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Sur l'arôme de viande de boeuf grillée II. Dihydro‐6,7‐5 H ‐cyclopenta[ b ]pyrazines, identification et mode de formation
Author(s) -
Flament Ivon,
Kohler Margrit,
Aschiero Roland
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590703
Subject(s) - chemistry , aroma , alkyl , flavor , pyrazine , ammonia , organic chemistry , stereochemistry , medicinal chemistry , food science
Identification of alkyl‐5 H ‐6,7‐dihydrococyclopenta[ b ]pyrazines in roasted meat flavor. Model reaction used as basis for natural product formation and new synthesis. Seven alkyl‐5 H ‐6,7‐dihydrocyclopenta[ b ]pyrazines have been identified in a roasted meat aroma obtained by thermolysis of the hydrosoluble flavor precursors of raw meat. Formation of these heterocyclics by condensation of hydroxycyclopentenones with aliphatic α‐dicarbonyl compounds in the presence of ammonia has been confirmed by a model reaction. Alkyl‐5 H ‐cyclopenta[ b ]pyrazines and dicyclopenta [ b,e ]pyrazines are also obtained from this reaction, but have not yet been identified in roasted flavors. Preparation of the intermediates of the model reaction enabled development of an economical synthesis of 2,3,5‐trimethyl‐5 H ‐6,7‐dihydrocyclopenta[ b ]pyrazine.