|Preferred IUPAC name
Isovaleral, Isovaleric Aldehyde
3D model (JSmol)
CompTox Dashboard (EPA)
|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|
|Occupational safety and health (OHS/OSH):|
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:
A small amount of 2,2-dimethylpropanal side product is also generated.
Another method of production involves the isomerization of 3-methylbut-3-en-1-ol using CuO–ZnO as a catalyst. A mixture of 3-methylbut-3-en-1-ol and 3-methylbut-2-en-1-ol may also be used. These starting materials are obtained from a reaction between isobutene and formaldehyde:
- CH3CH3CCH2 + CH2O → (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-dimethylbut-2-ene, and is then converted to 2,3-dimethylbutane-2,3-diol and methyl tert-butyl ketone, 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., ed. (2007). Hawley's Condensed Chemical Dictionary (15th ed.). New York, NY: John Wiley. p. 719.
- Cserháti, T.; Forgács, E. (2003). "Flavor (Flavour) Compounds: Structures and Characteristics". Encyclopedia of Food Sciences and Nutrition (2nd ed.). Elsevier Science. pp. 2509–2517.
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- Bamforth, C. W. (2003). "Chemistry of Brewing". Encyclopedia of Food Sciences and Nutrition (2nd ed.). pp. 440–447.
- Owuor, P. O. (2003). "Tea: Analysis and Tasting". Encyclopedia of Food Sciences and Nutrition (2nd ed.). pp. 5757–5762.