inchiInChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3inchikeyROWKJAVDOGWPAT-UHFFFAOYSA-Npolar_surface_area37.3refractivity22.39polarizability9.14rotatable_bond_count1acceptor_count2donor_count1physiological_charge0formal_charge0Specdb::CMs20865Specdb::CMs29430Specdb::CMs38554Specdb::CMs99801Specdb::CMs132900Specdb::CMs140634Specdb::EiMs1627Specdb::NmrOneD1939Specdb::NmrOneD3890Specdb::NmrOneD4163Specdb::NmrOneD135420Specdb::NmrOneD135421Specdb::NmrOneD135422Specdb::NmrOneD135423Specdb::NmrOneD135424Specdb::NmrOneD135425Specdb::NmrOneD135426Specdb::NmrOneD135427Specdb::NmrOneD135428Specdb::NmrOneD135429Specdb::NmrOneD135430Specdb::NmrOneD135431Specdb::NmrOneD135432Specdb::NmrOneD135433Specdb::NmrOneD135434Specdb::NmrOneD135435Specdb::NmrOneD135436Specdb::NmrOneD135437Specdb::NmrOneD135438Specdb::NmrOneD135439Specdb::NmrOneD166336Specdb::NmrOneD166562Specdb::MsMs2218Specdb::MsMs2219Specdb::MsMs2220Specdb::MsMs5865Specdb::MsMs7067Specdb::MsMs7068Specdb::MsMs7069Specdb::MsMs13739Specdb::MsMs13740Specdb::MsMs13741Specdb::MsMs2252531Specdb::MsMs2253939Specdb::MsMs2290713Specdb::MsMs2290714Specdb::MsMs2290715Specdb::MsMs2644881Specdb::MsMs2644882Specdb::MsMs2644883Specdb::NmrTwoD1874HMDB0324321105851C00466AcetoinKanehisa, 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-D114.22080510van 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 80:2939-2948.18331064Bertagnolli, B. L., Hager, L. P. (1993). "Role of flavin in acetoin production by two bacterial pyruvate oxidases." Arch Biochem Biophys 300:364-371.8424670Hirooka 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):185-91.3275321Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6.2758593Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73.2589871Otsuka 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):215-20.1400754http://hmdb.ca/system/metabolites/msds/000/002/826/original/HMDB03243.pdf?1358461989Pyruvate dehydrogenase [cytochrome]P07003POXB_ECOLIpoxBhttp://ecmdb.ca/proteins/P07003.xml