Isopropyl methoxypyrazine

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

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

## Presence in wine grapes

[edit]

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

[edit]

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

[edit]

* Alkylpyrazines

## References

[edit]

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.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H315]: H315: Causes skin irritation
*[H319]: H319: Causes serious eye irritation
*[H335]: H335: May cause respiratory irritation
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.