Isopropyl methoxy pyrazine

Isopropyl methoxy pyrazine
IUPAC name

2-methoxy-3-propan-2-ylpyrazine
Other names

IPMP
2-Isopropyl-3-methoxypyrazine
3-Isopropyl-2-methoxypyrazine
Identifiers
CAS number 25773-40-4 Y
PubChem 33166
Jmol-3D images Image 1
Properties
Molecular formula C8H12N2O
Molar mass 152.19 g/mol
Exact mass 152.094963 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Isopropyl methoxy pyrazine (IPMP) is a methoxypyrazine, a class of chemical compounds that produce odors. The odor is rather undesirable and is produced by the Asian lady beetle or by the actinomycete Streptomyces sp.[1]

Presence in wine grapes

The odor of IPMP tends to be undesirable in the case of certain wines.[2]

Cabernet Sauvignon have high levels of methoxypyrazines.[3][4] Two methoxypyrazine compounds, 3-isobutyl-2-methoxypyrazine (IBMP) and 3-isopropyl-2-methoxypyrazine, are considered to be important determinants of green flavours in Sauvignon blanc wines.[5]

See also

References

  1. ^ Three highly odorous metabolites from an actinomycete: 2-Isopropyl-3-methoxy-pyrazine, methylisoborneol, and geosmin. Nancy N. Gerber, Journal of chemical ecology, Volume 3, Number 4, pp. 475-482, doi:10.1007/BF00988190
  2. ^ Trace flavour components of grapes
  3. ^ winepros.com.au Oxford Companion to Wine methoxypyrazines
  4. ^ Oz Clarke Encyclopedia of Grapes pg 223 Harcourt Books 2001 ISBN 0-15-100714-4
  5. ^ Marais, J., Hunter, J.J., & Haasbroek, P.D. (1999). Effect of microclimate, season and region on Sauvignon blanc grape composition and wine quality. South African Journal of Enology and Viticulture, 20, 19-30.