Acetoin, also known as 3-hydroxybutanone or acetyl methyl carbinol, is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula CH
3CH(OH)C(O)CH
3. It is a colorless
liquid
A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, a ...
with a pleasant, buttery odor. It is
chiral
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is distinguishable from ...
. The form produced by bacteria is (''R'')-acetoin.
[Albert Gossauer: ''Struktur und Reaktivität der Biomoleküle'', Verlag Helvetica Chimica Acta, Zürich, 2006, Seite 285, .]
Production in bacteria
Acetoin is a neutral, four-carbon molecule used as an external energy store by a number of
fermentative bacteria. It is produced by the
decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ...
of alpha-
acetolactate
α-Acetolactic acid is a precursor in the biosynthesis of the branched chain amino acids valine and leucine. α-Acetolactic acid is produced from two molecules of pyruvic acid by acetolactate synthase. α-Acetolactic acid can also be decarboxylat ...
, a common precursor in the biosynthesis of
branched-chain amino acid
A branched-chain amino acid (BCAA) is an amino acid having an aliphatic side-chain with a branch (a central carbon atom bound to three or more carbon atoms). Among the proteinogenic amino acids, there are three BCAAs: leucine, isoleucine, and va ...
s. Owing to its neutral nature, production and excretion of acetoin during exponential growth prevents over-acidification of the
cytoplasm
In cell biology, the cytoplasm is all of the material within a eukaryotic cell, enclosed by the cell membrane, except for the cell nucleus. The material inside the nucleus and contained within the nuclear membrane is termed the nucleoplasm. The ...
and the surrounding medium that would result from accumulation of acidic metabolic products, such as
acetic acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
and
citric acid
Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in t ...
. Once superior carbon sources are exhausted, and the culture enters
stationary phase, acetoin can be used to maintain the culture density. The conversion of acetoin into
acetyl-CoA
Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for ...
is catalysed by the
acetoin dehydrogenase
Acetoin dehydrogenase (, ''acetoin dehydrogenase complex'', ''acetoin dehydrogenase enzyme system'', ''AoDH ES'') is an enzyme with systematic name ''acetyl-CoA:acetoin O-acetyltransferase''. This enzyme catalyses the following chemical reaction
...
complex, following a mechanism largely analogous to the
pyruvate dehydrogenase
Pyruvate dehydrogenase is an enzyme that catalyzes the reaction of pyruvate and a lipoamide to give the acetylated dihydrolipoamide and carbon dioxide. The conversion requires the coenzyme thiamine pyrophosphate.
Pyruvate dehydrogenase is us ...
complex; however, as acetoin is not a
2-oxoacid, it does not undergo decarboxylation by the
E1 enzyme; instead, a molecule of
acetaldehyde
Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
is released.
In some bacteria, acetoin can also be reduced to
2,3-butanediol by
acetoin reductase/2,3-butanediol dehydrogenase.
The
Voges-Proskauer test is a commonly used microbiological test for acetoin production.
Uses
Food ingredients
Acetoin, along with
diacetyl
Diacetyl (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacet ...
, is one of the compounds that gives
butter
Butter is a dairy product made from the fat and protein components of churned cream. It is a semi-solid emulsion at room temperature, consisting of approximately 80% butterfat. It is used at room temperature as a spread, melted as a condiment ...
its characteristic
flavor
Flavor or flavour is either the sensory perception of taste or smell, or a flavoring in food that produces such perception.
Flavor or flavour may also refer to:
Science
*Flavors (programming language), an early object-oriented extension to Lis ...
. Because of this, manufacturers of partially
hydrogenated
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic co ...
oils
An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
typically add
artificial butter flavor
Artificial butter flavoring is a flavoring used to give a food the taste and smell of butter. It may contain diacetyl, acetylpropionyl, or acetoin, three natural compounds in butter that contribute to its characteristic taste and smell. Manu ...
– acetoin and diacetyl – (along with
beta carotene
Beta (, ; uppercase , lowercase , or cursive ; grc, βῆτα, bē̂ta or ell, βήτα, víta) is the second letter of the Greek alphabet. In the system of Greek numerals, it has a value of 2. In Modern Greek, it represents the voiced labio ...
for the yellow color) to the final product.
Acetoin can be found in
apple
An apple is an edible fruit produced by an apple tree (''Malus domestica''). Apple fruit tree, trees are agriculture, cultivated worldwide and are the most widely grown species in the genus ''Malus''. The tree originated in Central Asia, wh ...
s,
yogurt
Yogurt (; , from tr, yoğurt, also spelled yoghurt, yogourt or yoghourt) is a food produced by bacterial Fermentation (food), fermentation of milk. The bacteria used to make yogurt are known as ''yogurt cultures''. Fermentation of sugars in t ...
,
asparagus
Asparagus, or garden asparagus, folk name sparrow grass, scientific name ''Asparagus officinalis'', is a perennial flowering plant species in the genus ''Asparagus''. Its young shoots are used as a spring vegetable.
It was once classified in ...
,
blackcurrant
The blackcurrant (''Ribes nigrum''), also known as black currant or cassis, is a deciduous shrub in the family Grossulariaceae grown for its edible berries. It is native to temperate parts of central and northern Europe and northern Asia, whe ...
s,
blackberries
The blackberry is an edible fruit produced by many species in the genus ''Rubus'' in the family Rosaceae, hybrids among these species within the subgenus ''Rubus'', and hybrids between the subgenera ''Rubus'' and ''Idaeobatus''. The taxonomy of ...
,
wheat
Wheat is a grass widely cultivated for its seed, a cereal grain that is a worldwide staple food. The many species of wheat together make up the genus ''Triticum'' ; the most widely grown is common wheat (''T. aestivum''). The archaeologi ...
,
broccoli
Broccoli (''Brassica oleracea'' var. ''italica'') is an edible green plant in the cabbage family (family Brassicaceae, genus ''Brassica'') whose large flowering head, stalk and small associated leaves are eaten as a vegetable. Broccoli is cl ...
,
brussels sprouts
The Brussels sprout is a member of the Gemmifera cultivar group of cabbages (''Brassica oleracea''), grown for its edible buds. The leaf vegetables are typically 1.5–4.0 cm (0.6–1.6 in) in diameter and resemble miniature cabbages ...
,
cantaloupe
The cantaloupe, rockmelon (Australia and New Zealand, although cantaloupe is used in some states of Australia), sweet melon, or spanspek (Southern Africa) is a melon that is a variety of the muskmelon species (''Cucumis melo'') from the fami ...
s, and
maple syrup
Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple tree ...
.
Acetoin is used as a food
flavor
Flavor or flavour is either the sensory perception of taste or smell, or a flavoring in food that produces such perception.
Flavor or flavour may also refer to:
Science
*Flavors (programming language), an early object-oriented extension to Lis ...
ing (in baked goods) and as a
fragrance
An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently vol ...
.
Electronic cigarettes
It is used in
liquids
A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, an ...
for
electronic cigarette
An electronic cigarette is an electronic device that simulates tobacco smoking. It consists of an atomizer, a power source such as a battery, and a container such as a cartridge or tank. Instead of smoke, the user inhales vapor. As such ...
s to give a buttery or caramel flavor.
[{{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]
See also
*
Diacetyl
Diacetyl (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacet ...
*
Acetylpropionyl
References
Acyloins
Flavors
Perfume ingredients