<abstract xmlns="http://www.w3.org/1999/xhtml"><p>Employment of 1-hydroxy-acetone as a carbon source and NH<sub>4</sub>OH as a source of base and nitrogen, has enabled arrays of pyrazines to be synthesized. Reaction conditions such as temperature, time, carbon/nitrogen mole ratios and pH were optimized to maximize the quantity of pyrazines, thereby providing the synthesis of at least 19–20 structurally different pyrazines. Addition of amino acids, selected aldehydes, and hydrolyzed tobacco-derived F1 protein has positively impacted the array of pyrazines from both qualitative and quantitative aspects. Results further showed that by changing the carbon source from 1-hydroxy-acetone to 1-hydroxy-2-butanone and/or 2-hydroxy-3-butanone, control of the type of pyrazines being synthesized could be realized in that the qualitative and quantitative distributions of the pyrazine array were shifted to higher molecular weight derivatives. A relatively large scale reaction (1.5 L) employing optimized parameters yielded > 2 g of a diverse array of pyrazines dominated by multiple dimethylpyrazine derivatives. While systematically varying reaction conditions and reagent mole ratios can predictably alter the distribution and yield of pyrazines, the two most overwhelmingly significant factors governing these two pyrazine product characteristics included the structure of the carbon source and the presence or absence of aldehydes and free amino acids.</p></abstract>

Employment of 1-hydroxy-acetone as a carbon source and NH4OH as a source of base and nitrogen, has enabled arrays of pyrazines to be synthesized. Reaction conditions such as temperature, time, carbon/nitrogen mole ratios and pH were optimized to maximize the quantity of pyrazines, thereby providing the synthesis of at least 19–20 structurally different pyrazines. Addition of amino acids, selected aldehydes, and hydrolyzed tobacco-derived F1 protein has positively impacted the array of pyrazines from both qualitative and quantitative aspects. Results further showed that by changing the carbon source from 1-hydroxy-acetone to 1-hydroxy-2-butanone and/or 2-hydroxy-3-butanone, control of the type of pyrazines being synthesized could be realized in that the qualitative and quantitative distributions of the pyrazine array were shifted to higher molecular weight derivatives. A relatively large scale reaction (1.5 L) employing optimized parameters yielded > 2 g of a diverse array of pyrazines dominated by multiple dimethylpyrazine derivatives. While systematically varying reaction conditions and reagent mole ratios can predictably alter the distribution and yield of pyrazines, the two most overwhelmingly significant factors governing these two pyrazine product characteristics included the structure of the carbon source and the presence or absence of aldehydes and free amino acids.

Optimal Synthesis of Substituted and Branched Pyrazines via Reaction of Alpha Hydroxy Ketones with Selected Nitrogen Sources

Contributions to Tobacco & Nicotine Research

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Employment of 1-hydroxy-acetone as a carbon source and NH4OH as a source of base and nitrogen, has enabled arrays of pyrazines to be synthesized. Reaction...

Optimal Synthesis of Substituted and Branched Pyrazines via Reaction of Alpha Hydroxy Ketones with Selected Nitrogen Sources

Published Online: Aug 30, 2019

Page range: 267 - 277

Received: Jun 29, 2018

Accepted: Jul 02, 2019

DOI: https://doi.org/10.2478/cttr-2019-0006

© 2019 Mehdi Ashraf-Khorassani et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.