Pyrazine, 2-ethyl-6-methyl-
- Formula: C7H10N2
- Molecular weight: 122.1677
- IUPAC Standard InChI: InChI=1S/C7H10N2/c1-3-7-5-8-4-6(2)9-7/h4-5H,3H2,1-2H3
- IUPAC Standard InChIKey: RAFHQTNQEZECFL-UHFFFAOYSA-N
- CAS Registry Number: 13925-03-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 2-Ethyl-6-methylpyrazine; 2-Methyl-6-ethylpyrazine; 2,6-Methylethylpyrazine; Pyrazine, 6-ethyl-2-methyl
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Normal alkane RI, polar column, temperature ramp
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-Innowax | FFAP | DB-Wax | HP-Innowax | ZB-Wax |
| Column length (m) | 15. | 30. | 60. | 50. | 60. |
| Carrier gas | Helium | Nitrogen | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.20 | 0.32 |
| Phase thickness (μm) | 0.50 | 0.50 | 0.50 | 0.33 | 0.50 |
| Tstart (C) | 40. | 35. | 40. | 50. | 40. |
| Tend (C) | 250. | 250. | 210. | 250. | 220. |
| Heat rate (K/min) | 3. | 4. | 2. | 10. | 4. |
| Initial hold (min) | 5. | 5. | 5. | ||
| Final hold (min) | 45. | 70. | 6. | 5. | |
| I | 1362. | 1398. | 1408. | 1372. | 1420. |
| Reference | Puvipirom and Chaisei, 2012 | Budryn, Nebesny, et al., 2011 | Moon and Shibamoto, 2009 | Du, Clery, et al., 2008 | Marin, Pozrl, et al., 2008 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | FFAP | DB-Wax | DB-Wax | TC-Wax |
| Column length (m) | 30. | 30. | 30. | 60. | 60. |
| Carrier gas | He | N2 | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.5 | 0.25 | 0.25 | 0.5 |
| Tstart (C) | 50. | 35. | 40. | 50. | 40. |
| Tend (C) | 230. | 320. | 230. | 200. | 230. |
| Heat rate (K/min) | 4. | 4. | 4. | 2. | 3. |
| Initial hold (min) | 5. | 2. | 8. | ||
| Final hold (min) | 15. | 45. | 15. | 90. | |
| I | 1375. | 1398. | 1375. | 1357. | 1396. |
| Reference | Characterization of Pyrazines in Some Chinese Liquors and Their Approximate Concentrations, 2007 | Nebesny, Budryn, et al., 2007 | Fan and Qian, 2006 | Fujioka and Shibamoto, 2006 | Ishikawa, Ito, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | HP-Wax | HP-Wax | DB-Wax | TC-Wax |
| Column length (m) | 30. | 60. | 60. | 30. | 60. |
| Carrier gas | He | He | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.5 | 0.5 | 0.25 | 0.25 |
| Tstart (C) | 50. | 40. | 40. | 30. | 50. |
| Tend (C) | 180. | 199. | 190. | 250. | 230. |
| Heat rate (K/min) | 3. | 3. | 3. | 4. | 2. |
| Initial hold (min) | 6. | 6. | 1. | ||
| Final hold (min) | 40. | ||||
| I | 1415. | 1411. | 1411. | 1392. | 1383. |
| Reference | Yanagimoto, Ochi, et al., 2004 | Andueza, Maeztu, et al., 2003 | Andueza, de Peña, et al., 2003 | Tanaka, Yamauchi, et al., 2003 | Fukami, Ishiyama, et al., 2002 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-Wax | DB-Wax | HP-Wax | HP-Wax | DB-Wax |
| Column length (m) | 60. | 30. | 60. | 60. | 60. |
| Carrier gas | He | He | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.53 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.5 | 1. | 0.5 | 0.5 | |
| Tstart (C) | 40. | 40. | 40. | 40. | 30. |
| Tend (C) | 190. | 225. | 190. | 190. | 170. |
| Heat rate (K/min) | 3. | 6. | 3. | 3. | 2. |
| Initial hold (min) | 6. | 5. | 6. | 6. | 4. |
| Final hold (min) | 30. | 60. | |||
| I | 1411. | 1380. | 1411. | 1411. | 1380. |
| Reference | Sanz, Maeztu, et al., 2002 | Cadwallader and Heo, 2001 | Maeztu, Sanz, et al., 2001 | Sanz, Ansorena, et al., 2001 | Buttery, Orts, et al., 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | DB-Wax | CP-Wax 52CB | DB-Wax | DB-Wax |
| Column length (m) | 30. | 60. | 50. | 60. | 60. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.53 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | ||||
| Tstart (C) | 60. | 30. | 50. | 40. | 60. |
| Tend (C) | 210. | 170. | 210. | 200. | 180. |
| Heat rate (K/min) | 4. | 2. | 1.5 | 2. | 4. |
| Initial hold (min) | 4. | 5. | 2. | 4. | |
| Final hold (min) | 30. | 10. | 30. | ||
| I | 1394. | 1380. | 1399. | 1382. | 1367. |
| Reference | Iwatsuki, Mizota, et al., 1999 | Buttery and Ling, 1998 | Chyau, Lin, et al., 1997 | Umano, Hagi, et al., 1995 | Eiserich, Macku, et al., 1992 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | DB-Wax | Carbowax 20M | DB-Wax | Carbowax 20M |
| Column length (m) | 50. | 50. | 30. | 50. | |
| Carrier gas | He | 30 | He | Hydrogen | |
| Substrate | |||||
| Column diameter (mm) | 0.33 | 0.25 | 0.22 | 0.25 | 0.20 |
| Phase thickness (μm) | |||||
| Tstart (C) | 60. | 30. | 80. | 70. | 50. |
| Tend (C) | 200. | 240. | 200. | 160. | 200. |
| Heat rate (K/min) | 3. | 50. | 2. | 2. | 1. |
| Initial hold (min) | 10. | 8. | |||
| Final hold (min) | 35. | ||||
| I | 1350. | 1364. | 1353. | 1381. | 1367. |
| Reference | Vernin, Metzger, et al., 1992 | Pfannhauser, 1990 | Mihara and Masuda, 1988 | Wong and Bernhard, 1988 | Wu, Liou, et al., 1987 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M |
| Column length (m) | 50. | 150. | 39. | 100. | 100. |
| Carrier gas | N2 | H2 | |||
| Substrate | |||||
| Column diameter (mm) | 0.22 | 0.64 | 0.30 | 0.25 | 0.25 |
| Phase thickness (μm) | |||||
| Tstart (C) | 80. | 50. | 60. | 70. | 70. |
| Tend (C) | 200. | 170. | 220. | 170. | 170. |
| Heat rate (K/min) | 2. | 1. | 2. | 1. | 1. |
| Initial hold (min) | 30. | ||||
| Final hold (min) | 60. | ||||
| I | 1353. | 1390. | 1372. | 1388. | 1392. |
| Reference | Mihara and Enomoto, 1985 | Buttery, Ling, et al., 1983 | Liardon and Ledermann, 1980 | Shibamoto and Russell, 1977 | Shibamoto and Russell, 1977 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane RI, polar column, temperature ramp, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Puvipirom and Chaisei, 2012
Puvipirom, J.; Chaisei, S.,
Contribution of roasted grains and seeds in aroma of oleang (Thai coffee drink),
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Budryn, Nebesny, et al., 2011
Budryn, G.; Nebesny, E.; Kula, J.; Majda, T.; Krysiak, W.,
HS-SPME/GC/MS Profiles of convectively and microwave roasted Ivory Coast Robusta coffee brews,
Czech. J. Food Sci., 2011, 29, 2, 151-160. [all data]
Moon and Shibamoto, 2009
Moon, J.-K.; Shibamoto, T.,
Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans,
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Du, Clery, et al., 2008
Du, Z.; Clery, R.; Hammond, C.J.,
Volatile organic nitrogen-containing constituents in ambrette seed Abelmoschus moschatus Medik (Malvaceae),
J. Agric. Food Chem., 2008, 56, 16, 7388-7392, https://doi.org/10.1021/jf800958d
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Marin, Pozrl, et al., 2008
Marin, K.; Pozrl, T.; Zlatic, E.; Plestenjak, A.,
A new aroma index to determine the aroma quality of roasted and ground coffee during storage,
Food Technol. Biotechnol., 2008, 46, 4, 442-447. [all data]
Characterization of Pyrazines in Some Chinese Liquors and Their Approximate Concentrations, 2007
Characterization of Pyrazines in Some Chinese Liquors; Their Approximate Concentrations,
W. Fan; Y. Xu; Y. Zhang,
J. Agric. Food Chem., 2007, 55, 9956-9962. [all data]
Nebesny, Budryn, et al., 2007
Nebesny, E.; Budryn, G.; Kula, J.; Majda, T.,
The effect of roasting method on headspace composition of robusta coffee bean aroma,
Eur. Food Res. Technol., 2007, 225, 1, 9-19, https://doi.org/10.1007/s00217-006-0375-0
. [all data]
Fan and Qian, 2006
Fan, W.; Qian, M.C.,
Characterization of Aroma Compounds of Chinese Wuliangye and Jiannanchun Liquors by Aroma Extract Dilution Analysis,
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Fujioka and Shibamoto, 2006
Fujioka, K.; Shibamoto, T.,
Quantitation of volatiles and nonvolatile acids in an extract from coffee beverages: correlation with antioxidant activity,
J. Agric. Food Chem., 2006, 54, 16, 6054-6058, https://doi.org/10.1021/jf060460x
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Ishikawa, Ito, et al., 2004
Ishikawa, M.; Ito, O.; Ishizaki, S.; Kurobayashi, Y.; Fujita, A.,
Solid-phase aroma concentrate extraction (SPACE ): a new headspace technique for more sensitive analysis of volatiles,
Flavour Fragr. J., 2004, 19, 3, 183-187, https://doi.org/10.1002/ffj.1322
. [all data]
Yanagimoto, Ochi, et al., 2004
Yanagimoto, K.; Ochi, H.; Lee, K.-G.; Shibamoto, T.,
Antioxidative activities of fractions obtained from brewed coffee,
J. Agric. Food Chem., 2004, 52, 3, 592-596, https://doi.org/10.1021/jf030317t
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Andueza, Maeztu, et al., 2003
Andueza, S.; Maeztu, L.; Pascual, L.; Ibanez, C.; de Pena M.P.; Cid, C.,
Influence of extraction temperature on the final quality of espresso coffee,
J. Sci. Food Agric., 2003, 83, 3, 240-248, https://doi.org/10.1002/jsfa.1304
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Andueza, de Peña, et al., 2003
Andueza, S.; de Peña, M.P.; Cid, C.,
Chemical and sensorial characteristics of espresso coffee as affected by grinding and torrefacto roast,
J. Agric. Food Chem., 2003, 51, 24, 7034-7039, https://doi.org/10.1021/jf034628f
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Tanaka, Yamauchi, et al., 2003
Tanaka, T.; Yamauchi, T.; Katsumata, R.; Kiuchi, K.,
Comparison of volatile components in commercial Itohiki-Natto by solid phase microextraction and gas chromatography,
Nippon Shokuhin Kagaku Kogaku Kaishi, 2003, 50, 6, 278-285, https://doi.org/10.3136/nskkk.50.278
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Fukami, Ishiyama, et al., 2002
Fukami, K.; Ishiyama, S.; Yaguramaki, H.; Masuzawa, T.; Nabeta, Y.; Endo, K.; Shimoda, M.,
Identification of distinctive volatile compounds in fish sauce,
J. Agric. Food Chem., 2002, 50, 19, 5412-5416, https://doi.org/10.1021/jf020405y
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Sanz, Maeztu, et al., 2002
Sanz, C.; Maeztu, L.; Zapelena, M.J.; Bello, J.; Cid, C.,
Profiles of volatile compounds and sensory analysis of three blends of coffee: influence of different proportions of Arabica and Robusta and influence of roasting coffee with sugar,
J. Sci. Food Agric., 2002, 82, 8, 840-847, https://doi.org/10.1002/jsfa.1110
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Cadwallader and Heo, 2001
Cadwallader, K.R.; Heo, J.,
Aroma of roasted sesame oil: characterization by direct thermal desorption-gas chromatography-olfactometry and sample dilution analysis,
Am. Chem. Soc. Symp. Ser., 2001, 782, 187-202. [all data]
Maeztu, Sanz, et al., 2001
Maeztu, L.; Sanz, C.; Andueza, S.; de Peña, M.P.; Bello, J.; Cid, C.,
Characterization of espresso coffee aroma by static headspace GC-MS and sensory flavor profile,
J. Agric. Food Chem., 2001, 49, 11, 5437-5444, https://doi.org/10.1021/jf0107959
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Sanz, Ansorena, et al., 2001
Sanz, C.; Ansorena, D.; Bello, J.; Cid, C.,
Optimizing headspace temperature and time sampling for identification of volatile compounds in ground roasted Arabica coffee,
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Buttery, Orts, et al., 1999
Buttery, R.G.; Orts, W.J.; Takeoka, G.R.; Nam, Y.,
Volatile flavor components of rice cakes,
J. Agric. Food Chem., 1999, 47, 10, 4353-4356, https://doi.org/10.1021/jf990140w
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Iwatsuki, Mizota, et al., 1999
Iwatsuki, K.; Mizota, Y.; Kubota, T.; Nishimura, O.; Masuda, H.; Sotoyama, K.; Tomita, M.,
Aroma extract dilution analysis. Evluation of aroma of pasteurized and UHT processed milk by aroma extract dilution analysis,
Nippon Shokuhin Kagaku Kogaku Kaishi, 1999, 46, 9, 587-597, https://doi.org/10.3136/nskkk.46.587
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Buttery and Ling, 1998
Buttery, R.G.; Ling, L.C.,
Additional studies on flavor components of corn tortilla chips,
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Chyau, Lin, et al., 1997
Chyau, C.-C.; Lin, Y.-C.; Mau, J.-L.,
Storage stability of deep-fried shallot flavoring,
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Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T.,
Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system,
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Eiserich, Macku, et al., 1992
Eiserich, J.P.; Macku, C.; Shibamoto, T.,
Volatile antioxidants formed from an L-cysteine/D-glucose Maillard model system,
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. [all data]
Vernin, Metzger, et al., 1992
Vernin, G.; Metzger, J.; Boniface, C.; Murello, M.-H.; Siouffi, A.; Larice, J.-L.; Parkanyi, C.,
Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds,
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Pfannhauser, 1990
Pfannhauser, W.,
Fluchtige Verbindungen aus extrudaten von triticale,
Deutsche Lebensmittel-Rundschau, 1990, 86, 3, 69-72. [all data]
Mihara and Masuda, 1988
Mihara, S.; Masuda, H.,
Structure-odor relationships for disubstituted pyrazines,
J. Agric. Food Chem., 1988, 36, 6, 1242-1247, https://doi.org/10.1021/jf00084a029
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Wong and Bernhard, 1988
Wong, J.M.; Bernhard, R.A.,
Effect of nitrogen source on pyrazine formation,
J. Agric. Food Chem., 1988, 36, 1, 123-129, https://doi.org/10.1021/jf00079a032
. [all data]
Wu, Liou, et al., 1987
Wu, C.-M.; Liou, S.-E.; Chang, Y.-H.; Chiang, W.,
Volatile compounds of the wax gourd (Benincasa hispida, Cogn) and a wax gourd beverage,
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Mihara and Enomoto, 1985
Mihara, S.; Enomoto, N.,
Calculation of retention indices of pyrazines on the basis of molecular structure,
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Buttery, Ling, et al., 1983
Buttery, R.G.; Ling, L.C.; Teranishi, R.; Mon, T.R.,
Insect attractants: volatiles of hydrolizyed protein insect baits,
J. Agric. Food Chem., 1983, 31, 4, 689-692, https://doi.org/10.1021/jf00118a003
. [all data]
Liardon and Ledermann, 1980
Liardon, R.; Ledermann, S.,
volatile components of fermented soya hydrolysate. II. Composition of basic fraction,
Z. Lebensm. Unters. Forsch., 1980, 170, 3, 208-213, https://doi.org/10.1007/BF01042542
. [all data]
Shibamoto and Russell, 1977
Shibamoto, T.; Russell, G.F.,
A study of the volatiles isolated from a D-glucose-hydrogen sulfide-ammonia model system,
J. Agric. Food Chem., 1977, 25, 1, 109-112, https://doi.org/10.1021/jf60209a054
. [all data]
Notes
Go To: Top, Normal alkane RI, polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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