Formula C5H10O | Appearance Colorless Liquid | |
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Isovaleraldehyde organic compound, 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. It can be produced commercially and is used as a reagent for the production of pharmaceuticals and pesticides.
Contents
Synthesis
Synthetic routes for the production of isovaleraldehyde vary. One method is by the hydroformylation of isobutene:
CH3CH3CCH2 + H2 + CO → (CH3)2CHCH2CHOA small amount of 2,2-dimethylpropanal side product is also generated. Another method of production involves the isomerization of 3-methyl-3-butene-1-ol using CuO-ZnO as a catalyst. A mixture of 3-methyl-3-butene-1-ol and 3-methyl-2-butene-1-ol may also be used. These starting materials are obtained from a reaction between isobutene and formaldehyde:
CH2CH3CCH2 + (CH3)2CCH2 → (CH3)2CHCH2CHOFinally, in beer the compound is produced via a reaction between the amino acid leucine and reductones in the malt.
Occurrences and Uses
As it stems 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 such foods as beer, cheese, coffee, chicken, fish, chocolate, olive oil, and tea.
The compound is used as a reactant in the synthesis of a number of compounds. Notably it is used to synthesize 2,3-dimethyl-2-butene, and is then converted to 2,3-dimethylbutane-2,3-diol and methyltert-butylketone, better known as 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.