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Isopropyl methoxypyrazine

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Isopropyl methoxy pyrazine
Chemical structure of isopropyl methoxypyrazine
Names
Preferred IUPAC name 2-Methoxy-3-(propan-2-yl)pyrazine
Other names 2-Isopropyl-3-methoxypyrazine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.042.946 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3Key: NTOPKICPEQUPPH-UHFFFAOYSA-N
  • InChI=1/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3Key: NTOPKICPEQUPPH-UHFFFAOYAE
SMILES
  • CC(C)C1=NC=CN=C1OC
Properties
Chemical formula C8H12N2O
Molar mass 152.19 g/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Isopropyl methoxypyrazine (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. It can be detected by human taste at concentrations of as low as 2 nanograms per litre.

Presence in wine grapes

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

Cabernet Sauvignon has high levels of methoxypyrazines. 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.

Presence in coffee

IPMP is also an important flavour compound in coffee and is responsible for causing an off-taste called "potato taste" in East African coffee. The insects Antestiopsis are also implicated in causing the taste.

See also

References

  1. GHS: sigma-aldrich 243132 Archived 2024-05-01 at the Wayback Machine
  2. 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
  3. Cristina Sala; Olga Busto; Josep Guasch; Fernando Zamora. Factors affecting the presence of 3-alkyl-2- methoxypyrazines in grapes and wines. A review (PDF) (Report). Archived (PDF) from the original on 2016-03-03. Retrieved 2012-04-01.
  4. "Trace flavour components of grapes". Archived from the original on 2012-02-06. Retrieved 2011-12-24.
  5. winepros.com.au Oxford Companion to Wine methoxypyrazines Archived 2012-02-29 at the Wayback Machine
  6. Oz Clarke Encyclopedia of Grapes pg 223 Harcourt Books 2001 ISBN 0-15-100714-4
  7. 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.
  8. Czerny, M.; Grosch, W. (2000). "Potent Odorants of Raw Arabica Coffee. Their Changes during Roasting". Journal of Agricultural and Food Chemistry. 48 (3): 868–872. Bibcode:2000JAFC...48..868C. doi:10.1021/jf990609n. PMID 10725165.
  9. B. Bouyjou; B. Decazy; G. Fourny. "L'élimination du " goût de pomme de terre " dans le café Arabica du Burundi" [Removing the "potato taste" from Burundian Arabica]. Plantations, Recherche, Développement (in French). 6 (2): 107–115. Archived from the original on 2012-03-11. Retrieved 2012-04-01.
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