Isopropyl methoxypyrazine

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

PubChem CID

* 33166

UNII |

* 1FL7L111A6 Y

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 pictograms |
GHS Signal word | warning

GHS hazard statements

| HH315Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors, HH335Script error: No such module "Preview warning".Category:GHS errors

GHS precautionary statements

| PP302 + P352Script error: No such module "Preview warning".Category:GHS errors, PP305 + P351 + P338Script error: No such module "Preview warning".Category:GHS errors

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

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]

## Contents

* 1 Presence in wine grapes
* 2 Presence in coffee
* 3 See also
* 4 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

## References

1. ↑ GHS: sigma-aldrich 243132
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.﻿ (Report). http://www.tesisenred.net/bitstream/handle/10803/8653/15-PaperC2.pdf. Retrieved 2012-04-01.
4. ↑ "Trace flavour components of grapes". http://www.regional.org.au/au/roc/1991food/p-13.htm.
5. ↑ winepros.com.au Oxford Companion to Wine methoxypyrazines
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. doi:10.1021/jf990609n. PMID 10725165. Bibcode: 2000JAFC...48..868C.
9. ↑ B. Bouyjou; B. Decazy; G. Fourny. "L'élimination du " goût de pomme de terre " dans le café Arabica du Burundi" (in fr). Plantations, Recherche, Développement 6 (2): 107–115. http://publications.cirad.fr/une_notice.php?dk=392315. Retrieved 2012-04-01.

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*[CID]: Compound ID