3-Isobutyl-2-methoxypyrazine

3-Isobutyl-2-methoxypyrazine

Names
IUPAC name 2-Methoxy-3-(2-methylpropyl)pyrazine
Other names 2-Isobutyl-3-methoxypyrazine; IBMP
Identifiers
CAS Number	24683-00-9
Jmol interactive 3D	Image
PubChem	32594
InChI InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3 Key: UXFSPRAGHGMRSQ-UHFFFAOYSA-N
SMILES CC(C)CC1=NC=CN=C1OC
Properties
Chemical formula	C9H14N2O
Molar mass	166.22 g·mol^−1
Appearance	Liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Isobutyl-2-methoxypyrazine (2-isobutyl-3-methoxypyrazine^[1]) is a methoxypyrazine that is very similar to isopropyl methoxy pyrazine except that the alkyl side-group contains an isobutyl group attached to the carbon alpha to the methoxy sidegroup instead of an isopropyl side-group at that same carbon position.

The molecule is produced by some plants and is a contributor to the aroma of several plant-based foods.^[2][3]

Bombyx mori pheromone binding protein bound to 3-isobutyl-2-methoxypyrazine (bell pepper odorant) PDB entry 2p70^[4]

References

1. 2-Isobutyl-3-methoxypyrazine in Sigma-Aldrich Catalogue
2. Kaneko, S.; Sakai, R.; Kumazawa, K.; Usuki, M.; Nishimura, O. (2013). "Key aroma compounds in roasted in-shell peanuts". Bioscience, Biotechnology, and Biochemistry 77 (7): 1467–1473. doi:10.1271/bbb.130112. PMID 23832337.
3. Koch, A.; Doyle, C. L.; Matthews, M. A.; Williams, L. E.; Ebeler, S. E. (2010). "2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype". Phytochemistry 71 (17–18): 2190–2198. doi:10.1016/j.phytochem.2010.09.006. PMID 20965529.
4. Lautenschlager, C.; Leal, W. S.; Clardy, J. (2007). "Bombyx mori Pheromone-Binding Protein Binding Nonpheromone Ligands: Implications for Pheromone Recognition". Structure 15 (9): 1148–1154. doi:10.1016/j.str.2007.07.013. PMC 2072049. PMID 17850754.