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] Commercially it is used as a reagent for the production of pharmaceuticals, perfumes and pesticides.[3]

Isovaleraldehyde
Names
Preferred IUPAC name
3-Methylbutanal
Other names
Isovaleral, Isovaleric Aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.811
UNII
  • InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
    Key: YGHRJJRRZDOVPD-UHFFFAOYSA-N
  • InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
    Key: YGHRJJRRZDOVPD-UHFFFAOYAE
  • CC(C)CC=O
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
 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:

(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 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]

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]

2,4,6-Triisobutyl-1,3,5-trioxane

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]

References
  1. Lewis, R. J., Sr., ed. (2007). Hawley's Condensed Chemical Dictionary (15th ed.). New York, NY: John Wiley. p. 719.{{cite book}}: CS1 maint: multiple names: editors list (link)
  2. Cserháti, T.; Forgács, E. (2003). "Flavor (Flavour) Compounds: Structures and Characteristics". Encyclopedia of Food Sciences and Nutrition (2nd ed.). Elsevier Science. pp. 2509–2517.
  3. Kohlpaintner, C. "Aliphatic Aldehydes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 9. doi:10.1002/14356007.a01_321.pub3.
  4. Bamforth, C. W. (2003). "Chemistry of Brewing". Encyclopedia of Food Sciences and Nutrition (2nd ed.). pp. 440–447.
  5. Owuor, P. O. (2003). "Tea: Analysis and Tasting". Encyclopedia of Food Sciences and Nutrition (2nd ed.). pp. 5757–5762.
  6. Boeckman, Robert; Tusch, Douglas J.; Biegasiewiczjournal=Organic Syntheses, Kyle F. (2015). "Organocatalyzed Direct Asymmetric α-Hydroxymethylation of Aldehydes". 92: 320–327. doi:10.15227/orgsyn.092.0320. {{cite journal}}: Cite journal requires |journal= (help)
  7. Poulsen, Pernille; Overgaard, Mette; Jensen, Kim L.; Jørgensenjournal=Organic Syntheses, Karl Anker (2014). "Enantioselective Organocatalytic α-Arylation of Aldehydes". 91: 175–184. doi:10.15227/orgsyn.091.0175. {{cite journal}}: Cite journal requires |journal= (help)
  8. Donald Arthur Withycombe, et al. U.S. Patent 4,093,752, U.S. Patent 4,191,785 (1978 to International Flavors and Fragrances Inc).
  9. http://lmrnaturals.iff.com/en/site-services/flavor-online-compendium-iframe#3-methylbutyraldehyde
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