Selective Substituted Pyrazine Formation via Hydroxy Ketone Carbon Sources

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Solution Overview

Problem

Conventional methods for producing pyrazines using sugars as carbon sources often result in dominant production of undesirable pyrazine and methylpyrazine, which lack desirable sensory notes and volatility characteristics, making them less suitable for certain applications, such as tobacco products.

Innovation Solution

The use of tobacco-derived carbon sources like hydroxy ketones and nitrogen sources like amino acids or ammonium ions in controlled reaction conditions to selectively produce specific substituted pyrazines, minimizing the formation of pyrazine and methylpyrazine and allowing for the production of desirable pyrazines with improved flavor profiles.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If sugars are used as carbon sources in pyrazine production, then pyrazine and methylpyrazine are produced in high quantities, but the sensory quality and volatility characteristics deteriorate

Engineering Contradiction:
Improvepyrazine production quantityVSAvoidsensory quality and volatility characteristics
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the carbon source from conventional sugars to hydroxy ketones (such as acetoin, acetyl methyl carbinol, acetol). This parameter change in the carbon source structure fundamentally alters the reaction pathway, enabling selective formation of substituted pyrazines with desirable sensory characteristics while avoiding dominant production of pyrazine and methylpyrazine.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If conventional sugar-based methods are used, then the reaction process is simple and well-established, but the product selectivity and flavor profile control are poor

Engineering Contradiction:
Improvereaction process simplicityVSAvoidproduct selectivity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The invention modifies the chemical composition parameter of the carbon source to hydroxy ketones, which inherently directs the Maillard reaction toward substituted pyrazine formation. This parameter change maintains reaction simplicity while achieving superior product selectivity and flavor profile control.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If free amino acids are added to reduce pyrazine and methylpyrazine formation, then the amount of undesirable products decreases, but the overall pyrazine yield and complexity of the mixture increase

Engineering Contradiction:
Improveundesirable pyrazine contentVSAvoidtotal pyrazine yield
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent extracts or removes sugar from the conventional carbon source mixture and replaces it with hydroxy ketones. This extraction of the problematic sugar component eliminates the pathway to pyrazine and methylpyrazine formation while maintaining productive pyrazine synthesis through the hydroxy ketone route.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

By changing the carbon source parameter from sugar to hydroxy ketone, the reaction selectively produces substituted pyrazines with desirable sensory properties, achieving both reduction of undesirable products and maintenance of high productivity in a single parameter change.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach enables the controlled formation of specific substituted pyrazines with desirable flavor profiles, such as roasted and toasted notes, which can be incorporated into tobacco products, enhancing their sensory attributes.

Implementation Method 1

Pyrazines are produced by reactions (e.g., Maillard) of a carbon source with nitrogenous compounds

Methodology Applied
Scientific EffectMaillard reaction: Chemical Bonding

Implementation Method 2

heating the reaction solution to a reaction temperature and holding the reaction solution at the reaction temperature for a time sufficient to produce a reaction product comprising at least one substituted pyrazine

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Data Source

PatentUS11891364B2Methods of selectively forming substituted pyrazines
Publication Date: 2024.02.06 R J REYNOLDS TOBACCO COMPANY
  • US11891364B2 patent drawing
  • US11891364B2 patent drawing
  • US11891364B2 patent drawing

AI summary

Methods of selectively forming substituted pyrazines are provided. Methods of the present invention can include receiving a reaction solution including at least one carbon source and at least one nitrogen source, and heating the reaction solution to a reaction temperature and holding the reaction solution at the reaction temperature for a time sufficient to produce a reaction product comprising at least one substituted pyrazine. The carbon source can be selected from the group consisting of hydroxy ketone(s), sugar(s) treated with at least one buffer, and combinations thereof. Tobacco products incorporating substituted pyrazines are also provided.