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Acetoin information


Acetoin
3-Hydroxybutanone
Names
Preferred IUPAC name
3-Hydroxybutan-2-one
Other names
3-Hydroxybutanone
Acetyl methyl carbinol
Identifiers
CAS Number
  • 513-86-0 (R/S) checkY
  • 53584-56-8 (R) checkY
  • 78183-56-9 (S) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15688 checkY
ChemSpider
  • 21105851 checkY
ECHA InfoCard 100.007.432 Edit this at Wikidata
EC Number
  • 208-174-1
KEGG
  • C01769 checkY
PubChem CID
  • 179
RTECS number
  • EL8790000
UNII
  • BG4D34CO2H checkY
CompTox Dashboard (EPA)
  • DTXSID0024399 Edit this at Wikidata
InChI
  • InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3 checkY
    Key: ROWKJAVDOGWPAT-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
    Key: ROWKJAVDOGWPAT-UHFFFAOYAD
SMILES
  • CC(=O)C(C)O
Properties
Chemical formula
C4H8O2
Molar mass 88.106 g·mol−1
Appearance colorless liquid
Odor bland, yogurt-like
Density 1.012 g/cm3
Melting point 15 °C (59 °F; 288 K)
Boiling point 148 °C (298 °F; 421 K)
Solubility in water
1000 g/L (20 °C)
Solubility in other solvents Soluble in alcohol
Slightly soluble in ether, petroleum ether
Miscible in propylene glycol
Insoluble in vegetable oil
log P -0.36
Acidity (pKa) 13.72
Chiral rotation ([α]D)
-39.4
Refractive index (nD)
1.4171
Hazards
Flash point 41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
> 5000 mg/kg (rat, oral)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 chiral. The form produced by bacteria is (R)-acetoin.[1]

  1. ^ Albert Gossauer: Struktur und Reaktivität der Biomoleküle, Verlag Helvetica Chimica Acta, Zürich, 2006, Seite 285, ISBN 978-3-906390-29-1.

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Acetoin

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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...

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Acetoin dehydrogenase

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Acetoin dehydrogenase (EC 2.3.1.190, acetoin dehydrogenase complex, acetoin dehydrogenase enzyme system, AoDH ES) is an enzyme with systematic name acetyl-CoA:acetoin...

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Acetoin racemase

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an acetoin racemase (EC 5.1.2.4) is an enzyme that catalyzes the chemical reaction (S)-acetoin ⇌ {\displaystyle \rightleftharpoons } (R)-acetoin This...

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Diacetyl

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industrially by dehydrogenation of 2,3-butanediol. Acetoin is an intermediate. Diacetyl and acetoin are two compounds that give butter its characteristic...

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List of chemical compounds in coffee

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Putrescine, Theophylline, Trigonelline Quinic acid, Acetoin Harmane Norharman 3,5-Di-caffeoylquinic acid Acetoin Dimethyl disulfide 3,5-Di-caffeoylquinic acid...

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Diacetyl reductase

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reductase is the name of two acetoin forming enzymes: Diacetyl reductase ((R)-acetoin forming) Diacetyl reductase ((S)-acetoin forming) This set index page...

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C4H8O2

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The molecular formula C4H8O2 may refer to: Acetoin cis-Butene-1,4-diol Butyric acid Dioxanes 1,2-Dioxane 1,3-Dioxane 1,4-Dioxane Ethyl acetate 3-Hydroxybutanal...

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Acetolactate decarboxylase

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\rightleftharpoons } (R)-2-acetoin + CO2 Hence, this enzyme has one substrate, (S)-2-hydroxy-2-methyl-3-oxobutanoate, and two products, (R)-2-acetoin and CO2. This...

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Staphylococcus haemolyticus

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glycerol, maltose, sucrose, and trehalose. It also tests positive for acetoin production, arginine, dihydrolase, benzidine, catalase, hemolysis, and...

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Kefir

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contribute to the flavor of kefir are pyruvic acid, acetic acid, diacetyl and acetoin (both of which contribute a "buttery" flavor), citric acid, acetaldehyde...

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Aroma compound

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known) Phosphine (zinc phosphide poisoned bait) Diacetyl (butter flavor) Acetoin (butter flavor) Nerolin (orange flowers) Tetrahydrothiophene (added to...

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Flavoring

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Chemical Odor Manzanate Apple Diacetyl, acetylpropionyl, acetoin Buttery Isoamyl acetate Banana Benzaldehyde Bitter almond, cherry Cinnamaldehyde Cinnamon...

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Streptococcus mitis

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Mannose Positive Sucrose Positive Starch Negative Enzymatic Reactions Acetoin Negative Acid Phosphatase Variable Alkaline Phosphatase Positive Hyaluronidase...

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Malolactic fermentation

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products of malolactic fermentation are lactic acid, diacetyl, acetic acid, acetoin, and various esters. The amount and exact nature of these products depends...

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Pelobacter propionicus

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propionicus is a species of bacteria that ferments 2,3-butanediol and acetoin. It is Gram-negative, strictly anaerobic and non-spore-forming. Ott Bd...

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Artificial butter flavoring

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taste and smell of butter. It may contain diacetyl, acetylpropionyl, or acetoin, three natural compounds in butter that contribute to its characteristic...

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Histone deacetylase

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expression. Together with the acetylpolyamine amidohydrolases and the acetoin utilization proteins, the histone deacetylases form an ancient protein...

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Cronobacter

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galacturonate and D-maltose. Cronobacter spp. are also generally positive for acetoin production (Voges–Proskauer test) and negative for the methyl red test...

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List of additives in cigarettes

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U V W X Y Z See also References External links Acetanisole Acetic acid Acetoin Acetophenone 6-Acetoxydihydrotheaspirane 2-Acetyl-3-ethylpyrazine 2-Acetyl-5-methylfuran...

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IMViC

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potassium hydroxide to test for the presence of acetylmethylcarbinol (acetoin), an intermediate of the 2,3-butanediol fermentation pathway. After adding...

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Streptococcus anginosus

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sequence analysis. The majority of Streptococcus anginosus strains produce acetoin from glucose, ferment lactose, trehalose, salicin, and sucrose, and hydrolyze...

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