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 ;
3D model (JSmol)	Interactive image;
ChemSpider	30649 ;
PubChem CID	33166;
UNII	1FL7L111A6 ;
	InChI InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3 Key: NTOPKICPEQUPPH-UHFFFAOYSA-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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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]

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]

References

↑ GHS: sigma-aldrich 243132
↑ 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
↑ 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.
↑ Trace flavour components of grapes
↑ winepros.com.au Oxford Companion to Wine methoxypyrazines
↑ Oz Clarke Encyclopedia of Grapes pg 223 Harcourt Books 2001 ISBN:0-15-100714-4
↑ 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.
↑ 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.
↑ 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.

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[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.

[regional-4] Trace flavour components of grapes

[5] winepros.com.au Oxford Companion to Wine methoxypyrazines

[Clarke_pg_223-6] 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.

[bou-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.

Isopropyl Methoxypyrazine

Contents

Presence in wine grapes

Presence in coffee

See also

References