N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE

CAS: 608514-55-2 FLAVORING AGENT OR ADJUVANT

N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE is a synthetic flavoring agent noted for its meaty and herb-like aroma and is used to enhance savory profiles in various food applications.

What It Is

N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE is a chemical compound classified as a flavoring agent used in the formulation of food flavors. It has the CAS Registry Number 608514-55-2 and is identified by multiple synonyms and structural descriptors that reflect its molecular configuration and nomenclature. As a member of the amide class of compounds, this ingredient exhibits a backbone structure typical of fatty amides, with a cyclopropyl substituent on a nonadienamide chain. In industrial and regulatory databases, it is associated with identifiers such as FEMA Number 4087 and JECFA Flavor Number 1597, indicating its evaluation by flavor and food additive expert panels with respect to flavor use. Its sensory characteristics are described as meaty and herb-like, making it suitable for contributing savory notes to flavor blends designed for food products that benefit from such profiles. The compound’s molecular identity and properties, such as molecular formula C12H19NO and average mass, are recorded across chemical information repositories that support research, formulation, and regulatory reference activities. The ingredient has been cataloged by authoritative chemical registries, indicating a recognized set of structural and nomenclature identifiers that facilitate its use in flavor science and regulatory contexts. The array of names reflects the various naming conventions encountered in flavor chemistry, regulatory inventories, and technical literature, and underscores the importance of precise chemical definition for ingredient specification. Comprehensive understanding of what it is involves recognizing it as a specifically structured amide with sensory function that contributes aromatic complexity to formulated foods.

How It Is Made

The manufacturing of N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE involves synthetic organic chemistry techniques typical for constructing fatty amides with defined unsaturated carbon chains. At a high level, production begins with the preparation of a nonadienic acid or derivative that has the desired double-bond configuration (trans at the 2 position and cis at the 6 position) on a nine-carbon backbone. This intermediate is then coupled with cyclopropylamine or an appropriate cyclopropyl precursor through amide bond formation. Amide synthesis methods such as coupling reagents or activation of the acid component are standard techniques in flavor and fragrance chemical production. After the key chemical synthesis step, purification processes like distillation, crystallization, or chromatography are applied to isolate the target compound at a level of purity suitable for flavor use. During industrial-scale production, stringent quality control measures monitor the structural integrity, isomeric purity, and absence of by-products to ensure that the compound meets specifications for sensory performance and safety in food applications. Quality control often involves analytical methods such as gas chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy, which confirm the desired chemical structure and the configuration of double bonds. The production environment for such synthetic flavor compounds is typically a controlled chemical manufacturing facility equipped to handle reactive intermediates and to comply with safety standards for chemical synthesis. Given the specialized nature of the compound, its production routes are developed by chemists familiar with amide chemistry and flavor compound synthesis, and are optimized to balance yield, purity, and maintainability of defined sensory characteristics.

Why It Is Used In Food

N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE is used in food primarily for its role as a flavoring agent to enhance savory and meaty characteristics in flavor formulations. In the field of flavor science, specific compounds are selected for their ability to impart distinct sensory attributes that complement or improve the overall flavor profile of a product. This ingredient’s herb-like and meaty aroma profile contributes complexity and depth to savory flavor systems, making it useful in applications such as meat analogues, sauces, gravies, snack seasonings, and other products that benefit from nuanced savory notes. The compound is incorporated into flavor blends at concentrations appropriate to achieve the desired sensory impact without overpowering other components. Its use is guided by flavor formulation practices that consider interactions with other ingredients, such as enhancers, sweeteners, and texturizing agents, to achieve a balanced and appealing sensory experience. Flavor chemists leverage the aromatic qualities of compounds like this one to mimic or enhance natural food flavors, particularly when formulating reduced-fat, plant-based, or composite food products where sensory richness may be diminished. By integrating this compound into carefully designed flavor matrices, manufacturers can achieve targeted sensory goals, aligning with consumer expectations for robust and distinctive taste and aroma. The selection of this ingredient is driven by its sensory efficacy in contributing to specific flavor notes that are difficult to replicate with more conventional or natural flavoring agents alone. The technical rationale for its use also involves considerations of stability and compatibility within diverse food systems, enabling consistent performance under typical processing and storage conditions.

Adi Example Calculation

To illustrate how Acceptable Daily Intake concepts apply in a hypothetical calculation, consider a scenario where an expert committee has established an ADI for a flavoring compound. Suppose that an ADI is set at a numeric value that reflects conservative safety assessment. For an illustrative example, if an ADI for a flavor compound were stated at a hypothetical numeric value of X milligrams per kilogram of body weight per day, an individual weighing 70 kilograms could theoretically consume up to 70 times X milligrams per day without exceeding the ADI threshold. If X were 0.1 mg/kg body weight, this would correspond to a daily intake of up to 7 milligrams for a 70-kilogram person. This calculation is intended solely to demonstrate how ADI values are scaled to body weight and is not a recommendation for consumption levels. Actual intake from food products is typically far below such thresholds, as flavor compounds are used at very low concentrations to achieve desired sensory effects. It is important to understand that an ADI is a regulatory construct based on risk assessment, designed to ensure that routine dietary exposure to a compound remains within safe boundaries. Flavor chemists, regulatory authorities, and risk assessors use ADI concepts along with exposure estimates to evaluate whether ingredient usage patterns align with safety expectations, and to guide labeling and formulation practices.

Safety And Health Research

Safety and health research related to N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE focuses on evaluating its hazard potential and exposure in the context of use as a flavoring agent. Expert committees and flavor industry panels, such as those convened by JECFA and FEMA, assess data on chemical structure, metabolism, and anticipated intake from typical food use levels to determine whether any safety concerns arise under normal usage conditions. These evaluations consider attributes such as genotoxicity, subacute and subchronic toxicity, and any evidence from reproductive or developmental studies, where available, to form a comprehensive picture of safety. Based on available evaluations, expert panels have concluded that at current levels of intake associated with its role as a flavor ingredient, there is no safety concern, with such conclusions often conditioned on continued adherence to defined use levels. Such assessments are published in formal reports summarizing the methodology and rationale for safety determinations and are used by regulatory authorities and industry stakeholders to guide responsible formulation practices. In research contexts, the absence of adverse effects at typical use levels is interpreted within the framework of risk assessment, which accounts for both the potency of the compound and the magnitude of consumer exposure. Scientific assessments do not imply therapeutic benefits but rather aim to establish whether the compound poses undue risk when incorporated into foods for its intended functional purpose. Ongoing monitoring of emerging data and revisions to flavor evaluation frameworks ensure that safety considerations remain aligned with the best available scientific evidence. The collective body of safety research emphasizes data-driven evaluation, hazard characterization, and exposure assessment as central to understanding the health implications of flavor compounds in the diet.

Regulatory Status Worldwide

N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE is cataloged in regulatory inventories relevant to food ingredient use in major markets. In the United States, it appears in the Food and Drug Administration’s Substances Added to Food (formerly EAFUS) database, where it is listed with its CAS Registry Number and identified for use as a flavoring agent or adjuvant. This listing indicates recognition of the compound in the context of food ingredient inventories, although it does not by itself convey specific numeric usage limits or a formal regulation in Title 21 of the Code of Federal Regulations. The FEMA (Flavor and Extract Manufacturers Association) has assigned it FEMA Number 4087, and it is referenced in FEMA flavor library entries that provide context for expert panel evaluations of flavoring substances. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated the substance as part of flavoring group evaluations, with assessment summaries indicating consideration of intake levels and safety at typical use levels. Such evaluations are documented in expert committee reports that discuss exposure estimates and conditional safety conclusions when used as a flavoring agent. The compound’s regulatory status in other jurisdictions may be informed by similar flavor ingredient inventories or flavoring group evaluations by regional food safety authorities, although specific numeric authorizations and use-level limits are often established through detailed regulatory processes. As with many flavoring agents, its presence in these inventories reflects a path of review by technical expert panels and regulators familiar with flavor compound evaluation frameworks. Regulatory approaches worldwide prioritize ingredient safety assessment, and listings in such databases are part of the broader governance that enables formulation and labeling in compliance with local food laws.

Taste And Functional Properties

The taste and functional properties of N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE are centered on its ability to deliver sensory complexity, particularly in the savory dimension. Organoleptically, it is described as having a meaty and herb-like aroma, making it suitable for enhancing umami-like characteristics in flavor blends. The presence of unsaturated hydrocarbon chains and the cyclopropyl group contribute to the volatility and interaction with olfactory receptors, which underpins its sensory impact. In practical terms, this compound is not a direct taste agent in the way that salt or sweetness modulators are, but it functions as part of a flavor profile that influences perceived taste through aroma. Its solubility properties reflect those of many flavor compounds; it is typically more soluble in alcohol and oil media than in water, which aligns with its integration into oil-based flavor systems or emulsified flavor carriers. Such solubility behavior affects formulation strategies, as flavorists often use carriers or solvents that promote dispersion and stability in the final product matrix. The compound exhibits functional stability within a defined range of processing conditions, although like many unsaturated organic compounds, it may be sensitive to extreme heat or prolonged exposure to oxidative environments. This stability profile informs how it is incorporated during food processing, with consideration given to when flavor additions are made to preserve intended sensory attributes. Overall, the compound’s functional profile combines aromatic potency with formulation versatility, enabling its use in a variety of flavored food categories where meaty and herb notes are desired.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) represents a value derived by expert committees to define the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. ADIs are often expressed in milligrams per kilogram of body weight and are based on toxicology data, safety factors, and exposure estimates. In the context of flavoring agents such as N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE, expert panels analyze available toxicity and exposure data to determine whether a formal ADI is necessary or whether intake from typical use is sufficiently low that safety concerns do not emerge. When an ADI is established for food additives with extensive toxicological data, it provides a benchmark for regulatory authorities and formulators to ensure that ingredient usage remains within safe boundaries. For many flavor compounds, estimated intakes from food use are orders of magnitude below levels that would trigger toxicological concern, and this understanding is integrated into risk assessment frameworks. An ADI is not a recommended target for consumption but rather a conservative threshold to protect public health, incorporating safety margins to account for uncertainty and variability among individuals. In the absence of a formally established numeric ADI for a specific flavoring agent, risk assessors rely on expert evaluations of exposure relative to potential hazard endpoints to determine that use at typical levels does not pose significant risk. This approach underscores the principle that safety evaluation in food chemistry balances exposure, hazard, and conservative safety factors to protect diverse populations.

Comparison With Similar Additives

When comparing N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE with other flavoring agents, it is useful to consider similarities and differences in sensory profile, functional role, and typical usage. For example, compounds such as 2,4-decadienal and certain pyrazines also contribute savory, roasted, or meaty notes in flavor systems, and are selected by flavorists to achieve specific aromatic goals. While pyrazines may impart nutty or roasted characteristics, N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE emphasizes herbaceous and meaty nuances, illustrating how different chemical classes can influence overall flavor perception. Other amide-based flavor compounds may share structural features, such as carbon chain length and unsaturation, which affect volatility and olfactory receptor interaction. The choice among these ingredients depends on the desired sensory target and the balance of notes within a flavor formulation. Compared to sweet flavor enhancers or salt potentiators, savory-focused agents like this one are used in conjunction with other modulators to create a rounded sensory impression, rather than functioning as primary taste drivers. The diversity of flavor compounds available enables formulators to tailor profiles with precision, selecting ingredients that complement one another and align with product goals, whether enhancing savory depth in snacks or balancing aromatic complexity in sauces. Understanding the functional niches of similar additives supports informed formulation strategies, leveraging the unique contributions of each compound to achieve desired flavor outcomes.

Common Food Applications Narrative

In the context of food applications, N-CYCLOPROPYL-TRANS-2-CIS-6-NONADIENAMIDE is employed to enrich the savory character of formulated foods across a range of categories. Its sensory profile lends itself to products where depth of flavor and complexity are important to consumer perception. For example, in savory snacks where a robust flavor backbone is sought, this ingredient can be part of a flavor blend that supports notes of roasted meat, herbs, and umami-enhancing impressions. Similarly, in soups, sauces, and gravies, formulators may incorporate it to elevate the overall aromatic intensity and complement other savory ingredients like hydrolyzed vegetable proteins or yeast extracts. Ready-to-cook meal kits and prepared dishes that aim to deliver rich, home-style flavors can also benefit from its inclusion, particularly in systems where natural flavors alone may not achieve the desired sensory balance. Beyond snack and meal applications, it may play a role in seasoning blends for plant-based meat analogues, contributing aromatic complexity that consumers associate with traditional protein-rich foods. Its use in condiments—such as savory spreads, marinades, and dressings—can enhance the perception of depth and roundness in flavor. The compound’s integration into such products is carried out with precision, as flavorists tailor the level of addition to achieve a harmonious interaction with other components in the formula. The end result is a sensory profile that elevates the eating experience, bringing forward nuanced savory and aromatic notes that resonate with consumer taste expectations. Across these applications, the ingredient’s value lies in its ability to support and reinforce complementary flavor elements, making it a useful tool in the flavor chemist’s repertoire for creating compelling and enjoyable food products.

Safety & Regulations

FDA

  • Notes: Listed in Substances Added to Food inventory; specific CFR authorization not verified.

EFSA

  • Notes: No explicit numeric EFSA ADI found in authoritative sources.

JECFA

  • Notes: JECFA evaluations referenced; no explicit numeric ADI or year confirmed on d documents.

Sources

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