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] Commercially it is used as a reagent for the production of pharmaceuticals, perfumes and pesticides.[3]
Names | |
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Preferred IUPAC name
3-Methylbutanal | |
Other names
Isovaleral, Isovaleric Aldehyde
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Identifiers | |
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3D model (JSmol)
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.008.811 |
PubChem CID
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UNII |
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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).
Infobox references
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Synthetic routes for the production of isovaleraldehyde vary. One method is by the hydroformylation of isobutene:
A small amount of 2,2-dimethylpropanal ((CH3)2C−C(CHO)CH3 side product is also generated.[3]
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:[3]
Finally, in beer the compound is produced via a reaction between the amino acid leucine and reductones in the malt.[4]
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-1,3,5-trioxane [68165-40-2]. This is a flavouring agent that can be used in confectionary, tobacco, and other foodstuffs, toothpastes and the like.[8] It is described as imparting a creamy, dairy, vanilla chocolate and berry flavour.
According to IFF, isovaleraldehyde is used as a food flavorant additive.[9]
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