2-methoxypyrazine is a kind of pyrazine derivative. It emits a kernels and cocoa-like aroma. It is a commonly used daily, food flavoring agent. It has many kinds of flavoring derivatives such as 3-Isobutyl-2-methoxypyrazine, 3-sec-butyl-2-methoxypyrazine, 3-alkyl-2-methoxypyrazines and 3-isopropyl-2-methoxypyrazine. There derivatives could be found in wine and many kinds of fruits such as berry and grapes.
Murray, K. E., J. Shipton, and F. B. Whitfield. "2-methoxypyrazines and the flavour of green peas (Pisum sativum). " Chemistry & Industry 27.14(1970):897-898.
Hashizume, Katsumi, and Takashi Samuta. "Grape maturity and light exposure affect berry methoxypyrazine concentration." American Journal of Enology and Viticulture 50.2 (1999): 194-198.
Hartmann, Peter J., Harold M. McNair, and Bruce W. Zoecklein. "Measurement of 3-alkyl-2-methoxypyrazine by headspace solid-phase microextraction in spiked model wines." American Journal of Enology and Viticulture 53.4 (2002): 285-288.
HASHiZUME, Katsumi, and Norihiko Umeda. "Methoxypyrazine content of Japanese red wines." Bioscience, biotechnology, and biochemistry 60.5 (1996): 802-805.
Lacey, Michael J., et al. "Methoxypyrazines in Sauvignon blanc grapes and wines." American Journal of Enology and Viticulture 42.2 (1991): 103-108.
Methoxypyrazine has an odor threshold of 700 ppb in water. Methoxypyrazine may be prepared from 2-hydroxypyrazine by various
routes.
Methoxypyrazine has a sweet, nutty, cocoa odor. Methoxypyrazine contributes a distinctive “green, capsicum (bell
pepper), herbaceous and earthy” aroma that is quite characteristic of certain wines, such as sauvignon blanc and cabernet sauvignon.
Present at ultra-trace levels in sauvignon blanc and cabernet sauvignon grapes and wine. Methoxypyrazine
contributes a distinctive wine aroma, even at low parts per trillion levels. Also reported found in cooked beef, cocoa, malt and krill.
2-Methoxypyrazine is used as a daily-use and edible flavoring. GB 2760-2002 stipulates that it is a permitted food flavoring, mainly used in the formulation of roasted flavorings.
From 2-hydroxypyrazine by various routes.
ChEBI: Methoxypyrazine is an aromatic ether and a member of pyrazines.
Skin and eye irritant.
When heated to decomposition it emits
toxic fumes of NOx.
