3-Methylbutanoic acid

3-Methylbutanoic acid
IUPAC name 3-Methylbutanoic acid
Other names Delphinic acid 3-Methylbutyric acid Isopentanoic acid
Identifiers
CAS number	503-74-2 Y
ChemSpider	10001 Y
UNII	1BR7X184L5 Y
DrugBank	DB03750
KEGG	C08262 Y
ChEBI	CHEBI:28484 Y
ChEMBL	CHEMBL568737 Y
Jmol-3D images	Image 1
SMILES O=C(O)CC(C)C
InChI InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7) Y Key: GWYFCOCPABKNJV-UHFFFAOYSA-N Y InChI=1/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7) Key: GWYFCOCPABKNJV-UHFFFAOYAV
Properties
Molecular formula	C5H10O2
Molar mass	102.13 g/mol
Density	0.925 g/cm³
Melting point	-29 °C, 244 K, -20 °F
Boiling point	175–177 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3-Methylbutanoic acid, or more commonly isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but extremely soluble in most common organic solvents.

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^[2] when it is produced by skin bacteria metabolising leucine. Isovaleric acid is what gives stale hops its characteristically cheesy aroma and flavor.

Other synonyms include delphinic acid, 3-methylbutyric acid, and isopentanoic acid.

See also

• Isovaleric acidemia

References

1. ^ Eadie, Mervyn J (2004-11-01). "Could Valerian Have Been the First Anticonvulsant?". Epilepsia 45 (11): 1338–1343. doi:10.1111/j.0013-9580.2004.27904.x. ISSN 1528-1167. http://onlinelibrary.wiley.com/doi/10.1111/j.0013-9580.2004.27904.x/abstract. Retrieved 2012-05-09. 
2. ^ Ara, Katsutoshi; Masakatsu Hama, Syunichi Akiba, Kenzo Koike, Koichi Okisaka, Toyoki Hagura, Tetsuro Kamiya, Fusao Tomita (2006-04). "Foot odor due to microbial metabolism and its control". Canadian Journal of Microbiology 52 (4): 357–364. doi:10.1139/w05-130. ISSN 1480-3275 0008-4166, 1480-3275. http://www.nrcresearchpress.com/doi/abs/10.1139/w05-130. Retrieved 2012-05-09. 

External links

• PubChem 10430