3-Methylbutanoic acid

3-Methylbutanoic acid

3-Methylbutanoic acid
Skeletal formula of 3-methylbutanoic acid
Ball-and-stick model of 3-methylbutanoic acid
Names
IUPAC name
3-Methylbutanoic acid
Other names
Delphinic acid
3-Methylbutyric acid
Isopentanoic acid
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
DrugBank  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
Properties
C5H10O2
Molar mass 102.13 g/mol
Density 0.925 g/cm3
Melting point −29 °C (−20 °F; 244 K)
Boiling point 175 to 177 °C (347 to 351 °F; 448 to 450 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

3-Methylbutanoic acid, or more commonly isovaleric acid, is an essential oils.

Isovaleric acid has a strong pungent cheesy or sweaty smell, but its volatile esters have pleasing scents and are used widely in perfumery. It has been proposed that it is the anticonvulsant agent in valerian.[1] It is a major component of the cause of unpleasant foot odor, as it is produced by skin bacteria metabolizing leucine.[2]

Isovaleric acid is seen as the primary cause of the flavors added to wine caused by Brettanomyces yeasts.[3] Other compounds produced by Brettanomyces yeasts include 4-ethylphenol, 4-vinylphenol, and 4-ethylguaiacol.[4] An excess of isovaleric acid in wine is generally seen as a defect,[4] as it can smell sweaty, leathery, or like a barnyard, but in small amounts it can smell smokey, spicy, or medicinal.[3] These phenomena may be prevented by killing any Brettanomyces yeasts, such as by sterile filtration, by the addition of relatively large quantities of sulfur dioxide and sometimes sorbic acid, by mixing in alcoholic spirit to give a fortified wine of sufficient strength to kill all yeast and bacteria, or by pasteurization. Isovaleric acid can also be found in beer, and, excepting some English–style ales, is usually considered a flaw.[5] It can be produced by the oxidation of hop resins, or by Brettanomyces yeasts present.[5]

See also

References

  1. ^ Eadie, Mervyn J. (November 2004). "Could Valerian Have Been the First Anticonvulsant?". Epilepsia 45 (11): 1338–1343.  
  2. ^ Ara, Katsutoshi; Hama, Masakatsu; Akiba, Syunichi; Koike, Kenzo; Okisaka, Koichi; Hagura, Toyoki; Kamiya, Tetsuro; Tomita, Fusao (April 2006). "Foot odor due to microbial metabolism and its control". Canadian Journal of Microbiology 52 (4): 357–364.  
  3. ^ a b Jackson, Ron S. (2008). Wine Science: Principles and Applications (3rd ed.). Academic Press. p. 495.  
  4. ^ a b Kirk-Othmer (2007). "Wine". Food and Feed Technology, Volume 2. John Wiley & Sons. p. 702.  
  5. ^ a b Oliver, Garrett, ed. (2012). The Oxford Companion to Beer. Oxford University Press. p. 498.