Isovaleraldehyde

Isovaleraldehyde
Names
	Preferred IUPAC name 3-Methylbutanal
	Other names Isovaleral, Isovaleric Aldehyde
Identifiers
CAS Number	590-86-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16638;
ChemSpider	11065;
ECHA InfoCard	100.008.811
PubChem CID	11552;
UNII	69931RWI96 ;
CompTox Dashboard (EPA)	DTXSID1021619 ;
	InChI 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;
	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)	−57.5×10−6 cm3/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 [77 °F], 100 kPa). Infobox references

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]

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]

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

^ ^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.
^ ^a ^b ^c ^d 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.
^ 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.
^ 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.
^ 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.
^ Donald Arthur Withycombe, et al. U.S. patent 4,093,752, U.S. patent 4,191,785 (1978 to International Flavors and Fragrances Inc).
^ "LMR Naturals".

[Dictionary-1] ^ ^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.

[Flavor-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.

[Ullmann-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.

[Beers-4] Bamforth, C. W. (2003). "Chemistry of Brewing". Encyclopedia of Food Sciences and Nutrition (2nd ed.). pp. 440–447.

[Tea-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".

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