Isovaleraldehyde

Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO. It is an aldehyde, a colorless liquid at STP,[1] and found in low concentrations in many types of food.[2] It can be produced commercially and is used as a reagent for the production of pharmaceuticals and pesticides.[3]

Isovaleraldehyde
Names
IUPAC name
3-methylbutyraldehyde
Systematic IUPAC name
3-Methylbutanal
Other names
Isovaleral, Isovaleric Aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.811
UNII
Properties
C5H10O
Molar mass 86.13[1]
Appearance Colorless Liquid[1]
Density 0.785 g/mL at 20 °C[1]
Melting point −51 °C (−60 °F; 222 K)[1]
Boiling point 92 °C (198 °F; 365 K)[1]
Soluble in alcohol and ether, slightly soluble in water[1]
-57.5·10−6 cm3/mol
Hazards
Main hazards Combustible[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

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.[3] 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:[3]

CH3CH3CCH2 + CH2O → (CH3)2CHCH2CHO

Finally, in beer the compound is produced via a reaction between the amino acid leucine and reductones in the malt.[4]

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.[2][5]

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.[3]

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References
  1. Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 719
  2. 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
  3. Kohlpaintner, C. Ullmann's Encyclopedia of Industrial Chemistry: Aldehydes, Aliphatic, Wiley-VCH, 2000, Pg. 9 doi:10.1002/14356007.a01_321.pub3
  4. Bamforth, C.W. Encyclopedia of Food Sciences and Nutrition (Second Edition) | Chemistry of Brewing, 2003, Pg. 440-447
  5. Owuor, P.O. Encyclopedia of Food Sciences and Nutrition (Second Edition) TEA | Analysis and Tasting, 2003, Pg. 5757-5762
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