Alkylpyrazines are chemical compounds based on

pyrazine Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2. It is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. It is a ''"deliquescent crystal or wax-lik ...

with different substitution patterns. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including cocoa, baked goods, coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions.

Examples

File:2-Methylpyrazine.svg , 2-Methylpyrazine (found in roasted sesame) File:2,3-Dimethylpyrazine.svg , 2,3-Dimethylpyrazine (found in roasted sesame) File:2,5-Dimethylpyrazine.svg , 2,5-Dimethylpyrazine (asparagus, tea, crispbread, malt, shrimp, soy, squid, Swiss cheese, bread, roasted sesame) File:Tetramethylpyrazine v2.svg , 2,3,5,6-Tetramethylpyrazine (nattō, fermented cocoa beans)

2-Methylpyrazine

2-Methylpyrazine was the volatile odorant found at the highest concentration in roasted

sesame Sesame (; ''Sesamum indicum'') is a plant in the genus '' Sesamum'', also called benne. Numerous wild relatives occur in Africa and a smaller number in India. It is widely naturalized in tropical regions around the world and is cultivated for ...

seed oil.

2,3-Dimethylpyrazine

2,3-Dimethylpyrazine is a component of the aroma of roasted sesame seeds.

2,5-Dimethylpyrazine

2,5-Dimethylpyrazine is used as flavor additive and

odorant An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

in foods such as

cereals A cereal is a grass cultivated for its edible grain. Cereals are the world's largest crops, and are therefore staple foods. They include rice, wheat, rye, oats, barley, millet, and maize (Corn). Edible grains from other plant families, suc ...

and products such as

cigarettes A cigarette is a narrow cylinder containing a combustible material, typically tobacco, that is rolled into thin paper for smoking. The cigarette is ignited at one end, causing it to smolder; the resulting smoke is orally inhaled via the oppo ...

. It occurs naturally in

asparagus Asparagus (''Asparagus officinalis'') is a perennial flowering plant species in the genus ''Asparagus (genus), Asparagus'' native to Eurasia. Widely cultivated as a vegetable crop, its young shoots are used as a spring vegetable. Description ...

, black or green

tea Tea is an aromatic beverage prepared by pouring hot or boiling water over cured or fresh leaves of '' Camellia sinensis'', an evergreen shrub native to East Asia which probably originated in the borderlands of south-western China and nor ...

crispbread Crispbread is a flat and dry type of bread, containing mostly rye flour. Crispbreads are lightweight and keep fresh for a very long time due to their lack of water. Crispbread is a staple food and was for a long time considered a poor man's diet ...

malt Malt is any cereal grain that has been made to germinate by soaking in water and then stopped from germinating further by drying with hot air, a process known as "malting". Malted grain is used to make beer, whisky, malted milk, malt vinegar, ...

, raw

shrimp A shrimp (: shrimp (American English, US) or shrimps (British English, UK)) is a crustacean with an elongated body and a primarily Aquatic locomotion, swimming mode of locomotion – typically Decapods belonging to the Caridea or Dendrobranchi ...

Soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...

squid A squid (: squid) is a mollusc with an elongated soft body, large eyes, eight cephalopod limb, arms, and two tentacles in the orders Myopsida, Oegopsida, and Bathyteuthida (though many other molluscs within the broader Neocoleoidea are also ...

, Swiss cheeses, and

wheat bread Brown bread is bread made with significant amounts of whole grain flours, usually wheat sometimes with corn and or rye flours. Brown breads often get their characteristic dark color from ingredients such as molasses or coffee. In Canada, the ...

. It's also found in roasted sesame. The chemical formula is C₆H₈N₂.

2,6-Dimethylpyrazine

2,6-Dimethylpyrazine is also used as flavor additive and odorant in foods such as cereals and products such as cigarettes. It occurs naturally in baked

potato The potato () is a starchy tuberous vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are underground stem tubers of the plant ''Solanum tuberosum'', a perennial in the nightshade famil ...

, black or green tea, crispbread,

French fries French fries, or simply fries, also known as chips, and finger chips (Indian English), are '' batonnet'' or '' julienne''-cut deep-fried potatoes of disputed origin. They are prepared by cutting potatoes into even strips, drying them, and f ...

, peated malt, raw asparagus, roasted

barley Barley (), a member of the grass family, is a major cereal grain grown in temperate climates globally. It was one of the first cultivated grains; it was domesticated in the Fertile Crescent around 9000 BC, giving it nonshattering spikele ...

, roasted filberts or

pecans The pecan ( , , ; ''Carya illinoinensis'') is a species of hickory native to the Southern United States and northern Mexico in the region of the Mississippi River. The tree is cultivated for its seed primarily in the U.S. states of Georgia, ...

, squid, wheat bread,

wild rice Wild rice, also called manoomin, mnomen, psíŋ, Canada rice, Indian rice, or water oats, is any of four species of grasses that form the genus ''Zizania'', and the grain that can be harvested from them. The grain was historically and is sti ...

(Zizania aquatica), and

wort Wort () is the liquid extracted from the mashing process during the brewing of beer or whisky. Wort contains the sugars, the most important being maltose and maltotriose, that will be Ethanol fermentation, fermented by the brewing yeast to prod ...

. It's also found in roasted sesame. The chemical formula is C₆H₈N₂.

2,3,5,6-Tetramethylpyrazine

Tetramethylpyrazine Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans. In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter. When purified ...

(ligustrazine) is found in

nattō is a traditional Japanese cuisine, Japanese food made from whole soybeans that have been Fermentation in food processing, fermented with Bacillus subtilis, ''Bacillus subtilis'' var. ''natto''. It is often served as a breakfast food with rice. ...

and in fermented

cocoa bean The cocoa bean, also known as cocoa () or cacao (), is the dried and fully fermented seed of ''Theobroma cacao'', the cacao tree, from which cocoa solids (a mixture of nonfat substances) and cocoa butter (the fat) can be extracted. Cacao tree ...

s.Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550.

References

{{reflist Pyrazines