Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acetoin: Difference between pages

{{distinguish|Acetone}}

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 477239174

|ImageFile = Acetoin-2D.svg

|ImageSize = 200px

|ImageName = 3-Hydroxybutanone

|PIN = 3-Hydroxybutan-2-one

|OtherNames = 3-Hydroxybutanone<br />Acetyl methyl carbinol

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 21105851

|ChemSpiderID1 = 388445

|ChemSpiderID1_Comment = (''R'')

|ChemSpiderID2 = 394765

|ChemSpiderID2_Comment = (''S'')

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = BG4D34CO2H

|KEGG = C00466

|KEGG1 = C00810

|KEGG1_Comment = (''R'')

|KEGG2 = C01769

|KEGG2_Comment = (''S'')

|InChI = 1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3

|InChIKey = ROWKJAVDOGWPAT-UHFFFAOYAD

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = ROWKJAVDOGWPAT-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 513-86-0

|CASNo_Comment = <small>(''R''/''S'')</small>

|CASNo1_Ref = {{cascite|correct|CAS}}

|CASNo1 = 53584-56-8

|CASNo1_Comment = <small>(''R'')</small>

|CASNo2_Ref = {{cascite|correct|CAS}}

|CASNo2 = 78183-56-9

|CASNo2_Comment = <small>(''S'')</small>

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 15688

|ChEBI1 = 15686

|ChEBI1_Comment = (''R'')

|ChEBI2 = 15687

|ChEBI2_Comment = (''S'')

|SMILES = CC(=O)C(C)O

|SMILES1 = CC(=O)[C@@H](C)O

|SMILES1_Comment = (''R'')

|SMILES2 = CC(=O)[C@H](C)O

|SMILES2_Comment = (''S'')

|PubChem = 179

|PubChem1 = 439314

|PubChem1_Comment = (''R'')

|PubChem2 = 447765

|PubChem2_Comment = (''S'')

|EINECS = 208-174-1

|RTECS = EL8790000

|Section2={{Chembox Properties

|C=4 | H=8 | O=2

|Appearance = colorless liquid

|Odor = bland, yogurt-like

|Density = 1.012 g/cm³

|MeltingPtC = 15

|BoilingPtC = 148

|Solubility = 1000 g/L (20&nbsp;°C)

|SolubleOther = Soluble in [[ethanol|alcohol]] <br /> Slightly soluble in [[diethyl ether|ether]], [[petroleum ether]] <br /> Miscible in [[propylene glycol]] <br /> Insoluble in [[vegetable oil]]

|Solvent = other solvents

|LogP = -0.36

|RefractIndex = 1.4171

|SpecRotation = -39.4

|pKa = 13.72

|Section3={{Chembox Hazards

|ExternalSDS = [http://www.thegoodscentscompany.com/msds/md102388.html MSDS]

|FlashPtC = 41

|LD50 = > 5000 mg/kg (rat, oral)

}}

'''Acetoin''', also known as '''3-hydroxybutanone''' or '''acetyl methyl carbinol''', is an [[organic compound]] with the formula CH₃CH(OH)C(O)CH₃. It is a colorless [[liquid]] with a pleasant, buttery odor. It is [[chirality (chemistry)|chiral]]. 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>

==Production in bacteria==

Acetoin is a neutral, four-carbon molecule used as an external energy store by a number of [[Fermentation|fermentative]] bacteria. It is produced by the [[decarboxylation]] of alpha-[[acetolactate]], a common precursor in the [[biosynthesis]] of [[branched-chain amino acid]]s. Owing to its neutral nature, production and excretion of acetoin during exponential growth prevents over-acidification of the [[cytoplasm]] and the surrounding medium that would result from accumulation of acidic metabolic products, such as [[acetic acid]] and [[citric acid]]. Once superior carbon sources are exhausted, and the culture enters [[Stationary phase (biology)|stationary phase]], 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 [[acetyl-CoA]] is catalysed by the [[acetoin dehydrogenase]] complex, following a mechanism largely analogous to the [[pyruvate dehydrogenase]] complex; however, as acetoin is not a [[2-oxo acid|2-oxoacid]], it does not undergo decarboxylation by the [[E1 enzyme]]; instead, a molecule of [[acetaldehyde]] 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>

In some bacteria, acetoin can also be reduced to [[2,3-butanediol]] by [[(R,R)-butanediol dehydrogenase|acetoin reductase/2,3-butanediol dehydrogenase]].

The [[Voges-Proskauer]] 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>

==Uses==

===Food ingredients===

Acetoin, along with [[diacetyl]], is one of the compounds that gives [[butter]] its characteristic [[Flavoring|flavor]]. Because of this, manufacturers of partially [[Hydrogenation|hydrogenated]] [[Vegetable fats and oils|oils]] typically add [[artificial butter flavor]] – acetoin and diacetyl – (along with [[beta carotene]] 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>

Acetoin can be found in [[apple]]s, [[yogurt]], [[asparagus]], [[blackcurrant]]s, [[blackberry|blackberries]], [[wheat]], [[broccoli]], [[brussels sprouts]], [[cantaloupe]]s, and [[maple syrup]].<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 &#124; STEM}}</ref><ref>{{Cite web|url=https://www.fks.com/learningcenter/acetoin.html|title=Evaluation of Natural Acetyl Methyl Carbinol&#124;Flavorist|website=www.fks.com}}</ref>

Acetoin is used as a food [[Flavoring|flavor]]ing (in [[baked goods]]) and as a [[fragrance]].

===Electronic cigarettes===

It is used in [[construction of electronic cigarettes#E-cigarette liquid|liquids]] for [[electronic cigarette]]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>

==See also==

* [[Diacetyl]]

* [[Acetylpropionyl]]

==References==

<references/>

[[Category:Acyloins]]

[[Category:Flavors]]

[[Category:Perfume ingredients]]