isovaleraldehyde
{{Chembox
| ImageFile = 3-Methylbutyraldehyde.svg
| ImageSize = 180px
| ImageAlt =
| PIN = 3-Methylbutanal
| OtherNames = Isovaleral, Isovaleric Aldehyde
|Section1={{Chembox Identifiers
| CASNo = 590-86-3
| CASNo_Ref = {{cascite|correct}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 69931RWI96
| ChEBI = 16638
| PubChem = 11552
| ChemSpiderID = 11065
| SMILES = CC(C)CC=O
| InChI = 1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
| InChIKey = YGHRJJRRZDOVPD-UHFFFAOYAE
| StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
| StdInChIKey = YGHRJJRRZDOVPD-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
| C = 5 | H = 10 | O = 1
| Appearance = Colorless Liquid
| Density = 0.785 g/mL at 20 °C
| MeltingPtC = −51
| BoilingPtC = 92
| Solubility = Soluble in alcohol and ether, slightly soluble in water
| MagSus = {{val|-57.5e-6|u=cm3/mol}}
}}
|Section3={{Chembox Hazards
| FlashPt =
| AutoignitionPt =
}}
}}
Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO. It is an aldehyde, a colorless liquid at STP,{{cite book|editor-last=Lewis |editor-first=R. J. Sr. |title=Hawley's Condensed Chemical Dictionary |edition=15th |publisher=John Wiley |location=New York, NY |date=2007 |page=719}} and found in low concentrations in many types of food.{{cite encyclopedia|last1=Cserháti |first1=T. |last2=Forgács |first2=E. |encyclopedia=Encyclopedia of Food Sciences and Nutrition |edition=2nd |entry=Flavor (Flavour) Compounds: Structures and Characteristics |publisher=Elsevier Science |date=2003 |pages=2509–2517}} Commercially it is used as a reagent for the production of pharmaceuticals, perfumes and pesticides.{{Ullmann|last=Kohlpaintner |first=C. |title=Aliphatic Aldehydes |page=9 |doi=10.1002/14356007.a01_321.pub3}}
Synthesis
Synthetic routes for the production of isovaleraldehyde vary. One method is by the hydroformylation of isobutene:
:{{chem2|(CH3)2C\dCH2 + H2 + CO → (CH3)2CH\sCH2CHO}}
A small amount of 2,2-dimethylpropanal ({{chem2|(CH3)2C(CHO)CH3}}) side product is also generated.
Another method of production involves the isomerization of isoprenol using CuO–ZnO as a catalyst. A mixture of isoprenol and prenol 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.{{cite encyclopedia|last1=Bamforth |first1=C. W. |encyclopedia=Encyclopedia of Food Sciences and Nutrition |edition=2nd |entry=Chemistry of Brewing |date=2003 |pages=440–447}}
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.{{cite encyclopedia|last=Owuor |first=P. O. |encyclopedia=Encyclopedia of Food Sciences and Nutrition |edition=2nd |entry=Tea: Analysis and Tasting |date=2003 |pages=5757–5762}}
The compound is used as a reactant in the synthesis of a number of compounds. Notably it is used to synthesize tetramethylethylene, and is then converted to pinacol and 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.{{cite journal |doi=10.15227/orgsyn.092.0320|title=Organocatalyzed Direct Asymmetric α-Hydroxymethylation of Aldehydes |year=2015 |last1=Boeckman |first1=Robert |first2=Douglas J.|last2=Tusch|first3=Kyle F.|last3=Biegasiewiczjournal=Organic Syntheses |journal=Organic Syntheses |volume=92 |pages=320–327 |doi-access=free }}{{cite journal |doi=10.15227/orgsyn.091.0175|title=Enantioselective Organocatalytic α-Arylation of Aldehydes |year=2014 |last1=Poulsen |first1=Pernille |first2=Mette|last2=Overgaard|first3=Kim L.|last3=Jensen|first4=Karl Anker|last4= Jørgensenjournal=Organic Syntheses |journal=Organic Syntheses |volume=91 |pages=175–184 |doi-access=free }}
File:2,4,6-Triisobutyl-1,3,5-trioxane.svg]]
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.Donald Arthur Withycombe, et al. {{US patent|4093752}}, {{US patent|4191785}} (1978 to International Flavors and Fragrances Inc).
It is described as imparting a creamy, dairy, vanilla chocolate and berry flavour.
According to IFF, isovaleraldehyde is used as a food flavorant additive.{{cite web | url=http://lmrnaturals.iff.com/en/site-services/flavor-online-compendium-iframe#3-methylbutyraldehyde | title=LMR Naturals }}