Isovaleraldehyde
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Isovaleraldehyde
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO. It is an aldehyde, a colorless liquid at STP, and found in low concentrations in many types of food. Commercially it is used as a reagent for the production of pharmaceuticals,
perfume Perfume (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...
s and
pesticides Pesticides are substances that are used to pest control, control pest (organism), pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for a ...
.


Synthesis

Synthetic routes for the production of isovaleraldehyde vary. One method is by the
hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
of isobutene: : A small amount of 2,2-dimethylpropanal () side product is also generated. Another method of production involves the isomerization of isoprenol using CuOZnO as a catalyst. A mixture of isoprenol and prenol may also be used. These starting materials are obtained from a reaction between isobutene and formaldehyde: :CH3CH3CCH2 + CH2O → (CH3)2CHCH2CHO Finally, in beer the compound is produced via a reaction between the
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
leucine and reductones in the
malt Malt is any cereal grain that has been made to germinate by soaking in water and then stopped from germinating further by drying with hot air, a process known as "malting". Malted grain is used to make beer, whisky, malted milk, malt vinegar, ...
.


Occurrences and uses

As it can be derived from leucine, the occurrence of isovaleraldehyde is not limited to beer. The compound has found to be a flavor component in many different types of foods. It is described as having a malty flavor and has been found in
cheese Cheese is a type of dairy product produced in a range of flavors, textures, and forms by coagulation of the milk protein casein. It comprises proteins and fat from milk (usually the milk of cows, buffalo, goats or sheep). During prod ...
, coffee,
chicken The chicken (''Gallus gallus domesticus'') is a domesticated subspecies of the red junglefowl (''Gallus gallus''), originally native to Southeast Asia. It was first domesticated around 8,000 years ago and is now one of the most common and w ...
,
fish A fish (: fish or fishes) is an aquatic animal, aquatic, Anamniotes, anamniotic, gill-bearing vertebrate animal with swimming fish fin, fins and craniate, a hard skull, but lacking limb (anatomy), limbs with digit (anatomy), digits. Fish can ...
,
chocolate Chocolate is a food made from roasted and ground cocoa beans that can be a liquid, solid, or paste, either by itself or to flavoring, flavor other foods. Cocoa beans are the processed seeds of the cacao tree (''Theobroma cacao''); unprocesse ...
,
olive oil Olive oil is a vegetable oil obtained by pressing whole olives (the fruit of ''Olea europaea'', a traditional Tree fruit, tree crop of the Mediterranean Basin) and extracting the oil. It is commonly used in cooking for frying foods, as a cond ...
, and tea. The compound is used as a reactant in the synthesis of a number of compounds. Notably it is used to synthesize tetramethylethylene, and is then converted to pinacol and pinacolone. Pinacolone itself is then used in synthesis for number of pesticides. Additionally, a range of pharmaceuticals, such as butizide, are synthesized from isovaleraldehyde and its corresponding acid. It is a common reagent or building block in organic synthesis. Acid-catalyzed cyclic trimerization of Isovaleraldehyde gives 2,4,6-Triisobutyl- 1,3,5-trioxane 8165-40-2 This is a flavouring agent that can be used in confectionary, tobacco, and other foodstuffs, toothpastes and the like. It is described as imparting a creamy, dairy, vanilla chocolate and berry flavour. According to IFF, isovaleraldehyde is used as a food flavorant additive.


References

{{reflist Flavors Alkanals