Isovaleraldehyde
Names | |
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Preferred IUPAC name
3-Methylbutanal | |
Other names
Isovaleral, Isovaleric Aldehyde
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.008.811 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Combustible[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isovaleraldehyde
Synthesis
Synthetic routes for the production of isovaleraldehyde vary. One method is by the hydroformylation of isobutene:
- (CH3)2C=CH2 + H2 + CO → (CH3)2C−CH2CHO
A small amount of 2,2-dimethylpropanal ((CH3)2C−C(CHO)CH3 side product is also generated.[3]
Another method of production involves the
- 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 can be derived 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 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-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.[3] It is a common reagent or building block in organic synthesis.[6][7]
Acid-catalyzed cyclic trimerization of Isovaleraldehyde gives 2,4,6-Triisobutyl-
According to IFF, isovaleraldehyde is used as a food flavorant additive.[9]
References
- ^ a b c d e f g h Lewis, R. J. Sr., ed. (2007). Hawley's Condensed Chemical Dictionary (15th ed.). New York, NY: John Wiley. p. 719.
- ^ a b Cserháti, T.; Forgács, E. (2003). "Flavor (Flavour) Compounds: Structures and Characteristics". Encyclopedia of Food Sciences and Nutrition (2nd ed.). Elsevier Science. pp. 2509–2517.
- ^ ISBN 978-3527306732.
- ^ 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.
- )
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- ^ Donald Arthur Withycombe, et al. U.S. patent 4,093,752, U.S. patent 4,191,785 (1978 to International Flavors and Fragrances Inc).
- ^ http://lmrnaturals.iff.com/en/site-services/flavor-online-compendium-iframe#3-methylbutyraldehyde