S-nitrosothiol Meat Preservatives Reducing Nitrosamine Formation

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Solution Overview

Problem

Current nitrite substitutes for meat preservation, such as S-nitrosocysteine, fail to effectively reduce N-nitrosamine formation and often exhibit similar or increased reactivity with secondary amines, posing health risks due to carcinogenic compounds.

Innovation Solution

Modified S-nitroso-cysteine derivatives, like S-nitroso-N-acetylcysteine, are used in combination with inhibitors like ascorbic acid to significantly reduce N-nitrosamine formation, offering a safer preservative alternative by minimizing reaction with secondary amines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If nitrite is used as a preservative in meat, then antimicrobial activity and color preservation are improved, but N-nitrosamine formation increases

Engineering Contradiction:
Improvepreservative activityVSAvoidN-nitrosamine formation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical structure parameter of nitrite by introducing organic groups (R1 and R2) to create organic nitrites with the general formula R1-N(O)-R2. This structural modification reduces reactivity with secondary amines while maintaining preservative properties, directly addressing the contradiction between effectiveness and harmful byproduct formation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite nitrosyl compounds combining organic moieties with nitrosyl groups. These composite structures exhibit modified chemical behavior compared to inorganic nitrite, achieving both preservation efficacy and reduced carcinogenic potential through the synergistic combination of organic and inorganic components

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If S-nitrosocysteine is used as a nitrite substitute, then N-nitrosamine formation is reduced, but antimicrobial activity is insufficient

Engineering Contradiction:
ImproveN-nitrosamine formationVSAvoidantimicrobial activity
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The invention modifies the S-nitrosocysteine structure by introducing various organic groups (R1 and R2) to create a series of derivatives with formula R1-N(O)-R2 where at least one R group contains a thiol or amino group. This systematic structural parameter change optimizes both antimicrobial activity and reduced nitrosamine formation simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific functional groups (thiol, amino, carboxyl) at specific positions in the molecular structure to confer localized functions. The thiol or amino group provides antimicrobial activity, while the overall structure maintains low reactivity with secondary amines, achieving different functions at different molecular locations

Inventive Principle:
Principle #3Local quality

3Object-generated harmful factors

If nitrite is replaced with traditional substitutes, then N-nitrosamine formation is addressed, but preservative effectiveness is lost

Engineering Contradiction:
ImproveN-nitrosamine formationVSAvoidpreservative effectiveness
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The organic nitrosyl compounds are designed to perform multiple functions simultaneously: antimicrobial activity, color preservation, and flavor contribution. This multi-functionality replaces the traditional single-function approach of nitrite, achieving both safety and effectiveness in one compound

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The organic nitrosyl compounds act as intermediaries between nitrite and meat components. They provide the necessary nitrosyl groups for preservation while their organic structure mediates reduced reactivity with harmful amines, bridging the gap between effectiveness and safety

Inventive Principle:
Principle #24Intermediary (Mediator)

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

S-nitroso-N-acetylcysteine derivatives generate substantially lower amounts of nitrosamines compared to sodium nitrite or S-nitrosocysteine, providing effective antimicrobial activity and color preservation in meat products while maintaining flavor, even under varying storage conditions.

Implementation Method 1

The reaction of nitrite and secondary amines leads to the formation of N-nitrosamines... Modified S-nitroso-cysteine derivatives, like S-nitroso-N-acetylcysteine, are used in combination with inhibitors like ascorbic acid to significantly reduce N-nitrosamine formation

Methodology Applied
Scientific EffectNitrosation reaction: Chemical Bonding

Implementation Method 2

auxiliary additives intended to suppress formation of N-nitrosamines, e.g., chiefly ascorbic acid, isoascrobic acid or salts thereof, are conventionally incorporated into nitrite-cured meat products to act as nitrosamine blocking agents

Methodology Applied
Scientific EffectChemical inhibition: Chemical Bonding

Implementation Method 3

S-Nitrosothiols are compounds represented, in their most general form, by Formula II... Incze et al. reported that a compound of Formula II where R is cysteine exhibits antimicrobial activity higher than nitrite on various bacteria

Methodology Applied
Scientific EffectAntimicrobial action: Preservative

Implementation Method 4

nitrite has been traditionally used by the meat industry as an additive to serve a multifold purpose: preservation of meet... development of the characteristic pink to red color of the meat

Methodology Applied
Scientific EffectColor preservation:

Data Source

PatentUS11632972B2S-nitrosothiol compounds and their combinations with nitrosamine blocking agents for safe food preservation
Publication Date: 2023.04.25 YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD
  • US11632972B2 patent drawing
  • US11632972B2 patent drawing
  • US11632972B2 patent drawing

AI summary

The invention relates to a process for treating food, in particular for curing meat, comprising adding to the food a compound of Formula III, which is a derivative of S-nitroso-cysteine. Use of the compound of Formula III as food preservative and compositions for curing meat are also provided by the invention.