|Systematic IUPAC name
Isovaleral, Isovaleric Aldehyde
3D model (JSmol)
|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 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:
- CH3CH3CCH2 + H2 + CO → (CH3)2CHCH2CHO
A 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)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
- Cserháti, T. and Forgács, E. Encyclopedia of Food Sciences and Nutrition (Second Edition): Flavor (Flavour) Compounds | Structures and Characteristics, Elsevier Science Ltd., 2003, Pg. 2509-2517
- Kohlpaintner, C. Ullmann's Encyclopedia of Industrial Chemistry: Aldehydes, Aliphatic, Wiley-VCH, 2000, Pg. 9 doi:10.1002/14356007.a01_321.pub3
- Bamforth, C.W. Encyclopedia of Food Sciences and Nutrition (Second Edition) | Chemistry of Brewing, 2003, Pg. 440-447
- Owuor, P.O. Encyclopedia of Food Sciences and Nutrition (Second Edition) TEA | Analysis and Tasting, 2003, Pg. 5757-5762