Isovaleraldehyde
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| Names | |
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IUPAC name
3-methylbutyraldehyde
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Systematic IUPAC name
3-Methylbutanal
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| Other names
Isovaleral, Isovaleric Aldehyde
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| Identifiers | |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.008.811 |
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PubChem CID
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| Properties | |
| C5H10O | |
| Molar mass | 86.13 |
| Appearance | Colorless Liquid |
| 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 | |
| -57.5·10−6 cm3/mol | |
| Hazards | |
| Main hazards | Combustible |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
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-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:
Finally, in beer the compound is produced via a reaction between the amino acid leucine and reductones in the malt.
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.
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