2,2-DIBROMO-3-NITRILOPROPIONAMIDE

CAS: 10222-01-2 ANTIMICROBIAL AGENT

2,2-DIBROMO-3-NITRILOPROPIONAMIDE is a synthetic antimicrobial agent with industrial applications and specific indirect food contact uses regulated under federal food additive provisions. It is not a direct food additive for consumption, and its use in food processing contexts is limited to controlled antimicrobial functions in industrial production and food contact materials.

What It Is

2,2-DIBROMO-3-NITRILOPROPIONAMIDE is a synthetic antimicrobial agent recognized by the Chemical Abstracts Service with CAS number 10222-01-2 and a stable crystalline form. It is broadly classified as an antimicrobial agent, meaning it inhibits or suppresses the growth of microorganisms such as bacteria and fungi. Its general structure includes brominated acetamide functionality, which contributes to its antimicrobial effectiveness. As a compound, it is not typically used directly as a food ingredient for direct consumption but rather in industrial contexts where microbial control is needed. From a regulatory perspective, it is referenced in a set of indirect food additive regulations that specify conditions under which the chemical can be used in food contact materials. These include provisions for controlling microorganisms in sugar mill environments (referencing 21 CFR 173.320) and use as a preservative in adhesives and paperboard components that may contact food (21 CFR 175.105, 176.170, 176.300). The inclusion of this compound in these regulations underscores its specialized function rather than general food additive use. In chemical databases, this compound appears under multiple synonyms but is most commonly referred to by its DBNPA abbreviation in scientific literature. The structural features and functional groups of this molecule provide it with broad antimicrobial properties, making it suitable for industrial applications where microbial contamination is a concern.

How It Is Made

The synthesis of 2,2-DIBROMO-3-NITRILOPROPIONAMIDE involves halogenation reactions that introduce bromine atoms into an acetamide backbone. Typical laboratory and industrial syntheses begin with a cyanoacetamide precursor, which undergoes controlled bromination under specific pH and temperature conditions to yield the dibrominated product. The production process is designed to ensure a consistent crystalline quality of the final compound, which aids in its handling and formulation for end uses. Because of the reactive nature of brominated compounds, synthesis requires careful control to avoid side reactions and ensure purity. Reagents are selected to introduce bromine atoms without degrading other functional elements of the molecule. After synthesis, the compound is purified and characterized using standard analytical techniques such as chromatography and spectrometry to confirm its identity and purity. The physical form of the resulting product is typically a white to off-white crystalline solid, stable under normal storage conditions. In industrial practice, manufacturers establish internal specifications for chemical purity, which may include maximum levels of residual solvents or byproducts. These specifications help maintain consistent performance when the compound is later incorporated into formulations intended for antimicrobial applications. Given its function, handling during manufacture and formulation prioritizes protective measures to avoid exposure and minimize environmental release.

Why It Is Used In Food

2,2-DIBROMO-3-NITRILOPROPIONAMIDE is used in food-related contexts not as a direct edible additive, but for its antimicrobial properties in processes where controlling microorganisms is essential. Its role in food processing arises from the need to limit microbial contamination in environments like sugar mills, where the presence of bacteria can interfere with product quality and safety. Under 21 CFR 173.320, certain chemicals including antimicrobial agents can be used to control microorganisms in cane sugar and beet sugar mills, provided conditions of use are met. Additionally, this compound has been approved under indirect food additive regulations for use as a preservative in adhesives applied to food packaging and as a component in coatings and paperboard that may contact food. These uses are governed by sections such as 21 CFR 175.105 (adhesives) and 21 CFR 176.170 and 176.300 (components of paper and paperboard in contact with foods). In these contexts, the compound helps prevent microbial degradation of materials that come into contact with food, thereby supporting food safety and quality. The technological justification for using an antimicrobial agent like this in food contact applications lies in its ability to suppress microbial growth on surfaces and materials. By incorporating it into adhesives or coatings, manufacturers aim to maintain the integrity of packaging materials and food processing environments, reducing spoilage and the risk of contamination during storage and transport. The compound’s effectiveness at low concentrations and compatibility with material substrates make it suitable for such applications under controlled regulatory limits.

Adi Example Calculation

Because 2,2-DIBROMO-3-NITRILOPROPIONAMIDE is not assigned a specific acceptable daily intake (ADI) value in regulatory frameworks, calculating an ADI example using a hypothetical body weight is not applicable in the same way it would be for a conventional food additive. Typically, an ADI example would illustrate how a numeric ADI value translates into exposure amounts for individuals of varying body weights. In the case of indirect food contact substances, exposure is instead controlled through limits on migration and specific conditions of use that ensure any incidental exposure remains minimal. For example, if a migration limit were established for a compound used in food packaging, regulators would assess the maximum amount that could migrate into food over time and compare that to established safety thresholds. These thresholds integrate uncertainty factors and toxicological data to ensure safety across populations. In the absence of a defined numeric ADI, exposure assessments rely on compliance with regulatory specifications that implicitly maintain safety margins.

Safety And Health Research

Safety and health research on 2,2-DIBROMO-3-NITRILOPROPIONAMIDE focuses on its toxicological profile and implications for handlers, industrial users, and incidental exposures. Toxicology reports from industrial assessments indicate that the compound has moderate acute toxicity and can cause irritation upon contact with skin, eyes, or respiratory tissues if protective measures are not taken. These findings underscore the importance of safe handling practices in industrial environments where the compound is formulated or applied. Regulatory evaluations for indirect food contact uses consider the compound’s potential for migration from materials into food and the associated exposure levels. Studies on similar antimicrobial agents typically assess parameters such as dermal toxicity, inhalation effects, and potential for environmental impacts, though detailed published research on this compound’s specific effects at low exposure levels may be limited. Regulatory provisions for indirect use hinge on the assumption that, when properly applied, migration remains low and does not pose a risk to consumers beyond accepted safety margins. Given its antimicrobial function, safety assessments also consider the compound’s mechanisms of action and potential unintended interactions with non-target organisms. However, the primary focus remains on ensuring that any incidental exposure from food contact materials falls within established limits of safety. Occupational and industrial safety guidelines provide further context on protective measures for workers handling this compound in manufacturing and application settings.

Regulatory Status Worldwide

In the United States, the regulatory status of 2,2-DIBROMO-3-NITRILOPROPIONAMIDE is defined through its inclusion in specific sections of Title 21 of the Code of Federal Regulations. These sections address indirect food additive uses, such as the control of microorganisms in sugar mill environments and the inclusion of antimicrobial preservatives in adhesives and coatings used on food contact materials. The regulations referenced under 21 CFR 173.320, 175.105, 176.170, and 176.300 provide the legal framework for these applications, specifying conditions of safe use. The compound is not approved as a direct food additive intended for ingestion. Instead, its use is permitted in industrial and indirect food contact applications where its antimicrobial properties can be harnessed without resulting in substantive direct consumption. Because of this specialized regulatory status, its presence in foods is incidental and subject to migration limits established in the relevant CFR sections. International regulatory frameworks may also address antimicrobial agents and food contact substances, but specific approvals and limitations can vary by jurisdiction. In many cases, a compound used in food contact applications in one region must undergo separate evaluations in others. For 2,2-DIBROMO-3-NITRILOPROPIONAMIDE, the primary documented regulatory context remains within U.S. federal food additive regulations that govern indirect contact uses and microbial control in processing environments.

Taste And Functional Properties

In terms of sensory properties, 2,2-DIBROMO-3-NITRILOPROPIONAMIDE itself is not used for taste or sensory effects in food. It is not intended for ingestion and therefore its taste profile is largely irrelevant in approved uses. Its physical form is a crystalline solid with limited solubility in water, and it does not contribute to flavor or functional food properties in the way sugars, acids, or emulsifiers do. Functionally, the compound’s properties are best understood in relation to its antimicrobial effectiveness. It is designed to interfere with microbial physiology in environments where controlling the presence of bacteria and fungi is necessary. The compound’s molecular structure allows it to interact with biological systems of microorganisms, leading to inhibited growth or death in situations where microbial activity would otherwise cause degradation of materials or contamination. Because it is not intended for ingestion, its use is restricted to applications where it does not directly impart taste or quality attributes to food. When incorporated into adhesives or coatings, it remains bound within those matrices, and any potential interaction with food components is limited and controlled under regulatory provisions. As such, discussions of taste or functional attributes in the context of food do not typically apply to this compound.

Acceptable Daily Intake Explained

The concept of acceptable daily intake (ADI) is a regulatory tool used to estimate the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For compounds like 2,2-DIBROMO-3-NITRILOPROPIONAMIDE that are not used as direct food additives, an ADI value specific to dietary intake may not be established in the same way as for conventional food additives. Instead, regulatory limits focus on controlling migration into food contact materials to ensure that any exposure remains minimal. In this context, the relevant CFR sections that govern indirect food contact use set conditions under which migration is considered safe. These conditions implicitly assume that any exposure resulting from use of the compound in adhesives or coatings will remain within acceptable boundaries, obviating the need for a separate ADI value. Therefore, while the ADI framework is a cornerstone of direct food additive safety assessments, indirect food contact substances such as this compound are regulated through migration limits and conditions of use rather than a formal ADI number. Understanding ADI helps readers recognize that safety evaluations integrate toxicological data, expected exposure levels, and safety factors to determine whether a substance can be used in food-related applications. In the absence of a defined numeric ADI for this compound, the regulatory approach emphasizes minimizing exposure through controlled use conditions and monitoring migration into food contact surfaces.

Comparison With Similar Additives

When comparing 2,2-DIBROMO-3-NITRILOPROPIONAMIDE with other antimicrobial agents used in food contact and industrial applications, it is useful to consider aspects such as function, regulatory context, and application scope. For example, organic acids such as sorbic acid and benzoic acid are used as direct food preservatives with established ADI values and broad approvals for use in food products. These compounds are ingested in controlled amounts and evaluated for safety based on dietary exposure. In contrast, 2,2-DIBROMO-3-NITRILOPROPIONAMIDE is used in indirect food contact settings and industrial microbial control rather than direct addition to food. Its regulatory status reflects this distinction: it is permitted under specific CFR sections for use in materials that may contact food but is not intended as a direct food additive. Other antimicrobial agents used in food contact applications, such as silver-based agents in packaging, also fall under indirect use provisions and are evaluated based on migration and exposure limits rather than direct ingestion standards. This comparison highlights the different regulatory pathways for antimicrobial additives depending on their intended use. Direct food preservatives undergo rigorous evaluation for dietary safety and have defined ingestion limits. Indirect food contact antimicrobial agents are governed by separate regulations that prioritize controlling exposure through material design and use conditions. As a result, understanding the functional role and regulatory framework for each type of additive is key to interpreting their safety profiles and appropriate applications.

Common Food Applications Narrative

Although 2,2-DIBROMO-3-NITRILOPROPIONAMIDE is not used directly as a food ingredient, its applications intersect with food manufacturing and packaging processes in specific ways due to its antimicrobial properties. In sugar milling operations, microbial growth can pose challenges to processing and product quality, leading manufacturers to use antimicrobial agents to keep equipment and product streams free of contamination. Under regulations for controlling microorganisms in sugar mills, antimicrobial agents including this compound may be employed under specified conditions to maintain hygiene standards and reduce spoilage. Another context in which this compound sees application is in the formulation of adhesives and coatings that come into indirect contact with food. For packaged foods such as boxed cereals, dry goods, or other products housed in paperboard packaging, adhesives and coatings play a crucial role in maintaining structural integrity. Incorporating an antimicrobial agent into these materials enables manufacturers to mitigate microbial growth on the surface of packaging, helping to preserve product quality during storage and transport. These uses reflect scenarios where an antimicrobial agent does not become a food ingredient itself but supports processes and materials that interact with food. When properly applied according to regulatory guidelines, the compound enhances the safety of food contact surfaces by reducing the potential for contamination. As with all indirect food additive uses, manufacturers must comply with limits and conditions of use outlined in relevant regulatory sections to ensure that any migration into food remains within acceptable bounds.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 173.320, 175.105, 176.170, 176.300

EFSA

  • Notes: No specific EFSA evaluation database link available for this compound

JECFA

  • Notes: No JECFA evaluation found for dietary intake

Sources

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