Misplaced Pages

Isovaleraldehyde

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from 3-methylbutanal)
Isovaleraldehyde
Names
Preferred IUPAC name 3-Methylbutanal
Other names Isovaleral, Isovaleric Aldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.811 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3Key: YGHRJJRRZDOVPD-UHFFFAOYSA-N
  • InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3Key: YGHRJJRRZDOVPD-UHFFFAOYAE
SMILES
  • CC(C)CC=O
Properties
Chemical formula 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)
Solubility in water Soluble in alcohol and ether, slightly soluble in water
Magnetic susceptibility (χ) −57.5×10 cm/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Combustible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.

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:

CH3CH3CCH2 + CH2O → (CH3)2CHCH2CHO

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

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.

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. It is a common reagent or building block in organic synthesis.

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

Acid-catalyzed cyclic trimerization of Isovaleraldehyde gives 2,4,6-Triisobutyl-1,3,5-trioxane . This is a flavouring agent that can be used in confectionary, tobacco, and other foodstuffs, toothpastes and the like. It is described as imparting a creamy, dairy, vanilla chocolate and berry flavour.

According to IFF, isovaleraldehyde is used as a food flavorant additive.

References

  1. ^ Lewis, R. J. Sr., ed. (2007). Hawley's Condensed Chemical Dictionary (15th ed.). New York, NY: John Wiley. p. 719.
  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. ISBN 978-3527306732.
  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". Organic Syntheses. 92: 320–327. doi:10.15227/orgsyn.092.0320.
  7. Poulsen, Pernille; Overgaard, Mette; Jensen, Kim L.; Jørgensenjournal=Organic Syntheses, Karl Anker (2014). "Enantioselective Organocatalytic α-Arylation of Aldehydes". Organic Syntheses. 91: 175–184. doi:10.15227/orgsyn.091.0175.
  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. "LMR Naturals".
Categories: