| Revision as of 19:52, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 475776939 of page Acetoin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:19, 26 May 2024 edit Teaktl17 (talk | contribs)Extended confirmed users18,243 edits Chembox: + PubChem R,S |
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{{distinguish|Acetone}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 445129962 |
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|Watchedfields = changed |
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| ImageFile = 3-Hydroxybutanone.svg |
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|verifiedrevid = 477239174 |
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| ImageSize = 100px |
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|ImageFile = Acetoin-2D.svg |
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| ImageName = 3-Hydroxybutanone |
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|ImageSize = 200px |
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| OtherNames = 3-Hydroxybutanone<br />Acetyl methyl carbinol |
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|ImageName = 3-Hydroxybutanone |
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| Section1 = {{Chembox Identifiers |
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|PIN = 3-Hydroxybutan-2-one |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames = 3-Hydroxybutanone<br />Acetyl methyl carbinol |
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| ChemSpiderID = 21105851 |
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|Section1={{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = BG4D34CO2H |
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|ChemSpiderID = 21105851 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChemSpiderID1 = 388445 |
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| KEGG = C01769 |
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|ChemSpiderID1_Comment = (''R'') |
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| InChI = 1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 |
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|ChemSpiderID2 = 394765 |
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| InChIKey = ROWKJAVDOGWPAT-UHFFFAOYAD |
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|ChemSpiderID2_Comment = (''S'') |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChI = 1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 |
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|UNII = BG4D34CO2H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG = C00466 |
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| StdInChIKey = ROWKJAVDOGWPAT-UHFFFAOYSA-N |
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|KEGG1 = C00810 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|KEGG1_Comment = (''R'') |
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| CASNo = 513-86-0 |
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|KEGG2 = C01769 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|KEGG2_Comment = (''S'') |
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| ChEBI = 15688 |
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|InChI = 1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 |
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| SMILES = CC(=O)C(C)O |
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|InChIKey = ROWKJAVDOGWPAT-UHFFFAOYAD |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = ROWKJAVDOGWPAT-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 513-86-0 |
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|CASNo_Comment = <small>(''R''/''S'')</small> |
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|CASNo1_Ref = {{cascite|correct|CAS}} |
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|CASNo1 = 53584-56-8 |
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|CASNo1_Comment = <small>(''R'')</small> |
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|CASNo2_Ref = {{cascite|correct|CAS}} |
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|CASNo2 = 78183-56-9 |
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|CASNo2_Comment = <small>(''S'')</small> |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 15688 |
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|ChEBI1 = 15686 |
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|ChEBI1_Comment = (''R'') |
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|ChEBI2 = 15687 |
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|ChEBI2_Comment = (''S'') |
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|SMILES = CC(=O)C(C)O |
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|SMILES1 = CC(=O)(C)O |
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|SMILES1_Comment = (''R'') |
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|SMILES2 = CC(=O)(C)O |
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|SMILES2_Comment = (''S'') |
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|PubChem = 179 |
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|PubChem1 = 439314 |
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|PubChem1_Comment = (''R'') |
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|PubChem2 = 447765 |
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|PubChem2_Comment = (''S'') |
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|EINECS = 208-174-1 |
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|RTECS = EL8790000 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=4|H=8|O=2 |
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|C=4 | H=8 | O=2 |
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|Appearance = colorless liquid |
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| Density = 1.012 g/cm³ |
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|Odor = bland, yogurt-like |
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| MeltingPtC = 15 |
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|Density = 1.012 g/cm<sup>3</sup> |
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| BoilingPtC = 148 |
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|MeltingPtC = 15 |
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|BoilingPtC = 148 |
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|Solubility = 1000 g/L (20 °C) |
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|SolubleOther = Soluble in ] <br /> Slightly soluble in ], ] <br /> Miscible in ] <br /> Insoluble in ] |
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|Solvent = other solvents |
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|LogP = -0.36 |
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|RefractIndex = 1.4171 |
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|SpecRotation = -39.4 |
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|pKa = 13.72 |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| ExternalMSDS = |
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|ExternalSDS = |
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|FlashPtC = 41 |
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| MainHazards = |
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|LD50 = > 5000 mg/kg (rat, oral) |
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| FlashPt = |
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| Autoignition = }} |
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}} |
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}} |
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}} |
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'''Acetoin''', also known as '''3-hydroxybutanone''' or '''acetyl methyl carbinol''', is an ] with the formula CH<sub>3</sub>CH(OH)C(O)CH<sub>3</sub>. It is a colorless ] with a pleasant, buttery odor. It is ]. The form produced by bacteria is (''R'')-acetoin.<ref name=Gossauer>Albert Gossauer: ''Struktur und Reaktivität der Biomoleküle'', Verlag Helvetica Chimica Acta, Zürich, 2006, Seite 285, {{ISBN|978-3-906390-29-1}}.</ref> |
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==Production in bacteria== |
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Acetoin is a neutral, four-carbon molecule used as an external energy store by a number of ] bacteria. It is produced by the ] of alpha-], a common precursor in the ] of ]s. Owing to its neutral nature, production and excretion of acetoin during exponential growth prevents over-acidification of the ] and the surrounding medium that would result from accumulation of acidic metabolic products, such as ] and ]. Once superior carbon sources are exhausted, and the culture enters ], acetoin can be used to maintain the culture density.<ref>{{cite journal | doi = 10.1080/10408410701364604 |author1=Xiao, Z. |author2=Xu, P. | year = 2007 | title = Acetoin metabolism in bacteria | journal = Crit Rev Microbiol | volume = 33 | issue = 2 | pages = 127–140 | pmid = 17558661|s2cid=46151943 }}</ref> The conversion of acetoin into ] is catalysed by the ] complex, following a mechanism largely analogous to the ] complex; however, as acetoin is not a ], it does not undergo decarboxylation by the ]; instead, a molecule of ] is released.<ref>{{cite journal |author1=Oppermann, F.B. |author2=Steinbuchel, A. | year = 1994 | title = Identification and molecular characterization of the aco genes encoding the Pelobacter carbinolicus acetoin dehydrogenase enzyme system | journal = J. Bacteriol. | volume = 176 | issue = 2 | pages = 469–485 | pmid = 8110297 | pmc = 205071 | doi=10.1128/jb.176.2.469-485.1994}}</ref> |
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In some bacteria, acetoin can also be reduced to ] by ]. |
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The ] test is a commonly used microbiological test for acetoin production.<ref>{{cite journal |author1=Speckman, R.A. |author2=Collins, E.B. | year = 1982 | title = Specificity of the Westerfeld adaptation of the Voges-Proskauer test | journal = Appl Environ Microbiol | volume = 44 | issue = 1 | pages = 40–43 |doi=10.1128/aem.44.1.40-43.1982 | pmid = 6751225 | pmc = 241965|bibcode=1982ApEnM..44...40S }}</ref> |
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==Uses== |
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===Food ingredients=== |
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Acetoin, along with ], is one of the compounds that gives ] its characteristic ]. Because of this, manufacturers of partially ] ] typically add ] – acetoin and diacetyl – (along with ] for the yellow color) to the final product.<ref>Pavia et al., ''Introduction to Organic Laboratory Techniques'', 4th ed., {{ISBN|978-0-495-28069-9}}</ref> |
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Acetoin can be found in ]s, ], ], ]s, ], ], ], ], ]s, and ].<ref>{{cite web| url = http://www.aresok.org/npg/nioshdbs/oshamethods/validated/1012/1012.html| url-status = dead| archive-url = https://web.archive.org/web/20180604002419/http://www.aresok.org/npg/nioshdbs/oshamethods/validated/1012/1012.html| archive-date = 2018-06-04| title = Sampling and Analytical Methods: Acetoin, Diacetyl, 1012}}</ref><ref>{{Cite web|url=https://allendalecolumbia.org/tag/stem/page/11/|title=Allendale Columbia | STEM}}</ref><ref>{{Cite web|url=https://www.fks.com/learningcenter/acetoin.html|title=Evaluation of Natural Acetyl Methyl Carbinol|Flavorist|website=www.fks.com}}</ref> |
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Acetoin is used as a food ]ing (in ]) and as a ]. |
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===Electronic cigarettes=== |
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It is used in ] for ]s to give a buttery or caramel flavor.<ref name=EatonChapt5>{{cite book |chapter-url=https://www.nap.edu/read/24952/chapter/8?term=Diacetyl#175 |author1=Committee on the Review of the Health Effects of Electronic Nicotine Delivery Systems, National Academies of Sciences|editor1-last=Eaton |editor1-first=David L. |editor2-last=Kwan |editor2-first=Leslie Y. |editor3-last=Stratton |editor3-first=Kathleen |title=Public Health Consequences of E-Cigarettes |date=2018 |publisher=National Academies Press |isbn=9780309468343 |page=175 |language=en |pmid=29894118|chapter=Chapter 5: Toxicology of E-Cigarette Constituents}}</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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<references/> |
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] |
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] |
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] |