|Systematic IUPAC name
Isovaleral, Isovaleric Aldehyde
|Jmol 3D model||Interactive image|
|Density||0.785 g/mL at 20 °C|
|Melting point||−51 °C (−60 °F; 222 K)|
|Boiling point||92 °C (198 °F; 365 K)|
|Soluble in alcohol and ether, slightly soluble in water|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Isovaleraldehyde is a small 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.
Synthetic routes for the production of isovaleraldehyde vary. One method is by the hydroformylation of isobutene, which forms a small amount of 2,2-dimethylpropanal as a side product. The balanced reaction is given below
CH3CH3CCH2 + H2 + CO → (CH3)2CHCH2CHO 95% + (CH3)3CCHO 5%
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 + CuO-ZnO (Catalytic Amounts) → (CH3)2CHCH2CHO
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.
- Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 719
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