Isopropyl methoxypyrazine
Chemical compound
From Wikipedia, the free encyclopedia
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, and yeast, specifically Saccharomyces cerevisiae. [2] It can be detected by human taste at concentrations of as low as 2 nanograms per litre.[3]
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| Names | |
|---|---|
| Preferred IUPAC name
2-Methoxy-3-(propan-2-yl)pyrazine | |
| Other names
2-Isopropyl-3-methoxypyrazine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.042.946 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H12N2O | |
| Molar mass | 152.19 g/mol |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| H315, H319, H335 | |
| P302+P352, P305+P351+P338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Presence in wine grapes
The odor of IPMP tends to be undesirable in the case of certain wines.[4]
Cabernet Sauvignon has high levels of methoxypyrazines.[5][6] 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.[7]
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.[8] The insects Antestiopsis are also implicated in causing the taste.[9]