Isopropyl methoxypyrazine

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.^[2] It can be detected by human taste at concentrations of as low as 2 nanograms per litre.^[3]

Isopropyl methoxy pyrazine

Chemical structure of isopropyl methoxy pyrazine
Names
Preferred IUPAC name 2-Methoxy-3-(propan-2-yl)pyrazine
Other names 2-Isopropyl-3-methoxypyrazine
Identifiers
CAS Number	25773-40-4 Y
3D model (JSmol)	Interactive image
ChemSpider	30649 N
ECHA InfoCard	100.042.946
PubChem CID	33166
UNII	1FL7L111A6 Y
CompTox Dashboard (EPA)	DTXSID4067147
InChI InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3 N Key: NTOPKICPEQUPPH-UHFFFAOYSA-N N InChI=1/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3 Key: NTOPKICPEQUPPH-UHFFFAOYAE
SMILES CC(C)C1=NC=CN=C1OC
Properties
Chemical formula	C8H12N2O
Molar mass	152.19 g/mol
Hazards
GHS labelling:[1]
Pictograms
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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]

See also

• Alkylpyrazines