The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients

Adams, Timothy B.; Doull, John; Feron, V.J.; Goodman, Jay I.; Marnett, Lawrence J.; Munro, I.C.; Newberne, Paul M.; Portoghese, Philip S.; Smith, Robert L.; Waddell, William J.; Wagner, Bernard M.

doi:10.1016/s0278-6915(01)00123-5

Cited by 93 publications

(64 citation statements)

References 46 publications

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“…They are a common constituent of foods, and are generated primarily from a heat-induced condensation between amino acids and sugars through the Strecker degradation. 1 Pyrazine derivatives exhibit a wide variety of aromas in food. For example, 2,5-dimethylpyrazine and tetramethylpyrazine are important flavor components in cocoa, 2 and 2-ethenyl-3,5-dimethylpyrazine and 2-ethenyl-3-ethyl-5-dimethylpyrazine are also important as earthy smelling compounds in coffee products.…”

Section: Introductionmentioning

confidence: 99%

An Abnormal Temperature Dependence of Alkylpyrazines’ Retention in Reversed-Phase Liquid Chromatography

et al. 2011

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Retention behaviors of pyrazine and alkylpyrazines on various stationary phases in reversed-phase liquid chromatography were examined. An abnormal temperature effect on the retention of alkylpyrazines with a mobile phase consisting of acetonitrile and water was observed when changing the column temperature. On the other hand, no similar trend was found with a methanol-water mobile phase. For all the columns investigated in this work, the above tendency to the temperature-dependence was consistently observed, suggesting that the abnormal temperature effect on the retention of alkylpyrazines could be mainly induced by an acetonitrile-based mobile phase.

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Section: Introductionmentioning

confidence: 99%

An Abnormal Temperature Dependence of Alkylpyrazines’ Retention in Reversed-Phase Liquid Chromatography

et al. 2011

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“…1 comprises a classical trans-square planar coordination complex (Fig. 1), whereas 2 has an unusual structure in which six-membered rings comprising [Cu 3 Cl 3 ] units (Fig. 2) are linked together into infinite chains by bridging pyrazine groups, thus forming double chains within a macroscopic one-dimensional zig-zag chain structure (Fig.…”

Section: Results and Discussion Preparation And Structural Studiesmentioning

confidence: 99%

Coordination complexes of functionalized pyrazines with metal ions: reagents for the controlled release of flavourant molecules at elevated temperatures

et al. 2006

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“…In contrast to the above findings, DM was not degraded under anaerobic conditions, indicating that the transformation of DM into DHM requires molecular oxygen. The hydroxylation of heterocyclic compounds by oxidases found in mammals and rats (in most cases, by xanthine oxidase) is well established (1,12,30,37,40). The formation of 2-hydroxymorpholine by cytochrome P450-dependent monooxygenase was suggested as the initial step in morpholine degradation by Mycobacterium strain RP1 (24).…”

Section: Discussionmentioning

confidence: 99%

“…Pyrazines are found mainly in processed food, where they are formed during dry heating processes. They are also found naturally in many vegetables, insects, terrestrial vertebrates, and marine organisms, and they are produced by microorganisms during their primary or secondary metabolism (1,3,36,39). Many alkylated and methoxylated pyrazines exhibit strong odorous properties and are important flavoring compounds in a variety of food products (11,19,27).…”

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confidence: 99%

Degradation of 2,3-Diethyl-5-Methylpyrazine by a Newly Discovered Bacterium, Mycobacterium sp. Strain DM-11

Rappert

Botsch

Nagorny

et al. 2006

Appl Environ Microbiol

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A bacterium was isolated from the waste gas treatment plant at a fishmeal processing company on the basis of its capacity to use 2,3-diethyl-5-methylpyrazine (DM) as a sole carbon and energy source. The strain, designated strain DM-11, grew optimally at 25°C and had a doubling time of 29.2 h. The strain did not grow on complex media like tryptic soy broth, Luria-Bertani broth, or nutrient broth or on simple carbon sources like glucose, acetate, oxoglutarate, succinate, or citrate. Only on Löwenstein-Jensen medium was growth observed. The 16S rRNA gene sequence of strain DM-11 showed the highest similarity (96.2%) to Mycobacterium poriferae strain ATCC 35087 T . Therefore, strain DM-11 merits recognition as a novel species within the genus Mycobacterium. DM also served as a sole nitrogen source for the growth of strain DM-11. The degradation of DM by strain DM-11 requires molecular oxygen. The first intermediate was identified as 5,6-diethyl-2-hydroxy-3-methylpyrazine (DHM). Its disappearance was accompanied by the release of ammonium into the culture medium. No other metabolite was detected. We conclude that ring fission occurred directly after the formation of DHM and ammonium was eliminated after ring cleavage. Molecular oxygen was essential for the degradation of DHM. The expression of enzymes involved in the degradation of DM and DHM was regulated. Only cells induced by DM or DHM converted these compounds. Strain DM-11 also grew on 2-ethyl-5(6)-methylpyrazine (EMP) and 2,3,5-trimethylpyrazine (TMP) as a sole carbon, nitrogen, and energy source. In addition, the strain converted many pyrazines found in the waste gases of food industries cometabolically.

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The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients

Cited by 93 publications

References 46 publications

An Abnormal Temperature Dependence of Alkylpyrazines’ Retention in Reversed-Phase Liquid Chromatography

An Abnormal Temperature Dependence of Alkylpyrazines’ Retention in Reversed-Phase Liquid Chromatography

Coordination complexes of functionalized pyrazines with metal ions: reagents for the controlled release of flavourant molecules at elevated temperatures

Degradation of 2,3-Diethyl-5-Methylpyrazine by a Newly Discovered Bacterium, Mycobacterium sp. Strain DM-11

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